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About This RoleAI processing…
At Gusto, we're 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 500,000 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.
Key Responsibilities
- 1Design 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.
- 2Build 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.
- 3Define 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.
- 4Apply retrieval-augmented generation (RAG) over contracts, policies, and legal knowledge bases to deliver grounded, citable answers for legal and business stakeholders.
- 5Evaluate, 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.
- 6Establish 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.
- 7Lead 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.
- 8Translate 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.
- 9Ensure 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.
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, 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.
- 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.
Perks & Benefits
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