Fitt Insider 327. Sam O'Keefe, Co-Founder & CEO of Flex
Feb 23, 2026
Sam O'Keefe, co-founder and CEO of Flex, builds a fintech that lets people pay with HSA and FSA funds at checkout. He talks about why health accounts are confusing and how Flex makes them seamless, the merchant benefits like higher conversion, API-first integrations with partners like Equinox, and trends across fitness, sleep, supplements and wearables.
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IRS Rules Explain HSA FSA Friction
- HSAs and FSAs were designed under IRS tax rules, not modern consumer health habits.
- Sam O'Keefe explains IRS code 213(d) defines medical expenses, creating the confusion and friction consumers face at checkout.
Add HSA FSA As A Checkout Payment
- Treat HSA and FSA as first-class payment methods in checkout to remove consumer friction.
- Flex integrates HSA/FSA like PayPal and handles compliance so merchants don't need to rework their checkout flows.
HSA FSA Increases Conversion And AOV
- Accepting HSA/FSA drives measurable merchant benefits beyond consumer goodwill.
- Sam cites data: checkout conversion up ~30%, average order value can more than double, and return rates fall when consumers pay with these accounts.