Senior Product Manager, Contractor Products

The Contractor Products team owns comprehensive contractor management solutions for small and medium businesses. This role focuses on building products from concept to scale, addressing substantial market opportunities in contractor onboarding, payments, and compliance across domestic and international markets. You'll shape long-term strategy while driving execution in one of Gusto's fastest-growing business segments.

This position requires leading research initiatives, defining market positioning, and translating strategic vision into actionable company-wide guidance. The role involves close collaboration across multiple functions to uncover insights, validate assumptions, and ensure successful delivery of customer-focused solutions.

• Drive long-term strategic planning including research, customer positioning, and product direction
• Build comprehensive vision for contractor product investments and competitive positioning
• Partner across Product, Engineering, Compliance, Legal, and Operations teams
• Lead execution as pace setter, using AI tools to solve complex customer problems
• Identify required investments and internal capabilities for business success
• Create shared understanding across cross-functional teams for optimal delivery

• 5+ years hands-on Product Management experience required
• Proven track record building products from concept to scale
• Experience with contractor management, payments, or compliance systems
• Strong collaboration skills across multiple business functions
• Demonstrated ability to translate strategy into actionable execution plans
• Active engagement with AI tools relevant to product management role

Gusto is a scale-up SaaS company supporting over 500,000 small businesses with payroll, HR, health insurance, and retirement services. The company operates across several US cities and integrates AI tools into its workflows.