Controller

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 We’re hiring our first Controller to build and own Crosby’s accounting and financial operations function from the ground up. This is not a maintenance role — it’s a systems-building role. You’ll design the financial infrastructure of an AI-native company from first principles, ensuring our accounting, reporting, and controls scale with the business. You’ll partner closely with the leadership team, and investors to deliver accurate, timely financials while building the processes and systems that support rapid growth. The right candidate is both deeply technical and highly pragmatic — someone who can operate at startup speed while maintaining institutional-grade rigor. WHAT YOU'LL DO - Oversee and execute all core accounting 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 WHO YOU ARE - 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 - Proficiency with modern accounting systems (experience with AI-native or automation-forward ERPs is a 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 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.