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Crosby is an AI-native law firm that combines human legal expertise with proprietary technology to help companies execute commercial contracts faster and with higher quality. The company was founded by experienced legal and startup operators and counts Cursor, Ramp, and Cognition among its customers.
As Product Manager, you will own one of Crosby's core AI products end-to-end, working with internal lawyers, external customers, and the Applied AI engineering team to ship products that deliver measurable improvements in quality and speed every quarter.
Key responsibilities:
- Drive product direction and own the vision, roadmap, and execution for the redlining product, taking it from 0→1 and scaling across all contract types to unlock full automation
- Design and operate the evaluation infrastructure that measures whether the redlining product is improving and why
- Partner deeply with the internal legal team and design partners to understand what good looks like, identify where the system breaks, and determine what's worth automating next
- Define and analyze metrics that translate quality, automation, and customer outcomes into measurable signals driving product direction
- Champion velocity by moving quickly under ambiguity, shipping, learning, and iterating
You'll spend significant time with lawyers, becoming a quasi-domain expert on legal contracts and review workflows. The role requires balancing technical rigor (eval design, agent architecture) with product intuition and startup agility.
REQUIREMENTS:
- 5+ years of product management experience with a track record building AI/ML-powered products at early-to-mid stage companies
- Hands-on experience building AI/ML-powered products in production
- Deep AI product knowledge: you've written evals, reasoned about model behavior, and made tradeoffs between agentic architectures; personal time spent in AI is a strong plus
- Experience working with domain experts to shape an AI product (legal, medical, financial, scientific)
- Background showing a product evolve from early stage to scale
- Detail-oriented and excited to go deep on a new domain
- Startup DNA: thrive in ambiguity, move with urgency, proven success in early-stage environments
- Technical fluency to engage with engineering on architecture, agent design, and eval infrastructure (coding not required)
- Bias to action: ship and iterate rather than over-plan
- Full ownership mentality: take responsibility for outcomes, not just deliverables
