Senior Product Designer

What you'll do

Build the end-to-end experience

• Own the core customer experience for medical, dental, and vision coverage, from understanding your coverage, to finding a doctor, staying healthy, and paying for care.
• Turn insurance-speak into plain language.
• Help people stay ahead of their health with tools that make preventive care easier, and support them when they're sick.
• Collaborate directly with the founders to shape what we build and why.
• Ship quickly, learn quickly, and keep improving.
• Raise the craft bar across the product.
• Prototype to think and move fast without sacrificing quality.
• Make health benefits feel like a real safety net: clear coverage, predictable costs, and confident next steps to get care and handle the bill when someone gets sick.

Partner with the team

• Work as peers with product and engineering leaders from Lemonade, Venmo, and Instacart — no layers between you and the decisions.
• You'll be one of two designers with high ownership and direct founder access.
• A remote-first team that operates on Central Time.

What you need

Experience

• 7+ years of product design experience, with 3+ years at a startup or high-growth company. Portfolio required.
• Built 0→1 products that shipped to real users and scaled, or led major redesigns with measurable impact.
• Strength in consumer-facing products that simplify complex decisions.
• Build and design with AI-native workflows.
• Strong judgment about which details matter most.

How you work

• You've shipped in environments where the roadmap didn't exist yet — and you helped write it.
• You know how to make sharp tradeoffs with limited resources and tight timelines.
• Strong taste paired with humility.
• You care about the people on the other side of the screen.

Skills

• Strong visual craft across typography, color, layout, and motion.
• Fluent in Figma and modern prototyping tools.
• Clear communicator across disciplines and seniority levels.

What you'll get

• Competitive salary + early-stage equity with significant upside, along with health benefits (of course).

Why this role, why now

• The American healthcare benefits system was built for a workforce that no longer exists—one job, one employer, full-time, forever. Ninety million workers today are independent 1099 professionals, gig, part-time, multi-income, or micro-shifting. The system wasn't built for them.
• Smirk is building the infrastructure that fixes this. We have the carriers, the payment rail, the employer pipeline, and a C-suite advisory council of former CHROs from some of the largest workforces in the country.
• This is a rare opportunity to join early, own meaningful outcomes, and help define a new category at the intersection of healthcare, AI, fintech, and the future of work.

About Smirk

• Smirk is building the AI health benefits infrastructure for the modern workforce: mobile, personalized coverage delivered with radical clarity. One in three adults today earns income from multiple sources, and traditional employer-tied benefits have failed the 90M+ workers who are independent 1099, flexible, gig-based, part-time, or between jobs.
• Our platform—the Smirk Wallet™ and Ailene™ AI care concierge—unifies coverage, payments, and care navigation into one intelligent system. We are carrier-backed (Chubb), Mastercard-partnered, live with Freelancers Union, and in active pilot design with Fortune 500 employers.
• We are seed-stage, post-product, post-traction, and accelerating.