Gusto, Inc. - Legal AI Engineer (Contractor)

• 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. • 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, Gusto's subsidiary, whose physical office is in Scottsdale. • 2-3 days • 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 it's 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.