Legal AI Engineer, Gusto
Contractor
Compensation will be $150/hr. + RSUs
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
Compensation will be $150/hr. + RSUs
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 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
What the job involves
- 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
- 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
- Approximately 20 hours per week, commensurate with experience and expertise. This is a 3-month engagement
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Co-Founder & Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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