Legal & Compliance Tech IT Product Manager

About the role

You own the end-to-end AI-first product strategy, roadmap, and delivery for all enterprise applications serving Gusto's Legal and Compliance organization. You reimagine how legal and compliance work gets done by embedding generative AI, AI agents, and intelligent automation into systems like contract lifecycle management, matter and legal-spend management, e-signature, entity and corporate records management, legal hold and e-discovery, and governance, risk, and compliance platforms. You act as the primary interface between Legal and Compliance teams and EAIT delivery resources, translating business needs into well-defined, AI-enabled product requirements and guiding solution design. You drive continuous improvement across core legal and compliance processes by designing agentic workflows and Model Context Protocols that connect legal systems to large language models while ensuring privilege protection, security, compliance, and measurable impact. This role blends product leadership with deep systems knowledge and a bias toward applying AI to every part of the legal technology stack.

Key facts

What you'll do

• 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 and 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.
• Translate complex legal and compliance workflows into clear product requirements, user stories, and acceptance criteria that guide solution design and engineering delivery.
• Partner with EAIT architects and delivery teams to design intelligent, context-aware platforms that shift legal operations from reactive, manual workflows to predictive and self-improving systems.
• Design and specify agentic workflows and Model Context Protocols (MCPs) that connect legal systems to large language models in a secure and compliant manner.
• Collaborate with data science and AI partners to evaluate, test, and iterate on AI features, ensuring they meet reliability, safety, and performance standards for enterprise legal environments.
• Facilitate discovery sessions, stakeholder interviews, and workshops with Legal and Compliance stakeholders to uncover pain points, opportunities, and requirements for AI-driven solutions.
• Prioritize features and enhancements based on strategic alignment, value, feasibility, and risk, balancing innovation with the practical realities of enterprise legal operations.
• Work closely with security, privacy, and compliance leaders to ensure all AI and automation solutions adhere to Gusto's policies, regulatory requirements, and data protection standards.
• Drive adoption of new AI tools and workflows through change management, training, and communication with legal and compliance users.
• Monitor and report on key product metrics, user feedback, and system performance to inform continuous improvements and future roadmap decisions.
• Partner with cross-functional teams across Enterprise Applications IT to ensure legal and compliance platforms integrate seamlessly with broader enterprise systems.
• Champion an AI-first mindset across the legal technology stack, exploring emerging tools, techniques, and best practices to keep the product vision ahead of industry trends.

Requirements

• Bachelor's degree in Computer Science, Information Technology, Engineering, Business, or a related field, or equivalent practical experience.
• 3+ years of product management experience, with at least 1 year focused on enterprise applications or B2B SaaS environments.
• Demonstrated experience managing AI-enabled products or features, with a portfolio that shows successful delivery of AI or automation initiatives.
• Strong understanding of enterprise legal operations, compliance processes, and the technology that supports them, including CLM, e-discovery, matter management, and GRC systems.
• Hands-on experience with AI technologies and methodologies, including prompt engineering, model evaluation, and integration patterns for LLMs in production environments.
• Excellent written and verbal communication skills, with the ability to translate technical concepts into clear narratives for both technical and non-technical stakeholders.
• Strong analytical and problem-solving skills, with comfort navigating ambiguity and complexity in fast-paced, matrixed organizations.
• Proven ability to influence and lead without direct authority, collaborating effectively with engineering, design, security, and operations teams.
• Deep commitment to building inclusive products and experiences, with awareness of how technology impacts diverse users and communities.
• Willingness to learn and adapt as AI technologies evolve, actively building fluency in new tools, frameworks, and best practices.

Nice to have

• Experience with contract lifecycle management, legal spend or matter management, e-signature, entity management, legal hold, e-discovery, or GRC platforms.
• Familiarity with Model Context Protocols (MCPs) and agentic workflow design for legal and compliance systems.
• Background in designing or implementing AI agents or generative AI solutions for enterprise legal or compliance use cases.
• Understanding of security, privacy, and compliance frameworks relevant to legal operations, including data governance and privilege protection considerations.
• Experience working in regulated industries or enterprise environments where risk, audit, and compliance controls are critical.

Practical notes

• This is a full-time position based in San Francisco, CA.
• Employees must comply with Gusto's policies and applicable legal and regulatory requirements.
• New-hire start dates are dependent on business needs and background check completion.