Job description

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! **Must reside in California for consideration, This position is not eligible for visa sponsorship or transfers.* 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 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. What You'll Do 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 What You'll Bring 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. In taking a market-based approach to compensation, base pay may vary depending on location. Additionally, base pay may vary considerably depending on job-related skills and experience. The current expected salary range for this position is: $200,000 - $220,000. 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. 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.

Requirements

Must-haves

If you want to use your talents to transform healthcare in the United States, come join us!
Must reside in California for consideration, This position is not eligible for visa sponsorship or transfers.*
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)
Bachelor’s or Master’s in a relevant field
What You'll Get
Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.

Nice-to-haves

Preferred: experience in healthcare, insurance, or other complex, regulated industries

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

aiaccessibilityllmmlsql

Platform: greenhouse
Effort: quick

Benefits

Benefits detected in the listing.

Health Insurance

Dental

Vision

401k