Head of Engineering, AI Platform

About this role

<div class="content-intro"><p style="line-height: 1.2;">&nbsp;</p> <hr> <p><strong>About Gusto</strong></p> <p>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.</p> <p>&nbsp;<br>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<a href="https://gusto.com/about/careers/total-rewards" target="_blank"> <u>Total Rewards philosophy</u></a>.</p> <p>&nbsp;<br>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.</p></div><p><span style="text-decoration: underline;">at Gusto</span></p> <p>San Francisco, CA</p> <h2><strong>About Gusto</strong></h2> <p>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.</p> <p>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.</p> <p>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.</p> <h2><strong>About the Role:</strong></h2> <p>Gusto is building AI agents that help small business owners get work done, whether by working alongside them or by automating their work entirely. AI Platform is the group that builds those agents and the underlying platform they run on, which other teams across Gusto also use to build agents of their own.</p> <p>We're looking for someone to lead the whole group: an organization of around 25 engineers, together with the managers who run each area. The platform is already in production and running a growing number of agents, so much of the work now is scaling it. That means helping the teams settle into their charters, working out what the shared platform should own versus what product teams build for themselves, and keeping the group's direction aligned with Gusto's broader AI strategy. There is considerable room for the group to grow from here.</p> <h2><strong>About the Team:</strong></h2> <p>AI Platform builds Gusto's agents and the platform they run on, along with the AI features customers use directly. One team owns the shared layer: it connects Gusto's products to the models, runs multi-step agent workflows reliably, and provides the model gateway, the tool and MCP registry, and the evaluation and observability tooling, so that any team can build an agent without recreating the same groundwork each time. It is built on LangGraph and the Vercel AI SDK. The other teams build the customer-facing agents on top of that platform, some working directly with customers and others running in the background to automate work on their behalf.</p> <p>It's already a highly cross-functional group, with product managers, designers, and data scientists working as part of the team alongside the engineers. It partners with product and AI/ML science teams across the rest of Gusto, and reports to the Head of Engineering, Core Experiences.</p> <h2><strong>Here's what you'll do day-to-day:</strong></h2> <ul> <li>You'll lead the group's technical strategy for building agents that assist and automate work for small business owners, and ensuring they're built on a platform other teams at Gusto can use.</li> <li>Set the technical direction and roadmap for the group, including the ongoing question of what the shared platform should own and what product teams build for themselves as more of the company comes to rely on it.</li> <li>Lead and empower the managers and tech leads in the group, supporting those already in place, hiring ahead of the group's growth, and building strong leadership for each of the teams as they take shape.</li> <li>Set the engineering standards for how agents behave, treating prompts, tools, and policies as production code and owning the evaluation and guardrail approach that keeps these non-deterministic systems reliable and cost-aware.</li> <li>Work closely with the product and data science partners in the group, and with the teams across Gusto that build on the platform, so that it meets their needs and becomes the way teams build agents across the company.</li> <li>Represent AI engineering to senior leadership, and keep the group's work connected to Gusto's broader AI strategy.</li> <li>Champion AI-native ways of working, and build a team that engineers and managers want to be part of and grow in.</li> </ul> <h2><strong>Here's what we're looking for:</strong></h2> <ul> <li>12+ years in engineering, including at least 5 leading through other managers and tech leads. You've grown other leaders and empowered them to run their teams.</li> <li>A track record of shipping AI or agent products that people rely on, with clear ownership of the engineering behind them. You understand how these systems work in depth: LLM agents, orchestration, tool calling, RAG, and the evaluation and monitoring that