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Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We’re assembling a team of passionate professionals—from tech leaders to healthcare experts—who want to fix a broken system and make it more personalized, transparent, and accessible.
We’re looking for a Director of Product Design to lead and scale our member experience efforts. This is a strategic, hands-on role focused on shaping how users access, understand, and engage with their healthcare across our digital products.
What You’ll Do
- Own the design strategy and execution for all member-facing products
- Partner with the VP of Member Experience and cross-functional teams to deliver user-centered design
- Provide creative direction across design projects to ensure clarity, quality, and consistency
- Lead initiatives that improve usability, engagement, and overall product quality
- Use design thinking and user insights to influence product vision and roadmap
- Foster a culture of design excellence and collaboration
- Build the foundation for a scalable design function as we grow
What They’re Looking For
- 7+ years designing and shipping consumer-facing mobile and web applications
- A portfolio that shows real user impact and strong product execution
- Strategic thinking with the ability to connect design work to business goals
- Experience leading design initiatives and providing creative direction
- Strong collaboration skills with Product, Engineering, and Marketing teams
- Experience mentoring or managing other designers is a plus
- Fluent in Figma, Sketch, or similar design/prototyping tools
- Deep understanding of UX best practices, accessibility, and design systems
- Clear communicator with the ability to influence stakeholders
- Passion for building great experiences and thriving in fast-paced environments
Why Join Sidecar Health
- Competitive salary, bonus potential, and equity package
- Medical, dental, and vision coverage
- 401k retirement plan
- Paid vacation and company holidays
- High-impact role at a mission-driven startup transforming U.S. healthcare
Sidecar Health is proud to be an Equal Opportunity Employer. We are committed to building a diverse, inclusive team and encourage candidates of all backgrounds to apply.
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