Legal AI Engineer (Contractor)

About Gusto 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. About the Role: We're looking for a Legal AI Engineer for a fixed engagement to build foundational legal team AI infrastructure. You'll design and stand up these systems, document them thoroughly, and hand them off to the team in a state where they can be maintained and iterated on internally. You'll provide services to a legal team that is already building its own AI tooling and infrastructure through Claude. Your engagement will be with the Senior Manager of Legal Contracting Operations AI Systems. Your project will be to add the technical depth that turns promising experiments into robust, shared systems, and to deliver a coherent stack of tools and workflows. During this engagement, you'll design workflows that are fast, measurable, and safe based on specifications from legal, legal ops, and cross-functional stakeholders. You'll leave behind documented systems and run books so the team can maintain and evolve what you've built. This engagement is equal parts legal infrastructure + applied AI, ideal for a hybrid legal/technical practitioner who can translate legal work into scalable systems and then make those systems real. Here’s what you’ll do day-to-day during this engagement: Connect the AI Stack Take the skills, workflows, and dashboards that individual team members have already built in Claude and package them into shared, maintainable assets the whole team can use. Wire together current AI tooling — build MCP integrations so data flows where it's needed without manual handoffs; engage with Gusto's AIT team on connections where native integrations don't exist. Further operationalize AI tools and integrations as agreed upon. Build a Legal Repository Stand up a structured, queryable knowledge layer fed by the team's existing research, positions, precedents, and playbooks — one that can be searched by any team member, can be invoked by automated workflows, and continuously ingests new information as the team works in the tool. Implement AI Workflows Working from priorities set by legal ops and attorneys, implement AI-assisted workflows for the team's highest-volume use cases — likely including contract first-pass review, matter intake and routing, litigation operations to enable intake, routing and response drafting for subpoenas, demand letters and notices and prompt libraries for recurring legal tasks. Document and Hand Off Deliver a maintenance runbook for every system built and train designated team members on administration, so nothing requires the contractor to maintain it after the engagement ends. Establish adoption baselines so the team can measure progress and know what to iterate on next. Here’s what we're looking for: Hands-on experience building and shipping AI-assisted workflows — not evaluating tools or writing specs, but actually standing systems up. Be ready to walk through something you built from prompt to production. Direct, working proficiency with Claude or comparable LLMs: prompt engineering, agentic workflows, and iterating on outputs until they're reliable. This is the core ... (truncated, view full listing at source)