Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.
The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.
If you want to use your talents to transform healthcare in the United States, come join us!
About the Role
With proven product-market fit, we’re on a mission to scale our platform and elevate the member experience across the entire healthcare journey. We’re looking for an experienced and strategic Director of Product Management to lead core initiatives that directly impact how members engage with and benefit from our product. This role will blend product vision, operational strategy, and team leadership—driving outcomes that are intuitive, scalable, and powered by modern technology, including AI. You’ll also manage a small team of product managers to help execute this vision and deliver impact across the business.
What You'll Do
- Own the end-to-end product strategy and roadmap for key member-facing features and experiences
- Lead a small team of product managers—providing guidance, mentorship, and alignment around goals and priorities
- Translate member pain points, business needs, and operational challenges into scalable product solutions
- Drive cross-functional collaboration with engineering, design, operations, member support, and compliance to bring products to life
- Evaluate and integrate third-party solutions where appropriate, and lead build-vs-buy decisions
- Define and track KPIs related to member engagement, product usage, and satisfaction to guide prioritization
- Partner closely with marketing and member operations to ensure member awareness, adoption, and feedback loops
- Champion an iterative, data-informed approach to product development with an emphasis on quality, accessibility, and ease of use
- Ensure member-facing experiences remain compliant, secure, and in alignment with regulatory requirements
What You'll Bring
- 8+ years of product management experience, with at least 1-2 years managing or mentoring product managers
- Demonstrated success owning consumer-facing product strategy and delivering seamless user experiences
- Experience working with or building AI/ML-powered products, especially to streamline or personalize experiences
- Strong collaboration skills across technical and non-technical teams
- Comfort working in ambiguous, fast-moving environments with a bias for action
- Excellent communication, storytelling, and documentation skills
- Strong data and analytical mindset (including proficiency in SQL)
- Bonus: experience in healthcare, insurance, or similarly complex, regulated industries
- Bachelor's or Master’s in a relevant field
What You'll Get
- Competitive salary, bonus opportunity, and equity package
- Comprehensive Medical, Dental, and Vision benefits
- A 401k retirement plan
- Paid vacation and company holidays
- Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.
Sidecar Health adopts a market-based approach to compensation, where base pay varies depending on location and is further influenced by job-related skills and experience. The current expected salary range for this position is $180,000 - $195,000.
Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.
Top Skills
What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
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