Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As an Engineer, you’ll have the unique opportunity to define and build the core technology stack that powers Crosby’s platform. You’ll work across the stack, building the robust back-end systems and tooling interfaces needed to deliver on our vision.
In this role, you’ll collaborate directly with the founders, define technical priorities, and ensure the scalability of our platform. You'll have a direct impact on our product and user experience as we create tools to make contract review faster and more efficient.
Design and implement scalable systems to process contracts at scale.
Build bleeding-edge agentic AI tools to help the Crosby Legal team review contracts faster.
Work closely with the founders and cross-functional teams to define and execute on technical priorities.
Establish the foundation for a robust and maintainable codebase as we grow.
Mentor and recruit engineers to help build out the team.
Experience: 3+ years of engineering experience, ideally including Python, TypeScript.
Problem-focused: Strong sense of the problem behind a problem, and attention to detail in delivering high-quality products.
Builder mindset: Excited about the opportunity to create and scale systems from the ground up.
Collaborative: Effective communicator who thrives in cross-disciplinary teams.
Ownership: Driven to take responsibility for projects from ideation through execution.
Curiosity: Passionate about learning and experimenting with new technologies.
Strong Python, TypeScript skill set
Strong experience with NLP, LLMs, RL, and Information Theory.
Experience with modern front-end frameworks (e.g., React, Vue, or Svelte).
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
This is not your typical bizops role. Operations are core to our business and are a competitive advantage, so we are designing an ambitious, world class org.
As a member of the Operations Team at Crosby, you will take full ownership of scaling the best law firm ever built – designing and optimizing complex human-in-the-loop workflows, cracking our automation, and ensuring quality.
Own mission-critical workflows that blend human and machine to deliver legal work faster and better than ever before
Design and implement new operational processes, from scoping to rollout, across legal delivery, quality control, training, and client success.
Partner with product and engineering to prototype and deploy internal tools that increase throughput and reduce error.
Define and operationalize Crosby’s evolving playbooks, training systems, and incentives as we scale.
2–5 years of experience in operations, consulting, finance, or a similarly analytical and high pressure, execution-focused environment. Priority given to former founders.
Deep curiosity about how things work—and how they can work better.
Proven ability to own complex systems or projects end-to-end, especially in ambiguous or high-stakes settings.
Excitement about working in-person with a team that values precision, pace, and constant reinvention.
An interest in law or legal services is a plus, but not required—this is an operations-first role.
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
We’re looking for a Founding Account Executive to build and own the commercial side of our business. As one of the first hires, you’ll partner closely with the founders to define our positioning, acquire early customers, and lay the foundation for scalable growth.
This role is ideal for a builder who thrives in ambiguity, can wear multiple hats, and is excited to create a playbook for sales and growth.
Build and execute the end-to-end sales motion: sourcing leads, running discovery, managing demos, negotiating contracts, and closing deals.
Develop our early marketing strategy: content, campaigns, events, and thought leadership.
Establish and manage our customer success approach to ensure adoption, retention, and advocacy.
Collect feedback from customers and the market to influence product roadmap and strategy.
Lay the foundation for a future sales teams by building processes, playbooks, and metrics.
3–8+ years in sales, business development or growth roles at high-growth startups (bonus if you’ve been an early hire).
Track record of closing enterprise or mid-market deals and building pipeline from scratch.
Strong understanding of B2B SaaS go-to-market motions (sales-led, PLG, partnerships).
Data-driven, but willing to experiment and move fast.
Excited about being a founding team member, with the associated risk/reward, ownership, and impact.
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Strategic Project Lead, you will be at the cutting edge of innovating on the way legal work gets practiced. You’ll own client relationships and work with your team of lawyers to optimize workflows for improved quality and efficiency. You’ll design and run experiments, leverage data to uncover insights, and identify best practices that can be scaled across the company.
Continuously evaluate workflows and processes, running data-driven experiments to improve speed, consistency, and quality.
Coordinate team resources to deliver timely, high-quality legal services tailored to client needs.
Manage and nurture relationships with clients to help realize value.
Partner with Product, Lawyers and Operations teams to implement new tools and processes.
Track and report on partnership performance, providing insights and recommendations for optimization.
3-5+ years of experience in operations, strategy consulting, project management, or a related field.
Ideally a professional or educational background in law or legal services.
Proven ability to lead and develop teams in a client-facing environment.
Strong analytical skills with experience using data to drive decision-making.
Demonstrated success in process design, workflow optimization, or operational strategy.
Excellent communication, relationship-building, and leadership skills.
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Research Engineer, you'll bridge research and production. You'll turn validated methods, benchmarks, and evaluation infrastructure from our research team into dependable, production-grade features. You’ll be responsible for the entire lifecycle of an AI feature—from building the underlying systems to customizing the models that make them run. Your work will involve both robust system design and the pragmatic application of advanced machine learning techniques, including model fine-tuning when necessary. This role is for a product-minded research engineer who knows how to get the most out of modern AI and is obsessed with shipping reliable, high impact features.
We also publish our work on legal AI at intelligence.crosby.ai — take a look at the kinds of problems you'd be working on.
Build core AI Systems: Design, build, and scale our primary AI features, including complex Retrieval Augmented Generation (RAG) pipelines and agentic workflows that make our models measurably better at contract review, playbook retrieval and docx editing.
Build RL fine-tuning infrastructure: Stand up and harden RL training infrastructure (PPO, GRPO, and related methods) so researchers can train quickly and reliably at scale.
