You could work anywhere. Why us?
Join a pre-IPO startup with capital, traction and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).
Work closely with brilliant leaders and team mates from companies like McKinsey, BCG, Bain, Nvidia, GEICO, Better, etc.
Disrupt a massive market and take us to a $10B business in the next few years.
Be immersed in a talent-dense environment and greatly accelerate your career growth.
About the opportunity:
As the Manager, Business Development and Partnerships, you’ll be a driving force behind the growth and success of our partner ecosystem. You’ll strategically manage and strengthen existing partnerships while identifying and securing high-value new collaborations that align with our long-term vision. By leveraging your deep understanding of market dynamics, you’ll propose innovative tools and product solutions that unlock scalable opportunities for both our business and our partners.
This high-impact role involves collaborating closely with cross-functional teams—product, operations, data, and sales—to craft and execute partnership strategies that deliver lasting business outcomes. Reporting directly to the VP of Partnerships, you’ll play a pivotal role in shaping the strategic direction of our partnership portfolio and accelerating growth across the organization.
Jerry is building the first super app to help people optimize all aspects of owning a car – insurance, buy/sell, registration, loans, safety, repairs, parking, etc – a $2T market in the U.S. We started with insurance in 2019, and since then we’ve launched loan refinancing, driving insights, a repair marketplace, car diagnostics, and a GenAI-powered chatbot & voicebot. We have amassed over 5M customers, raised $240MM in funding, scaled our revenue 60X and our team to 225 across 6 countries.
How you will make an impact:
Foster Strong Partner Relationships: Be the go-to person for building and nurturing deep, trusted relationships with existing partners. Your ability to serve as the primary point of contact will ensure long-term success and collaboration.
Drive Strategic Growth: Take ownership of developing and executing structured business plans or quarterly OKRs that align with each partner's unique goals, maximizing the potential of strategic partnerships through a deep understanding of their business.
Optimize Performance: Use your analytical skills to dive into data, uncover trends, and identify key opportunities for improving business KPIs. Your insights will be critical in driving smarter decisions and better outcomes for both sides.
Generate New Opportunities: Lead the charge in creating new growth opportunities with both existing and potential partners. Your expertise in negotiating will be key in structuring mutually beneficial deals that drive expansion.
Deliver Actionable Insights: Perform Analysis and regularly provide valuable insights and updates to both partners and internal teams, ensuring that everyone stays aligned, informed, and empowered to make the right decisions.
Resolve Challenges Quickly: Be the problem-solver, triaging operational and executional issues that arise across partners and internal teams. Your ability to act swiftly and decisively will keep everything running smoothly.
Ideal profile:
4+ years of experience in Business Development, Partnerships, or Management Consulting
Proven track record of successfully managing complex projects from inception to completion, with meticulous attention to detail and a strong bias for action.
A go-getter with a strong work ethic, a willingness to learn and adapt quickly, and a desire to contribute to the success of a high-growth company.
A data-driven approach to decision-making, with the ability to analyze complex situations and make informed, actionable decisions.
Excellent written and verbal communication, presentation, and interpersonal skills with the ability to effectively communicate complex ideas to both internal and external stakeholders.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all in one place. Since 2019, we’ve become one of the fastest-growing tech companies in the U.S.
We are looking for an Insurance Compliance & Regulatory Senior Lead to join our Insurance Operations team. Reporting directly to our Senior Manager of Insurance Ops, this role is ideal for an experienced insurance operations leader who excels at solving complex systemic issues, building rigorous compliance frameworks, and acting as the strategic bridge between our customers, carrier partners, state regulators, and internal product teams.
You write with judgment, not just accuracy. You can take a complicated file, determine what actually happened, and state a clear, complete, well-supported position under a deadline.
You solve problems at the root. You love digging beneath the surface to identify root causes and aren't afraid to roll up your sleeves to resolve complex edge cases while mentoring others to do the same.
You excel at high-stakes de-escalation. You possess executive-level composure and genuine empathy, easily navigating intense situations with customers, state regulators, and insurance carrier leaders.
You turn friction into product fixes. You naturally spot patterns in complaint data and have the strategic mindset to partner with tech, legal, and ops leaders to permanently fix underlying vulnerabilities.
You build and maintain operational rigor. You thrive in a remote environment, bringing organization, accountability, and process design to ensure compliance deadlines are met without exception.
Lead Escalation Operations: Oversee the end-to-end investigation and de-escalation framework for critical customer complaints, acting as the final point of escalation for complex issues.
Own DOI and Insurance Carrier Responses: Manage carrier audits and state regulatory complaint workflows; author, review, and finalize official correspondence to state departments of insurance, carrier partners, and consumers.
Systemic Root-Cause Resolution: Partner with Legal, Product, and Engineering to convert audit findings and complaint trends into product changes, automated checks, and process fixes.
Complaint Log & Compliance Controls: Own the complaint log and the workflows behind it, keeping records accurate and audit-ready for market conduct examinations and state data calls, and meeting statutory deadlines and internal SLAs.
Carrier Relationship & Claims Support: Serve as the primary operational liaison for carrier partners during high-stakes claims investigations, regulatory inquiries, and information audits.
Team Guidance & Coaching: Provide operational guidance, quality oversight, and subject-matter expertise to team members handling customer service, compliance, and claims support.
Regulatory Reporting & Documentation: Maintain accurate, audit-ready records of complaint trends, regulatory correspondence, and resolution timelines to support timely responses to DOI inquiries and to inform leadership of emerging compliance risk areas.
Active Property & Casualty (P&C) license required (or willingness to obtain it quickly)
5+ years of insurance experience, including 3+ years in state insurance and regulatory compliance.
2+ years in a team lead, managerial, or supervisory role preferred.
Proven track record of directly managing state regulatory inquiries (DOI complaints) and carrier audit relationships.
Working knowledge of NAIC model regulations, state insurance codes, and market conduct examination standards, with the ability to translate regulatory requirements into operational policy and team-level practice.
Exceptional executive-level written and verbal communication skills with an eye for legal and compliance detail.
Strong analytical mindset with experience using data to drive cross-functional product and operational improvements.
Bachelor’s degree preferred (or equivalent practical leadership experience).
Strategic Leadership & Impact: Work directly with Legal, Product, and Ops leadership to shape Jerry’s operational strategy and customer trust standards.
100% Remote Work: Work from home with all equipment provided.
Full Benefits: Comprehensive medical, dental, vision insurance, and 401(k) matching.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why We Exist
Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive.
Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace.
We've reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024. We're now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.
Why We’re Hiring
Our Data Science & Analytics team has been a force multiplier and accelerant to our business that has helped us reach these pivotal milestones in spite of headwinds and within a highly competitive market. They are a team of former McKinsey, BCG and Bain consultants who drive data & insights, and inform decision-making across every corner of our business. They are analytical powerhouses and first principles problem solvers who push forward our most important initiatives across product, growth, tech, and operations.
Every business unit has a Data Science team member embedded within it — someone who doesn't just run analyses and build dashboards, but shapes what questions we should ask, what data to pull, what conclusions to draw, what decisions to make, and then drives our teams towards our next goal: go from 5M to 50M customers and become a $10B business in the next 4 years.
As our business continues to expand, there is growing demand for more Data Science team members. We are hiring 2-3 people to drive impact in these areas:
Growth Marketing
Product Development
AI & Automation
Strategic Partnerships
On leveling: You may see job ads for this role at different job levels. Our priority is finding the right people, we can be flexible with job title/leveling.
Why You Will (Or Won't) Like Working Here
No slides: If you've worked in consulting, you know what it feels like to be up at 3am reformatting a deck. That doesn't exist here. The only work that gets done at Jerry is work that will materially change the trajectory of our business — an important product, a new growth channel, a key metric, a critical partner relationship, etc.
No corporate fluff: The Data Science & Analytics team is 14 insatiable learners who care deeply about solving difficult problems and making a tangible impact. Every person owns a critical domain. There is no bloat, unnecessary meetings, or waiting for approvals.
Hands-on: This is not a pure strategy role, you will also own execution. Your day-to-day will be surfacing analytical insights, driving decisions, and seeing them through end-to-end.
What You'll Own
You'll sit on our central Data Science & Analytics team but you’ll be embedded in one of Jerry's core business areas — growth, product, AI and automation, strategic partnerships — and own the analytical function for that business unit end-to-end.
Define the right problems: Before any analysis, understand what business question it's answering and what decision it will inform. Push back if the question is flawed.
Data and insights: Define metrics, build reports, run analyses, design experiments, and surface data insights that move your team's key metrics.
Drive outcomes: Bring recommendations to your counterparts in product, growth, finance or operations, tell them what's happening and why, and what next steps should be.
Who You Are
First principles thinker: You break ambiguous problems into clear hypotheses before touching data. You're analytically strong (comfortable with SQL or Python) but your instinct is to ask \"what are we trying to solve here?\" before jumping to \"what should I build?\"
Direct communicator: You can walk a skeptical stakeholder through a complex finding and get buy-in quickly. You write clearly, speak precisely, and don't bury the lede.
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
What You'll Bring
1+ years of experience at a consulting firm, investment bank, or high-growth technology company.
Strong analytical skills; ability to pull, structure, and interpret data independently.
Track record of owning ambiguous problems and delivering impact.
Clear, persuasive communicator who can influence decisions at the leadership level.
Our Tools
SQL (Clickhouse), Metabase, Python, Jupyter Hub, GitHub.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why We Exist
Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive.
Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace.
We've reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024. We're now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.
Why We’re Hiring
Our Data Science & Analytics team has been a force multiplier and accelerant to our business that has helped us reach these pivotal milestones in spite of headwinds and within a highly competitive market. They are a team of former McKinsey, BCG and Bain consultants who drive data & insights, and inform decision-making across every corner of our business. They are analytical powerhouses and first principles problem solvers who push forward our most important initiatives across product, growth, tech, and operations.
Every business unit has a Data Science team member embedded within it — someone who doesn't just run analyses and build dashboards, but shapes what questions we should ask, what data to pull, what conclusions to draw, what decisions to make, and then drives our teams towards our next goal: go from 5M to 50M customers and become a $10B business in the next 4 years.
