Lead Product Designer

Sidecar Health is redefining health insurance, aiming to make excellent healthcare affordable and attainable for everyone. As a Lead Product Designer, you will set the experience vision and direction across mobile and web, collaborating with Product and Engineering leadership to create simple and trusted experiences.

Responsibilities:

• End-to-end member + provider experiences across key journeys, surfaces, and teams
• Experience vision + strategy: a compelling north star, multi-quarter plan, and sequencing that makes it real
• Quality, consistency, and scalability through patterns, standards, and design system stewardship
• Cross-functional facilitation: driving alignment, clarity, and decisions through structured problem-solving
• Define and communicate a clear experience vision, principles, and strategic roadmap with Product + Engineering
• Facilitate cross-functional discovery and decision-making (workshops, critiques, working sessions) to align teams and resolve tradeoffs
• Influence problem framing, success metrics, and scope using both qualitative insights and quantitative signals
• Design hands-on: flows, IA, interaction models, UI, prototypes—making complex concepts feel obvious
• Translate real constraints (policy, operations, compliance, edge cases, data limits) into consumer-grade experiences that build trust
• Plan or guide research (interviews, usability tests, concept validation), synthesize findings into clear narratives, and drive shipped decisions
• Evolve and govern the design system: scalable patterns, accessibility, documentation, and adoption
• Mentor designers through critique, pairing, and calibration to level up craft and consistency
• Lead an AI-forward design practice: use AI tools to accelerate exploration, synthesis, prototyping, and production; share repeatable workflows that improve team velocity and outcomes

Requirements:

• 7+ years designing digital products (or equivalent) at a product/tech company—comfortable moving fast in scrappy, startup-style environments across consumer mobile and/or web
• A portfolio that shows you can simplify complex information through strong IA, hierarchy, and content craft
• Strong interaction + visual craft (layout, typography, systems thinking) and fluency building with design systems at scale
• Demonstrated thoughtful use of AI in day-to-day design practice—paired with a track record of teaching others and helping teams adopt new workflows
• Proven ability to lead multi-team, cross-functional initiatives and influence senior partners across Product, Engineering, Ops, Support, Compliance, and executive leadership
• Strong facilitation: you can run working sessions that drive clarity, alignment, and decisions
• Experience combining qualitative research with quantitative signals (funnels, analytics, experiments) to prioritize, iterate, and measure impact
• Ability to balance long-term vision and scalability with rapid, iterative delivery
• A strong commitment to accessibility and inclusive design
• Clear, concise communicator who can explain tradeoffs, document decisions, and drive crisp decision-making