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Flex

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Flex

Stripe for HSA/FSA payments

withflex.com
HQ: Remote
1-10
Fintech

Company research

Public company, workplace, funding, and market signals

Updated Aug 2, 2026

Overview

Flex Technology Co (Flex) is a San Francisco fintech/health-commerce company founded in 2023. It helps health and wellness brands and benefits platforms accept and grow HSA/FSA spending, while also operating a consumer marketplace for eligible products. Flex says its platform has processed 2M+ orders and supports more than 1,000 brands.

Primary product

HSA/FSA payments and commerce infrastructure: hosted or embedded checkout, real-time product eligibility, split-cart payments, Letters of Medical Necessity, recurring-payment support, merchant analytics, and an HSA/FSA marketplace.

Founded

2023

Headquarters

San Francisco, California, United States

Team size

30–40 employees (LinkedIn company data, July 2026); YC previously listed 8 employees.

Work style

Remote

Industry

Financial Services

Sub-industry

Healthcare payments, fintech infrastructure, and health/wellness commerce

Offices

San Francisco, California
Miami, Florida
New York, New York
Distributed workforce across the United States and Canada

Business model

B2B payments infrastructure for merchants
Merchant SaaS/API and e-commerce integrations
HSA/FSA eligibility and compliance services
Consumer HSA/FSA marketplace
Benefits-platform distribution partnerships

Funding

Stage

Series A

Total raised

$18M

Latest round

Series A · Sep 2025

Latest amount

$15M

Series A

Sep 2025 · First Round Capital and Core VC

$15M

Seed

Sep 2024

$3.2M

People & investors

Leadership

Sam O'Keefe

Co-Founder & CEO

Miguel Toledo

Co-Founder & CTO

Eugene L.

Head of Engineering

Benjamin Cole

Head of Compliance

Investors

Cameron Ventures
Core Innovation Capital
Core VC
Core VC / Core Innovation Capital
First Round Capital
Heirloom Ventures
Liquid 2 Ventures
Precursor Ventures
Rethink Impact
SV Angel
Y Combinator

Work & culture

Remote-first and early-stage: high ownership, direct access to founders and customers, small teams, fast execution, and responsibility for building payments, eligibility, compliance, and marketplace infrastructure. Public recruiting materials emphasize a diverse, vibrant team and quarterly in-person meetups.

Work style

Remote

Compensation

Public engineering postings show approximately $150,000–$220,000 annual base salary plus equity, depending on role. Sponsorship is not explicitly stated; postings mention hiring in the U.S., Canada, and Colombia.

Benefits

Medical insurance
Dental insurance
Vision insurance
Unlimited PTO
Unlimited sick days
Paid parental leave
Equity compensation
Quarterly in-person meetups

Product & market

Pricing

Not publicly disclosed. Flex appears to use a merchant/platform commercial model for payment acceptance, integrations, and related services; consumer marketplace pricing is product-specific.

Differentiators

  • —Purpose-built HSA/FSA payments infrastructure for e-commerce and wellness rather than general-purpose payments
  • —Real-time eligibility determination and compliance support
  • —Split payments for eligible and non-eligible items
  • —Letters of Medical Necessity during checkout
  • —Hosted checkout, APIs, and native e-commerce integrations
  • —Merchant analytics, attribution, merchandising, and marketing support
  • —Combines merchant infrastructure with a consumer marketplace
  • —Supports recurring payments and omnichannel use cases

Technology

Next.js
TypeScript
React
Rust
Node.js
Postgres
Redis
AWS
SQL
Snowflake or BigQuery
PyTorch
Hugging Face Transformers
ML/data pipelines

Customers

Dermstore
iFit
Therabody
Equinox
Ultrahuman
Forme
Kindred Bravely
Chilipad by Sleepme
JOON (benefits-platform partner)
SHOPLINE (platform partner)
RevenueCat (platform partner)

Competitors

Keyrails
Flex's adjacent alternatives include traditional HSA/FSA payment processors, reimbursement workflows, and large retailers such as Amazon and Walmart

Scale & contact

Estimated revenue

Approximately $1.5M–$2M annual revenue (third-party estimate for 2024; not company-reported or audited)

support@withflex.com

Latest news

Flex appoints Eugene L. as Head of Engineering

Flex on LinkedIn · Jul 2026

Flex announced Eugene L. as Head of Engineering; the role covers engineering teams building eligibility, marketplace, and payments infrastructure.