As our business continues to expand, there is growing demand for more Data Science team members. We are hiring 2-3 people to drive impact in these areas:
Growth Marketing
Product Development
AI & Automation
Strategic Partnerships
On leveling: You may see job ads for this role at different job levels. Our priority is finding the right people, we can be flexible with job title/leveling.
Why You Will (Or Won't) Like Working Here
No slides: If you've worked in consulting, you know what it feels like to be up at 3am reformatting a deck. That doesn't exist here. The only work that gets done at Jerry is work that will materially change the trajectory of our business — an important product, a new growth channel, a key metric, a critical partner relationship, etc.
No corporate fluff: The Data Science & Analytics team is 14 insatiable learners who care deeply about solving difficult problems and making a tangible impact. Every person owns a critical domain. There is no bloat, unnecessary meetings, or waiting for approvals.
Hands-on: This is not a pure strategy role, you will also own execution. Your day-to-day will be surfacing analytical insights, driving decisions, and seeing them through end-to-end.
What You'll Own
You'll sit on our central Data Science & Analytics team but you’ll be embedded in one of Jerry's core business areas — growth, product, AI and automation, strategic partnerships — and own the analytical function for that business unit end-to-end.
Define the right problems: Before any analysis, understand what business question it's answering and what decision it will inform. Push back if the question is flawed.
Data and insights: Define metrics, build reports, run analyses, design experiments, and surface data insights that move your team's key metrics.
Drive outcomes: Bring recommendations to your counterparts in product, growth, finance or operations, tell them what's happening and why, and what next steps should be.
Who You Are
First principles thinker: You break ambiguous problems into clear hypotheses before touching data. You're analytically strong (comfortable with SQL or Python) but your instinct is to ask \"what are we trying to solve here?\" before jumping to \"what should I build?\"
Direct communicator: You can walk a skeptical stakeholder through a complex finding and get buy-in quickly. You write clearly, speak precisely, and don't bury the lede.
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
What You'll Bring
2+ years of experience at a consulting firm, investment bank, or high-growth technology company.
Strong analytical skills; ability to pull, structure, and interpret data independently.
Track record of owning ambiguous problems and delivering impact.
Clear, persuasive communicator who can influence decisions at the leadership level.
Our Tools
SQL (Clickhouse), Metabase, Python, Jupyter Hub, GitHub.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why you should join us
Jerry.ai is a profitable, Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We’re building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
The opportunity is massive — car insurance alone is a $300B market in the U.S. We spent the last few years building our supply (we work with 100+ insurance carriers) and our technical infrastructure (60% of policies today are sold automatically without human intervention, 90% of inbound customer inquiries are resolved via AI and automation). The next chapter is about accelerating our growth — going from 5M to 50M customers by 2030.
About this role
The Growth team owns the entire customer sign-up and purchase funnel for our car insurance marketplace, and drives how millions of people discover, evaluate, and become a Jerry customer.
We’re looking for a Senior Product Manager to own the customer journey from first impression through purchase and beyond. This role sits at the heart of our business - you’ll take end-to-end ownership of high-impact funnels that directly move the needle on our north star goal. This is not a “growth hacking” role or one that prioritizes revenue at the cost of the customer experience and trust — we care about building a durable growth engine by creating a magical customer experience and providing unreasonable hospitality. You will need to investigate and understand customer needs across different personas, navigate complex backend systems, and translate that complexity into clear, trustworthy, and elegant user experiences.
This role reports to the VP of Growth. You’ll partner closely with Engineering, Design, Analytics, Marketing, and Leadership — including the CEO — to identify step-change opportunities and turn insight into shipped products that meaningfully moves the business.
What you will actually do
Things move quickly here and we just launched 5 big products this year, so there likely won’t be a “typical” day but here are some examples of things you could own:
Own landing pages, signup funnels, app download pages, including simplifying the user flow (insurance shopping is very complex and requires a lot of data inputs from the customer), personalizing the experience by user persona and marketing channel, building trust through designing delightful and helpful communication, copy and UI, etc
Own quote shopping, including improving the display of complex information to our customers without cognitive overload, integrating different insurance carriers (who all model risk and behave differently) into simple user experiences, balancing the needs and goals of our customers and our insurance carrier partners
Integrating other products (e.g., roadside assistance, home insurance, property tax appeals, motorcycle insurance, etc) into our car insurance shopping funnel
Why you will (or won't) like it here
Direct exposure: You'll report directly to our VP of Growth with visibility to the c-suite team. You'll have visibility into product strategy, business model tradeoffs, and roadmap decisions from Day One.
Time zone constraint: The engineering team is partly based overseas. Occasionally, you may need to overlap with their business hours.
Small team: The Growth team has 3 Product Managers (including you) and the surface area is huge, which means you'll have to be scrappy, but also that you'll have lots of scope and ownership.
Fast shipping culture: We run weekly sprints. Products that take 6-12 months to ship elsewhere, we launch in 1-2 months. This means faster learning and faster growth, but also a more demanding environment.
Who we get excited about
First principles thinker: You’re comfortable breaking ambiguous problems into clear hypotheses before reaching for a solution, as well as working with incomplete information.
Diligent: Your follow through is impeccable. When you own something, nothing falls through the cracks.
Customer-centric: You find customer feedback intrinsically interesting and not some box to check. You care deeply about understanding what drives how they think, feel and behave.
Strong communicator: You can work effectively across engineering, design, analytics, and marketing, including across time zones. You calibrate how much context others need and give it clearly.
What you bring
5+ years of experience in product management (ideally consumer-facing products)
Strong analytical skills; ability to pull, structure, and interpret data independently.
Track record of owning ambiguous problems and delivering impact.
Strong written and verbal communication skills, including the ability to synthesize messy signals into clear recommendations
Willingness to maintain regular daily overlap with global business hours for engineering coordination
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why you should join us
Jerry.ai is a profitable, Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We’re building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
The opportunity is massive — car insurance alone is a $300B market in the U.S. We spent the last few years building our supply (we work with 100+ insurance carriers) and our technical infrastructure (60% of policies today are sold automatically without human intervention, 90% of inbound customer inquiries are resolved via AI and automation). The next chapter is about accelerating our growth — going from 5M to 50M customers by 2030.
About this role
The Growth team owns the entire customer sign-up and purchase funnel for our car insurance marketplace, and drives how millions of people discover, evaluate, and become a Jerry customer.
We’re looking for a Product Manager to own the customer journey from first impression through purchase and beyond. This role sits at the heart of our business - you’ll take end-to-end ownership of high-impact funnels that directly move the needle on our north star goal. This is not a “growth hacking” role or one that prioritizes revenue at the cost of the customer experience and trust — we care about building a durable growth engine by creating a magical customer experience and providing unreasonable hospitality. You will need to investigate and understand customer needs across different personas, navigate complex backend systems, and translate that complexity into clear, trustworthy, and elegant user experiences.
This role reports to the VP of Growth. You’ll partner closely with Engineering, Design, Analytics, Marketing, and Leadership — including the CEO — to identify step-change opportunities and turn insight into shipped products that meaningfully moves the business.
What you will actually do
Things move quickly here and we just launched 5 big products this year, so there likely won’t be a “typical” day but here are some examples of things you could own:
Own landing pages, signup funnels, app download pages, including simplifying the user flow (insurance shopping is very complex and requires a lot of data inputs from the customer), personalizing the experience by user persona and marketing channel, building trust through designing delightful and helpful communication, copy and UI, etc
Own quote shopping, including improving the display of complex information to our customers without cognitive overload, integrating different insurance carriers (who all model risk and behave differently) into simple user experiences, balancing the needs and goals of our customers and our insurance carrier partners
Integrating other products (e.g., roadside assistance, home insurance, property tax appeals, motorcycle insurance, etc) into our car insurance shopping funnel
Why you will (or won't) like it here
Direct exposure: You'll report directly to our VP of Growth with visibility to the c-suite team. You'll have visibility into product strategy, business model tradeoffs, and roadmap decisions from Day One.
Time zone constraint: The engineering team is partly based overseas. Occasionally, you may need to overlap with their business hours.
Small team: The Growth team has 3 Product Managers (including you) and the surface area is huge, which means you'll have to be scrappy, but also that you'll have lots of scope and ownership.
Fast shipping culture: We run weekly sprints. Products that take 6-12 months to ship elsewhere, we launch in 1-2 months. This means faster learning and faster growth, but also a more demanding environment.
Who we get excited about
First principles thinker: You’re comfortable breaking ambiguous problems into clear hypotheses before reaching for a solution, as well as working with incomplete information.
Diligent: Your follow through is impeccable. When you own something, nothing falls through the cracks.
Customer-centric: You find customer feedback intrinsically interesting and not some box to check. You care deeply about understanding what drives how they think, feel and behave.
Strong communicator: You can work effectively across engineering, design, analytics, and marketing, including across time zones. You calibrate how much context others need and give it clearly.
What you bring
3+ years of experience in product management (ideally consumer-facing products)
Strong analytical skills; ability to pull, structure, and interpret data independently.
Track record of owning ambiguous problems and delivering impact.
Strong written and verbal communication skills, including the ability to synthesize messy signals into clear recommendations
Willingness to maintain regular daily overlap with global business hours for engineering coordination
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Join a pre-IPO startup with capital, traction, and runway ($240M funded | 40X revenue growth in 4 years | $2T market size).
Work closely with brilliant leaders and teammates from companies like McKinsey, BCG, Nvidia, Better, SoFi, etc.
Disrupt a massive market and help scale us to a $5B business in the next few years.
Be immersed in a talent-dense environment and accelerate your career growth exponentially.
Own end-to-end creative excellence and be a tastemaker at Jerry - from concepting and production to agency management.
At Jerry, we are redefining and radically improving how people manage car ownership, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry simplifies and automates car ownership while providing personalized services tailored to all car owners' needs. We are the #1 rated and most downloaded app in our category with a 4.7-star rating in the App Store and more than 5 million customers — and we're just getting started.
We're looking for a Senior Creative Strategist with sharp performance instincts and elevated visual taste. Someone who’s obsessed with advertising, and excited about how AI and new media are reshaping creative production. You'll own the full creative lifecycle: concepting, producing, and iterating ads that drive measurable results across TikTok, Meta, YouTube, and CTV, while raising the bar on craft and brand quality. You will be a driving force of Jerry’s creative engine with production chops to bring ideas to life yourself.
