Legal & Compliance Tech IT Product Manager

8+ years of experience in enterprise applications, legal operations / legal technology, business systems, or product management, with hands-on expertise supporting legal and/or compliance functions.

Demonstrated experience delivering AI-powered products or features—generative AI / large language models, AI assistants, or intelligent automation—ideally within legal, compliance, or enterprise applications, with a clear bias toward applying AI to solve business problems.

Working knowledge of leading LLM platforms (e.g., OpenAI, Anthropic, Gemini) and core GenAI techniques such as prompt engineering, retrieval-augmented generation (RAG), evaluation, and guardrails, with the ability to reason about model tradeoffs.

Familiarity with AI agent and orchestration frameworks (e.g., LangChain, CrewAI, Semantic Kernel) and Model Context Protocols (MCPs), and experience integrating AI with enterprise systems is a strong plus.

Hands-on experience with legal technology platforms such as contract lifecycle management (e.g., Ironclad, Agiloft, DocuSign CLM), matter management and e-billing (e.g., SimpleLegal, Brightflag, Legal Tracker), e-signature (e.g., DocuSign), entity management, legal hold / e-discovery, and/or GRC tools—including their native AI capabilities.

Experience evaluating, selecting, and deploying AI legal-tech vendors and running proofs-of-concept and build-vs-buy assessments.

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.