Lead Product Manager

The Mission: Eliminate Fear

Health insurance is complicated, expensive, and intimidating. At SimplyInsured, we are on a mission to eliminate that fear. We empower small business owners—the backbone of the economy—by making the enormous task of providing health insurance transparent, accessible, and dead-simple.

Born in Y-Combinator and backed by top-tier investors such as Polaris Partners and Bessemer Venture Partners, we are disrupting a convoluted industry through major partnerships with NetSuite, Toast, and Square. We arent just building a tool; were building the infrastructure for the future of health benefits.

As our Lead Product Manager, you will report directly to the CEO. You arent just managing a backlog; you are the architect of our next phase of growth. You will lead the "0-1" charge for new integrated partnerships and innovative product lines that will define SimplyInsured for the next decade.

This is a high-leverage role for a veteran PM who wants the autonomy to own product strategy and solve complex problems.

What Youll Do

• Architect the Roadmap: Define the vision and strategy for new integrated partnerships (e.g., embedding our engine into the worlds largest B2B platforms).
• Lead 0-1 Initiatives: Take raw ideas from the CEO or market feedback and turn them into validated, scalable products.
• Bridge the Gap: Act as the strategic glue between Engineering, Operations, and our high-profile external partners.
• Translate Complexity: Turn the "black box" of insurance regulations into an elegant, intuitive end-user experience that builds trust and removes fear.
• Build the Engine: Beyond shipping features, you will refine our product discovery processes, mentorship culture, and data-driven experimentation frameworks.
• Evangelize the "Why": Present actionable insights from competitive intel and industry data to the executive team to pivot or double down on key bets.
  
  

• The Experience: 7+ years in Product Management, specifically within early-stage Silicon Valley environments (Fintech, Healthtech, or Insurtech preferred).
• The "Founding" Spirit: Proven track record of taking a product from concept to launch (0-1) and scaling it to significant user/revenue milestones.
• Technical & Analytical Prowess: You are comfortable diving into API documentation one hour and SQL dashboards the next.
• High-Stakes Communication: Experience managing relationships with C-level stakeholders, both internally and at Fortune 500 partner companies.
• UX Obsession: A deep empathy for the small business owner and their employees; you understand that for our users, "simple" is a feature, not an aesthetic.
  
  

• True Ownership: A generous stock option package that reflects your impact as a leader in the company.
• Executive Access: A direct reporting line to the CEO and a seat at the table for major strategic decisions.
• Total Wellness: 100% Company-paid Medical, Dental, and Vision for you and your family.
• Flexibility: A remote-first environment with a "Take what you need" time off plan.
• Future-Proofing: 401k plan and a values-based culture that invests in your long-term career growth.