Why you will (or won’t) like working here
Large canvas: You won’t inherit a set-in-stone playbook. You will contribute meaningfully for our brand foundation. Your creative intuition will direct us to both what performs and what builds brand equity.
End-to-end ownership: This is a senior level role in scope and impact, but you also will be hands-on: concepting, directing production briefs, writing scripts, editing video, and using AI tools to move fast and unlock the next level.
Car ownership is not “sexy”: Insurance, maintenance, and safety are only topics people think about when they have a bill to pay, a flat tire to change, or when they get into an accident. Anyone can market something inherently exciting, but can you build enthusiasm and trust around a “dry” topic?
Concept and produce performance creative end-to-end: from ideation and scripting through editing and delivery, across paid social, CTV, and emerging channels.
Bring a sharp creative eye to every asset: elevating visual quality, pacing, and storytelling to raise Jerry's brand while keeping creative performance-driven.
Stay on top of platform trends, formats, and cultural shifts: ensuring Jerry's creative stays fresh, relevant, and effective.
Develop hooks, angles, and creative frameworks rooted in what actually drives performance, not just what looks good.
Translate performance data into creative direction: partnering with media and growth teams to turn signals into better ads.
Manage and maximize agency and production partners: writing briefs, providing creative direction, and quality-checking work to ensure external teams deliver at Jerry's standard.
Edit video directly: you're fluent in editing tools and comfortable cutting, iterating, and polishing ads at speed without sacrificing quality.
Leverage AI tools (for ideation, scripting, editing, asset generation, etc.) to accelerate workflows and unlock new creative possibilities.
5+ years in performance-driven creative production — ideally at a performance media agency and/or an in-house growth creative team at a DTC or app-based company.
Proven track record producing or directing high-performing creative for paid channels (Meta, TikTok, YouTube, CTV, etc.).
Strong performance creative intuition — you understand hooks, pacing, CTAs, and what makes people stop scrolling. You can concept ads that convert
Elevated visual taste — you have an eye for design, composition, and brand quality. You can take performance creative from functional to beautiful without losing effectiveness.
Video editing fluency — you can cut and iterate ads quickly yourself, making them look premium without needing heavy direction.
Collaborative and entrepreneurial mindset — thrives in fast-paced environments, comfortable bridging creative, media, and analytics teams.
AI fluency — you actively experiment with generative tools to speed up production, expand creative range, or improve output quality.
Bonus: experience in both a performance media agency and a brand or design agency, with exposure to brand-level creative craft. You know how to make ads that perform and ads that feel premium. You don't see those as tradeoffs.
Jerry's creative team has proven performance chops — but we're ready to level up our creative engine. This role is the key to unlocking exponentially more volume and creative diversity: someone with the taste to raise the bar, the production skills to move fast, and the performance instincts to ensure everything we ship drives results.
You'll be the connective tissue between idea and impact — helping us build a scalable creative system that blends craft, data, AI, and media strategy.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
About us:
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024.
Why we exist:
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat).
About this program:
Our next chapter is about accelerating growth – going from 5M to 50M customers by 2030.
This year alone, we launched 5 new products – home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance. Each of these new businesses comes with its own operational complexity, distinct user personas and painpoints, and its own path to scale.
As our business expands, we have a growing list of ideas but not enough people to execute them. This program exists to close that gap. We are looking for 2-3 associates to work directly with, and be mentored by, our Cofounder/CEO, and work on some of the highest-leverage problems in our business.
Reporting directly to our CEO, you will have a unique opportunity to develop the craft of product building, learn how a serial founder/CEO thinks and makes decisions, and see/understand a late stage tech startup’s day-to-day challenges as it goes through a rapid growth phase. You will be exposed to nearly every function at the company (i.e., product, growth, operations, finance, engineering, data), learn how to execute big-picture strategies and navigate the intricacies of a complex business.
A successful graduate will likely go on to become a product leader, growth leader, or run a function here or elsewhere. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you.
Who we get excited about:
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
First principles thinker: You break ambiguous problems into clear hypotheses, and your instinct is to ask \"What are we trying to accomplish here?\" before jumping to \"What is the solution?\".
Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.
Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.
What you bring:
2+ years of experience in management consulting, venture capital, private equity, or a startup environment
Bachelor's degree in a quantitative discipline such as STEM, economics, or similar
Ability to work in-person in our Palo Alto office alongside our CEO and executive team for the first 6-12 months
Compensation:
This position offers base salary and stock options. The base salary for this position within the San Francisco Bay Area is $120,000—$160,000 USD, but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with 4% employer matching, and wellness benefits, among others.
Location:
This role requires being in our Palo Alto office five days a week, at least until you are capable of operating independently.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
About us:
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024.
Why we exist:
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat).
Why we’re hiring:
Our next chapter is about accelerating growth – from 5M to 50M customers by 2030.
This year alone, we launched 5 new products – home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance. Each of these new businesses comes with its own operational complexity, distinct customer pain points, and its own path to scale.
As our business expands, we have a growing list of ideas but not enough people to execute them. This role exists to close that gap. We are looking for 2-3 Product Managers to work directly with, and be mentored by, our Cofounder/CEO (2x YC founder), and work on building or scaling one of our new product verticals.
Reporting directly to our CEO, you will have a unique opportunity to develop the craft of product building, learn how a serial founder/CEO thinks and makes decisions, and see/understand a late stage tech startup’s day-to-day challenges as it goes through a rapid growth phase. You will be exposed to nearly every function at the company (i.e., product, growth, operations, finance, engineering, data), learn how to execute big-picture strategies and navigate the intricacies of a complex business.
If you are successful, you will likely go on to become a product leader or commercial leader (e.g. owning P&L) here or elsewhere. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you.
Who we get excited about:
Insatiable learner: You are constantly seeking to deepen your knowledge, sharpen your skills, and master whatever craft or goal you’ve set your mind to.
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.
Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.
What you bring:
Ideally 1+ years of experience in a demanding environment such as management consulting, investment banking, venture capital, private equity, an early startup environment, or similar
Bachelor's degree in any discipline
Ability to work in-person in our Palo Alto office alongside our CEO and executive team at least for the first 6-12 months
Compensation:
This position offers base salary and stock options. The base salary for this position within the San Francisco Bay Area is 130,000—160,000 USD, but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with 4% employer matching, and wellness benefits, among others.
Location:
This role requires being in our Palo Alto office five days a week, at least until you are capable of operating independently.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Jerry.ai is a profitable, Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We’re building the first AI-powered advisor to manage all your physical assets. We started with the car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
About this role
We’re at an inflection point in our journey. After 2 years of profitable growth with a stable core business (car insurance marketplace), we’re ready to expand our product offerings and accelerate customer growth.
We’re looking for 2-3 Product Managers to drive progress across one of our key new product bets, including motorcycle insurance (just launched), home insurance (also just launched), new insurance products for other assets like boat and RV (concept phase), as well as non-insurance products to make car and home ownership easier such as helping customers save money on their property taxes (about to launch).
Each of these new product areas comes with its own operational complexity, its own customer personas and painpoints, and its own path to scale. And we’re looking for builders who are excited to take ownership of one of these new bets.
Why you will (or won't) like working here
0-to-1 scope: The products you will work on are new territory for us. There are no established frameworks, no prior PM who has figured it out.
Product complexity: Property tax rules vary county by county. Specialty vehicle insurance involves regulatory and product complexity that doesn't exist in standard auto. These are not clean, well-scoped problems to solve.
Real impact: You will have meaningful ownership. And what you do will likely materially impact the trajectory of our business over the next few years.
There are several new product bets in the motion. The specific product you will work on will largely depend on your prior experience, interests/preferences, and our business priorities when you join the team.
The goal in every case remains the same: ramp quickly on a new domain, distill data and insights to identify the highest leverage areas to prioritize (including quantitative data from our Data Science team and qualitative data from our Customer Insights & Research team), build and ship new products, get customer feedback quickly, apply learnings and iterate, and compound on what works.
Whether it’s home, motorcycle, boat or RV products, you will be a key contributor to our product roadmap and own execution from early concept or early launch to finding product-market fit, and scaling.
Who you are
A first-principles thinker: You approach problems with curiosity and use data to develop clear hypotheses before you reach for a solution. You're analytically strong but your instinct is to ask \"what are we trying to solve here?\" before jumping to \"what should I build?\"
An owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
Empathetic & Curious: You care deeply about understanding what drives how they think, feel and behave.
Diligent: Your follow through is impeccable. When you own something, nothing falls through the cracks.
5+ years in management consulting (MBB or equivalent), consumer-facing product management, or equivalent role at a high-growth startup
Consumer product instincts, either from direct product building experience or from close work alongside consumer product teams
Comfort with data: able to run your own analysis and build conviction from messy signals
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
About us:
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024.
Our purpose:
Your car, home, and motorcycle aren’t just purchases, they’re the physical embodiment of the life you’ve worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, and now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat).
About the role:
Our next chapter is about accelerating growth, from 5M to 50M customers by 2030.
This year alone, we launched 5 new products: home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance, among others within car and home ownership categories currently incubating. Each of these new businesses comes with its own operational complexity, distinct customer pain points, and its own path to scale.
We are looking for a General Manager to lead one of these new businesses. Reporting directly to our Cofounder/CEO, you will own the P&L, set the strategy, and be accountable for everything from product development, customer growth, partnerships, and operations. Depending on which product line, you may also lead a small team (1-2 people to start).
If you’re looking for an opportunity to build and scale a new business within a late-stage startup with an existing user base, product market fit, capital, traction, and a high caliber team, we’d love to hear from you!
Who we get excited about:
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside your swim lane.
Insatiable learner: You are constantly seeking to deepen your knowledge, sharpen your skills, and master whatever you’ve set your mind to.
Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.
Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.
What you bring:
6+ years of experience in venture capital, private equity, or hands-on operating roles in fast-growing startups
Bachelor’s degree in any discipline
Ability to work in person in our Palo Alto office alongside our CEO and executive team
Compensation:
This position offers base salary and stock options. The base salary for this position within the San Francisco Bay Area is $200,000— $250,000 USD, but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with 4% employer matching, and wellness benefits, among others.
