AI Engineer, Legal & Compliance

About Gusto

At Gusto were on a mission to grow the small business economy. We handle the hard stuff payroll health insurance 401(k)s and HR so owners can focus on their craft and their customers. With teams in Denver San Francisco and New York we support more than 500000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay benefits and equity (RSUs) because everyone who helps build Gusto should share in its success. Offer amounts are determined by role level and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

As a key member of Enterprise Applications IT (EAIT) the Legal & Compliance AI Engineer owns the AI-first strategy roadmap and delivery of the enterprise applications supporting Gustos 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 line with Gustos enterprise systems strategy you will help shift legal operations from reactive manual workflows to predictive context-aware and self-improving platformsdesigning agentic workflows and Model Context Protocols (MCPs) that connect legal systems to large language modelswhile 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 Gustos 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 teams capacity to operationalize AI within legal and compliance workflows and modernize the systems behind that work.

• 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 EAITs AI transformation strategy and enterprise architecture standards.
• Define success metrics and outcomesincluding AI adoption automation rate accuracy cycle-time reduction and cost-to-serveto measure business value and system effectiveness.

• 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 processessuch 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 featuresprompt design model selection and tradeoffs accuracy and hallucination testing human-in-the-loop review and continuous tuning.

• Lead end-to-end AI-augmented redesign of core legal workflowscontract 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 designsincluding where AI augments automates or fully owns a step and where humans stay in the loopfor 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.

• 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.

• 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.

• 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.

• 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.

• Bachelors 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 featuresgenerative AI / large language models AI assistants or intelligent automationideally 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 toolsincluding 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.

Our cash compensation amount for this role is targeted at $00 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.

Gusto has 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). The same office expectations apply to all Symmetry roles Gustos subsidiary whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office a secure reliable and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because its the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race color religion national origin age sex (including pregnancy childbirth or related medical conditions) marital status ancestry physical or mental disability genetic information veteran status gender identity or expression sexual orientation or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.

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