Legal Operations Manager

At Gusto, we’re on a mission to grow the small business economy. We handle payroll, health insurance, 401(k) s, and HR so owners can focus on their craft and 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  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.

We are seeking a hands‑on Legal Operations Manager to join the Legal & Compliance team. In this role you will own the systems, tools, and processes that enable our Legal & Compliance teams to build and scale, and be at the forefront of driving AI solutions for the teams. You will report to the Head of Legal Employment, Litigation & Legal Operations and work cross‑functionally as a true strategic partner to the team.

If you’re energized by building things that last, experimenting with emerging technology, and redefining what an in‑house legal team can achieve, this is your opportunity to make a lasting impact.

Gusto’s Legal & Compliance team partners with product teams to enable innovation, facilitate responsible company growth, accelerate the Gusto roadmap, and provide compliant products to our customers. The team delivers solution‑focused counsel on legal and business risks. We are passionate about using groundbreaking technology and excellent service to elevate the experience of small business owners and their employees. Each team member is a true owner and makes a tremendous impact every day.

• Drive the Legal & Compliance team’s operational strategy, understand operational challenges, identify opportunities to improve systems and workflows.
• Maintain and optimize a best‑in‑class AI‑driven tech stack. Partner cross‑functionally with AI and Contract Operations to identify technologies, negotiate with vendors, and drive implementation.
• Partner closely with Finance and Legal leadership to manage budget, forecasting, accruals, and track spend.
• Own planning cycles, OKRs, and data reporting and metrics.
• Manage outside counsel relationships, including new engagements, billing guidelines invoicing, and e‑billing. Drive outside counsel management strategy with a focus on cost discipline and operational accountability.
• Build and maintain knowledge‑management platforms and learning and development programs that keep the team current and operating effectively.
• Run the day‑to‑day operations of the Legal & Compliance team, driving efficiencies that enable the team to perform its best work (e.g., manage vendors, attorney memberships, internal practice guidelines, expenses, team meetings).
• Represent Gusto within the Legal Operations community and stay current on emerging technologies and best practices.

• 5+ years of legal operations experience at a high‑growth technology company.
• Hands‑on expertise with legal tooling‑selection, implementation, and day‑to‑day operation (CLM, e‑billing, matter management, procurement systems).
• Experience implementing AI and technology within legal operations.
• Hands‑on experience with AI‑assisted legal tools and a fluency (or path to fluency) in agentic / automated legal workflows.
• Experience engaging and managing outside counsel, legal spend, budgeting, and program management.
• Proven ability to build and maintain metrics and reporting frameworks, including operational KPIs.
• Exceptional communication skills and the ability to influence stakeholders across Legal, Finance, IT, Security, and Procurement.
• A builder’s mindset – demonstrated success building and improving processes, not just running them, with measurable results.

• Legal Operations community involvement…