Startups · AI

Principal Product Manager, AI Assistant

Gusto · Denver, CO - Hybrid; New York, NY - Hybrid; San Francisco, CA - Hybrid · Hybrid

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About Gusto

Backed by General Catalyst, Kleiner Perkins and Y Combinator.

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.

What they'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
More about this role

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 at Gusto. We 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.

  • 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...

Read the full posting on Gusto's site ↗

Product Management

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