Principal Product Manager, AI Assistant

By the Numbers:

Named #1 best software for small business of 2024 by G2

2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing

Over $500M in annual revenue

The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs

There are 6.2M employers in the US, 98% have fewer than 100 employees (1)

550,000 new businesses are created each year in the US (1)

What Product Management is like at Gusto:

Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools automating what slows teams down and amplifying what makes them creative and high-performing.

We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.

We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.

We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the CoreX AI team:

CoreX AI builds and powers AI experiences that make Gusto the best teammate for small businesses. Our largest AI bets embed directly in small business workflows whether that's answering a quick question or handling the task itself. Our customers trust us with their payroll, their employees' benefits, and their money decisions where mistakes have real, immediate consequences. We give small businesses trusted and powerful AI tools that supercharge how they work.

We're at an inflection point across everything we own, and we're looking for a product leader ready to accelerate our AI bets as we build toward that future. This is a role for builders who can work across Gusto, reason about API design and model behavior as comfortably as customer experience, and bring hands-on experience building with AI.

About the Role:

You'll define how Gusto's conversational assistant works, behaves, and earns customer trust and how small businesses use it to get real work done across payroll, benefits, HR, and beyond.

Develop a deep understanding of how small businesses actually work inside Gusto today the workflows they run, where they get stuck, and the work they'd hand off if they could

Lead the product vision for Gusto’s conversational assistant that gives small businesses superpowers, and turn it into a coherent strategy a sharp perspective on where the assistant earns real value, and what we build first

Expand what the assistant can actually do. You'll partner with domain teams to grow tool and domain coverage across payroll, time, benefits, and compliance, and hold the bar on quality as coverage grows measured in real actions customers complete, not conversations they have

Define how we show up in our customers’ ecosystem and the surfaces where work naturally happens third-party connectors, messaging channels, and AI clients and decide what earns priority against the depth we have in the app

Partner with engineering and data teams on technical trade-offs: how we expose Gusto's capabilities to agents through our API and MCP layer, how the assistant embeds into our first-party surfaces, and where we take on debt to move faster

Partner with design and UXR to understand how customers actually feel about AI acting on their behalf, and use that to shape how we build

Move fast. Speed is our top priority, and you'll set a pace that reflects it shipping narrow slices that get customers value early rather than waiting on the complete build

Here’s what we're looking for:

10+ years building as a product manager, with experience owning meaningful scope and driving broad product or platform-level decisions

You're comfortable in a high-visibility role engaging directly with Gusto leadership and product leaders across the company, and driving decisions that stick

You believe in what AI can do for small businesses, and you're excited to build it.

You understand what it takes to build trusted AI products: writing evals, holding a real point of view on AI quality, and assuming the responsibility of a product customers rely on day-to-day

You're hands-on and you'd rather build than delegate — and you thrive in a culture that expects it

You’re comfortable spanning both platform thinking and UX/experience judgment within the same role

You develop sharp perspectives on the systems AI products need — RAG, ontology, and a scalable API strategy for agent-accessible systems

You’re comfortable with a fluid, expanding charter. This isn't a role with a static roadmap, given how fast AI development and the competitive landscape are moving.

Our cash compensation amount for this role is $179,000,000/yr to $220,000/yr in Denver & most major metro locations, and $210,000/yr to $260,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate location, experience, and expertise, and may vary from the amounts listed above.