Legal AI Engineer (Contractor)

About Gusto

At Gusto were 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 500000 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:

Were looking for a Legal AI Engineer for a fixed engagement to build foundational legal team AI infrastructure. Youll 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.

Youll 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 youll design workflows that are fast measurable and safe based on specifications from legal legal ops and cross-functional stakeholders. Youll leave behind documented systems and run books so the team can maintain and evolve what youve 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.

Heres what youll 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 its needed without manual handoffs; engage with Gustos AIT team on connections where native integrations dont exist.
  • Further operationalize AI tools and integrations as agreed upon.
• Build a Legal Repository
  • Stand up a structured queryable knowledge layer fed by the teams 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 teams 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.

Heres what were 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 theyre reliable. This is the core technical skill for everything were building.
• Integration experience youve 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 dont 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.

Compensation will be $150/hr approximately 20 hours per week commensurate with experience and expertise. This is a 3-month engagement.

Gusto has physical office spaces in Denver San Francisco and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles Gustos subsidiary whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office a secure reliable and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because its the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race color religion national origin age sex (including pregnancy childbirth or related medical conditions) marital status ancestry physical or mental disability genetic information veteran status gender identity or expression sexual orientation or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.

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