Sidecar HealthSH

Director of Product Design

Sidecar Health is an American health insurance company offering transparent and affordable healthcare plans that give members control over their healthcare decisions and costs.

Sidecar Health

Employee count: 201-500

United States only

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.

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.

About the job

Apply before

Posted on

Job type

Full Time

Experience level

Director

Location requirements

Hiring timezones

United States +/- 0 hours

About Sidecar Health

Learn more about Sidecar Health and their company culture.

View company profile

At the heart of Sidecar Health's mission is a drive to make healthcare affordable and accessible for everyone in the United States. We are a team of problem solvers, embracing new ideas and developing creative solutions daily to achieve this goal. Our culture is built on ownership, where we hold ourselves and one another accountable. We value a strong bias for action, constantly moving forward to innovate within the health insurance industry. Leading with empathy is core to our interactions; we actively work to understand each other's perspectives. Sidecar Health is redefining health insurance with a modern, common-sense approach that puts consumers in control of their costs and choices. We believe that by offering complete transparency into coverage and costs, plus control over where care is received, we can significantly reduce healthcare expenses nationwide.

Our innovative model empowers members by allowing them to see any licensed healthcare provider they choose, eliminating the restrictions of traditional networks. We provide upfront pricing information, so members know what their plan will pay before they even see a doctor. This transparency, coupled with the Sidecar Health VISA benefit card for direct payments, simplifies the healthcare process and motivates cost-conscious decisions. If members spend less than their benefit amount, they share in the savings. This approach not only reshapes behavior and reduces costs but also cuts through the red tape that often defines traditional insurance, resulting in denial rates below 1%. We are committed to giving back to our communities and proudly donate to charitable organizations that promote better health. Our team is composed of passionate individuals from diverse backgrounds, including tech leaders, policymakers, and healthcare professionals, all united by the desire to fix a broken system and make it more personalized, affordable, and transparent.

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Sidecar Health

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