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Salary: USD 179,000 - 260,000 / annual
Gusto is seeking a Principal Product Manager to lead the vision and strategy for its conversational AI assistant, a core product that helps small businesses automate and streamline work across payroll, benefits, HR, and compliance.
In this role, you will:
- Develop deep understanding of small business workflows within Gusto, identifying where customers get stuck and what work they would delegate if possible
- Lead the product vision for Gusto's conversational assistant, translating it into a coherent strategy with clear perspective on where the assistant delivers real value and what to build first
- Expand the assistant's capabilities by partnering with domain teams to grow tool and domain coverage across payroll, time, benefits, and compliance, measured by real customer actions completed rather than conversation volume
- Define how the assistant shows up across customer ecosystems—third-party connectors, messaging channels, AI clients—and prioritize surfaces where work naturally happens
- Partner with engineering and data teams on technical trade-offs: API design, MCP layer architecture, embedding in first-party surfaces, and strategic technical debt decisions
- Collaborate with design and UXR to understand customer sentiment about AI acting on their behalf and shape product direction accordingly
- Move fast by shipping narrow, valuable slices early rather than waiting for complete builds
Gusto serves 500,000+ small businesses and is named #1 best software for small business by G2 (2024). The CoreX AI team is at an inflection point, building trusted AI experiences that customers rely on for critical business decisions. You'll work across the company with engineering, design, and domain experts, reasoning about API design and model behavior as comfortably as customer experience.
Gusto has hybrid offices in Denver, San Francisco, and New York, with expectations of 2-3 days per week in-office. The company is mission-driven, focused on lifting up small business owners building in an AI-first world.
REQUIREMENTS:
- 10+ years of product management experience with meaningful scope ownership and track record of driving broad product or platform-level decisions
- Comfortable in high-visibility roles engaging directly with Gusto leadership and driving decisions that stick
- Genuine belief in AI's potential for small businesses and excitement to build it
- Deep understanding of building trusted AI products: writing evals, holding strong perspectives on AI quality, and owning responsibility for products customers rely on daily
- Hands-on builder mentality; prefer building to delegating and thrive in a culture that expects it
- Ability to span both platform thinking and UX/experience judgment within the same role
- Sharp perspectives on AI product systems: RAG, ontology, and scalable API strategy for agent-accessible systems
- Comfort with fluid, expanding charters in a fast-moving AI landscape