Location:
This role is based in our Palo Alto office, 2-3 days a week.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why you should join us:
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We're building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, now we're expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
We're growing fast, which means our HR operations are getting more complex by the month, more states, more employees, more edge cases. Right now that complexity mostly lands on two people. We need someone who thrives doing the hands on work: real compliance problems to solve, policies to write, escalations that need judgment instead of a script. You'll also have room to bring AI into how we run HR ops to help cut the busywork so you can spend more time on the parts that matter.
The opportunity:
This isn't a role where you're processing paperwork and waiting for direction. You'll own the parts of HR operations that actually require judgment: multi-state compliance, policy drafting, and the payroll and benefits questions that come up when the answer isn't in a handbook. You've done this kind of work before, in-house, hands-on, and you're ready to be the person others come to when something's more complicated than usual.
You'll also have a real say in how AI fits into HR ops here, spending less time on the repetitive stuff and more time on the judgment calls that need a person.
What you'll own:
Multi-state compliance: tracking state-by-state law changes, drafting policy updates, and making sure they're actually implemented (not just written) across every employee classification and pay range
Our annual compliance audit and handbook refresh, yours to lead start to finish, in your first 90 days
Escalated payroll, benefits, and leave questions that need a more experienced hand
Reviewing and unblocking the work of our Payroll and HR Administration team members
Rearchitecting our HR ops processes with an AI-native mindset, not just using AI tools, but rethinking how the function should work
Growing into ownership of day-to-day HR operations management over time
Who you are:
Bachelor’s degree in any discipline
At least 2 years of real, hands-on HR generalist experience. You've personally drafted the policy, entered the payroll, handled the compliance filing, not just reviewed someone else's work
Genuine in-house, multi-state compliance experience
Comfortable in a small, high-intensity team where you touch payroll, benefits, and compliance yourself
Excited (not resistant) to build with AI.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why you should join us:
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We're building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, now we're expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
We're growing fast, which means our HR operations are getting more complex by the month, more states, more employees, more edge cases. Right now that complexity mostly lands on two people. We need someone who thrives doing the hands on work: real compliance problems to solve, policies to write, escalations that need judgment instead of a script. You'll also have room to bring AI into how we run HR ops to help cut the busywork so you can spend more time on the parts that matter.
The opportunity:
This isn't a role where you're processing paperwork and waiting for direction. You'll own the parts of HR operations that actually require judgment: multi-state compliance, policy drafting, and the payroll and benefits questions that come up when the answer isn't in a handbook. You've done this kind of work before, in-house, hands-on, and you're ready to be the person others come to when something's more complicated than usual.
You'll also have a real say in how AI fits into HR ops here, spending less time on the repetitive stuff and more time on the judgment calls that need a person.
What you'll own:
Multi-state compliance: tracking state-by-state law changes, drafting policy updates, and making sure they're actually implemented (not just written) across every employee classification and pay range
Our annual compliance audit and handbook refresh, yours to lead start to finish, in your first 90 days
Escalated payroll, benefits, and leave questions that need a more experienced hand
Reviewing and unblocking the work of our Payroll and HR Administration team members
Rearchitecting our HR ops processes with an AI-native mindset, not just using AI tools, but rethinking how the function should work
Growing into ownership of day-to-day HR operations management over time
Who you are:
Bachelor’s degree in any discipline
At least 2 years of real, hands-on HR generalist experience. You've personally drafted the policy, entered the payroll, handled the compliance filing, not just reviewed someone else's work
Genuine in-house, multi-state compliance experience
Comfortable in a small, high-intensity team where you touch payroll, benefits, and compliance yourself
Excited (not resistant) to build with AI.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
This job is what Jerry is all about: helping our customers take care of their most important assets, their car and home, with the kind of warmth and speed they didn't expect from an insurance company.
Car and home are people’s most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to help people manage it all.
The work is fast-paced, high-energy, team-oriented, and fully remote. A few things our team members love about working at Jerry:
Opportunities to shape the customer experience as the product and services are constantly evolving.
Competitive wage and benefits (medical, dental, vision insurance, 401K match, paid vacation time).
Equity (stock options) — we're a tech startup, and you own a piece of what you're building.
Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week.
Fully remote, with work equipment provided.
A career path in one of the largest industries in the world — insurance. We pay for your P&C insurance license if you don’t have one yet.
And, importantly, the colleagues you work alongside. Ask our team what they value most and the answer is almost always the same: the people and the culture. Jerry is full of people who take their work seriously and take helping each other just as seriously.
This role runs on two paths (sales and service). You don't have to know yet whether you're a sales person or a service person. We will figure this out together through the interview process.
As a member in the Customer Operations team, some of your responsibilities could include:
Taking great care of our customers. Our team members don't just answer the question asked — they catch the thing the customer didn't know to ask about. A coverage gap. A discount they qualify for. A renewal about to spike.
Answering inbound calls from customers shopping auto, home, motorcycle, and other policies, and from policyholders who need something changed.
Getting deep on the product. With a large panel of insurance companies to work from, knowing which one fits which customer is the craft of this job. Our app evolves constantly too, and knowing it inside out makes you the person customers trust to navigate it.
Problem solving to remove barriers between a customer and the right coverage.
Processing service requests — vehicles, drivers, lienholders, policy documents.
Making the product better. Tell us what you're hearing. The feedback loop here is short enough that you'll see your suggestions ship.
Who you are:
Prior work experience in customer service, sales, or hospitality is a plus, but not required
Genuinely friendly and positive attitude and willingness to work as a team
Strong work ethic
Strong problem solving skills
Strong communication skills
Compensation and perks:
Sales: Hourly wage of $19.00 - 21.00 plus uncapped commissions *Our most successful team members typically earn $100,000+ per year.
Service: Hourly wage of $19.00 - 21.00
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all with an unexpected level of warmth, speed, and simplicity.
We’re hiring Remote Inbound Sales Agents from premier retail and customer-service backgrounds (Apple Store, Microsoft, Lululemon, Nordstrom, Disney, Costco) who know that world-class experience is built on listening, educating, and making people feel cared for. You’ve mastered high-touch service on the sales floor; now bring those skills to a fully remote career with huge earning potential and professional growth.
Why Your Background Fits:
Consultative, Not Transactional: Zero cold calling or high-pressure tactics. Customers come to us through our app asking for help, and you’re there to deliver peace of mind and tailored advice.
Educate Like a Specialist: Just like guiding someone to the right tech gear or specialized fit, you’ll translate complex insurance details into clear, easy-to-understand choices.
High-Energy Warmth: You know how to multitask in a fast-paced environment while keeping every customer interaction positive, personal, and effortless.
How You’ll Care for Our Customers:
Welcome Inbound Shoppers: Connect with customers who started their search in our app, creating an immediate sense of trust and active engagement over the phone.
Simplify the Complex: Uncover policy nuances, hidden discounts, and coverage gaps across 55+ carrier options so customers get the best possible protection for their budget.
Solve with Empathy: Listen closely to hesitations, resolve concerns with patience, and make purchasing insurance feel refreshingly simple.
Guide to Completion: Help customers finalize their ideal policy right on the spot, leaving them confident in their coverage.
What You Bring:
The Service Standard: Experience in a high-standard retail, hospitality, or experience-driven environment (Apple, Lululemon, Nordstrom, Disney, etc.).
Empathetic Communication: A genuinely upbeat attitude, strong active listening skills, and the ability to connect naturally with people.
Tech-Savvy Multitasking: Comfort navigating internal tools and insurance platforms while maintaining a warm, fluid conversation.
Compensation & Perks:
Hourly wage: $19.00 - $21.00 plus uncapped commissions (*Our most successful team members typically earn $100,000+ per year).
Fully Funded Licensing: We cover 100% of your P&C licensing training and exam costs in your first two weeks.
Remote-First: 100% work-from-home with all computer equipment provided.
Full Benefits: Medical, dental, vision insurance, and 401(k) matching.
Flexible Schedules: Choose between a 5-day, 8-hour schedule or a 4-day, 10-hour workweek.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
About us:
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024.
Our purpose:
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat).
About this program:
Our next chapter is about accelerating growth – going from 5M to 50M customers by 2030.
This year alone, we launched 5 new products – home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance. Each of these new businesses comes with its own operational complexity, distinct user personas and pain points, and its own path to scale.
As our business expands, we have a growing list of ideas but not enough people to execute them. This program exists to close that gap. We are looking for 2-3 GMs-in-Training to work directly with, and be mentored by, our Cofounder/CEO, and work on some of the highest-leverage problems in our business.
Reporting directly to our CEO, you will have a unique opportunity to view and understand a company’s day-to-day challenges as it goes through a rapid growth phase. You will be exposed to every function at Jerry (i.e., product, growth, operations, finance, engineering, data), learn how to execute big-picture strategies and navigate the intricacies of a complex business.
A successful graduate will go on to own P&L for a business line here or elsewhere. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you.
Who we get excited about:
Insatiable learner: You are constantly seeking to deepen your knowledge, sharpen your skills, and master whatever craft or goal you’ve set your mind to.
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.
Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.
What you bring:
4+ years of experience in management consulting, venture capital, private equity, or a startup environment
Bachelor's degree in any discipline
Ability to work in-person in our Palo Alto office alongside our CEO and executive team for the first 6-12 months
Compensation:
This position offers base salary and stock options. The base salary for this position within the San Francisco Bay Area is $160,000—$200,000 USD, but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with 4% employer matching, and wellness benefits, among others.
Location:
This role requires being in our Palo Alto office five days a week, at least until you are capable of operating independently.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
About us:
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024.
Why we exist:
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat).
Why we’re hiring:
Our next chapter is about accelerating growth – from 5M to 50M customers by 2030.
This year alone, we launched 5 new products – home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance. Each of these new businesses comes with its own operational complexity, distinct customer pain points, and its own path to scale.
As our business expands, we have a growing list of ideas but not enough people to execute them. This program exists to close that gap. We are looking for 2-3 Product Managers-in-Training to work directly with, and be mentored by, our Cofounder/CEO (2x YC founder), and work on building or scaling one of our new product verticals.
