Principal Product Manager, AI Assistant

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k) s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done  expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

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.

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…