New The Skills of Tomorrow: how AI-exposed is every skill in 2026? See the data →
Gusto

Principal Product Manager, AI Assistant

Gusto
Apply →
hybrid senior full-time $179,000/yr to $220,000/yr in Denver & most major metro loca Denver, CO

First indexed 24 Sept 2026

Description

We're on a mission to grow the small business economy. You will 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.

AI is a fundamental part of how work gets done at Gusto. You will actively engage with AI tools relevant to your role and grow your fluency as the technology evolves.

As a Principal Product Manager, AI Assistant, you will 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.

Responsibilities:

  • Develop a deep understanding of how small businesses actually work inside Gusto today
  • Lead the product vision for Gusto’s conversational assistant
  • Expand what the assistant can actually do
  • Define how we show up in our customers’ ecosystem
  • Partner with engineering and data teams on technical trade-offs
  • Partner with design and UXR to understand how customers actually feel about AI acting on their behalf
  • Move fast and set a pace that reflects it

Requirements:

  • 10+ years building as a product manager
  • Experience owning meaningful scope and driving broad product or platform-level decisions
  • Comfortable in a high-visibility role engaging directly with Gusto leadership and product leaders across the company
  • Believe in what AI can do for small businesses, and you're excited to build it
  • Hands-on and you'd rather build than delegate
  • Comfortable spanning both platform thinking and UX/experience judgment within the same role

Benefits:

  • Competitive base pay
  • Benefits
  • Equity (RSUs)

Our cash compensation amount for this role is $179,000/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.

This listing is enriched and indexed by YubHub. To apply, use the employer's original posting: https://job-boards.greenhouse.io/gusto/jobs/8167750