Reporting directly to our CEO, you will have a unique opportunity to develop the craft of product building, learn how a serial founder/CEO thinks and makes decisions, and see/understand a late stage tech startup’s day-to-day challenges as it goes through a rapid growth phase. You will be exposed to nearly every function at the company (i.e., product, growth, operations, finance, engineering, data), learn how to execute big-picture strategies and navigate the intricacies of a complex business.
A successful graduate will likely go on to become a product leader or commercial leader (e.g. owning P&L) here or elsewhere. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you.
Who we get excited about:
Insatiable learner: You are constantly seeking to deepen your knowledge, sharpen your skills, and master whatever craft or goal you’ve set your mind to.
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.
Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.
What you bring:
Ideally 1+ years of experience in a demanding environment such as management consulting, investment banking, venture capital, private equity, an early startup environment, or similar
Bachelor's degree in any discipline
Ability to work in-person in our Palo Alto office alongside our CEO and executive team at least for the first 6-12 months
Compensation:
This position offers base salary and stock options. The base salary for this position within the San Francisco Bay Area is 130,000—160,000 USD, but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with 4% employer matching, and wellness benefits, among others.
Location:
This role requires being in our Palo Alto office five days a week, at least until you are capable of operating independently.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all in one place. Since 2019, we’ve become one of the fastest-growing tech companies in the U.S.
We are looking for Remote Inbound Sales Agents who come from top-tier retail/service backgrounds like the Apple Store, Chick-Fil-A, Trader Joe’s or Costco. We are hyper-focused on unreasonable hospitality and are looking for ambitious individuals who are friendly, hard-working, and are incredibly service-oriented.
This role may be a fit for you if:
You know that people don’t just come to a place for the product, they come for the experience. You know how to make a customer feel welcome, taken care of, and will go above and beyond to give them an incredible experience.
You’ve excelled in your retail job but are looking to transition into a long-term career with serious growth potential
You’re self-motivated and would enjoy a remote environment. This role can be done 100% remotely (goodbye, sore feet at the end of a long day!)
You thrive in a fast-paced & tech-focused environment: you’re used to handling several things at once while staying friendly. We’ll give you the best tools and tech to make that easy.
What you’ll actually do:
Go through (paid) training and insurance licensing (note: you must pass your licensing exam to legally sell insurance)
Guide engaged users through the insurance purchasing process. There’s no cold-calling, these people have already started their insurance search in our app
Simplify the Process: Help customers compare 55+ different insurance companies to find the one that fits their budget.
Solve Problems: Listen to a customer’s concerns and find a solution that makes them feel confident in their choice.
Close the Deal: Help customers finalize their new policy right then and there.
What’s in it for you?
Pay: $19.00 - $21.00 per hour plus uncapped commission. *Our most successful team members typically earn $100,000+ per year.
We Pay for Your License: Don't have an insurance license? No problem. We pay for your training and your exam (usually completed in your first two weeks).
Work From Home: 100% remote. We provide all the equipment you need.
Flexible Schedule: Choose between working five 8-hour days or four 10-hour days.
Full Benefits: Medical, dental, vision insurance, and 401K matching.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
More than 80% of Americans own a car and see it as one of their biggest financial commitments, yet managing one still means paperwork, long phone holds, and app switching. Jerry.ai built the first app to manage it all: insurance shopping, refinancing, safety, and repairs—bringing an unexpected level of warmth and speed to an industry stuck in the past. Since launching in 2019, we’ve grown to over 5M customers.
Every customer comes to us looking for a better, easier way to handle their insurance. As an Insurance Sales Agent, your mission is to deliver an exceptional, consultative experience that turns initial interest into long-term customer trust, matching each individual with the ideal coverage from Jerry’s panel of 55+ carrier partners.
Who You Are:
A top performer: You have 2+ years of experience in sales, consultative account management, or high-touch service environments.
A customer champion: You bring genuine empathy, warmth, and active listening skills to every interaction, with a true passion for helping people.
A natural problem solver: You manage competing priorities effortlessly while maintaining a high standard of service and attention to detail.
How You'll Wow Our Customers:
Deliver standout customer experiences: Handle inbound calls for auto, home, motorcycle, and specialty insurance with high energy, patience, and genuine care.
Educate and advocate: Go beyond standard answers to uncover savings or coverage gaps customers didn't know to look for, translating complex policy details into clear, easy-to-understand choices.
Guide and bind: Craft tailored policy packages across our 55+ carrier partners and finalize coverage with ease.
Navigate friction thoughtfully: Listen to customer hesitation with empathy, addressing concerns directly to ensure a smooth, transparent purchasing experience.
Elevate the product: Act as the voice of the customer by sharing direct feedback with our product team to continuously refine our app and service offerings.
Compensation and Perks:
Hourly wage: $19.00 - $21.00 plus uncapped commissions (*Our most successful team members typically earn $100,000+ per year).
Fully funded licensing: We pay 100% of the cost for your P&C license (expected within 2 weeks after starting).
Benefits: Medical, dental, vision insurance, and 401(k) match.
Remote-first: Work from home with all equipment provided, supported by ongoing training and active team mentorship.
Flexible scheduling: Choice between a 5-day, 8-hour schedule or a 4-day, 10-hour workweek.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
More than 80% of Americans own a car and see it as one of their biggest financial commitments, yet managing one still means paperwork, long phone holds, and app switching. Jerry.ai built the first app to manage it all: insurance shopping, refinancing, safety, and repairs—bringing an unexpected level of warmth and speed to an industry stuck in the past. Since launching in 2019, we’ve grown to over 5M customers.
Every customer comes to us looking for a better, easier way to handle their insurance. As a Remote Sales Agent, your mission is to deliver an exceptional, consultative experience that turns initial interest into long-term customer trust, matching each individual with the ideal coverage from Jerry’s panel of 55+ carrier partners.
Who You Are:
A top performer: You have 2+ years of experience in sales, consultative account management, or high-touch service environments.
A customer champion: You bring genuine empathy, warmth, and active listening skills to every interaction, with a true passion for helping people.
A natural problem solver: You manage competing priorities effortlessly while maintaining a high standard of service and attention to detail.
How You'll Wow Our Customers:
Deliver standout customer experiences: Handle inbound calls for auto, home, motorcycle, and specialty insurance with high energy, patience, and genuine care.
Educate and advocate: Go beyond standard answers to uncover savings or coverage gaps customers didn't know to look for, translating complex policy details into clear, easy-to-understand choices.
Guide and bind: Craft tailored policy packages across our 55+ carrier partners and finalize coverage with ease.
Navigate friction thoughtfully: Listen to customer hesitation with empathy, addressing concerns directly to ensure a smooth, transparent purchasing experience.
Elevate the product: Act as the voice of the customer by sharing direct feedback with our product team to continuously refine our app and service offerings.
Compensation and Perks:
Hourly wage: $19.00 - $21.00 plus uncapped commissions (*Our most successful team members typically earn $100,000+ per year).
Fully funded licensing: We pay 100% of the cost for your P&C license (expected within 2 weeks after starting).
Benefits: Medical, dental, vision insurance, and 401(k) match.
Remote-first: Work from home with all equipment provided, supported by ongoing training and active team mentorship.
Flexible scheduling: Choice between a 5-day, 8-hour schedule or a 4-day, 10-hour workweek.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why We Exist
Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive.
Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace.
We've reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024. We're now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.
Why We’re Hiring
Our Business Operations & Analytics team has been a force multiplier and accelerant to our business that has helped us reach these pivotal milestones in spite of headwinds and within a highly competitive market. They are a team of former McKinsey, BCG and Bain consultants who drive data & insights, and inform decision-making across every corner of our business. They are analytical powerhouses and first principles problem solvers who push forward our most important initiatives across product, growth, tech, and operations.
Every business unit has a Business Operations & Analytics team member embedded within it — someone who doesn't just run analyses and build dashboards, but shapes what questions we should ask, what data to pull, what conclusions to draw, what decisions to make, and then drives our teams towards our next goal: go from 5M to 50M customers and become a $10B business in the next 4 years.
As our business continues to expand, there is growing demand for more Business Operations & Analytics team members. We are hiring 2-3 people to drive impact in these areas:
Growth Marketing
Product Development
AI & Automation
Strategic Partnerships
On leveling: You may see job ads for this role at different job levels. Our priority is finding the right people, we can be flexible with job title/leveling.
Why You Will (Or Won't) Like Working Here
No slides: If you've worked in consulting, you know what it feels like to be up at 3am reformatting a deck. That doesn't exist here. The only work that gets done at Jerry is work that will materially change the trajectory of our business — an important product, a new growth channel, a key metric, a critical partner relationship, etc.
No corporate fluff: The Business Operations & Analytics team is 14 insatiable learners who care deeply about solving difficult problems and making a tangible impact. Every person owns a critical domain. There is no bloat, unnecessary meetings, or waiting for approvals.
Hands-on: This is not a pure strategy role, you will also own execution. Your day-to-day will be surfacing analytical insights, driving decisions, and seeing them through end-to-end.
What You'll Own
You'll sit on our central Business Operations & Analytics team but you’ll be embedded in one of Jerry's core business areas — growth, product, AI and automation, strategic partnerships — and own the analytical function for that business unit end-to-end.
Define the right problems: Before any analysis, understand what business question it's answering and what decision it will inform. Push back if the question is flawed.
Data and insights: Define metrics, build reports, run analyses, design experiments, and surface data insights that move your team's key metrics.
Drive outcomes: Bring recommendations to your counterparts in product, growth, finance or operations, tell them what's happening and why, and what next steps should be.
Who You Are
First principles thinker: You break ambiguous problems into clear hypotheses before touching data. You're analytically strong (comfortable with SQL or Python) but your instinct is to ask \"what are we trying to solve here?\" before jumping to \"what should I build?\"
Direct communicator: You can walk a skeptical stakeholder through a complex finding and get buy-in quickly. You write clearly, speak precisely, and don't bury the lede.
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
What You'll Bring
1+ years of experience at a consulting firm, investment bank, or high-growth technology company.
Strong analytical skills; ability to pull, structure, and interpret data independently.
Track record of owning ambiguous problems and delivering impact.
Clear, persuasive communicator who can influence decisions at the leadership level.
Our Tools
SQL (Clickhouse), Metabase, Python, Jupyter Hub, GitHub.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why We Exist
Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive.
Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace.
We've reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024. We're now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.
