Lead Product Designer, Sidecar Health
$160-180k
+ Bonus opportunity, and equity package
Digital health insurance platform
Be an early applicant
Digital health insurance platform
201-500 employees
Be an early applicant
$160-180k
+ Bonus opportunity, and equity package
201-500 employees
Company mission
To make healthcare affordable.
Role
Who you are
- 5+ 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
What the job involves
- We’re at an inflection point as we define a transformed Member Experience and build toward it. As Lead Product Designer, Member & Provider Experience, you’ll help set the experience vision and direction across mobile and web—partnering closely with Product and Engineering leadership to turn complexity into simple, trusted experiences.
- You’ll lead cross-functional problem solving, raise the bar on quality and craft, and help scale design through strong decision-making, reusable patterns, and a healthy design system that powers speed and quality of delivery
- 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
Our take
Sidecar Health’s insurtech platform allows users to tailor their own flexible healthcare plans based on their individual needs and budget. One of its main advantages outside of its flexibility is how the company doesn't use its own dedicated network of doctors, allowing the customer to see whomever they like while negating its own need to build nationwide networks.
On top of this it allows users to search and compare local health providers, and pay directly for care through its own payment card, often at a discount to what legacy insurance providers charge. Sidecar’s offering allows for better flexibility, more transparency and fewer financial burdens for unnecessary coverage areas.
The company has garnered plenty of praise, and financial backing, for its consumer-centric approach - and its latest raise positions Sidecar Health as a major disruptor in the market. That said, future growth will depend on how well it can expand its nationwide footprint, take on the legacy healthcare providers and work its way into employer and government-sponsored plans.
Steph
Company Specialist at Welcome to the Jungle
Insights
-28% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Jun 2024
$165m
SERIES D
Jan 2021
$125m
SERIES C
Total funding: $328m
Company benefits
- Comprehensive Medical, Dental, and Vision benefits
- Paid vacation and company holidays
- Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S
Company HQ
El Segundo, CA
Leadership
Patrick Quigley
(Co-Founder & CEO)Having worked at BEA Systems and QuinnStreet for a combined 8 years, they took an MBA at Wharton. They also served as CEO of Healthplans.com and Katch.
Veronica Osetinsky
(Co-Founder & COO)They studied at UCB before working at Bank of America and Paramax Capital. They worked at Quinstreet and Katch for 8 years prior to co-founding Sidecar Health.
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