Enable RL in a non-verifiable domain: Build reward pipelines, generators, and formal verification harnesses that make scalable RL possible in a domain like contract review.
Customize Models for Impact: Selectively fine tune and adapt language models to improve their performance on highly specific legal tasks where off the shelf solutions fall short
Ensure Production Quality: Develop evaluation and monitoring systems that catch regressions and reward hacking before they reach users.
Apply AI Pragmatically: Stay on the frontier of AI research and identify the most effective techniques and tools to solve immediate product challenges.
Collaborate to Ship: Work closely with product, backend, and our in house legal experts to deliver end to end solutions that make our users more effective.
Experience: 3+ years of professional software engineering experience building and shipping AI/ML-powered products, with deep proficiency in Python and a proven track record of scalable, production-grade systems.
Post-training expertise: Familiarity with post-training techniques such as SFT and GRPO, plus hands-on experience with the systems and frameworks that run them at scale—distributed model training, VERL, and vLLM.
Practical AI skills: Hands-on experience with LLM APIs (e.g., OpenAI, Anthropic), RAG, agentic workflows, and the full ML project lifecycle.
Analytical and pragmatic: A data-driven approach to problem solving and strong intuition for when to build complex infrastructure versus ship a simple solution.
Product-focused: Driven by user impact and skilled at making smart technical trade-offs to deliver value quickly.
Ownership: You thrive on taking full responsibility for features, from initial concept through deployment and iteration.
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Recruiter at Crosby, you'll play a pivotal role in scaling the team behind our AI-powered legal platform by identifying, engaging, and closing exceptional talent across Engineering, Product, and Design teams. You'll be a strategic partner to hiring managers and leadership by shaping hiring plans, translating business priorities into crisp role definitions, and guiding candidates through a high-bar, high-touch process. Beyond filling roles, you'll help build the foundation of Crosby's culture and velocity by ensuring we attract people who can reimagine how legal work gets done and can move fast in ambiguity.
Own the EPD talent pipeline: Lead full-cycle recruiting for Crosby's Engineering, Product, and Design organization.
Hunt for elite EPD talent: Go far beyond inbound. Proactively source and engage top-tier technical and creative talent through targeted outreach, creative search strategies, and deep network leverage.
Be the face of Crosby in the market: Serve as the first touchpoint for EPD candidates. Clearly articulate Crosby's ambition, product differentiation, and the opportunity to reshape an $18B legal services market — ensuring every candidate leaves with a compelling understanding of what we're building.
Deliver a world-class candidate experience: Ensure every candidate interaction is thoughtful, transparent, and high-integrity.
5+ years of EPD recruiting experience, ideally at a fast-growing startup
Proven track record rapidly scaling technical teams
Creativity in problem-solving and innovating across all stages of the hiring cycle
Experience aligning internal stakeholders on job descriptions, compensation bands and interview processes
Autonomous and excited about taking ownership over major hiring initiatives
Extreme passion for learning and growth
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
The Talent team partners directly with founders and functional leaders to build high-performing teams. We run structured, high-signal hiring processes designed to attract and assess exceptional technical talent.
We prioritize clarity, speed, and rigor at every stage of the recruiting cycle.
As a Talent Coordinator at Crosby, you'll play a critical role in supporting the recruiting engine behind our AI-powered legal platform by ensuring every part of the hiring process runs smoothly and efficiently. You’ll partner closely with recruiters, hiring managers, and candidates to coordinate interviews, manage scheduling across time zones, and maintain the operational backbone of our hiring process. Beyond logistics, you’ll help create a seamless and thoughtful candidate experience that reflects Crosby’s high standards and fast-moving culture.
Own recruiting coordination: Manage interview scheduling and coordination across go to market hiring processes while balancing complex calendars and time zones.
Deliver exceptional candidate logistics: Serve as a primary point of contact for candidates throughout the interview process, ensuring communication is timely, clear, and professional.
Maintain recruiting operations: Keep our ATS and recruiting systems accurate and organized, ensuring interview feedback, candidate records, and process documentation are up to date.
Support a world-class candidate experience: Ensure every interaction — from scheduling to interview preparation — reflects Crosby’s commitment to clarity, speed, and respect for candidates’ time.
1–3 years of experience in recruiting coordination, talent operations, or a similar role, ideally in a fast-paced startup environment
Highly organized with exceptional attention to detail and the ability to manage multiple scheduling priorities simultaneously
Strong communicator who can interact professionally with candidates, hiring managers, and executives
Comfortable working with recruiting tools such as ATS platforms, scheduling software, and productivity systems
Proactive, resourceful, and excited about building scalable recruiting operations that help teams grow quickly
Strong curiosity and a desire to learn how world-class teams hire and scale
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Data Scientist at Crosby, you'll play a critical role in developing the models and data systems that power our AI-driven legal platform. You’ll work across the full lifecycle — from data definition and labeling strategy to model development, evaluation, and iteration in production.
You’ll partner closely with engineers, product teams, and legal experts to translate complex legal workflows into structured machine learning systems. Beyond modeling, you’ll help ensure our systems are accurate, reliable, and continuously improving in real-world use.
Develop evaluation systems: Build metrics, benchmarks, and experimentation frameworks to measure and improve model performance.
Drive data strategy: Partner with legal and product teams to define labeling schemas, curate high-quality datasets, and improve data pipelines.
Support production systems: Work closely with engineering to deploy models, monitor performance, and iterate based on real-world usage.
