Legal & Compliance Tech IT Product Manager

Legal & Compliance Tech IT Product Manager

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. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done  expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

As a key member of Enterprise Applications IT (EAIT), the Legal Tech IT Product Manager owns the AI-first strategy, roadmap, and delivery of the enterprise applications supporting Gusto’s Legal & Compliance organization. This is an AI-forward product role: you will reimagine how legal and compliance work gets done by embedding generative AI, AI agents, and intelligent automation into systems like contract lifecycle management (CLM), matter and legal‑spend management, e‑signature, entity and corporate records management, legal hold and e‑discovery, and governance, risk, and compliance (GRC) platforms.

Acting as the primary interface between Legal & Compliance teams and EAIT delivery resources, you will translate business needs into well‑defined, AI‑enabled product requirements, guide solution design, and drive continuous improvement across core legal and compliance processes. In line with Gusto’s enterprise systems strategy, you will help shift legal operations from reactive, manual workflows to predictive, context‑aware, and self‑improving platforms—designing agentic workflows and Model Context Protocols (MCPs) that connect legal systems to large language models—while ensuring privilege protection, security, compliance, and measurable impact.

This role blends product leadership and deep systems knowledge with strong AI literacy and a bias toward applying AI to every part of the legal technology stack.

The Enterprise Applications IT (EAIT) team drives the intelligent transformation of Gusto’s enterprise systems, integrating AI, automation, and advanced analytics across our internal applications ecosystem to improve scalability, efficiency, and decision‑making. EAIT builds MCPs, AI agents, and intelligent workflows that connect systems and make enterprise processes smarter, faster, and more predictive, while providing reliable, secure, and scalable application platforms for critical business processes.

Within EAIT, this role provides dedicated, AI‑forward product ownership for the Legal & Compliance technology domain, complementing existing product and platform owners to establish a mature, well‑governed, and increasingly autonomous enterprise applications operating model. This is a new role, designed to expand the team’s capacity to operationalize AI within legal and compliance workflows and modernize the systems behind that work.

• Own the product vision, AI roadmap, and backlog for the legal and compliance technology portfolio within EAIT, with AI and automation as the default lens for every initiative.
• Set a multi‑year vision for an AI‑augmented legal function, identifying where generative AI, AI agents, and automation can eliminate manual effort, accelerate cycle times, and improve quality and risk outcomes.
• Align roadmap priorities with Legal & Compliance leadership, EAIT’s AI transformation strategy, and enterprise architecture standards.
• Define success metrics and outcomes—including AI adoption, automation rate, accuracy, cycle‑time reduction, and cost‑to‑serve—to measure business value and system effectiveness.

• Des…