Why We’re Hiring
Our Business Operations & Analytics team has been a force multiplier and accelerant to our business that has helped us reach these pivotal milestones in spite of headwinds and within a highly competitive market. They are a team of former McKinsey, BCG and Bain consultants who drive data & insights, and inform decision-making across every corner of our business. They are analytical powerhouses and first principles problem solvers who push forward our most important initiatives across product, growth, tech, and operations.
Every business unit has a Business Operations & Analytics team member embedded within it — someone who doesn't just run analyses and build dashboards, but shapes what questions we should ask, what data to pull, what conclusions to draw, what decisions to make, and then drives our teams towards our next goal: go from 5M to 50M customers and become a $10B business in the next 4 years.
As our business continues to expand, there is growing demand for more Business Operations & Analytics team members. We are hiring 2-3 people to drive impact in these areas:
Growth Marketing
Product Development
AI & Automation
Strategic Partnerships
On leveling: You may see job ads for this role at different job levels. Our priority is finding the right people, we can be flexible with job title/leveling.
Why You Will (Or Won't) Like Working Here
No slides: If you've worked in consulting, you know what it feels like to be up at 3am reformatting a deck. That doesn't exist here. The only work that gets done at Jerry is work that will materially change the trajectory of our business — an important product, a new growth channel, a key metric, a critical partner relationship, etc.
No corporate fluff: The Business Operations & Analytics team is 14 insatiable learners who care deeply about solving difficult problems and making a tangible impact. Every person owns a critical domain. There is no bloat, unnecessary meetings, or waiting for approvals.
Hands-on: This is not a pure strategy role, you will also own execution. Your day-to-day will be surfacing analytical insights, driving decisions, and seeing them through end-to-end.
What You'll Own
You'll sit on our central Business Operations & Analytics team but you’ll be embedded in one of Jerry's core business areas — growth, product, AI and automation, strategic partnerships — and own the analytical function for that business unit end-to-end.
Define the right problems: Before any analysis, understand what business question it's answering and what decision it will inform. Push back if the question is flawed.
Data and insights: Define metrics, build reports, run analyses, design experiments, and surface data insights that move your team's key metrics.
Drive outcomes: Bring recommendations to your counterparts in product, growth, finance or operations, tell them what's happening and why, and what next steps should be.
Who You Are
First principles thinker: You break ambiguous problems into clear hypotheses before touching data. You're analytically strong (comfortable with SQL or Python) but your instinct is to ask \"what are we trying to solve here?\" before jumping to \"what should I build?\"
Direct communicator: You can walk a skeptical stakeholder through a complex finding and get buy-in quickly. You write clearly, speak precisely, and don't bury the lede.
Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
What You'll Bring
2+ years of experience at a consulting firm, investment bank, or high-growth technology company.
Strong analytical skills; ability to pull, structure, and interpret data independently.
Track record of owning ambiguous problems and delivering impact.
Clear, persuasive communicator who can influence decisions at the leadership level.
Our Tools
SQL (Clickhouse), Metabase, Python, Jupyter Hub, GitHub.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
This job is what Jerry is all about: helping our customers take care of their most important assets, their car and home, with the kind of warmth and speed they didn't expect from an insurance company.
Car and home are people’s most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to help people manage it all.
The work is fast-paced, high-energy, team-oriented, and fully remote. A few things our team members love about working at Jerry:
Opportunities to shape the customer experience as the product and services are constantly evolving.
Competitive wage and benefits (medical, dental, vision insurance, 401K match, paid vacation time).
Stock equity (stock options) — we're a tech startup, and you own a piece of what you're building.
Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week.
Fully remote, with work equipment provided.
A career path in one of the largest industries in the world — insurance. We pay for your P&C insurance license if you don’t have one yet.
And, importantly, the colleagues you work alongside. Ask our team what they value most and the answer is almost always the same: the people and the culture. Jerry is full of people who take their work seriously and take helping each other just as seriously.
As a member in the Customer Operations team, some of your responsibilities could include:
Taking great care of our customers. Our team members don't just answer the question asked — they catch the thing the customer didn't know to ask about. A coverage gap. A discount they qualify for. A renewal about to spike.
Answering inbound calls from policyholders who need something changed.
Getting deep on the product. With a large panel of insurance companies to work from, knowing which one fits which customer is the craft of this job. Our app evolves constantly too, and knowing it inside out makes you the person customers trust to navigate it.
Problem solving to resolve customer inquiries effectively.
Processing service requests — vehicles, drivers, lienholders, policy documents.
Making the product better. Tell us what you're hearing. The feedback loop here is short enough that you'll see your suggestions ship.
Who you are:
Prior work experience in customer service, sales, or hospitality is a plus, but not required
Genuinely friendly and positive attitude and willingness to work as a team
Strong work ethic
Strong problem solving skills
Strong communication skills
Compensation and perks:
Hourly wage of $19.00 - 21.00 + equity (stock options)
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey — buy/sell, insurance, maintenance, repairs — is fragmented, complicated, and expensive.
Jerry.ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace.
We’ve reached 5M+ customers, raised $240M+, and scaled revenue 70X. We’re now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.
Jerry is expanding into several new markets at the same time. Capital allocation is now one of the most consequential decisions we make: each dollar committed to a new product line, a marketing channel, or a headcount is a dollar not available elsewhere.
We are hiring a Strategic Finance Manager, reporting to our VP of Finance, to build the analysis those decisions rest on. You will own the operating model and the planning cycle, partner with functional leaders across the company, and work closely with the CFO and the founders.
The operating core is the model, the planning cadence, and the spend discipline the company runs on. Alongside it, you are the analytical partner on new opportunities — the products, verticals, channels and partnerships we are deciding whether to back. And over your first year or two, as our newer products scale and the audience for our numbers widens beyond the people who already know the business, the reporting itself has to reach a standard that holds up to outside diligence.
Own the operating model and forecast cycle:
Own Jerry’s driver-based operating model for the base business and expand it as we launch new insurance products and business lines.
Run the annual budget and long-range planning process end to end — cadence, assumptions, stakeholder inputs, and the consolidated plan the executive team commits to.
Own the monthly and quarterly forecast cycle and variance analysis: Once Accounting closes the books, explain what moved against plan and prior period, why it moved, and what it means for the forecast.
Write the executive narrative: Translate the financial results into clear business insights for the CFO, the founders, the board, and our investors, at a standard that survives external diligence.
Lead monthly business reviews: Work with functional leaders and turn what the numbers show into the business decisions that need to be made.
Support the team in evaluating and implementing a planning system: Assess the options, make the recommendation, and own the rollout.
Build the financial case for new opportunities
Build the financial model for new product, vertical, channel or partnership: Size the market, model the economics, evaluate capital commitment and return profile.
Read results back against the case: Once something is live, compare the actual economics to what we underwrote and carry the lesson into the next decision. Monitor product and channel economics including CAC and payback, policy retention and lifetime value, contribution margin etc.
Support corporate development: Capital markets and investor workstreams through diligence, modeling, and transaction analysis as the need arises.
Frame build, buy or partner decisions: help refine the frameworks we use to compare the options and the return profile of each.
Underwrite vendor spend:
Build the business case before a commitment is made, support negotiation on terms, and give budget owners the visibility to manage their own numbers.
Accurate under deadline: Your numbers are right the first time, and they stay right when the deadline compresses. You check your own work before anyone else has to.
Picks the right question: No one hands you the workstream. You decide which analysis will actually change a decision, and leave the rest alone.
Direct communicator: You form a view, communicate it directly, and revise it when the evidence changes.
Executive-ready output: What you produce can go in front of the founders or the board without a rewrite — clear, precise, and honest about what the numbers do and do not show.
Owner: You take ownership of outcomes and are comfortable building process where none exists yet.
4+ years of relevant experience, ideally combining 2+ years at a reputable investment bank, corporate development group, or private equity firm with 2+ years in strategic finance or FP&A at a high-growth company.
A bachelor’s degree in finance, accounting, economics, or a similarly quantitative field.
Strong financial modeling skills: driver-based operating models, three-statement mechanics, scenario and sensitivity analysis, and a working command of accounting concepts and GAAP.
Experience with unit economics in a consumer or marketplace business, including CAC, LTV, payback, cohort retention, and contribution margin.
A track record of translating complex analysis into a clear narrative for an executive or investor audience.
Startup or high-growth experience strongly preferred, including building financial processes from scratch.
Hands-on fluency with AI tools for analysis, research, and workflow automation.
Nice to have:
Insurance, insurtech, fintech, or marketplace experience;
CFA certification;
vendor negotiation or procurement exposure;
finance tech stack experience (NetSuite, Ramp, planning tools).
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why we exist:
More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc.) is complicated, fragmented, and time-consuming, and the costs are staggering. At Jerry, we are building the first app to manage it all and make car ownership simple, transparent, and affordable.
Why we need you:
Redditors can smell a corporate ad from a mile away and will downvote low-effort marketing into oblivion. But when someone breaks down how car insurance premiums are actually calculated, or writes a step-by-step guide on negotiating a used car purchase, r/personalfinance and r/whatcarshouldibuy pay attention.
We need a Reddit Copywriter/Comedian who lives and breathes textual storytelling. You won't be writing marketing copy—you’ll be writing high-value, educational, human text posts that turn complex financial and automotive topics into top-voted Reddit threads. You know how to capture sub-culture tone, write hooky titles, and turn technical jargon into clear, engageable prose.
What you'll own:
Reddit Content Creation: Create genuinely helpful and entertaining content for relevant subreddits such as r/carinsurancehelp, r/mechanicadvice, r/idiotsincars, and r/frugal as well as Jerry's own subreddits.
Mastery of Reddit Voice: Craft long-form and short-form copy that bypasses corporate fluff, using tone, formatting, and structure that feels native, authentic, and upvote-worthy.
Thread Engagement Copy: Draft real-time, high-context replies to community comments and inquiries, balancing helpful expertise with a grounded, conversational voice.
Content Experimentation: Test different narrative hooks, post structures (TL;DRs, bulleted breakdowns, case studies), and post timings to maximize organic reach and community trust.
SEO & LLM Optimization: Write comprehensive, search-optimized Reddit copy designed to index well on Google search and serve as cited reference material for AI models.
