Senior Engineering Manager, Gusto

• A strong engineering foundation — you are a good enough engineer that you can engage with technical decisions at depth, even if you haven't written production code recently
• Management experience leading high-performing teams — you know how to hire well, develop people, and maintain a high bar without micromanaging
• A holistic thinker — you're as interested in why we're building something as how, and you naturally connect business context, user needs, and technical tradeoffs
• Genuine interest in AI and what it makes possible — not just as a buzzword, but as a tool you're curious about and want to understand well enough to make good bets on
• Comfort operating in ambiguity — you've led teams where the roadmap was being written in real time and the right process was the one that fit the moment
• A bias towards action — your instinct is to make it work, then make it work well, then make it scale
• Care for craft and user experience — you notice when something feels off in a product and it bothers you

Desirable

• We're looking for an engineering manager who wants to be close to the work. You'll lead a small team of engineers building at the frontier of what's possible with AI-powered professional tools — UX prototypers exploring new interaction models, founding engineers building new product lines, AI engineers designing agent systems
• The right person for this role isn't looking to manage from a distance or by dashboards. You think in terms of where the bottleneck is and what the team needs right now, not in terms of operating in a fixed mode
• You don't need to be writing code every day, but you should be deeply interested in understanding the work — the technical tradeoffs, the interaction design decisions, the product bets
• You should care about UX. You should care about the business. You should be the kind of manager who can look at a prototype and have a substantive opinion about it, and who can sit in an architecture discussion and push the thinking forward
• HR Labs is a new team inside Gusto using AI to fundamentally change how HR expertise is delivered to small businesses. We're building AI agents, intelligent automation, and novel tooling that allow a small team of HR professionals to deliver expert guidance at a scale that wasn't previously possible
• This is a startup-within-a-startup — one of Gusto's largest AI bets, scaling rapidly, with the freedom to experiment across both internal and customer-facing tools
• Set technical direction for a team building novel AI-powered tools and experiences — you'll need to understand the systems deeply enough to make good calls on what to build, how to sequence it, and when to pivot
• Work closely with product and design to shape what the team builds — in this environment, the engineering manager is a critical voice in product direction, not just a delivery partner
• Help your engineers navigate a fast-moving, ambiguous problem space — the right answer is often not obvious, and your job is to help the team find it faster
• Coach, mentor, and grow a small team of engineers with diverse skill sets — from UX prototypers to backend systems builders
• Build a team culture that values craft, speed, and intellectual honesty — where people challenge each other's ideas because they care about getting it right
• Identify where the bottleneck is and shift your own focus accordingly — some weeks that's hiring, some weeks it's unblocking a technical decision, some weeks it's sitting with an HR partner to understand their workflow