Head of Engineering

Who you are

• 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 What the job involves
• 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
• 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 Benefits
• Medical, dental, and vision insurance for employees and dependents
• Family care and support, including family planning and fertility benefits
• Gender-affirming care and support
• A variety of mental health resources
• Paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more
• Free meals and refreshments at the office (conversation and community is an added bonus!)