Support Engineer at Flex in Remote

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. 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 hiring a Support Engineer to help scale our support function as we grow. You’ll be the first hire under our founding Support Engineer, and you’ll play a key role in resolving merchant and customer issues, owning internal tooling, and helping build scalable support systems from the ground up.

This role is perfect for someone who loves solving problems, thrives in ambiguity, and is excited about building foundational support infrastructure at an early-stage startup.

What you’ll do

• Triage and respond to daily merchant and customer tickets via Slack and Pylon

• Ensure we meet SLA targets and maintain a high bar for customer satisfaction

• Deliver clear, thoughtful, and technically sound responses across internal and external communications

• Work closely with Engineering, Product, and Operations teams to unblock support issues and escalate bugs or system issues

• Contribute to internal tooling using Retool, Metabase, and SQL to help automate workflows and reduce support friction

• Collaborate on internal projects to help the Support team scale efficiently as we grow (e.g., bulk editing workflows, data validation tools, process documentation)

• Ensure the broader internal team has the tools and visibility they need to deliver a great customer experience

• Partner with Engineering to test new product functionality, edge cases, and backend fixes before rollout

• Build and maintain internal documentation for support workflows, product edge cases, and tooling tips

• Help define and improve tagging, categorization, and data structure for tickets to power better reporting and insights over time

Who You Are

• You have a foundational understanding of APIs, JSON, Postman, and Retool

• You’re curious, resourceful, and comfortable picking up technical tools on the fly

• You have strong written communication skills and a customer-first mindset

• You take initiative and thrive in fast-paced, scrappy environments

• You’re excited to wear many hats and aren’t afraid to build something from scratch

Why Join Flex

• Work directly with founders and leadership on high-impact initiatives.

• Equity compensation with competitive salary.

• Medical, dental, and vision plans.

• Unlimited PTO and sick days.

• Paid parental leave.

• Flexible, remote-first team with quarterly in-person meetups.

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.