Flex, a fast-growing platform that enables health and wellness retailers to accept Health Savings Account (HSA) and Flexible Spending Account (FSA) payments, has announced the close of a $15 million Series A funding round. This latest investment brings the company’s total capital raised to $18 million. It marks a significant step forward in its mission to unlock the vast, underutilized pool of pre-tax health spending. The funding round was led by First Round and Core VC, with additional support from Cameron Ventures, Rethink Impact, Y Combinator, and Liquid2.
Flex’s platform is already powering payments for hundreds of health and wellness brands, and its momentum is accelerating. Through new partnerships with major retailers like Dermstore, iFit, and Therabody, Flex is making it easier for consumers to use their pre-tax dollars on eligible products and services. By integrating directly into the checkout experience, Flex allows shoppers to apply their HSA/FSA funds seamlessly, often saving between 30$ and 40% on purchases. For merchants, this translates into higher conversion rates, larger average order values, and stronger customer retention—all driven by a payment method that many consumers didn’t even realize they could use for everyday wellness needs.
The company’s technology is designed to remove the friction that has long plagued HSA/FSA acceptance. From real-time eligibility checks to automated handling of Letters of Medical Necessity, Flex simplifies what has traditionally been a cumbersome process. It also supports subscription models and split-cart payments, making it easier for consumers to combine eligible and non-eligible items in a single transaction. On the backend, retailers benefit from a dashboard that provides clear visibility into performance metrics, usage trends, and revenue impact—without the need for manual claims processing or reimbursement delays.
With this new round of funding, Flex plans to scale its team, enhance its platform capabilities, and deepen its relationships with enterprise retailers. The goal is to position HSA/FSA payments not just as a niche offering, but as a mainstream growth channel that can drive meaningful business outcomes. As more consumers look for ways to manage their health expenses and invest in wellness, Flex is helping retailers meet that demand with a payment experience that is intuitive, compliant, and financially beneficial.
The broader context for Flex’s growth is the changing landscape of healthcare and consumer wellness. People are increasingly taking a proactive approach to their health, investing in products and services that support long-term well-being. At the same time, the complexity of the healthcare system often leaves consumers unsure of how to use the benefits available to them. Flex bridges that gap, turning HSA and FSA accounts into powerful tools for everyday health management.
Whether someone is recovering from a medical procedure, managing a chronic condition, or simply trying to live a healthier life, Flex offers a way to make those choices more affordable and accessible. The platform empowers consumers to use the money they’ve already set aside for health-related expenses, while helping retailers grow their businesses in a way that aligns with the values of transparency, affordability, and care.
How the funding will be used: The funding will enable Flex to expand its reach into the enterprise market, helping more retailers tap into the $150 billion in annual HSA/FSA spending that often goes unused or underleveraged.
KEY QUOTES:
“We’re building the financial infrastructure that connects people’s health benefits to the products and services that genuinely support their everyday wellbeing. This funding allows us to partner with the most influential health and wellness retailers, making it simple for millions of Americans to put their healthcare dollars to work. Health today extends far beyond the doctor’s office—it’s in our homes, our movement, and the daily choices we make. Our goal is to ensure the brands empowering healthier living are just as seamless to buy from as any other retailer.”
Sam O’Keefe, CEO of Flex
“We’re thrilled to back Flex as they unlock a smarter way for Americans to use their pre-tax dollars on everyday health and wellness. Their payments infrastructure serves the technical needs of companies at scale, and the retailers integrating Flex are seeing significant business impact.”
Liz Wessel, Partner at First Round