Apply AI pragmatically: Leverage LLMs and other modern techniques to solve product problems, balancing sophistication with reliability and speed.
Collaborate cross-functionally: Partner with engineering, product, and legal teams to deliver end-to-end systems that improve customer outcomes.
1–5 years of experience in data science, machine learning, or applied NLP, ideally in a fast-paced startup environment
Strong foundation in machine learning, statistics, and data analysis, with proficiency in Python
Hands-on experience working with LLMs, NLP systems, or unstructured text data
Experience working across the full ML lifecycle — from data curation and experimentation to deployment and monitoring
Highly analytical with strong problem-solving skills and the ability to translate ambiguous problems into structured solutions
Strong communicator who can collaborate effectively with both technical and non-technical stakeholders
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As Head of Data at Crosby, you'll play a critical role in defining and leading our data strategy across the company. You’ll be responsible for building the systems, pipelines, and teams that power our AI models, product analytics, and decision-making infrastructure.
You’ll work closely with engineering, product, and legal teams to ensure we are leveraging data as a core competitive advantage — from improving model performance to driving business insights. This is a highly strategic and hands-on role, requiring both technical depth and strong leadership.
Own data strategy: Define and execute Crosby’s data strategy across ML, analytics, and infrastructure.
Build and scale data systems: Design and implement robust data pipelines, storage systems, and tooling to support both product and modeling needs.
Enable AI performance: Partner closely with ML and engineering teams to improve data quality, labeling systems, and feedback loops that drive model performance.
Drive analytics and insights: Establish metrics, dashboards, and analytical frameworks to support product, business, and operational decision-making.
Lead and grow the team: Hire, mentor, and manage a high-performing data team across data science, analytics, and data engineering.
Ensure data quality and governance: Build systems and processes to ensure data accuracy, consistency, and reliability across the organization.
8+ years of experience in data science, data engineering, or analytics, with experience leading or managing teams
Strong technical foundation in data systems, including experience with data pipelines, warehousing, and large-scale data processing
Experience working closely with machine learning teams and understanding the data needs of ML systems
Proven ability to define metrics, build analytical frameworks, and drive data-informed decision-making
Strong leadership skills with experience building and scaling teams in fast-paced environments
Excellent communicator who can work effectively across technical and non-technical stakeholders
Highly organized, pragmatic, and motivated to build systems that drive real-world impact
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Security Engineer at Crosby, you'll play a critical role in designing and implementing the security foundations of our platform. You’ll be responsible for protecting sensitive legal data, securing our infrastructure, and embedding best-in-class security practices across the engineering organization.
You’ll work closely with engineering, product, and legal teams to identify risks, implement controls, and ensure our systems meet the highest standards of security and compliance. This role is for someone who is both deeply technical and highly pragmatic — able to balance strong security guarantees with the speed required in a fast-moving environment.
Own application and infrastructure security: Design and implement security controls across our application, APIs, and cloud infrastructure.
Protect sensitive data: Build systems and processes to safeguard confidential legal and customer data.
Drive security best practices: Establish and enforce secure development practices, including code reviews, threat modeling, and vulnerability management.
Monitor and respond: Implement monitoring, alerting, and incident response processes to detect and respond to security threats.
Ensure compliance readiness: Support security and compliance efforts (e.g., SOC 2), including documentation, controls, and audits.
Collaborate across teams: Partner with engineering and product teams to embed security into the development lifecycle without slowing velocity.
4+ years of experience in security engineering, infrastructure security, or a related role
Strong understanding of application security, cloud security (e.g., AWS/GCP), and common vulnerability classes
Experience securing production systems, including authentication, authorization, and data protection
Proficient in at least one programming language (e.g., Python, Go) and comfortable working with engineering teams
Experience with security tooling, monitoring systems, and incident response workflows
Highly pragmatic — able to prioritize risks and implement effective, scalable solutions
Strong ownership mindset with the ability to operate independently in ambiguous environments
Clear communicator who can work effectively with engineers, product teams, and leadership
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As an Infrastructure Engineer at Crosby, you'll play a critical role in building and scaling the systems that power our platform. You’ll be responsible for designing and maintaining reliable, scalable infrastructure across compute, storage, and deployment systems.
You’ll work closely with backend, AI, and product engineers to ensure our systems are performant, observable, and easy to operate. This role is for someone who cares deeply about reliability and developer velocity — building infrastructure that enables teams to ship quickly and confidently.
Build and scale infrastructure: Design and maintain cloud infrastructure across compute, storage, and networking.
Own deployment systems: Develop and improve CI/CD pipelines and deployment workflows to enable fast, reliable releases.
Ensure reliability and performance: Implement monitoring, alerting, and observability systems to maintain high uptime and performance.
Support AI and data workloads: Optimize infrastructure for ML/AI systems, including batch processing, inference workloads, and data pipelines.
Improve developer velocity: Build tooling and systems that make it easier for engineers to build, test, and deploy software.
Collaborate across teams: Partner with engineering teams to ensure infrastructure supports product and system requirements.
