Lead, AI Assistant Platform for SMBs

Gusto; Denver, New York, San Francisco (CO, NY, CA); Hybrid; USD 179,000 - 220,000; Full time

Benefits offered by this job

Benefits

Equity (RSUs)

Job summary

Gusto seeks a seasoned Product Manager to lead our AI-powered conversational assistant. You will own the vision, collaborate with engineering, design, and data teams, and shape how SMBs use AI to handle payroll, HR, and benefits.

You will drive strategy for expanding capabilities, partner across domains, and ship fast with customer value in mind. A strong hands-on, platform-plus-UX mindset is essential.

Qualifications

• 10+ years building as a product manager with scope ownership and platform decisions
• High-visibility role engaging with company leadership and product leaders
• Belief in what AI can do for small businesses and excitement to build it
• Hands-on and prefer building over delegating, thriving in a fast-moving culture
• Ability to span platform thinking and UX/experience judgment within the same role
• Sharp perspectives on AI systems needs—RAG, ontology, scalable API strategy for agents

Responsibilities

• Lead the product vision for Gusto’s conversational assistant and define how it earns customer trust
• Expand the assistant's capabilities across payroll, time, benefits, and compliance
• Partner with domain teams to grow tool and domain coverage and ensure real user value
• Define surfaces where work happens (third-party connectors, messaging channels, AI clients) and set priorities
• Collaborate with engineering, data, design, and UX on technical trade-offs and API exposure
• Move fast by shipping narrow slices that deliver customer value early

Skills

Product management

AI fluency

Leadership

Cross-functional collaboration

Job description

Gusto seeks a seasoned Product Manager to lead our AI-powered conversational assistant. You will own the vision, collaborate with engineering, design, and data teams, and shape how SMBs use AI to handle payroll, HR, and benefits.

You will drive strategy for expanding capabilities, partner across domains, and ship fast with customer value in mind. A strong hands-on, platform-plus-UX mindset is essential.