Lead product strategy that transforms small-business health insurance into a clear, accessible, user-first experience.
About SimplyInsured
SimplyInsured is on a mission to eliminate fear in health insurance. We help small business owners navigate complex coverage decisions through transparency, simplicity, and exceptional customer experience. With more than 20,000 customers and partnerships that include Toast and Square, we’re reshaping an industry that has long been confusing and inaccessible. Founded out of Y Combinator and backed by Polaris Partners, Bessemer Venture Partners, New York Life Ventures, and AltaIR Capital, we’re building products that make healthcare easier for everyone.
Schedule
• Fully remote (U.S.-based)
• Standard Monday–Friday collaboration across Product, Engineering, and Operations
• Fast-paced environment with cross-functional alignment required
Responsibilities
• Gather, structure, and prioritize product requirements from internal teams and external stakeholders.
• Execute the product roadmap across the full technology stack to deliver industry-leading service at scale.
• Build strong cross-functional relationships to connect product goals, customer needs, and business value.
• Analyze competitive insights, industry trends, and customer feedback to guide strategic decisions.
• Propose innovative ways to improve product effectiveness and user experience.
• Collaborate with engineering and design teams to develop prototypes, mocks, and working solutions.
Requirements
• 5+ years of product management experience
• Experience with consumer-facing SaaS or marketplace products
• Ability to develop creative solutions to complex problems
• Strong analytical and strategic thinking
• Proactive, resourceful problem solver with strong communication skills
Benefits
• Base salary range: $150,000–$175,000
• Annual discretionary bonus
• Generous stock option package
• “Take what you need” time-off plan
• 100 percent employer-paid Medical, Dental, and Vision
• FSA plan
• 401(k)
• A values-driven culture anchored in transparency, growth, and ownership
If you’re excited about shaping the future of health insurance technology and building products that genuinely help small businesses, this role is built for you.
Happy Hunting,
~Two Chicks…