Legal & Compliance Tech IT Product ManagerActive$221K–$247K

Hybrid · San Francisco, CABusiness

The opportunity

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers.

What they're looking for

  • Define and prioritize Model Context Protocols (MCPs) and integrations that: securely connect legal systems (CLM, matter management, document management, GRC) to large language models and orchestration frameworks.
  • Apply retrieval-augmented generation (RAG) over contracts, policies, and: legal knowledge bases to deliver grounded, citable answers for legal and business stakeholders.
  • Evaluate, pilot, and scale AI legal-tech vendors and native AI features: (e.g., contract AI, AI assistants, e-discovery AI), running structured proofs-of-concept and build-vs-buy assessments.
  • Establish evaluation and quality processes for AI features—prompt design,: model selection and tradeoffs, accuracy and hallucination testing, human-in-the-loop review, and continuous tuning.