# Principal Product Manager, AI Assistant at Gusto

- Company: Gusto
- What the company does: Backed by General Catalyst, Kleiner Perkins and Y Combinator.
- Company website: http://www.gusto.com/
- Type: Startups (AI role)
- Level: Principal and up
- Location: Denver, CO - Hybrid; New York, NY - Hybrid; San Francisco, CA - Hybrid
- Work setup: Hybrid
- Posted: 2026-09-23
- Apply by: 2026-11-07
- Apply: https://job-boards.greenhouse.io/gusto/jobs/8167750
- Page: https://www.1752.vc/careers/jobs/gusto-principal-product-manager-ai-assistant/

## 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

Tags: Product Management