Product Lead

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 Product Lead, 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. What you'll do 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. Who you are 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 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.