4+ years of experience in infrastructure engineering, SRE, or backend systems
Strong experience with cloud platforms (e.g., AWS, GCP) and modern infrastructure tooling
Proficient in at least one programming language (e.g., Python, Go) and comfortable building internal tools
Experience with containerization and orchestration (e.g., Docker, Kubernetes)
Strong understanding of CI/CD systems, monitoring, and observability
Highly pragmatic with strong judgment around reliability vs speed trade-offs
Ownership mindset — you take responsibility for systems end-to-end
Comfortable operating in fast-paced, ambiguous environments
Benefits & Perks
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
We’re hiring our first Controller to build and own Crosby’s accounting and financial operations function from the ground up. Given Crosby is both an AI software company and law firm, accounting has particular strategic importance to the business. We’re looking for an ambitious, AI-native accounting leader who’s excited about the opportunity to lead a strategic accounting function at one of the fastest growing applied AI companies in NYC.
You’ll build on the early foundation we laid to take our accounting strategy to the next level, ensuring our accounting, reporting, and controls scale with the business. You will report to our VP Finance, and you’ll partner closely with the leadership team and investors to deliver high quality, timely financials while building the processes and systems that support rapid growth. The right candidate is excited about technical accounting strategy and pragmatic about efficiently delivering business outcomes, operating at startup speed while maintaining a high bar for accounting rigor.
Design accounting and tax strategy for a multi-entity, multi-owner, MSO style business with intercompany transactions
Oversee and execute all core accounting and tax activities across the business
Lead the monthly and annual close processes, including review/approval of journal entries, account reconciliations, flux analysis, and financial statement tie-outs to ensure accurate, timely, and decision-useful reporting
Drive audit readiness and execution by serving as the primary point of contact for external auditors and ensuring timely, high-quality completion of all deliverables
Design, implement, and enforce internal controls, policies, and standard operating procedures that strengthen risk management and support operational scale
Partner closely with leadership on fundraising initiatives, diligence processes, and financial storytelling
Bachelor’s degree in Accounting, Finance, or related field
CPA certification required
6+ years of progressive accounting experience, including 2+ years in high-growth startups or tech companies
Deep accounting expertise with a strong command of current US GAAP standards
Demonstrated experience building and scaling financial operations in a high-growth or “0→1” environment
Multi-entity consolidation experience required, experience with legal or healthcare MSO models and complex intercompany transactions a strong plus as well as cross-boarder consolidation
Proficiency with modern accounting systems (experience with AI-native or automation-forward ERPs is a strong plus) and broader financial tooling
Strong cross-functional collaborator; able to clearly communicate complex accounting and financial concepts to non-finance stakeholders
High attention to detail paired with strong operational judgment
A builder’s mindset, you operate with high ownership, move quickly, and proactively create structure where it doesn’t exist
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Product Manager, you'll own one of our core AI products end to end — the systems our internal lawyers and external customers use every day to do their work. You'll partner closely with those users, our Applied AI engineering team, and design to ship a product that delivers higher-quality output, faster, every quarter.
Drive product direction. Own the vision, product and roadmap end to end for our redlining product. Take the product surface from 0 → 1, then scale it across all contract types to unlock full automation.
Own the eval system. Design and operate the evaluation infrastructure that tells us whether the redlining product is improving and why.
Partner deeply with lawyers. Spend significant time with our internal legal team and design partners to surface what good looks like, where the system breaks, and what's worth automating next.
Define and analyze metrics. Translate quality, automation, and customer outcomes into measurable signals that drive direction.
Champion velocity. Move quickly under ambiguity; ship, learn, iterate.
Experience. 5+ years of product management experience, with a track record building AI/ML-powered products at an early-to-mid stage.
AI product depth. You've worked on AI applications: written evals, reasoned about model behavior, picked tradeoffs between agentic architectures. Personal time spent in the AI sauce is a strong plus.
Detail-oriented and excited to go deep on a new domain. You'll spend significant time with lawyers and become a quasi-domain-expert on legal contracts and review workflows.
Startup DNA. You thrive in ambiguity, move with urgency, and have proven success in early-stage startup environments.
Technical fluency. You can engage with engineering on architecture, agent design, and eval infrastructure. You don't need to write code.
Bias to action. You ship and iterate; you don't over-plan.
Ownership. You take full responsibility for outcomes, not just deliverables.
Hands-on experience building AI/ML-powered products in production
Experience working with domain experts to shape an AI product (legal, medical, financial, scientific)
Background that includes seeing a product evolve from early stage to scale
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Technical Generalist at Crosby, you'll play a critical role in building whatever matters most. This is not a narrowly defined role — we are looking for exceptional engineers and will shape the role around your strengths and where you can have the highest impact.
You’ll work across the stack — from product features to backend systems to AI workflows — and partner closely with engineering, product, and legal teams to solve high-leverage problems. If you’re someone who wants to operate with ownership, move quickly, and work on the hardest problems in the system, this is the role.
Build across the stack: Develop and ship features across frontend, backend, and AI systems.
Own end-to-end problems: Take ideas from concept to production, including design, implementation, and iteration.
Move quickly and pragmatically: Identify the highest-impact work and execute with speed while maintaining quality.
Improve systems continuously: Refactor, optimize, and scale systems as the product and team grow.
Collaborate closely: Work with product, design, and legal teams to deliver solutions that improve user outcomes.
Fill gaps where needed: Step into whatever area needs attention — whether that’s debugging, infrastructure, product features, or internal tooling.
We are simply looking for extremely strong engineers.
