Senior Director, Product Management, Fintech

What you'll do

Build the Smirk Health Wallet

• Own the end-to-end Smirk Health Wallet experience: funding from Smirk and employers in, spend on medical, pharmacy, and rewards out.
• Ship the wallet where customers already are: point of sale, Apple Wallet, and a GPR card in their pocket.
• Design how funds flow—from employer contributions and Smirk rewards into the wallet, out to providers, pharmacies, and merchants—so money is there the moment care is needed.
• Make the wallet the obvious, frictionless choice at checkout, whether it's a pharmacy counter, a hospital billing office, or a card reader at a clinic.
• Partner with engineering, design, our card issuing partner, compliance, fraud and risk, and CX to ship reliable, compliant money movement.
• Use AI tools across discovery, analysis, definition, and prototyping—pressure-test ideas in hours, not weeks.
• Collaborate directly with the founders to shape what we build and why.
• Ship quickly, measure what matters, and keep improving.

Partner with the team

• Work as peers with product and engineering leaders from Lemonade, Venmo, and Instacart — no layers between you and the decisions.
• High ownership and direct founder access on one of Smirk's most strategic products.
• A remote-first team that operates on Central Time.

What you need

Experience

• 7+ years of product management experience, with meaningful time in consumer fintech, payments, or digital wallets.
• Shipped a consumer card program, wallet, P2P, or payments product at scale—you've lived with the ops, the edge cases, and the fraud.
• Built 0→1 products that reached real users, or led major fintech launches with measurable impact.
• Deep consumer empathy—you think about the person at the pharmacy counter, not the persona deck.
• Fluent using AI tools for discovery, analysis, definition, and prototyping.
• Working knowledge of the regulatory surface area—KYC, card network rules, program management—enough to ship without tripping over it.

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 sweat the details that make or break trust—like turning a card decline at the pharmacy counter from a generic "transaction failed" into "your employer's deposit lands Friday, tap to cover the gap."
• You care about the people on the other side of the screen.

Skills

• Fluent in metrics, experimentation, and A/B testing.
• Clear communicator across engineering, design, compliance, and executive audiences.
• Comfortable diving into ledger mechanics, auth flows, and settlement when the work demands it.

What you'll get

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

About Smirk

• Smirk is building an AI-powered health insurance experience for the 90M 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.