Lead Product Manager, Member Experience

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!

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 Lead Product Manager 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.  

• →Own the end-to-end product strategy and roadmap for key member-facing features and experiences 
• →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

• 8+ years of product management experience, with a track record of owning high-volume consumer products (mobile and web) where onboarding, activation, and retention drive results 
• Experience shipping LLM- or ML-powered customer-facing experiences that personalize or simplify the user journey 
• Proven ability to simplify complex, confusing experiences into clear, intuitive ones 
• Fluency in experimentation (A/B testing), personalization, and journey-level metrics, not just feature-level metrics, plus proficiency in SQL 
• Close partnership with design and user research, including a habit of speaking directly with members 
• Ability to set direction in ambiguous, fast-moving environments and influence senior stakeholders and executives 
• Strong communication, storytelling, and documentation skills 
• Strong data and analytical mindset (including proficiency in SQL) 
• Preferred: experience in healthcare, insurance, or other 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.