8+ years of engineering people leadership experience, including managing senior engineers through ambiguous, rapidly-changing technical problems (not just well-scoped roadmap execution)
Direct, hands-on experience with agentic coding tools — you are a daily power user of Claude Code, Cursor, Codex, or equivalent, not someone who has read about them
Experience owning a significant vendor or infrastructure contract from technical requirements through legal and procurement close
Comfort making autonomy/risk tradeoff calls on AI systems without a dedicated security team making the call for you — you understand the shape of the risk (e.g., prompt injection, credential exposure, permission bypass) well enough to scope it yourself
Track record of leading through ambiguity across more than one nominally separate problem domain at once
Strong, direct communication — evidenced by briefing senior/executive stakeholders on strategy (not just status) and getting real decisions out of those conversations
Self-driven mindset, comfortable in Gusto's PE model: your job is removing roadblocks and setting direction, not command-and-control management
Our cash compensation amount for this role is targeted at $240,000-260,000 in Denver & most remote locations, and $290,000-305,000 for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate experience 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. This includes non-office days for hybrid employees
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
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