Collaborative Messaging: Work alongside the Content, SEO, and Product teams to adapt broader company insights into Reddit-first copy without losing brand accuracy.
Who you are:
A Reddit-First Writer: You are an active Reddit user with a deep library of work showing you can write for the platform. You understand post formatting, sub-culture nuances, and what makes a thread go viral versus what gets ignored.
3+ Years of Copywriting Experience: Proven track record writing short- and long-form copy, ideally within fintech, insurtech, automotive, or consumer tech.
Translator of Complexity: You can take \"boring,\" confusing, or frustrating topics (insurance policies, rate hikes, vehicle maintenance) and make them clear, useful, and compelling to read.
Obsessed with Value: You write to inform and help first, knowing that transparent, high-value writing builds more long-term brand equity than pushy calls-to-action.
Feedback-Resilient: You welcome raw feedback from both internal teams and public comments, using community reactions to refine and improve your writing style.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why we exist:
More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, and time-consuming, and the costs are staggering. In 2025, the cost of owning a car was more than 20% of the average household income, after tax. At Jerry.ai, we are building the first app to manage it all and make car ownership accessible to all.
Why we need you:
Jerry has built a product used by 5 million people, but the real conversations about car insurance and repair aren't happening in our apps—they’re happening on Reddit, Quora, and TikTok. We don’t want to just ‘manage’ these channels; we want to participate in them.
We’re looking for a Community Manager who can represent Jerry with authenticity and build trust with our current and future users! You’re someone who knows how to provide genuine value in an r/personalfinance thread and can just as easily navigate the high-energy culture of a TikTok comment section.
What you'll own:
Build and grow Jerry's organic presence across key channels like Reddit, Quora, YouTube, and TikTok — the places our customers actually congregate
Develop Jerry's playbook for how to show up in each community: when to post, when to reply, when to stay silent
Grow Jerry’s subreddits into active, trusted communities
Build a content and engagement strategy that scales without losing authenticity, leveraging AI where it helps
Work with Growth and Content teams to ensure consistency across channels
Measure what matters: sentiment, share of voice, referral traffic, and LLM citation
Who you are:
A platform native with a visceral dislike of corporate-speak — you write with a tone that earns upvotes and moves naturally across Reddit, TikTok, and Quora
3+ years in community management or organic social, ideally in fintech, insurtech, or another consumer facing and/or regulated category
A strategic operator who builds systems, not just vibes — you understand SEO and how LLMs cite sources
Proven ability to make \"boring\" or \"stressful\" categories feel human, authentic, and worth following
A patient, curious long-game player who values organic trust over quick PR wins
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why we exist: More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc.) is complicated, fragmented, and time-consuming, and the costs are staggering. At Jerry, we are building the first app to manage it all and make car ownership simple, transparent, and affordable.
Why we need you: Redditors can smell a corporate ad from a mile away and will downvote low-effort marketing into oblivion. But when someone breaks down how car insurance premiums are actually calculated, or writes a step-by-step guide on negotiating a used car purchase, r/personalfinance and r/whatcarshouldibuy pay attention.
We need a Reddit Copywriter who lives and breathes textual storytelling. You won't be writing marketing copy—you’ll be writing high-value, educational, human text posts that turn complex financial and automotive topics into top-voted Reddit threads. You know how to capture sub-culture tone, write hooky titles, and turn technical jargon into clear, engageable prose.
What you'll own:
Reddit Content Creation: Create genuinely helpful and entertaining content for relevant subreddits such as r/carinsurancehelp, r/mechanicadvice, r/idiotsincars, and r/frugal as well as Jerry's own subreddits.
Mastery of Reddit Voice: Craft long-form and short-form copy that bypasses corporate fluff, using tone, formatting, and structure that feels native, authentic, and upvote-worthy.
Thread Engagement Copy: Draft real-time, high-context replies to community comments and inquiries, balancing helpful expertise with a grounded, conversational voice.
Content Experimentation: Test different narrative hooks, post structures (TL;DRs, bulleted breakdowns, case studies), and post timings to maximize organic reach and community trust.
SEO & LLM Optimization: Write comprehensive, search-optimized Reddit copy designed to index well on Google search and serve as cited reference material for AI models.
Collaborative Messaging: Work alongside the Content, SEO, and Product teams to adapt broader company insights into Reddit-first copy without losing brand accuracy.
Who you are:
A Reddit-First Writer: You are an active Reddit user with a deep library of work showing you can write for the platform. You understand post formatting, sub-culture nuances, and what makes a thread go viral versus what gets ignored.
3+ Years of Copywriting Experience: Proven track record writing short- and long-form copy, ideally within fintech, insurtech, automotive, or consumer tech.
Translator of Complexity: You can take \"boring,\" confusing, or frustrating topics (insurance policies, rate hikes, vehicle maintenance) and make them clear, useful, and compelling to read.
Obsessed with Value: You write to inform and help first, knowing that transparent, high-value writing builds more long-term brand equity than pushy calls-to-action.
Feedback-Resilient: You welcome raw feedback from both internal teams and public comments, using community reactions to refine and improve your writing style.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Why we exist:
More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc.) is complicated, fragmented, and time-consuming, and the costs are staggering. At Jerry, we are building the first app to manage it all and make car ownership simple, transparent, and affordable.
Why we need you:
Car owners don't turn to press releases or corporate ads when their engine light comes on or their insurance rate hikes—they turn to Reddit. Subreddits like r/personalfinance, r/idiotsincars, r/mechanicadvice, and r/whatcarshouldibuy are ground zero for real, unfiltered advice about car ownership.
We aren't looking to spam threads with marketing pitch decks. We need a dedicated Reddit Social Media Manager who understands sub-culture, respects community guidelines, and knows how to build genuine authority. You will lead Jerry’s presence across Reddit, turning complex auto financial topics into high-value, upvote-worthy engagement.
What you'll own:
Reddit Operations & Strategy: Own Jerry’s official presence across Reddit, including brand-owned subreddits and organic engagement in broader automotive, financial, and consumer communities.
Community Playbook: Establish Jerry’s Reddit voice—knowing precisely when to offer technical advice, when to drop a well-timed meme, and when to lurk without interrupting the discussion.
Content Creation: Craft high-effort, informative text posts, deep-dive guides, and visual breakdowns on car ownership, insurance savings, and maintenance tactics tailored to specific subreddit cultures.
Reputation & Crisis Management: Act as the first line of defense in threads discussing Jerry, turning frustrated posts into trust-building service moments through transparent, helpful responses.
Analytics & Insight: Track key metrics including Karma growth, thread sentiment, share of voice, referral traffic, and how Reddit community discussions influence search indexability and LLM citations.
Cross-Functional Feedback: Feed organic Reddit insights, emerging car-owner pain points, and trending topics back to our Product and Content teams.
Who you are:
A Reddit Native: You have a deep understanding of karma, subreddit dynamics, automods, shadowbans, and the unspoken rules of the platform. You possess a visceral dislike of corporate-speak and know how to write naturally for Redditors.
Experienced Community Marketer: 2+ years managing organic social or community strategy, with a heavy emphasis on Reddit, ideally within consumer tech, fintech, or insurtech, or a demonstrated track record of growing other types of social accounts
Value-First Strategist: You understand that long-term trust and high-upvote educational posts build far more brand equity than quick conversion pushes.
Technical & Search-Aware: You understand how Reddit content feeds into Google SGE, LLMs, and organic SEO, structuring posts so they rank as permanent resources for car owners.
Thick-Skinned & Empathetic: You can handle pushback, skepticism, and tough questions in public threads with grace, humor, and complete honesty.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
You could work anywhere. Why us?
Join a pre-IPO startup with capital, traction and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).
Work closely with brilliant leaders and team mates from companies like McKinsey, BCG, Bain, Nvidia, GEICO, Better, etc.
Disrupt a massive market and take us to a $10B business in the next few years.
Be immersed in a talent-dense environment and greatly accelerate your career growth.
About the opportunity:
As the Director, Business Development and Partnerships, you’ll be a driving force behind the growth and success of our partner ecosystem. You’ll strategically manage and strengthen existing partnerships while identifying and securing high-value new collaborations that align with our long-term vision. By leveraging your deep understanding of market dynamics, you’ll propose innovative tools and product solutions that unlock scalable opportunities for both our business and our partners.
This high-impact role involves collaborating closely with cross-functional teams—product, operations, data, and sales—to craft and execute partnership strategies that deliver lasting business outcomes. Reporting directly to the VP of Partnerships, you’ll play a pivotal role in shaping the strategic direction of our partnership portfolio and accelerating growth across the organization.
Jerry is building the first super app to help people optimize all aspects of owning a car – insurance, buy/sell, registration, loans, safety, repairs, parking, etc – a $2T market in the U.S. We started with insurance in 2019, and since then we’ve launched loan refinancing, driving insights, a repair marketplace, car diagnostics, and a GenAI-powered chatbot & voicebot. We have amassed over 5M customers, raised $240MM in funding, scaled our revenue 60X and our team to 225 across 6 countries.
How you will make an impact:
Foster Strong Partner Relationships: Be the go-to person for building and nurturing deep, trusted relationships with existing partners. Your ability to serve as the primary point of contact will ensure long-term success and collaboration.
Drive Strategic Growth: Take ownership of developing and executing structured business plans or quarterly OKRs that align with each partner's unique goals, maximizing the potential of strategic partnerships through a deep understanding of their business.
Optimize Performance: Use your analytical skills to dive into data, uncover trends, and identify key opportunities for improving business KPIs. Your insights will be critical in driving smarter decisions and better outcomes for both sides.
Generate New Opportunities: Lead the charge in creating new growth opportunities with both existing and potential partners. Your expertise in negotiating will be key in structuring mutually beneficial deals that drive expansion.
Deliver Actionable Insights: Perform Analysis and regularly provide valuable insights and updates to both partners and internal teams, ensuring that everyone stays aligned, informed, and empowered to make the right decisions.
Resolve Challenges Quickly: Be the problem-solver, triaging operational and executional issues that arise across partners and internal teams. Your ability to act swiftly and decisively will keep everything running smoothly.
Ideal profile:
8+ years of experience in Business Development, Partnerships, or Management Consulting
Proven track record of successfully managing complex projects from inception to completion, with meticulous attention to detail and a strong bias for action.
