Director of Product Management - Remote

Overview

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.

In Short

• 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

Requirements

• 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

Benefits

• 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.