Principal Product Manager, Agentic Benefits Operations

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . By the Numbers: Named #1 best software for small business of 2024 by G2 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing Over $500M in annual revenue The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs There are 6.2M employers in the US, 98% have fewer than 100 employees (1) 550,000 new businesses are created each year in the US (1) What Product Management is like at Gusto: Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing. We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care. We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence. We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto. About the Team: Gusto operates a scaled, full-suite benefits brokerage and is building a Professional Employer Organization (PEO) offering to serve more complex small businesses with a bundled solution for HR, payroll, benefits, and compliance. Our existing brokerage business is among the largest in the US serving the SMB market, and our PEO bet is one of our most strategic new initiatives, with FY26 focused on developing the foundation and FY27 aimed at launching a differentiated, scalable customer experience. We're looking for a Product Manager to lead the transformation of Gusto's benefits administration platform, the product that powers benefits for tens of thousands of SMBs and their employees. This role owns what happens after benefit selections are made: implementing plans with carriers, fulfilling enrollments, and giving customers visibility into the status of their benefits. It is a broad scope, encompassing agentic workflows, customer-facing experiences, internal tooling, and carrier integrations. Here’s what you’ll do day-to-day: Ownership: Lead long-term strategy. This includes driving research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for success. You’ll translate this strategy into actionable guidance that informs company-wide planning and execution. North Star: Focus the organization on what matters most. Identify the highest-leverage investments and decisions across functions that will unlock long-term success, reduce ambiguity, and ensure that Gusto is building toward a cohesive and differentiated Benefits PEO offering. Collaborate: Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations to uncover insights, validate assumptions, and build alignment. You’ll help create shared understanding and ensure cross-functional teams are set up to deliv ... (truncated, view full listing at source)