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Flex

Stripe for HSA/FSA payments

Flex is a payment platform for businesses to accept HSA/FSA, unlocking the $150B per year sitting in HSA/FSA accounts.
Jobs at Flex
New York, NY, US / Remote (New York, NY, US)
$60K - $120K
3+ years
US / Remote (US)
$165K - $212K
3+ years
New York, NY, US / Remote (New York, NY, US)
$100K - $200K
6+ years
Flex
Founded:2023
Team Size:8
Status:
Active
Group Partner:Dalton Caldwell
Active Founders

Sam O'Keefe, Founder

Sam is a cofounder at Flex. Her previous roles include product leadership at a growth stage fintech (Unit21), EIR in Area120, and global head of startup programs at Google, and an editor at TechCrunch. Sam has also been a writer and producer of South of Market, the Musical.
Sam O'Keefe
Sam O'Keefe
Flex

Miguel Toledo, Founder

Miguel is a cofounder at Flex. Previously built software to make machine learning infrastructure and data pipelines work at Lyft Level 5, fraud and AML products at Unit 21, and monitoring systems at Google Cloud.
Miguel Toledo
Miguel Toledo
Flex
Company Launches
Flex Market: Marketplace for HSA/FSA
See original launch post ›

We’re excited to introduce Flex Market, a new marketplace designed to make health and wellness more accessible.

Here’s a glimpse of what you’ll find on Flex Market:

  • 🏋️‍♀️ Fitness programs and equipment
  • 🧴 Supplements
  • 💆‍♀️ Sleep and recovery products
  • ⌚ Wearables
  • 🏥 Traditional OTC health products (eyeglasses, women’s health products etc)

Why Flex Market is Unique

For products like supplements, fitness equipment or other “dual use” items, consumers are required to have a doctor's note, or Letter of Medical Necessity (LMN), to qualify to spend their HSA/FSA funds.

Flex is the only place where consumers can both shop for traditional healthcare products (think what you might expect to find at a CVS) as well as those items that require a Letter of Medical Necessity (LMN). For those that require the latter, consumers can initiate a two minute telehealth consultation immediately, qualify, and receive their LMNs later that day.

Quick HSA/FSA Background

Health Savings Accounts and Flexible Spending Accounts are tax advantaged accounts that are designated to be spent on healthcare related purchases. Historically these funds have only been able to be spent on trips to the doctor’s office or buying items at CVS.

FSAs are use-it-or-lose-it, meaning that at the end of the year any funds that aren't spent are forfeited. On average, individuals lose about $450 per year, resulting in nearly $10B of lost benefits.

Why it Matters

Flex Market isn’t just a shopping platform – it’s part of a larger mission to make health and wellness more accessible.

By addressing the barriers of traditional HSA/FSA spending, we’re helping people:

  • Avoid forfeiting their hard-earned HSA/FSA funds
  • Discover new ways to invest in their health
  • Making health products and services more accessible

Check Us Out Today!

If you or someone you know has FSA funds to spend before year-end or is gearing up for health-related purchases as part of a New Year’s resolution, check out Flex Market! If you’re interested in seeing your brand on the marketplace, reach out to us here.

Thanks so much for your support – and here’s to a healthier 2025! 💪

Other Company Launches

💪 Flex: Stripe for HSA/FSA payments

We enable businesses to unlock the $120B per year sitting in HSA/FSA accounts.
Read Launch ›