The opportunity
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 Gusto’s Legal & Compliance organization. This is an AI-forward product role: you will reimagine…
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 & 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.
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.
What they're looking for
- Bachelor’s degree in Information Systems, Business Administration, Legal Studies, or a related field.
- + 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 features—generative: AI / large language models, AI assistants, or intelligent automation—ideally 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 tools—including 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.
