Senior Product Manager - Benefits & PEO (Multiple Roles)

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 hiring for three roles in the Benefits and PEO product roles: 

• 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!). 

• Workers’ Compensation: This Senior Product Manager will own building out our PEO Workers Compensation product from scratch. You will own the end to end product vision and strategy for PEO Workers’ Comp, and influence our operational workflows and carrier relationships. The PM will partner with engineering to architect and build complex technical capabilities around pricing, underwriting, and billing.

• Benefits AI: We’re looking for a Senior Product Manager to drive an industry-first 0-to-1 AI initiative and lead a team responsible for an existing product driving $XXm in new ARR each year.

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:

• 5+ years of product management experience, ideally with additional professional experience in roles that involved leading large, complex, and cross-functional initiatives

  • PEO Growth: Minimum of at least 1 year in a PEO  

  • Workers’ Compensation: Minimum of at least 1 year in a PEO or tech forward commercial P&C Insurance company

  • Benefits AI: 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 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. 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. We are actively hiring for the following Centers of Gravity: Toronto, Canada, Atlanta, GA, Austin, TX, Chicago, IL, Denver, CO, Los Angeles, CA, Miami, FL, and Seattle, WA. Our open roles will specify on the careers page and in the job description where the position is eligible for work. 

 (1) Business Applications with Planned Wages (www.census.gov)