Skip to content
GustoGustoSan Francisco, CA

Legal & Compliance Tech IT Product Manager

Product manager owning the AI-first roadmap and delivery of enterprise legal and compliance technology at Gusto. Reimagine legal workflows with generative AI, agents, RAG, and MCPs across CLM, matter management, GRC and related platforms while ensuring security, privilege protection, and compliance.

Salary not listed
On-site5+ YOEProduct Management

About the role

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 AI tools and transformed processes across the Legal & Compliance organization through training, communication, and change management.
  • Act as an AI fluency champion, helping legal and compliance professionals integrate generative AI and agents into daily workflows.

Requirements

  • 5+ years of product management experience, ideally in legal tech, enterprise applications, or AI-enabled SaaS products.
  • Strong AI literacy with hands-on experience designing or shipping generative AI features, AI agents, RAG systems, or agentic workflows.
  • Deep knowledge of legal and compliance technology stack (CLM, matter management, e-billing, GRC, e-signature, e-discovery).
  • Proven ability to translate complex business and legal requirements into technical specifications and roadmaps.
  • Experience with enterprise systems implementation, integrations, and platform ownership.
  • Strong stakeholder management and cross-functional leadership skills, especially partnering with legal, compliance, security, and engineering teams.
  • Understanding of data privacy, security, compliance (including SOX), and attorney-client privilege considerations in AI systems.
  • Bachelor's degree in a relevant field (Computer Science, Law, Business, or equivalent experience).

Nice-to-Haves

  • Experience in a high-growth tech company or scaling legal operations.
  • Familiarity with Model Context Protocols (MCPs), orchestration frameworks, or building AI agents.
  • Background in legal (JD or paralegal experience) or prior work in Legal Operations (LegalOps).
  • Experience with specific platforms like LinkSquares, SirionLabs, Thomson Reuters, or ServiceNow GRC.
  • Track record of measuring and reporting on AI ROI and operational metrics.

Skills

Product ManagementGenerative AIAI AgentsRAGClmGRCLegal TechMcpContract Lifecycle ManagementEdiscoveryResponsible AiStakeholder Management
Airtable

Product Manager

AirtableSan Francisco, CA +1

Own end-to-end AI-native product experiences at Airtable, focusing on how humans and AI agents collaborate on structured data and workflows. Requires 5+ years PM experience, deep AI fluency, high agency, and strong product taste for building trustworthy AI interactions.

187k – 235k
On-site5+ YOEProduct Management
Datadog

Product Manager II

DatadogNew York, NY

Product Manager on the Developer Engagement team responsible for building integrations and AI-powered experiences that embed Datadog observability, CI/CD, security, and automation directly into developer workflows, pull requests, and code review tools.

156k – 195k
Hybrid3+ YOEProduct Management
Stripe

Product Manager, Cash Platform

StripeNew York, NY

Product Manager owning strategy and roadmap for Stripe's FX, cross-border payouts, and Cash Platform. Requires 5+ years PM experience, technical depth (former engineer/data scientist preferred), domain expertise in financial infrastructure, and strong cross-functional execution focused on cost, performance, and monetization.

Salary not listed
On-site5+ YOEProduct Management
Stripe

AI Product Manager, Professional Services

StripeNew York, NY +1

Own the AI product roadmap and drive adoption for a global Professional Services organization. Requires 5+ years in product/transformation roles, strong technical credibility with LLMs and agentic AI, and exceptional influence skills in ambiguous, cross-functional environments.

Salary not listed
Hybrid5+ YOEProduct Management
Anthropic

Product Manager, Safeguards Generalist-2

AnthropicSan Francisco, CA

Product Manager on Anthropic's Safeguards team owning ideation, design, development and deployment of safety systems, detections, evals, interventions and UX to protect users from risks of frontier AI models across platforms. Requires deep technical expertise in safeguards, 5+ years PM experience, and ability to collaborate with research, policy, and engineering teams in ambiguous, fast-moving environments.

305k – 385k
Hybrid5+ YOEProduct Management