4+ years of experience building and shipping production systems, with evidence of exceptional ability
Technically sharp with strong fundamentals — you can reason clearly about systems, tradeoffs, and complexity
Fast learner who can quickly ramp across new domains, tools, and parts of the stack
High agency — you don’t wait for direction, you identify important problems and drive them to resolution
Strong builder — you’ve shipped meaningful work and know how to execute quickly without sacrificing quality
Comfortable with ambiguity and excited to work in an environment where the problem space evolves quickly
Clear thinker and communicator who can collaborate across disciplines
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As an AI Developer Experience Engineer at Crosby, you'll play a critical role in building the internal systems that enable our team to develop, evaluate, and ship AI features quickly and reliably. You’ll focus on improving the developer experience around LLMs, data, and experimentation — creating tools and infrastructure that accelerate iteration while maintaining quality.
You’ll partner closely with engineers, data scientists, and researchers to streamline workflows across prompting, evaluation, fine-tuning, and deployment. This role is for someone who is obsessed with leverage — building systems that make other engineers dramatically more productive.
Build AI developer tooling: Design and implement internal tools for prompt management, evaluation, experimentation, and model iteration.
Improve iteration speed: Create systems that enable rapid testing, debugging, and comparison of model outputs across different approaches.
Own evaluation infrastructure: Develop frameworks for benchmarking, regression testing, and monitoring AI system performance.
Streamline data workflows: Build pipelines and tooling to support data collection, labeling, and feedback loops for model improvement.
Support production systems: Partner with engineering teams to ensure AI features are reliable, observable, and easy to maintain in production.
Enable the team: Identify bottlenecks in the development process and build systems that increase developer velocity and confidence.
3+ years of software engineering experience, ideally working on developer tools, infrastructure, or platform teams
Strong proficiency in Python and experience building backend systems and internal tooling
Hands-on experience working with LLMs, APIs (e.g., OpenAI, Anthropic), and modern AI workflows
Experience building systems for experimentation, evaluation, or data pipelines
Strong systems thinking with the ability to design tools that scale across teams
Highly pragmatic with a focus on improving developer velocity and real-world outcomes
Strong communicator who can work closely with engineers, researchers, and product teams
Proactive, resourceful, and excited about building foundational systems in a fast-moving environment
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
This is not your typical bizops role. Operations are core to our business and are a competitive advantage, so we are designing an ambitious, world class org.
As a member of the Operations Team at Crosby, you will take full ownership of scaling the best law firm ever built – designing and optimizing complex human-in-the-loop workflows, cracking our automation, and ensuring quality.
Own mission-critical workflows that blend human and machine to deliver legal work faster and better than ever before
Design and implement new operational processes, from scoping to rollout, across legal delivery, quality control, training, and client success.
Partner with product and engineering to prototype and deploy internal tools that increase throughput and reduce error.
Define and operationalize Crosby’s evolving playbooks, training systems, and incentives as we scale.
2–5 years of experience in operations, consulting, finance, or a similarly analytical and high pressure, execution-focused environment. Priority given to former founders.
Deep curiosity about how things work—and how they can work better.
Proven ability to own complex systems or projects end-to-end, especially in ambiguous or high-stakes settings.
Excitement about working in-person with a team that values precision, pace, and constant reinvention.
An interest in law or legal services is a plus, but not required—this is an operations-first role.
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
Sequoia. Goldman. Wachtell. The best services firms have sterling reputations. One of their most durable moats is the incredible brand each has built over decades. At Crosby, we are building a third type of company: neither software nor services, but a neofirm.
Our brand is one of our most important assets. You will own Crosby’s brand as we remake one of the most important industries and build the best AI law firm in the world.
Brand strategy and positioning: work with the founders, head of marketing, and other stakeholders to build the foundation for what Crosby’s brand stands for. Build a brand that stands out and captures attention, while feeling premium and trustworthy.
Visual identity and brand system: make Crosby’s brand show up consistently across varied canvases from billboards to conference booths to how our swag feels.
Signature campaigns and creative direction: partner with the founders and head of marketing to develop Crosby’s next major brand campaign for 2027, building on the recognition created by the “Death of the Billable Hour.” Drive the central idea and its execution across out-of-home, digital, social, and other relevant channels.
Website and market-facing storytelling: help transform Crosby’s website into a more complete expression of the company, services, and technology. Shape page narratives, visual concepts, headlines, and concise brand copy with product, design, and a dedicated writer.
Cross functional partnership: work with design, product marketing, events, content, and other teams to consistently build affinity for Crosby’s brand with every interaction a customer or prospect has.
4-8 years of experience building a standout brand in tech, consumer, or at an agency. This could be at an admired brand, through a standout campaign or agency project, or while building an emerging company.
Proven ability to build a brand from the ground up, either as the first or second hire focused on brand.
Exceptional taste and a clear point of view. Compelling examples of distinctive, high-quality brand work and the ability to explain why creative choices were right for the company, audience, and objective.
Visual fluency. The judgment to guide identity and visual expression across different formats, plus enough comfort with rough mockups or concepts to communicate direction. Being a production designer is not required.
Conviction and collaborative judgment. Comfort navigating strong opinions from founders, marketing, Product, Sales, and designers. The ability to defend sound creative decisions, incorporate useful feedback, and move projects forward.
End-to-end creative leadership. Experience translating a brand idea into campaigns, a website, customer moments, or other shipped work, with clear ownership of concept, feedback, and delivery.
Resourcefulness and momentum. A bias for shipping high-quality work in an evolving organization, building practical systems, and managing tradeoffs without waiting for perfect resources or direction.
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
Build the growth motion at Crosby by helping us turn raw demand into a scalable system. We are building a third type of company: neither software nor services, but a neofirm. We are rethinking tech’s growth playbook, keeping what works for our business, and dropping what is brand detractive.
