Senior Head of Product

Senior Product Manager, Benefits & PEO (Multiple Roles)
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We handle the hard stufflike payroll, health insurance, 401(k)s, and HRso owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, were proud to support more than 400,000 small businesses across the country, and were building a workplace that represents and celebrates the customers we serve. Named #1 best software for small business of 2024 by G2
~Youll move fast by pairing sharp product judgment with fluency in AI tools automating what slows teams down and amplifying what makes them creative and highperforming.
Youll prototype, automate, design, and ship using AI as your cobuilder to turn problems into durable solutions that deliver customer value with urgency and care.
Gusto has a strong missiondriven culture, and we care deeply about lifting up these business owners building technology for an AIfirst world that gives them the superpowers to run and grow their businesses with confidence.
Gusto operates a scaled, fullsuite 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.
PEO Growth: We are looking for a Senior Product Manager to play a key part in developing the endtoend PEO customer experience. Youll define how we serve these customers, what capabilities we need to build, and how we ensure were delivering a cohesive endtoend product experience. This PM should spike on core UX and building AIenabled experiences (or a willingness to learn how).
This Senior Product Manager will own building out our PEO Workers Compensation product from scratch. Benefits AI: Were looking for a Senior Product Manager to drive an industryfirst 0to1 AI initiative and lead a team responsible for an existing product driving $XXm in new ARR each year.
This includes driving research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for success. Youll translate this strategy into actionable guidance that informs companywide planning and execution.
Identify the highestleverage investments and decisions across functions that will unlock longterm success, reduce ambiguity, and ensure that Gusto is building toward a cohesive and differentiated Benefits & PEO offering.
Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations to uncover insights, validate assumptions, and build alignment. Youll help create shared understanding and ensure crossfunctional teams are set up to deliver.
Whether its clarifying requirements, kicking off strategic initiatives, or embedding with a team to drive execution, youll help move the work forward by creating clarity, building momentum, and enabling others to succeed.
Minimum of at least 1 year in a PEO or tech forward commercial P&C Insurance company
~ Strong strategic thinking and the ability to connect work across customer needs, product design, internal operations, pricing, and gotomarket
Our cash compensation amount for this role is targeted at $152,000 to $190,000/yr in Denver & most major metro locations, and $184,000 to $230,000/yr for San Francisco, New York, & Seattle. 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.
Fulltime
Software Development
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.
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