Lead Product Manager at Si

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 aren't just building a tool; we’re building the infrastructure for the future of health benefits. As our Lead Product Manager, you will report directly to the CEO. You aren't 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 You’ll Do • Architect the Roadmap: Define the vision and strategy for new integrated partnerships (e.g., embedding our engine into the world's 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. What You’ll Bring • 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. What We Offer • 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. Compensation Starting Base Salary Range: $170,000 - $200,000 Note: This is just one part of total compensation, which includes performance bonuses and significant equity upside. Our Culture We value radical transparency, a bias for action, and the obligation to dissent. We hold each other to extremely high standards because our mission—protecting families' health and finances—demands it. SimplyInsured is an equal opportunity employer. We strongly encourage candidates from underrepresented backgrounds to apply. If you’re excited about the mission but don’t check every single box, apply anyway—we want to hear how your unique perspective can amplify our team.