Technical Generalist

About Crosby

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

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.

What you'll do

• 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.

Who you are

• 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

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

Equal Opportunity

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.