About Flex
Flex was founded to solve a simple but costly problem: making it easy for health and wellness brands to accept HSA and FSA payments online.We're backed by First Round, Core VC, Rethink Capital power checkout for Equinox, Dermstore, Therabody, and Ultrahuman to name a few. For years, only giants like Amazon and Walmart could process these payments at checkout, leaving smaller merchants — and their customers — to deal with frustrating reimbursement paperwork.
Our technology verifies product eligibility in real time, handles split payments for eligible and non-eligible items, and can even issue Letters of Medical Necessity during checkout. With $150 billion in annual HSA/FSA spending potential, we’re giving brands the tools to unlock new revenue and making it easier for consumers to use the benefits they’ve earned.
About the Role
We're looking for a Director of Operations to be our first operations hire - building a new venture from the ground up, from concept to delivery. You'll own the operational infrastructure and compliance foundation that scales.
The right person has done this before at an early-stage healthtech company. They know what it takes to move fast without cutting corners on the things that matter. This is a role for someone who thrives in ambiguity, takes initiative, and wants to build something from scratch.
What You’ll Do
Own the operational backbone of this venture from day one - concept through execution
Drive regulatory readiness and stay ahead of the compliance requirements that come with operating in a regulated healthcare environment
Design and improve the workflows that keep the operation running - and running well.
Stand up the full network: recruiting, onboarding, and performance management
Define the metrics that matter - turnaround time, quality, throughput, compliance - and build the dashboards and rituals around them
Partner with Flex's product and engineering teams to translate operational needs into platform requirements
Write the playbooks, policies, and documentation that let this operation scale beyond you
Who You Are
You've built or scaled an operation before - ideally as one of the first operations hires at an early-stage healthtech company
You've worked closely with outside counsel and know how to turn legal guidance into operational decisions without losing momentum
You've designed workflows that balance compliance, experience, and speed - and you've measured and improved them
You operate with high ownership, write clearly, and make decisions with incomplete information
You're energized by greenfield builds, lean teams, and the ambiguity that comes with both
Why Join Flex
A mission-driven team making healthcare spending effortless
Early-stage impact - your work will directly shape our growth and success
Collaborative, high-trust, and transparent culture
Competitive compensation and equity package
Flexible, remote-friendly work environment