Legal & Compliance AI Engineer

Gusto

Legal AI product leader modernizing Gusto’s payroll, HR, and compliance enterprise systems. Embedding LLMs, agents, automation, and MCPs into legal workflows.

Posted 8/15/2026full-timeSan Francisco • California • 🇺🇸 United StatesSeniorLead💰 $221,000 - $247,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in AI-augmented legal technology, including the design and delivery of generative AI capabilities, while ensuring compliance with privacy and security standards. Proven ability to translate business requirements into functional specifications and manage cross-functional partnerships for successful AI adoption.

Highest-signal resume keywords

AI-Powered Product DevelopmentGenerative AI ExpertiseLegal Technology PlatformsStakeholder ManagementPrompt Engineering

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

AI Adoption MetricsContract Drafting AutomationLegal Workflow RedesignMCP IntegrationRAG ApplicationModel SelectionHallucination TestingAI Feature EvaluationLegal Operations ManagementBusiness Requirements Translation

Soft Skills

Cross-Functional PartnershipInfluencing Without AuthorityGrowth MindsetCommunication SkillsChange Management

Tools & Technologies

OpenAILangChainCrewAISemantic KernelCLM ToolsE-Billing SystemsE-Signature SolutionsLegal Hold ToolsGRC ToolsAI Agents

Certifications & Qualifications

PMPProduct Management CertificationAI/ML CertificationLegal Operations Certification

Industry Keywords

Legal TechnologyCompliance StandardsEnterprise ApplicationsAI WorkflowsProofs-of-Concept

Tech Stack

Tools & technologies

PMP

About the role

Key responsibilities & impact

Own the product vision, AI roadmap, and backlog for Gusto’s legal and compliance technology portfolio
Set a multi-year vision for an AI-augmented legal function
Define success metrics for AI adoption, automation, accuracy, cycle-time reduction, and cost-to-serve
Design and deliver generative-AI capabilities for contract drafting, review, redlining, clause extraction, summarization, search, and risk flagging
Build and productize AI agents for legal intake, contract self-service, obligation tracking, policy Q&A, and regulatory-change monitoring
Define and prioritize MCPs and integrations connecting legal systems to LLMs and orchestration frameworks
Apply RAG over contracts, policies, and legal knowledge bases
Evaluate and scale AI legal-tech vendors and native AI features through proofs-of-concept and build-vs-buy assessments
Establish AI feature evaluation and quality processes, including prompt design, model selection, hallucination testing, human-in-the-loop review, and continuous tuning
Lead AI-augmented redesign of legal workflows including CLM, matter management, legal spend, e-signature, entity management, legal hold, e-discovery, and GRC
Translate business requirements into functional specifications and solution designs
Ensure solutions meet privacy, security, internal controls, compliance, privilege-protection, and auditability standards
Partner with engineers, administrators, architects, platform owners, Legal, Compliance, Security, risk, audit, data, BI, and AI teams
Manage intake, prioritization, delivery, change management, training, documentation, and AI adoption
Define KPIs, dashboards, analytics, and AI-driven insights for legal and compliance operations

Requirements

What you’ll need

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 expertise supporting legal and/or compliance functions
Experience delivering AI-powered products or features using generative AI, LLMs, AI assistants, or intelligent automation
Working knowledge of LLM platforms such as OpenAI, Anthropic, or Gemini
Knowledge of prompt engineering, RAG, evaluation, guardrails, and model tradeoffs
Familiarity with AI agent and orchestration frameworks such as LangChain, CrewAI, or Semantic Kernel
Familiarity with MCPs and experience integrating AI with enterprise systems is a strong plus
Hands-on experience with legal technology platforms including CLM, matter management, e-billing, e-signature, entity management, legal hold/e-discovery, and/or GRC tools
Experience evaluating, selecting, and deploying AI legal-tech vendors and running proofs-of-concept and build-vs-buy assessments
Experience embedding privacy, privilege protection, audit controls, and SOX-aligned governance into AI workflows
Experience owning or managing enterprise application products in an IT or EAIT-style organization
Ability to translate business needs into product roadmaps, functional requirements, and delivered solutions
Strong stakeholder management and cross-functional partnership skills
Excellent written and verbal communication skills
Ability to influence without authority
Growth mindset and ability to operate in ambiguity and scale AI solutions from proof-of-concept to enterprise adoption
Relevant PMP, product management, AI/ML, or legal operations/CLM certifications are a plus

Benefits

Comp & perks

Competitive base pay
Health insurance
401(k)
Equity (RSUs)
Secure, reliable, and consistent internet connection required when working outside a Gusto office
Reasonable accommodations for qualified individuals with disabilities and disabled veterans