You’ll own the strategy and execution that drive pipeline growth across channels: mapping our potential buyers, brainstorming creative ways to get in front of them, and constantly thinking about how to improve conversion at every step of the funnel. You’ll productize the channels that are working for us, build a single source of truth for our funnel, fix the issues our funnel reveals, and experiment to develop the investment case for strong channels we aren’t running yet.
Partner closely with sales to build a repeatable outbound motion: draft a prioritized target list, messaging, and sequencing; automate other ancillary touchpoints like gifting and event invites
Paid channels: figure out a brand accretive way to use paid channels like ads to drive awareness among buying committees
Experiment: come up with and execute endless campaigns to test new channels and messaging that can drive pipeline and conversion; cut the losers and double down on the winners
Help drive ROI at events & conferences: measure ICP and TAM overlap to prioritize conferences and dinner invites; partner with events lead to build a machine to send event invites, automate follow ups, and measure ROI
Analytics: track campaign performance, analyze funnel data, and own ways insights from this data can be immediately used to drive pipeline or improve funnel conversion
2-6 years experience leading growth at a startup building marketing channels from 0-1 and scaling marketing channels from 1-10
Creative enough to come up with experiments, and analytical enough to measure what's working
High agency: you take a broad mandate and get it done. You see an opportunity in the funnel math in the morning and ship a new campaign to take advantage of it by the afternoon.
Willing to test unconventional ideas.
Great judgment: you know that Crosby is building a trusted brand as a law firm, and know the line between creative, eye-catching campaign and an idea that is harmful to our brand and goals
Analytical: you own CAC, conversion, activation, and payback by channel. You build the dashboards, track the funnel, and read the cohorts by yourself.
Low ego: you know that the best way to test hypotheses is by sending the email or building the ad creative yourself. No task is beneath you.
You move quickly, communicate clearly, and thrive in ambiguous, fast-paced environments.
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
Hosting great events are a critical way we bring on new clients and retain existing clients at Crosby. Our customers are very busy people: CROs, GCs, and CFOs at the fastest growing AI startups and Fortune 500 companies. We need to throw exceptional, can’t miss events that busy people with many options will make time for.
Host incredible events from Michelin starred dinners to suites at can’t miss sports games to creative “I never thought a company could sponsor that” experiences; throw events you personally are dying to go to, not bland corporate events.
Own the details from idea through execution, including venues, vendors, budgets, creative, guest lists, programming, production, and on-site execution.
Partner with the Head of Marketing to shape our events strategy, including what personas and geographies to prioritize and which conferences to sponsor, and tying IRL experiences into broader campaigns and business goals.
Build our very first customer conference, bringing together Crosby customers for an elevated day of sharing best practices and forging deep relationships.
Partner with the Head of Marketing, Head of Brand, and sales to stand out at industry conferences with unique booths, speaking opportunities, and upscale experiences so every conference appearance gives attendees a reason to seek us out.
Build the playbook for our events program: establish repeatable concepts, creative standards, and production processes; measure performance, gather learnings, and constantly raise the bar so we can double down on what works and drop what doesn’t.
2-6 years of experience in world class hospitality, whether in the hospitality industry or field marketing
Creative host: you can dream up and pull off experiences that people genuinely want to attend, from compelling activations at major industry conferences to intimate dinners
Exceptional taste and a clear point of view: compelling examples of high end events you have helped run, and the ability to explain why one creative choice is better than anotehr for the company’s business goals
Detail oriented execution machine: you know all the hard work that goes into taking an event from a B+ to an A+ and put the time and effort in to polish the finest details.
Equally comfortable dreaming up a new concept, sweating the details, and getting in the weeds to make it happen. Excitement about travel and working in a fast-paced startup environment is important.
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Product Engineer at Crosby, you'll own defined surfaces of the product end to end. You'll work across the stack — data models, backend services, APIs, and the interfaces our users work in every day — and go deep on the complex legal and AI workflows that sit underneath.
You'll partner closely with product, design, and our in-house legal team to shape what we build and how it works. Beyond shipping features, you'll set patterns, make foundational technical decisions, and help raise the bar for engineering as we scale. If you want to own real scope and ship fast, this is the role.
Build end to end: Design and ship features across the stack, from Python services and APIs to the React and TypeScript interfaces on top of them
Work on AI workflows: Build and improve the AI systems the product runs on
Design the systems: Model complex legal workflows into the data models, services, and APIs the rest of the team builds on
Prototype and iterate fast: Work closely with product and our in-house legal team to rapidly prototype and iterate on features
Grow the team: Mentor and help recruit world-class engineers
Experience: 5+ years building production software, with real backend depth and enough frontend fluency to ship a polished interface without waiting on a handoff. We work in Python and TypeScript but we care more about judgment than a specific stack
Systems thinking: You're comfortable designing schemas, APIs, and services that other engineers depend on, and you think about failure modes before they reach users
Product sense: You have strong instincts for what to build and a low tolerance for experiences that technically work but feel bad to use
Builder mindset: You're excited to create and scale systems from the ground up and make foundational technical decisions
Ownership: You take full responsibility for projects from ideation through execution and delivery
Collaborative: An effective communicator who works well with product, design, and domain experts
Curiosity: Passionate about learning and experimenting with new technologies to solve hard problems
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
Our two founders run very different halves of the company — Ryan on the legal and go-to-market side, John on product and engineering — and their time is the company's scarcest resource. This role exists to protect and scale it.
