Principal Product Manager, AI Assistant
About this role
Defining how Gusto's conversational assistant works, behaves, and earns customer trust, you will lead the product vision that gives small businesses superpowers across payroll, benefits, and HR. Operating within the CoreX AI team, you will partner with domain, engineering, and data teams to expand what the assistant can actually do, holding the bar on quality as coverage grows. You will prototype, automate, design, and ship using AI as your co-builder to turn problems into durable solutions while maintaining a fast pace of execution.
Gusto serves over 500,000 small businesses nationwide by handling payroll, health insurance, 401(k)s, and HR so owners can focus on their craft. The product team operates in a lean, boundaryless environment where product managers do whatever it takes to deliver outcomes with urgency and care. Ideal candidates thrive in ambiguity, possess a hands-on building mentality, and combine sharp product judgment with deep fluency in AI tools and system architecture.
What you will do
- Lead the product vision for Gusto's conversational assistant, translating customer needs into a coherent strategy and defining what gets built first.
- Partner with domain teams to expand tool and domain coverage across payroll, time, benefits, and compliance while maintaining high quality standards measured in real actions completed.
- Define surface integrations across third-party connectors, messaging channels, and AI clients to determine where work naturally happens for customers.
- Collaborate with engineering and data teams on technical trade-offs involving API design, the Model Context Protocol layer, and first-party surface embedding.
- Work alongside design and user research teams to understand customer sentiment regarding AI actions and use those insights to shape product development.
- Set a rapid pace of execution by shipping narrow slices that deliver early customer value rather than waiting for complete builds.
What you need
- Bring 10 or more years of experience building as a product manager, including owning meaningful scope and driving broad product or platform-level decisions.
- Demonstrate hands-on experience building trusted AI products, which includes writing evaluations and holding a clear perspective on AI quality.
- Combine platform systems thinking for technologies like RAG, ontology, and scalable APIs with strong user experience judgment.
- Thrive in a hands-on culture where you prefer building over delegating and can engage comfortably with company leadership.
- Navigate a fluid, expanding charter and changing competitive landscape with curiosity, experimentation, and comfort with ambiguity.
Benefits
- Competitive base pay
- Benefits package
- Equity in the form of RSUs
Skills and tech stack
Questions candidates ask
What are the office and remote work expectations for this role?
Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office on designated days approximately 2 to 3 days per week.
What is the compensation range for this position?
The cash compensation amount is $179,000 to $220,000 per year in Denver and most major metro locations, and $210,000 to $260,000 per year for San Francisco, Seattle, and New York. Final offer amounts are determined by multiple factors including candidate location, experience, and expertise.
What team will this person join?
This role sits on the CoreX AI team, which builds and powers AI experiences that make Gusto the best teammate for small businesses. The team embeds AI directly into small business workflows to handle tasks and answer questions where mistakes have immediate consequences.
What kind of AI experience is expected for the role?
Candidates must have hands-on experience building trusted AI products, including writing evaluations, holding a point of view on AI quality, and reasoning about API design and model behavior as comfortably as customer experience.