Senior AI Product Manager, Conversational Assistant

The Wrap; New York (NY); Hybrid; USD 179,000 - 260,000; Full time

Job summary

Gusto is seeking a senior product manager to define and accelerate our conversational assistant, shaping how small businesses work with payroll, benefits, HR, and beyond. You will own the strategy, partner with engineering, design, and data teams, and drive rapid delivery of valuable features.

You will operate across multiple domains, ensure AI quality, and balance platform thinking with user experience to earn customer trust and scale impact in a fast-moving, AI‑driven environment.

Qualifications

• 10+ years building as a product manager with broad scope.
• Experience owning platform-level decisions and working with executives.
• Belief in AI's potential for small businesses; able to build trust.
• Hands-on builder who values action over delegation.
• Able to bridge platform thinking with UX/experience judgment.
• Develop perspectives on systems AI products: RAG, ontology, API strategy.

Responsibilities

• Define how Gusto's conversational assistant works, behaves, and earns customer trust.
• Lead the product vision for the assistant and translate it into a strategy with clear first steps.
• Expand assistant capabilities by partnering with domain teams across payroll, time, benefits, and compliance.
• Define how the assistant appears in ecosystems, including third-party connectors and AI clients.
• Collaborate with engineering and data teams on API exposure and integration decisions.
• Partner with design and UXR to test user sentiment and shape implementation.
• Move fast by shipping narrow slices that deliver customer value early.

Skills

Product management

Leadership exposure

AI product mindset

Trusted AI

Hands-on

Platform thinking

UX judgment

AI systems

Flexible scope

Job description

Gusto is seeking a senior product manager to define and accelerate our conversational assistant, shaping how small businesses work with payroll, benefits, HR, and beyond. You will own the strategy, partner with engineering, design, and data teams, and drive rapid delivery of valuable features.

You will operate across multiple domains, ensure AI quality, and balance platform thinking with user experience to earn customer trust and scale impact in a fast-moving, AI‑driven environment.