Sr Engineering Manager, HR Labs

About the Role:

We're looking for a sr 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 experience — you notice when something feels off in a product and it bothers you

Preferred:

• Experience managing teams building AI-powered products or working with LLMs, agents, or AI-driven workflows
• Experience in a high-growth or early-stage environment where you wore multiple hats
• Background as a generalist — you've worked across frontend, backend, or multiple domains and you're comfortable context-switching
• Experience in, or interest working in, Ruby on Rails
• You've founded a company — or it's something you see yourself doing someday