As Executive Assistant to the Founders, you'll own the calendars, inboxes, and travel of both the CEO and CTO, and you'll be the person who makes sure the highest-leverage meeting happens on the right day with the right prep in hand. You'll operate with real judgment and real context: you'll know what matters this quarter, who the important clients and candidates are, and what can wait. This is a craft role for someone who takes genuine pride in doing it at the highest level, with a direct line into how the company is run.
Own the calendars of both founders — triaging competing priorities, protecting deep work, and making the call on tradeoffs without needing to ask.
Manage inboxes: triage, draft replies in each founder's voice, flag what needs their attention, and make sure nothing important goes quiet.
Run meeting prep and follow-through — agendas, briefing notes, background on who's in the room, and clean notes and action items afterward.
Book and manage domestic and international travel, and rebuild plans quickly when they change mid-trip.
Coordinate client, investor, and candidate scheduling with care — often the first impression someone has of Crosby.
Handle expenses, reimbursements, and vendor and subscription logistics for both founders.
Support off-sites, board meetings, and leadership sessions end-to-end, from logistics to materials.
Be the trusted holder of sensitive information across legal, financial, personnel, and client matters.
2+ years supporting founders or C-suite executives, ideally at a high-growth startup or a firm where the pace and stakes were high.
Exceptionally organized and fast — you close loops the same day and never need a second reminder.
Excellent written communication. You can draft on someone else's behalf and have it sound like them.
Comfortable making judgment calls with incomplete information, and comfortable saying no on a founder's behalf.
Discreet by instinct. You've handled confidential material and treated it as a given, not a burden.
Fluent with modern tools and genuinely curious about AI — we expect you to use it to make yourself faster.
Excited to work in person, five days a week, alongside a team that values precision and pace.
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
The Role:
Sit at the center of modern deal-making. You’ll review and negotiate the commercial contracts that get deals to signature for companies like Cursor, Ramp, and Cognition.
Direct AI, don’t babysit it. You’ll orchestrate Crosby’s tooling over a contract and spend your judgment where it counts.
Own outcomes end-to-end and chase the small touches that turn a closed deal into one a client can’t help but tell others about at dinner.
This is a high-impact role for a lawyer excited to apply AI to their own practice, obsessive about quality execution, and drawn to leverage over billable hours.
What You'll Do:
Review and negotiate commercial contracts with speed and precision, catching the obligations, risks, and off-market terms that matter.
Collaborate with other Crosby legal team members to interpret contract terms and surface the anomalies and edge cases that need an expert’s read.
Spot inefficiencies and recurring patterns in how contracts get reviewed, and turn them into improvements that sharpen how the whole team works.
Help standardize and codify recurring contract types and playbooks so the team’s judgment compounds instead of resetting on every deal.
Partner with engineering and operations to evolve our legal service delivery model.
Who You Are:
Admitted to practice and in good standing in at least one US state
An Australian practising certificate, or foreign lawyer registration (or eligibility to register)
Australian citizenship, permanent residency, or a visa with unrestricted work rights (we’re unable to sponsor)
4+ years reviewing US commercial contracts in private practice or in-house
You have impeccable attention to detail, and sound, commercial judgment. You catch buried clauses, the wrong cross-reference, and can distinguish signal from noise.
You hold a high bar for your own work and get restless when something could be better.
You embrace change and move confidently in a fast-paced, sometimes ambiguous environment.
You write and speak clearly, and can explain a hard call simply.
You’re already tinkering with AI, or excited to, and drawn to the frontier of legal work.
Benefits & Perks
Equity and bonus compensation
Private health insurance
Fully remote
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
As a Recruiter at Crosby, you’ll play a pivotal role in scaling the team behind our AI-powered legal platform by identifying, engaging, and closing exceptional talent across our Go-To-Market organization, including Sales and Operations. You’ll be a strategic partner to GTM leadership and hiring managers by shaping hiring plans, translating revenue and growth priorities into crisp role definitions, and guiding candidates through a high-bar, high-touch process. Beyond filling roles, you’ll help build the foundation of Crosby’s culture and commercial velocity by ensuring we attract people who can reimagine how legal work gets bought and sold, and who can move fast in ambiguity.
Own the GTM talent pipeline: Lead full-cycle recruiting for Crosby’s Sales and Operations teams, from Account Executives and SDRs to RevOps, BizOps, and GTM leadership.
Hunt for elite GTM talent: Go far beyond inbound. Proactively source and engage top-performing sellers and operators through targeted outreach, creative search strategies, and deep network leverage, including within legal tech and vertical SaaS.
Assess for performance, not just pedigree: Partner with hiring managers to design interview processes that evaluate quota attainment, deal complexity, and operational rigor, so we hire people who consistently deliver results.
Be the face of Crosby in the market: Serve as the first touchpoint for GTM candidates. Clearly articulate Crosby’s ambition, product differentiation, and the opportunity to reshape an $18B legal services market, ensuring every candidate leaves with a compelling understanding of what we’re building and why it’s a winning story to sell.
Deliver a world-class candidate experience: Ensure every candidate interaction is thoughtful, transparent, and high-integrity.
