Legal AI Engineer (Contractor)

gusto· 84 open roles

Remote RemoteFull-time1 months ago

Salary

$78,000 - $93,600

Experience

Mid

Job Type

Full-time

Posted

1 months ago

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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

1
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.
2
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.
3
Further operationalize AI tools and integrations as agreed upon.
4
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.
5
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.
6
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.

Requirements

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 technical skill for everything we're building.
Integration experience — you've wired tools together using APIs, MCPs, or similar patterns, and you know what breaks and why. Coordinating with engineering or IT teams to scope and execute those connections is second nature to you.
Comfort operating in ambiguity. You can take a business problem and context from attorneys or legal ops — not a technical spec — and turn it into a working system. You know how to ask the right questions, fill in gaps with judgment, and move forward.
Comfort working within internal technology governance processes. You know how to communicate with an IT or AI team on tool approvals, data access, and security reviews — and you don't try to go around them. You build within the guardrails, and you help the team understand why those guardrails matter.
Bonus: Experience working alongside attorneys: you understand contracting workflows, matter intake, research cycles, and how legal teams make decisions.

Perks & Benefits

Bonus: Experience working alongside attorneys: you understand contracting workflows, matter intake, research cycles, and how legal teams make decisions.

We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success.