Senior Product Designer

Ninety million Americans—freelancers, part-time, seasonal workers, and 1099 contractors—are left out of benefits built for full-time jobs. As a product designer at Smirk, you'll give them tools to choose, understand, and use their health benefits—across medical, dental, and vision. Your work gives people a safety net, so if they get sick they can get access to care and navigate the system with clarity, support, and confidence. 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. 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. #J-18808-Ljbffr Smirk Health