5+ years of GTM recruiting experience (Sales, Revenue Operations, BizOps, or similar), ideally at a fast-growing B2B SaaS startup
Proven track record rapidly scaling sales and operations teams
Fluency in GTM roles and metrics, with the ability to dig into quota attainment, OTE structures, and sales cycles to separate real performers from strong interviewers
Creativity in problem-solving and innovating across all stages of the hiring cycle
Experience aligning internal stakeholders on job descriptions, compensation bands (including variable comp and OTE) and interview processes
Autonomous and excited about taking ownership over major hiring initiatives
Extreme passion for learning and growth
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
The Role:
Sit at the center of modern deal-making. You’ll review and negotiate the commercial contracts that get deals to signature for companies like Cursor, Ramp, and Cognition.
Direct AI, don’t babysit it. You’ll orchestrate Crosby’s tooling over a contract and spend your judgment where it counts.
Own outcomes end-to-end and chase the small touches that turn a closed deal into one a client can’t help but tell others about at dinner.
This is a high-impact role for a lawyer excited to apply AI to their own practice, obsessive about quality execution, and drawn to leverage over billable hours.
What You'll Do:
Review and negotiate commercial contracts with speed and precision, catching the obligations, risks, and off-market terms that matter.
Collaborate with other Crosby legal team members to interpret contract terms and surface the anomalies and edge cases that need an expert’s read.
Spot inefficiencies and recurring patterns in how contracts get reviewed, and turn them into improvements that sharpen how the whole team works.
Help standardize and codify recurring contract types and playbooks so the team’s judgment compounds instead of resetting on every deal.
Partner with engineering and operations to evolve our legal service delivery model.
Who You Are:
4+ years reviewing commercial contracts in private practice or in-house
You have impeccable attention to detail, and sound, commercial judgment. You catch buried clauses, the wrong cross-reference, and can distinguish signal from noise.
You hold a high bar for your own work and get restless when something could be better.
You embrace change and move confidently in a fast-paced, sometimes ambiguous environment.
You write and speak clearly, and can explain a hard call simply.
You’re already tinkering with AI, or excited to, and drawn to the frontier of legal work.
Benefits & Perks
Equity and bonus compensation
Flexible, generous PTO
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
About the role
Build the systems behind Crosby’s next stage of growth.
You’ll own the processes, data, and tools that help us turn demand into lasting client relationships. Working closely with the COO and leaders across Sales, Growth, Finance, and Legal Operations, you’ll bring clarity to how we acquire clients, convert pilots, grow accounts, and plan for what comes next.
Our business requires understanding both what clients commit to and how they actually use Crosby. You’ll connect pipeline, commercial terms, client activity, and revenue so we can make better decisions about where to invest and how to scale.
This is a hands-on role with broad ownership. You should be equally comfortable building a forecast, configuring a CRM workflow, and helping a sales leader understand why conversion changed.
What you’ll do
Own our commercial systems: Build and maintain the CRM, integrations, and workflows our teams rely on. Establish clear account ownership, pipeline stages, lead routing, and data standards—and make the systems easy to use.
Make revenue performance clear: Build reporting that connects pipeline, pilot conversion, signed commitments, client usage, retention, and expansion. Partner with Finance to keep bookings, billed revenue, and collections clearly defined and reconciled.
Run forecasting and pipeline reviews: Establish a consistent cadence with Sales and Finance. Pressure-test assumptions, identify stalled deals and risks, and turn the forecast into specific actions.
Help scale the sales team: Build capacity and hiring models, account assignments, quota recommendations, and ramp reporting. Partner with leadership and Finance on compensation plans and accurate commission calculations.
Improve conversion across the client journey: Find where prospects and clients get stuck—from initial inquiry through pilot, onboarding, and expansion. Work with the relevant teams to fix those gaps and measure whether the changes work.
Connect the sale to delivery: Make sure pricing, commitments, and client expectations transfer cleanly into onboarding and billing. Give Legal Operations visibility into expected demand so we can plan capacity as we grow.
Automate repetitive work: Use AI, integrations, and practical tooling to reduce manual updates, improve data quality, and give the team more time with clients. Own adoption and reliability after launch.
Who you are
You’ve built before: You have 5–8 years of experience in Revenue Operations, Sales Operations, or a closely related function, including meaningful ownership at a fast-growing B2B company.
You get into the systems yourself: You’ve configured a CRM, built workflows and integrations, and resolved the data issues behind unreliable reporting. Experience with Attio, Salesforce, or HubSpot is relevant.
You’re analytically strong: You can build a forecast, capacity model, or cohort analysis yourself and explain what it means. You’re excellent in spreadsheets; SQL and experience with BI tools are a plus.
You understand commercial nuance: You can distinguish a signed commitment from realized revenue and translate pilots, variable usage, and expansion into useful reporting and planning.
You make teams more effective: You earn trust with salespeople, introduce processes people actually follow, and hold a high standard for accuracy and accountability.
You have strong judgment: You know when to build something durable and when a simple solution will get the team moving. You can prioritize a broad mandate without waiting for a detailed roadmap.
You’re curious and resourceful: You actively use AI and automation in your work, learn unfamiliar tools quickly, and take responsibility for seeing projects through.
What success looks like
Leadership has a clear, trusted view of pipeline and revenue. Salespeople spend less time on administrative work. Pilots, onboarding, and expansion have clear owners and measurable outcomes. Hiring and capacity decisions are grounded in data. The systems you build help Crosby grow while keeping the team fast.
Benefits & Perks
Unlimited PTO
Lunch & dinner in the office every day
Medical insurance (multiple plan options through Anthem & Cigna)
HSA or FSA, depending on your plan choice
Dental insurance
Vision insurance
One Medical membership
401(k) match
In-office desk setup stipend
Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.