Director of Product Design

Summary

Join Sidecar Health, a company redefining health insurance, as their Director of Product Design. This leadership role focuses on driving design vision, strategy, and execution across consumer-facing products. You will collaborate with cross-functional teams and external partners to create high-quality user experiences, lead initiatives to improve usability and engagement, and influence product vision. The position requires managing design resources and contributing to a design-centric culture. Growth opportunities exist as the company scales. Sidecar Health offers a competitive salary, bonus, equity, comprehensive benefits, 401k, paid time off, and the chance to impact healthcare.

Requirements

• 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
• 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

Responsibilities

• 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

Preferred Qualifications

Previous experience managing or mentoring designers

Benefits

• 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