hsa-fsa-payments
(3)
I V Y Labs
I V Y Labs is a San Francisco mobile-first company building simple, HIPAA-secure tools for independent mental health providers. Its flagship product, Ivy Pay, lets therapists charge a client's credit, debit, HSA or FSA card on file with a single button push - no card readers, checks or monthly fees - at a flat 2.75% per transaction. Founded by former Yelp executive Mandy Silverman, the company set out to remove the awkward friction of getting paid so therapists can focus on care, and has expanded toward helping clients discover and connect with the right therapist.
Prado
Prado is an Austin-based Food-as-Medicine platform that lets clinicians prescribe medically tailored meals and lets patients pay for them with pre-tax HSA/FSA dollars. It stitches together the parts that usually don't talk to each other - a compliant Letter of Medical Necessity, HIPAA- and IRS-approved checkout, white-label storefronts, and fulfillment - so healthy prepared food becomes both prescribable and reimbursable. Founded in 2020 by former Snap Kitchen CEO Jon Carter, Prado has supported the sale of more than 25 million meals and connects food operators to a network of 70M+ tax-advantaged account holders.
Sam O'Keefe
Sam O'Keefe is the co-founder and CEO of Flex, the San Francisco fintech often called 'Stripe for HSA/FSA payments.' Flex lets health and wellness brands accept the roughly $150 billion of tax-advantaged health-account money that Americans leave sitting unused every year, turning a confusing benefits process into a one-tap checkout. A two-time Y Combinator founder who previously built fraud and risk software at Unit21 and led startup programs at Google, O'Keefe raised a $15M Series A in September 2025 to make 'pay with HSA/FSA' as ordinary at checkout as PayPal.