Senior Product Manager, Contractor Products

Gusto Gusto · Fintech · Boston, MA +1 · Remote · Product Management

Senior Product Manager for Gusto's Contractor Products team, focusing on end-to-end contractor management for SMBs. The role involves leading long-term strategy, defining product vision, and driving execution, with an expectation to actively use AI tools in the product development process.

What you'd actually do

  1. 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.
  2. Build a long-term vision for how Gusto invests in contractor products—defining how we can simplify contractor management for SMBs and create durable competitive advantage
  3. 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.
  4. Be the pace setter. Drive execution as a boundaryless builder — doing whatever it takes to achieve outcomes. You will use AI as your co-builder to turn complex problems into durable, customer-loved solutions with urgency and care.

Skills

Required

  • 5+ years of hands-on Product Management experience
  • Proven track record of building 0-to-1 products—taking ideas from discovery through launch and iteration
  • Strong customer discovery and product research skills with the ability to translate insights into actionable product strategies
  • Solid data acumen with the ability to use data to inform decisions, set goals, and measure success
  • Experience with AI tools and a vision for how AI can transform product experiences
  • Exceptional cross-functional collaborator and leader—a great listener who naturally brings teams and stakeholders along, yet doesn't hesitate to make hard decisions when needed
  • Ability to identify emerging opportunities, build business cases, define product vision, and create supporting roadmaps
  • Entrepreneurial mindset, driven by our mission, with deep empathy for small business owners and their contractor workforce challenges
  • A proven track record of building products that customers love

What the JD emphasized

  • building 0→1
  • AI tools