Director of Product Design

Position Overview

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• Job Type: Not Specified
• Salary: Not Specified

Sidecar Health is revolutionizing health insurance with the mission to make excellent healthcare affordable and accessible. We seek driven individuals who are passionate about fixing a broken system and making it more personalized, affordable, and transparent. Join us if you want to use your talents to transform healthcare in the United States.

About the Role

We are seeking a Director of Product Design to lead and scale our member experience design efforts. This is a strategic, hands-on leadership role focused on driving design vision, strategy, and execution for our consumer-facing products. You will collaborate closely with the VP of Member Experience and cross-functional leaders to shape how members interact with their healthcare. The role includes managing internal and external design resources, with opportunities for growth as the company scales.

Responsibilities

• Drive the end-to-end design strategy and execution for member-facing products.
• Guide and collaborate with cross-functional teams and 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 to 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 foster a culture that values great design.
• Contribute to building the foundation for future growth of the design function.

Requirements

• 7+ years of experience designing and shipping consumer-facing mobile and web applications.
• A strong portfolio demonstrating user impact and business results.
• 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 (Product, Engineering, Marketing, external partners).
• Previous experience managing or mentoring designers is preferred.
• Strong communication skills with the ability to present design rationale and influence stakeholders.
• Proficiency in design and prototyping tools (e.g., Figma, Sketch).
• 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.

Why Join Us

• Competitive salary, bonus opportunity, and equity package.
• Comprehensive Medical, Dental, and Vision benefits.
• 401k retirement plan.
• Paid vacation and company holidays.
• Opportunity to make a significant impact at a rapidly growing, mission-driven company transforming healthcare in the U.S.

Company Information

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.