Legal & Compliance Tech IT Product Manager

About the Role

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.

Responsibilities

AI-First Product Ownership & Roadmap (Legal & Compliance Technology)

• 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.

AI, Automation & Agentic Workflows

• Design and deliver generative-AI capabilities across the legal stack: AI-assisted contract drafting, review, redlining, clause extraction, and risk flagging; AI summarization of matters, contracts, and legal documents; and natural-language search across legal knowledge.
• Build and productize AI agents that execute or augment core legal and compliance processes,such as legal intake triage and routing, NDA and standard-contract self-service, obligation and renewal tracking, policy Q&A, and regulatory-change monitoring.
• 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.

Business Process & Solution Design

• Lead end-to-end, AI-augmented redesign of core legal workflows,contract lifecycle management, matter intake and management, outside-counsel and legal-spend (e-billing), e-signature, entity and corporate records management, and legal hold and e-discovery.
• Translate business requirements into clear functional specifications and solution designs,including where AI augments, automates, or fully owns a step, and where humans stay in the loop,for EAIT delivery teams.
• Ensure solutions are scalable, auditable, and aligned with data privacy, security, internal controls, and compliance standards, including protection of privileged and sensitive information in all AI workflows.

Enterprise Applications Enablement

• Partner with EAIT engineers, administrators, AI architects, and platform owners to design and deliver enhancements, integrations, MCPs, and AI agents across legal technology platforms.
• Review and approve configurations, workflows, integrations, prompts, and agent designs to ensure they meet business, legal, and IT governance requirements.
• Guide prioritization of enhancements, AI capabilities, upgrades, and technical-debt remediation across legal-managed platforms.

Stakeholder Partnership & Delivery

• Serve as the primary EAIT point of contact for Legal & Compliance stakeholders and as a champion for AI-first ways of working across the legal function.
• Manage intake, prioritization, and delivery of requests, balancing stakeholder needs with EAIT capacity and the AI roadmap.
• Lead cross-functional initiatives from discovery through deployment, ensuring clear communication, change management, and timely execution.

Responsible AI, Controls, Privacy & Insights

• Govern the full lifecycle of AI agents and MCPs in the legal domain, ensuring responsible-AI practices: guardrails, privilege protection, data governance, access controls, auditability, and human oversight.
• Partner with Legal, IT risk, Security, and audit teams to ensure AI-enabled systems and processes support privacy, regulatory, and SOX-related requirements and safeguard attorney-client privilege and sensitive data.
• Define and oversee KPIs and operational metrics for legal and compliance systems, including AI accuracy, reliability, adoption, and ROI.
• Collaborate with data, BI, and AI teams to deliver dashboards, analytics, and AI-driven insights that support data-driven legal operations.

Change Management, AI Enablement & Adoption

• Drive successful adoption of new AI capabilities through training, documentation, prompt and playbook libraries, and hands-on change management.
• Coach legal and compliance teams on safe, effective, and confident use of AI tools, and act as the subject-matter expert for legal AI and technology within EAIT, promoting best practices and standardization.

Requirements

• Bachelor’s degree in Information Systems, Business Administration, Legal Studies, or a related field.
• 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.
• Strong commitment to responsible, secure, and explainable AI, with experience embedding privacy, privilege protection, audit controls, and SOX-aligned governance into AI-enabled workflows.
• Experience owning or managing enterprise application products within an IT or EAIT-style organization, and the ability to translate business needs into product roadmaps, functional requirements, and delivered solutions.
• Strong stakeholder management skills and the ability to partner effectively across Legal, Compliance, IT, and executive leadership, with excellent written and verbal communication and the ability to influence without authority.
• Growth mindset and the ability to operate in ambiguity, define standards where none exist, and scale AI solutions from proof-of-concept to enterprise-wide adoption.
• Relevant certifications (PMP, product management, AI/ML, or legal operations / CLM certifications) are a plus.

Benefits

• Cash compensation amount targeted at $221,000-247,000 in San Francisco Bay Area.
• Stock equity is additional.
• Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.
• Physical office spaces in Denver, San Francisco, and New York City.
• Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role).