A go-getter with a strong work ethic, a willingness to learn and adapt quickly, and a desire to contribute to the success of a high-growth company.
A data-driven approach to decision-making, with the ability to analyze complex situations and make informed, actionable decisions.
Excellent written and verbal communication, presentation, and interpersonal skills with the ability to effectively communicate complex ideas to both internal and external stakeholders.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
This job is what Jerry is all about: helping our customers take care of their most important assets, their car and home, with the kind of warmth and speed they didn't expect from an insurance company.
Car and home are people’s most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to help people manage it all.
The work is fast-paced, high-energy, team-oriented, and fully remote. A few things our team members love about working at Jerry:
Opportunities to shape the customer experience as the product and services are constantly evolving.
Competitive wage and benefits (medical, dental, vision insurance, 401K match, paid vacation time).
Stock equity (stock options) — we're a tech startup, and you own a piece of what you're building.
Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week.
Fully remote, with work equipment provided.
A career path in one of the largest industries in the world — insurance. We pay for your P&C insurance license if you don’t have one yet.
And, importantly, the colleagues you work alongside. Ask our team what they value most and the answer is almost always the same: the people and the culture. Jerry is full of people who take their work seriously and take helping each other just as seriously.
As a member in the Customer Operations team, some of your responsibilities could include:
Taking great care of our customers. Our team members don't just answer the question asked — they catch the thing the customer didn't know to ask about. A coverage gap. A discount they qualify for. A renewal about to spike.
Answering inbound calls from policyholders who need something changed.
Getting deep on the product. With a large panel of insurance companies to work from, knowing which one fits which customer is the craft of this job. Our app evolves constantly too, and knowing it inside out makes you the person customers trust to navigate it.
Problem solving to resolve customer inquiries effectively.
Processing service requests — vehicles, drivers, lienholders, policy documents.
Making the product better. Tell us what you're hearing. The feedback loop here is short enough that you'll see your suggestions ship.
Who you are:
Prior work experience in customer service, sales, or hospitality is a plus, but not required
Genuinely friendly and positive attitude and willingness to work as a team
Strong work ethic
Strong problem solving skills
Strong communication skills
Compensation and perks:
Hourly wage of $19.00 - 21.00 + equity (stock options)
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
This job is what Jerry is all about: helping our customers take care of their most important assets, their car and home, with the kind of warmth and speed they didn't expect from an insurance company.
Car and home are people’s most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to help people manage it all.
The work is fast-paced, high-energy, team-oriented, and fully remote. A few things our team members love about working at Jerry:
Opportunities to shape the customer experience as the product and services are constantly evolving.
Competitive wage and benefits (medical, dental, vision insurance, 401K match, paid vacation time).
Stock equity (stock options) — we're a tech startup, and you own a piece of what you're building.
Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week.
Fully remote, with work equipment provided.
A career path in one of the largest industries in the world — insurance. We pay for your P&C insurance license if you don’t have one yet.
And, importantly, the colleagues you work alongside. Ask our team what they value most and the answer is almost always the same: the people and the culture. Jerry is full of people who take their work seriously and take helping each other just as seriously.
As a member in the Customer Operations team, some of your responsibilities could include:
Taking great care of our customers. Our team members don't just answer the question asked — they catch the thing the customer didn't know to ask about. A coverage gap. A discount they qualify for. A renewal about to spike.
Answering inbound calls from policyholders who need something changed.
Getting deep on the product. With a large panel of insurance companies to work from, knowing which one fits which customer is the craft of this job. Our app evolves constantly too, and knowing it inside out makes you the person customers trust to navigate it.
Problem solving to resolve customer inquiries effectively.
Processing service requests — vehicles, drivers, lienholders, policy documents.
Making the product better. Tell us what you're hearing. The feedback loop here is short enough that you'll see your suggestions ship.
Who you are:
Prior work experience in customer service, sales, or hospitality is a plus, but not required
Genuinely friendly and positive attitude and willingness to work as a team
Strong work ethic
Strong problem solving skills
Strong communication skills
Compensation and perks:
Hourly wage of $19.00 - 21.00 + equity (stock options)
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
You could work anywhere. Why us?
Join a pre-IPO startup with capital, traction and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).
Work closely with brilliant leaders and team mates from companies like McKinsey, BCG, Bain, Nvidia, GEICO, Better, etc.
Disrupt a massive market and take us to a $10B business in the next few years.
Be immersed in a talent-dense environment and greatly accelerate your career growth.
About the opportunity:
As the Director, Business Operations (Business Development), you’ll be a driving force behind the growth and success of our partner ecosystem. You’ll strategically manage and strengthen existing partnerships while identifying and securing high-value new collaborations that align with our long-term vision. By leveraging your deep understanding of market dynamics, you’ll propose innovative tools and product solutions that unlock scalable opportunities for both our business and our partners.
This high-impact role involves collaborating closely with cross-functional teams—product, operations, data, and sales—to craft and execute partnership strategies that deliver lasting business outcomes. Reporting directly to the VP of Partnerships, you’ll play a pivotal role in shaping the strategic direction of our partnership portfolio and accelerating growth across the organization.
Jerry is building the first super app to help people optimize all aspects of owning a car – insurance, buy/sell, registration, loans, safety, repairs, parking, etc – a $2T market in the U.S. We started with insurance in 2019, and since then we’ve launched loan refinancing, driving insights, a repair marketplace, car diagnostics, and a GenAI-powered chatbot & voicebot. We have amassed over 5M customers, raised $240MM in funding, scaled our revenue 60X and our team to 225 across 6 countries.
How you will make an impact:
Foster Strong Partner Relationships: Be the go-to person for building and nurturing deep, trusted relationships with existing partners. Your ability to serve as the primary point of contact will ensure long-term success and collaboration.
Drive Strategic Growth: Take ownership of developing and executing structured business plans or quarterly OKRs that align with each partner's unique goals, maximizing the potential of strategic partnerships through a deep understanding of their business.
Optimize Performance: Use your analytical skills to dive into data, uncover trends, and identify key opportunities for improving business KPIs. Your insights will be critical in driving smarter decisions and better outcomes for both sides.
Generate New Opportunities: Lead the charge in creating new growth opportunities with both existing and potential partners. Your expertise in negotiating will be key in structuring mutually beneficial deals that drive expansion.
Deliver Actionable Insights: Perform Analysis and regularly provide valuable insights and updates to both partners and internal teams, ensuring that everyone stays aligned, informed, and empowered to make the right decisions.
Resolve Challenges Quickly: Be the problem-solver, triaging operational and executional issues that arise across partners and internal teams. Your ability to act swiftly and decisively will keep everything running smoothly.
Ideal profile:
8+ years of experience in Business Development, Partnerships, or Management Consulting
Proven track record of successfully managing complex projects from inception to completion, with meticulous attention to detail and a strong bias for action.
A go-getter with a strong work ethic, a willingness to learn and adapt quickly, and a desire to contribute to the success of a high-growth company.
A data-driven approach to decision-making, with the ability to analyze complex situations and make informed, actionable decisions.
Excellent written and verbal communication, presentation, and interpersonal skills with the ability to effectively communicate complex ideas to both internal and external stakeholders.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
You could work anywhere. Why us?
Join a pre-IPO startup with capital, traction and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).
Work closely with brilliant leaders and team mates from companies like McKinsey, BCG, Bain, Nvidia, GEICO, Better, etc.
Disrupt a massive market and take us to a $10B business in the next few years.
Be immersed in a talent-dense environment and greatly accelerate your career growth.
About the opportunity:
As the Manager, Business Operations (Business Development), you’ll be a driving force behind the growth and success of our partner ecosystem. You’ll strategically manage and strengthen existing partnerships while identifying and securing high-value new collaborations that align with our long-term vision. By leveraging your deep understanding of market dynamics, you’ll propose innovative tools and product solutions that unlock scalable opportunities for both our business and our partners.
This high-impact role involves collaborating closely with cross-functional teams—product, operations, data, and sales—to craft and execute partnership strategies that deliver lasting business outcomes. Reporting directly to the VP of Partnerships, you’ll play a pivotal role in shaping the strategic direction of our partnership portfolio and accelerating growth across the organization.
Jerry is building the first super app to help people optimize all aspects of owning a car – insurance, buy/sell, registration, loans, safety, repairs, parking, etc – a $2T market in the U.S. We started with insurance in 2019, and since then we’ve launched loan refinancing, driving insights, a repair marketplace, car diagnostics, and a GenAI-powered chatbot & voicebot. We have amassed over 5M customers, raised $240MM in funding, scaled our revenue 60X and our team to 225 across 6 countries.
How you will make an impact:
Foster Strong Partner Relationships: Be the go-to person for building and nurturing deep, trusted relationships with existing partners. Your ability to serve as the primary point of contact will ensure long-term success and collaboration.
Drive Strategic Growth: Take ownership of developing and executing structured business plans or quarterly OKRs that align with each partner's unique goals, maximizing the potential of strategic partnerships through a deep understanding of their business.
Optimize Performance: Use your analytical skills to dive into data, uncover trends, and identify key opportunities for improving business KPIs. Your insights will be critical in driving smarter decisions and better outcomes for both sides.
Generate New Opportunities: Lead the charge in creating new growth opportunities with both existing and potential partners. Your expertise in negotiating will be key in structuring mutually beneficial deals that drive expansion.
Deliver Actionable Insights: Perform Analysis and regularly provide valuable insights and updates to both partners and internal teams, ensuring that everyone stays aligned, informed, and empowered to make the right decisions.
Resolve Challenges Quickly: Be the problem-solver, triaging operational and executional issues that arise across partners and internal teams. Your ability to act swiftly and decisively will keep everything running smoothly.
Ideal profile:
4+ years of experience in Business Development, Partnerships, or Management Consulting
Proven track record of successfully managing complex projects from inception to completion, with meticulous attention to detail and a strong bias for action.
A go-getter with a strong work ethic, a willingness to learn and adapt quickly, and a desire to contribute to the success of a high-growth company.
A data-driven approach to decision-making, with the ability to analyze complex situations and make informed, actionable decisions.
Excellent written and verbal communication, presentation, and interpersonal skills with the ability to effectively communicate complex ideas to both internal and external stakeholders.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.
Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.