Staff Product Designer (contractor)

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 strong Staff Product Designer (Contractor) to help overhaul our member experience. This role is pivotal in shaping a high-consumer-grade app that empowers people to navigate healthcare confidently. You’ll report to and work closely with the VP of Member Experience, supporting key initiatives that improve how members engage with our product. You should be equally comfortable with big-picture thinking and hands-on design execution.

What You'll Do

• Own and lead end-to-end product design initiatives for members, including the onboarding experience for new users
• Shape strategy to educate and guide members toward more informed healthcare decisions across the entire journey
• Present and communicate design concepts to cross-functional stakeholders and senior leadership, adjusting your approach based on fidelity and audience
• Collaborate with Product, Engineering, and Marketing to ensure a cohesive and engaging user experience
• Validate and iterate on designs through user research and usability testing
• Maintain a high level of detail during implementation by working closely with Engineering and QA teams
• Advocate for user-centered design principles and design best practices across the organization

What You'll Bring

• 7+ years of design experience designing consumer-facing mobile and web applications, with a portfolio that highlights impact on end users
• A collaborative partner who’s worked closely with Product Managers, Engineers, and Researchers to ship high-quality product solutions
• Comfortable presenting design rationale to cross-functional teams and executive stakeholders
• Experienced at incorporating both qualitative and quantitative insights into your design process
• Strategic and able to translate business goals into thoughtful, innovative design solutions
• Proficient in tools like Figma, Sketch, or similar
• Detail-oriented with excellent visual design skills
• Self-motivated and able to manage multiple projects independently

Why Join Us:

• Be part of a mission-driven company that is transforming the health insurance industry.
• Work in a dynamic and collaborative environment with a passionate team.
• Opportunity to make a significant impact on the member experience and help shape the future of healthcare.