Director of Product Design

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

We’re looking for a Director of Product Design to lead and scale our member experience design efforts. This is a strategic and hands-on leadership role focused on driving design vision, strategy, and execution across our consumer-facing products. You’ll work closely with the VP of Member Experience and cross-functional leaders to shape how members access, understand, and engage with their healthcare. The role includes oversight of design resources—both internal and external—with room to grow and expand the function as the company scales.

What You'll Do 

• Drive the end-to-end design strategy and execution for our member-facing products
• Guide and collaborate with cross-functional teams, as well as external design partners, to deliver high-quality, user-centered experiences
• Provide creative direction and feedback across design workstreams to ensure consistency, clarity, and impact
• Lead key initiatives that improve usability, member engagement, and overall product design quality
• Influence product vision and roadmap through design thinking and user insights
• Champion design excellence across the organization and contribute to a culture that values great design
• Help lay the foundation for future growth of the design function as the business evolves

What You'll Bring 

• 7+ years of experience designing and shipping consumer-facing mobile and web applications, with a strong portfolio that demonstrates user impact and business results
• A strategic mindset with the ability to connect design decisions to product and business outcomes
• Proven track record of leading design initiatives, providing creative direction, and driving high-quality execution
• Experience collaborating with cross-functional teams, including Product, Engineering, Marketing, and external partners
• Previous experience managing or mentoring designers preferred
• Strong communication skills with the ability to present design rationale and influence stakeholders at all levels
• Proficient in design and prototyping tools like Figma, Sketch, or similar
• Deep understanding of design systems, accessibility standards, and best practices for intuitive UX
• Passion for crafting exceptional user experiences and a bias for action in fast-moving environments
• Leadership potential with a desire to shape and grow the design function over time

Why Join Us: 

• 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.