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 — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers.
What this role actually needs.
About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. Responsibilities: - 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. - 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 Requirements: - 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) Benefits: - 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) Company context: Gusto builds payroll and HR software with broad product, platform, security, and data hiring across North America.
Day-to-day expectations
Gusto lists these responsibilities for the Principal Product Manager, Agentic Benefits Operations role.
- 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.
- 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
What a strong candidate brings
These requirements are extracted from the source listing and normalized for UpJobz readers.
- 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)
Why people would want this job
Gusto published these compensation, benefits, or working-context details with the role.
- 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)
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Source: job-boards.greenhouse.io · Source ID: 7665272 · Confidence: 91/100 · Last checked: May 7, 2026
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