Senior Product Manager, PEO (Multiple Roles)
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. 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.
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.
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.
About the Team: Gusto is building a Professional Employer Organization (PEO) offering to serve more complex small businesses with a bundled solution for HR, payroll, benefits, and compliance. It’s one of our most strategic initiatives, with FY26 focused on developing the foundation and FY27 aimed at launching a differentiated, scalable customer experience.
PEO Growth: We are looking for a Senior Product Manager to play a key part in developing the end to end PEO customer experience. You’ll define how we serve these customers, what capabilities we need to build, and how we ensure we’re delivering a cohesive end to end product experience. This PM should spike on core UX and building AI‑enabled experiences (or a willingness to learn how!).
This Senior Product Manager will own building out our PEO Workers Compensation product from scratch. The PM will partner with engineering to architect and build complex technical capabilities around pricing, underwriting, and billing.
Ownership: Lead the development of Gusto’s long‑term PEO strategy. This includes driving research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for a successful launch. You’ll translate this strategy into actionable guidance that informs company‑wide planning and execution.
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 PEO offering.
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 on the PEO opportunity.
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.
Strong strategic thinking and the ability to connect work across customer needs, product design, internal operations, pricing, and go‑to‑market.
• Experience with PEOs, workers compensation, payroll systems, business insurance, benefits administration, or bundled HR services is strongly preferred.
• A bias toward action, comfort operating without a clear playbook, and a desire to drive meaningful progress on long‑term company priorities.
We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. 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 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. 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.
Interested in building your career at Gusto, Inc.?
