Support Engineer

Flex; Oregon; Hybrid; USD 90,000 - 120,000; Full time

Benefits offered by this job

Equity compensation

Medical, dental, and vision plans

Unlimited PTO and sick days

Paid parental leave

Flexible, remote-first team with in‑p

Quarterly in-person meetups

Job summary

Flex is hiring a Support Engineer to scale our support function within Engineering, blending customer-facing support with technical problem solving. You’ll triage merchant and customer tickets, contribute to internal tooling with Retool, Metabase, and SQL, and collaborate with Engineering, Product, and Operations to unblock issues.

This remote-first role offers equity, health plans, unlimited PTO, parental leave, and quarterly in-person meetups, with an opportunity to build foundational support

Qualifications

• Foundational understanding of APIs, JSON, Postman and Retool.
• Strong written communication and a customer-first mindset.
• Self-starter who builds processes in ambiguity and takes initiative.
• Comfort with AI tools and automation to accelerate work.

Responsibilities

• Triage and respond to daily merchant and customer tickets via Slack and Pylon.
• Meet SLA targets and maintain high customer satisfaction.
• Provide clear, thoughtful, technically sound responses across communications.
• Collaborate with Engineering, Product, and Operations to unblock issues.
• Contribute to internal tooling using Retool, Metabase, and SQL.
• Develop AI-assisted workflows and automation to speed support.
• Help scale the Support team with data-driven improvements.

Skills

Self-starter

APIs

JSON

Postman

Retool

SQL

Slack

Customer-first mindset

Written communication

AI tools

Tools

Retool

Postman

Metabase

SQL

Slack

Pylon

Job description

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, 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. Not everything here has a process yet. We're looking for someone with real judgment and common sense: when you hit a problem nobody has solved before, you think it through, figure out the right steps, and fix it, rather than waiting for a playbook.

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 elevate bugs or system issues
• Contribute to internal tooling using Retool, Metabase, and SQL to help automate workflows and reduce support friction
• Use AI tools and automation to make support faster and smarter, from scripts and integrations to AI-assisted workflows and internal agents
• 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're a self-starter with strong critical thinking. When there's no process, you figure out the right steps and help build one
• 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
• You're comfortable using AI tools (Claude, ChatGPT, etc.) and automation platforms to work faster

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