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About the Role
Define how Gusto's conversational assistant works, behaves, and earns customer trust, enabling small businesses to accomplish real work across payroll, benefits, HR, and more. This role involves developing a deep understanding of small business workflows within Gusto, leading the product vision for the conversational assistant, expanding its capabilities, defining its ecosystem presence, and partnering with engineering, data, design, and UXR teams on technical and user experience aspects. The focus is on moving fast and shipping narrow slices of value to customers early.
Responsibilities
- Define how Gusto's conversational assistant works, behaves, and earns customer trust.
- 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 by partnering with domain teams.
- Define how we show up in our customers’ ecosystem and the surfaces where work naturally happens.
- 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 ship narrow slices that get customers value early.
Requirements
- 10+ years building as a product manager, with 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.
- Belief in what AI can do for small businesses and excitement to build it.
- Understanding of 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.
- Hands-on approach, preferring to build rather than delegate.
- Comfortable spanning both platform thinking and UX/experience judgment within the same role.
- Ability to develop sharp perspectives on the systems AI products need — RAG, ontology, and a scalable API strategy for agent-accessible systems.
- Comfortable with a fluid, expanding charter given the pace of AI development and the competitive landscape.
Skills
- AI tools
- Product judgment
- Prototyping
- Automation
- Design
- Shipping products
- API design
- Model behavior
- Customer experience
- Building with AI
- RAG
- Ontology
- Scalable API strategy
Location
- Denver
- San Francisco
- New York City
- Scottsdale
Work Type
- Hybrid
- Onsite
Experience Level
- 10+ years of product management experience
Salary/Compensations
- $179,000/yr to $220,000/yr in Denver & most major metro locations
- $210,000/yr to $260,000/yr for San Francisco, Seattle & New York
Benefits
- Competitive base pay
- Benefits
- Equity (RSUs)
About the Company
- Gusto is on a mission to grow the small business economy by handling payroll, health insurance, 401(k)s, and HR.
- Teams are located in Denver, San Francisco, and New York.
- Supports more than 500,000 small businesses nationwide.
- Named #1 best software for small business of 2024 by G2.
- Has 2,700+ employees in the United States, Canada, Mexico, and Turkiye.
- Generates over $500M in annual revenue.
- The SMB market is large and growing with huge opportunities for Gusto.
- 98% of US employers have fewer than 100 employees.
- 550,000 new businesses are created each year in the US.
Equal Opportunity
- Gusto is proud to be an equal opportunity employer.
- Does not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic.
- Considers qualified applicants with criminal histories, consistent with applicable federal, state and local law.
- Is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures.
- Wants to see candidates perform to the best of their ability.
- Provides a process for requesting medical or religious accommodations during the candidate journey.