Flex Partners with JOON to Bring HSA/FSA Shopping to Employer Benefits Platforms

GlobeNewswire · May 2026

Flex integrated its HSA/FSA marketplace into JOON's employer benefits platform, extending distribution to employer clients and employees.

Flex Partners with Equinox to Unlock HSA/FSA Funds for Members

Fitt Insider · Feb 2026

Flex announced an Equinox partnership covering HSA/FSA use for selected memberships, training, recovery, and wellness offerings.

Flex + SHOPLINE: Enabling HSA/FSA Payments for In-App Subscriptions

Flex blog · Nov 2025

Major partnership announcing HSA/FSA payment acceptance for SHOPLINE’s merchants via Flex.

Flex + RevenueCat: Enabling HSA/FSA Payments for In-App Subscriptions

Flex blog · Nov 2025

Launch of Flex’s HSA/FSA payment support inside RevenueCat-managed iOS, Android, and web subscriptions.

Announcements categoryBlogBusiness product pageCareersCareersContact salesDeveloper documentationEngineering / product blogHomepageInstagram
SourcesFlex official websiteFlex Series A announcementFlex Series A—GlobeNewswireYC company profileYC LaunchLinkedIn company pageFlex careers listingFlex backend engineering listingGetLatka third-party metricsFlex contact page

Jobs and careers at Flex

39 jobs at Flex

Senior Staff Software Engineer, Partner Integrations

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New York, NY; Salt Lake City, UT; San Francisco, CA; New York, NY; Salt Lake City, UT; San Francisco, CA
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Staff Software Engineer, Backend

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4d ago
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Senior Software Engineer, Backend

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4d ago
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Staff Software Engineer, Martech

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4d ago
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Senior Manager, Capital Markets

On-site
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New York, NY; Salt Lake City, UT; San Francisco, CA; New York, NY; Salt Lake City, UT; San Francisco, CA
4d ago
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Sales Development Representative I

On-site
Revenue
Salt Lake City, UT
1w ago
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Lifecycle Marketing Manager

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New York, NY; San Francisco, CA; New York, NY; San Francisco, CA
1w ago
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Director, Strategic Partnerships

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New York, NY; San Francisco, CA; New York, NY; San Francisco, CA
1w ago
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Sr. Staff Analytics Engineer

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1w ago
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Staff Data Scientist

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1w ago
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Senior Director, Product Partnerships

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New York, NY; San Francisco, CA; New York, NY
2w ago
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Senior Manager, Account Management (Rent)

On-site
Revenue
New York, NY; Salt Lake City, UT; San Francisco, CA; New York, NY
2w ago
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Staff Software Development Engineer in Test (SDET)

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2w ago
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Staff Data Scientist, New Verticals

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Director, Sales Solutions Engineering

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2w ago
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Associate Director, Product Compliance

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New York, NY; Salt Lake City, UT; San Francisco, CA; New York, NY
3w ago
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Sr Staff Data Scientist, New Verticals

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3w ago
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Staff Product Designer, Consumer

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Design
New York, NY; Salt Lake City, UT; San Francisco, CA; New York, NY; Salt Lake City, UT; San Francisco, CA
4w ago
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Principal Product Designer, Consumer

On-site
Design
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4w ago
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Senior Software Development Engineer in Test (SDET)

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4w ago
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Senior Director of Product, New Venture

On-site
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1mo ago
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Staff Product Designer (Contract)

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Senior Director, Revenue Strategy & Operations

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Senior Staff Decision Science (Risk)

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Director, Financial Systems & Transformation

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2mo ago
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Strategic Account Executive, New Vertical Sales

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Associate General Counsel

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2mo ago
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Director, Account Management

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2mo ago
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Senior Director, Product Compliance

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2mo ago
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Strategic Account Manager

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2mo ago
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Associate General Counsel, Product & Regulatory

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3mo ago
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Director of Product, Payments Platform

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3mo ago
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Senior Manager, Strategic Partnerships

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3mo ago
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Vice President, Business Development & Strategic Partnerships

On-site
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4mo ago
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Manager, Corporate Accounting

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Accounting
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4mo ago
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Senior Director, Business Development (New Verticals)

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6mo ago
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