Flex

Founding Solutions Architect

United States · Exec

Sponsorship not specified$160k-$260kDetected 84 days ago

RailsSketchSalesLogisticsProcurementCustomer Success

About the role

This is the highest-leverage Solutions Architecting job we'll ever hire for.
You won't be parachuted in for a single demo and pulled back out.
You'll be embedded with sales from first call through contract, integration, and expansion, and you'll be the person who turns "this looks interesting" into a signed and live merchant.

You'd be the first dedicated SA at a category-creating company in a $150B market. The deals you close and the assets you build define how Flex sells to enterprise for years
As our Founding Solutions Architect, you own the technical motion for every strategic and enterprise deal at Flex.
The technical narrative for every enterprise deal, from first discovery call through security review, integration design, and go-live
Remote-first, with quarterly in-person meetups. Expect ~25% travel for prospect on-sites, partner conversations, and industry events
The category we're building didn't exist two years ago, and the enterprise opportunity in front of us is the next chapter.

7+ years in Solutions Architecture, Sales Engineering, or Solutions Engineering, with at least 3 years selling into enterprise
You can read API docs, sketch an integration on a whiteboard, and ship a working POC when a deal calls for it.
You've been at a seed or Series A/B company before and you know what "first one in the seat" actually feels like
You can tell us in six months which assets moved deals and which didn't

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.

making it easy for health and wellness brands to accept HSA and FSA payments online.
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.
Meaningful founding-team equity
Medical, dental, and vision plans
Unlimited PTO and sick days
Paid parental leave

Comfortable in early-stage chaos. You've been at a seed or Series A/B company before and you know what "first one in the seat" actually feels like
You get energy from being in front of customers, not behind a deck

complex direct API integrations, payments rails, eligibility logic, and healthcare compliance
Flex is an equal opportunity employer and encourages applicants from all backgrounds and life experiences.
We celebrate diversity and do not discriminate based on race, religion, color, national origin, sexual orientation, gender identity, gender expression, age, veteran status, disability status, or any other legally protected characteristic.

This listing is sourced directly from Flex's careers page and normalized into a canonical job model.