Senior Product Designer

Ninety million Americans—freelancers, part-time, seasonal workers, and 1099 contractors—either don't have health insurance or can't afford to use it. ACA marketplace plans exist, but when you're making $600/week, high deductibles can make you functionally uninsured. As a senior product designer at Smirk, you'll give people tools to choose, understand, and use health insurance—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 insurance, 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 insurance 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

• Build alongside product and engineering leaders from Lemonade, Venmo, and Instacart.
• A remote-first team that operates on Central Time.

What you need

Experience

• Senior-level product design experience shipping consumer products. Portfolio required.
• Built 0→1 products 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

• Comfortable with ambiguity. You define problems before solving them.
• 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
• Company equity
• Health benefits include medical, dental, and vision insurance
• 401(k) retirement plan
• Up to 3-weeks paid PTO

About Smirk

Smirk is building an AI-powered health insurance experience for the 60M workers traditional insurance forgot: freelancers, gig workers, and small-business employees—people who deserve better than paperwork, surprise bills, and legalese masquerading as "coverage."

We've got the nation's largest collection of freelancers and Fortune 20 customers in the pipeline, Chubb as our carrier partner, and CHROs from Starbucks and McDonald's advising us.

How to apply

Send your portfolio and a short note about why this work matters to you to careers@smirkhealth.com