Head of Engineering

Gusto is on a mission to grow the small business economy, handling payroll, health insurance, 401(k)s, and HR for over 500,000 small businesses nationwide. We are building a workplace that reflects the people we serve.

• 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

• 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 footing