Legal & Compliance Tech IT Product Manager
Gusto is a payroll and HR platform that helps small businesses pay domestic and international employees, manage benefits, and automate compliance.
Maintainer signals as of 8/12/2026
Projects
About Gusto
Gusto serves small and mid-sized businesses with payroll processing, employee benefits administration, and HR tools in one platform. Users can run payroll, manage health insurance, hire globally, and pay international contractors in local currency or USDC stablecoins. The platform automates payroll tax filings across multiple states and integrates with tools like QuickBooks and Xero.
Skills
Candidate Availability
Required and preferred rules are kept separate and reflect the wording in the original posting.
About the Role
You own the AI-first strategy, roadmap, and delivery of legal and compliance enterprise applications. You translate business needs into product requirements, redesign legal workflows, deliver AI agents and integrations, govern responsible AI, and drive adoption of new capabilities.
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
- Hands-on experience supporting legal or compliance functions
- Experience delivering AI-powered products or features
- Knowledge of leading LLM platforms
- Knowledge of prompt engineering, retrieval-augmented generation, evaluation, and guardrails
- Familiarity with AI agent and orchestration frameworks and Model Context Protocols
- Experience with legal technology platforms
- Experience evaluating and deploying AI legal-tech vendors
- Responsible AI, privacy, privilege protection, and audit control experience
- Experience owning enterprise application products
- Strong stakeholder management and communication skills
Responsibilities
- Own the legal and compliance technology product vision, AI roadmap, and backlog
- Set a vision for an AI-augmented legal function
- Align roadmap priorities with stakeholders and architecture standards
- Define success metrics for AI adoption and system effectiveness
- Design generative AI capabilities across the legal technology stack
- Build and productize AI agents for legal and compliance processes
- Define Model Context Protocols and system integrations
- Apply retrieval-augmented generation to legal knowledge
- Evaluate and scale AI legal-tech vendors
- Establish evaluation and quality processes for AI features
- Redesign core legal workflows
- Translate business requirements into functional specifications and solution designs
- Partner with engineers, administrators, architects, and platform owners
- Manage intake, prioritization, and delivery of requests
- Govern AI agents and Model Context Protocols
- Drive adoption through training, documentation, and change management
Benefits
- Health insurance
- 401(k)
- Equity (RSUs)
