Principal Product Manager, AI Assistant

At Gusto, we're on a mission to grow the small business economy.

As a Principal Product Manager, AI Assistant, 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.

Key Responsibilities:

• Develop a deep understanding of how small businesses work with Gusto today, including their workflows, pain points, and tasks they'd like to hand off.
• Lead the product vision for Gusto's conversational assistant, turning it into a coherent strategy that delivers customer value with urgency and care.
• Expand the assistant's capabilities by partnering with domain teams to grow tool and domain coverage across payroll, time, benefits, and compliance.
• Define how the assistant shows up in customers' ecosystems and prioritize surfaces where work naturally happens.
• Partner with engineering and data teams on technical trade-offs, such as exposing Gusto's capabilities to agents through APIs and MCP layers.
• Collaborate with design and UXR to understand how customers feel about AI acting on their behalf and shape how we build.
• Move fast, shipping narrow slices that deliver customer value early.

Requirements:

• 10+ years of experience as a product manager, with a track record of 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.
• Belief in the potential of AI to empower small businesses, with excitement to build it.
• Understanding of what it takes to build trusted AI products, including writing evals and holding a point of view on AI quality.
• Hands-on and willing to build rather than delegate, thriving in a culture that expects it.
• Comfortable spanning platform thinking and UX/experience judgment within the same role.
• Sharp perspectives on the systems AI products need, including RAG, ontology, and scalable API strategies.

Benefits:

• Competitive base pay, benefits, and equity (RSUs).
• Physical office spaces in Denver, San Francisco, and New York City, with flexible work arrangements.

Salary Range: $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.