Job description

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, most merchants lacked the infrastructure to process these payments at checkout, leaving customers to deal with frustrating reimbursement paperwork instead. 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 joining a small but growing Support Engineering team embedded within Engineering, working at the intersection of customer-facing support and technical problem solving. This role blends hands-on merchant and customer support with real engineering work — building internal tooling, automating workflows, and partnering closely with the broader Engineering team to ship fixes and improve our systems. 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

Requirements

Must-haves

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

Nice-to-haves

None flagged.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

sql

Platform: ashby
Effort: quick

Benefits

Benefits detected in the listing.

Dental

Vision

Pto

Parental Leave

Wellness