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 deliver. Accelerate Execution: Step into the highest‑priority gaps that stand in the way of success. Whether it’s clarifying requirements, kicking off strategic initiatives, or embedding with a team to drive execution, you’ll help move the work forward by creating clarity, building momentum, and enabling others to succeed. Here’s what we’re looking for 8+ years of product management experience, ideally with additional professional experience in roles that involved leading large, complex, and cross‑functional initiatives A systems thinker with experience in AI‑driven workflows, operations platforms, and process transformation. Benefits experience is a plus, but not a requirement. Strong strategic thinking and the ability to connect work across customer needs, product design, internal operations, pricing, and go‑to‑market Excellent communication and storytelling skills, with a talent for making complexity understandable and actionable A bias towards action, comfort operating without a clear playbook, and a desire to drive meaningful progress on long‑term company priorities If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we’re looking for someone excited to join the team. Our cash compensation amount for this role is $179,000/yr to $224,000/yr in Denver & most major metro locations, and $210,000/yr to $263,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Where do PMs at Gusto work? We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. Our open roles will specify on the careers page and in the job description where the position is eligible for work. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2–3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non‑office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it’s the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do 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. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice. #J-18808-Ljbffr