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

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.