Head of Engineering, AI Platform

at Gusto

San Francisco, CA

About Gusto

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.

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:

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.

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.

About the Team:

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.

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.

Here's what you'll do day-to-day:

• 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.
• 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.
• 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.
• 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.
• 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.
• Represent AI engineering to senior leadership, and keep the group's work connected to Gusto's broader AI strategy.
• Champion AI-native ways of working, and build a team that engineers and managers want to be part of and grow in.

Here's what we're looking for:

• 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.
• 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 keep them dependable.
• The ability to set technical strategy across several teams and see it through, including aligning teams you don't directly manage around shared outcomes.
• Enough technical depth to engage senior engineers on a difficult architecture decision, without needing to write the code yourself.
• Experience growing an engineering organization, ideally somewhere that was still finding its shape.
• You treat reliability, evaluation, and guardrails as core engineering work rather than a step left to the end.
• Comfort leading a cross-functional group, working closely with product managers, designers, and data scientists as much as with engineers.
• You develop and empower other leaders, communicate clearly with technical and non-technical audiences, and work well across many teams.

It's a plus if you've worked across both platform and product engineering, built with a framework like LangGraph or the Vercel AI SDK, or have led in fintech or another regulated environment.

Our cash compensation amount for this role is targeted at $274,000 to $305,000 in Denver and most remote locations, and $321,000 to $356,000 for San Francisco, New York, and Seattle. Annual cash incentives and Stock equity is additional. Final offer amounts are determined by multiple factors including candidate experience, level, and expertise and may vary from the amounts listed above.

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.

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.

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.

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.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

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