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About FlexFlex was founded to solve a simple but costly problem: 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.We're backed by First Round, Core VC, Rethink Capital power checkout for Equinox, Dermstore, Therabody, and Ultrahuman to name a few. The category we're building didn't exist two years ago, and the enterprise opportunity in front of us is the next chapter.About the RoleThis is the highest-leverage Solutions Architecting job we'll ever hire for. As our Founding Solutions Architect, you own the technical motion for every strategic and enterprise deal at Flex. You'll be embedded with sales from first call through contract, integration, and expansion—turning “this looks interesting” into a signed and live merchant.You'll be the loudest voice of the customer inside Flex: patterns you spot in enterprise conversations, integration shapes prospects keep asking for, compliance gaps that block deals, and capabilities competitors are claiming all flow directly into product and engineering's roadmap. You work directly with our VP of Sales and CTO, alongside our founders, sales team, and engineering org.What You'll OwnThe technical narrative for every enterprise deal, from first discovery call through security review, integration design, and go-liveCustom integration architectures for complex merchant-built checkouts (primarily direct API integration with sophisticated, custom commerce stacks)Live POCs, sandbox demos, and integration walkthroughs that move six- and seven-figure deals across the lineThe structured feedback loop into product and engineering, synthesizing what enterprise prospects need, where we're losing on capability, and where the next durable bet isReusable enablement assets, including reference architectures, integration playbooks, security and compliance one-pagers, and ROI models that scale the GTM teamSmooth handoff to customer success and engineering for post-sale implementationWho You Are7+ years in Solutions Architecture, Sales Engineering, or Solutions Engineering, with at least 3 years selling into enterpriseOwned the technical side of complex, multi-stakeholder deals involving a CTO, a CISO, a head of e-commerce, and procurementCan read API docs, sketch an integration on a whiteboard, and ship a working POC when a deal calls for it (without needing an engineer in the room)Background in payments, fintech, e-commerce, or healthtech is strongly preferred; HSA/FSA, benefits, or regulated payments is a major plusBuilt feedback channels into product orgs that engineers actually trustWrites well: crisp follow-ups, clean architecture diagrams, briefs an exec can read in 90 secondsComfortable in early-stage chaos; has been at a seed or Series A/B company and knows what “first one in the seat” feels likeHow You ThinkTranslates fluently between a CTO, a compliance officer, and a marketing lead, knowing which version of the answer each needsGets energy from being in front of customers, not behind a deckInstruments what you do and can explain which assets moved deals and which didn’tA builder: the first version of every playbook here will have your fingerprints on itCompensation & LogisticsOTE: $160,000 to $260,000, structured as base plus variable tied to enterprise pipeline and closed-won attainmentMeaningful founding-team equityMedical, dental, and vision plansUnlimited PTO and sick daysPaid parental leaveRemote-first, with quarterly in-person meetups; expect ~25% travel for prospect on-sites, partner conversations, and industry eventsWhy This Role, Why NowYou'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 yearsYou'd work directly with founders on deals and product decisions that shape the companyThe technical surface area is meaty: complex direct API integrations, payments rails, eligibility logic, and healthcare complianceFlex 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.
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