Engineering Manager, HR Labs

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . About the Role: 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. About the Team: 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. Here’s what you’ll do day-to-day: 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 Here’s what we're looking for: 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 expe ... (truncated, view full listing at source)