Stripe for HSA/FSA payments

Founding AE

$60K - $120K
San Francisco, CA, US / Remote (US)
Job Type
1+ years
Connect directly with founders of the best YC-funded startups.
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Sam O'Keefe
Sam O'Keefe

About the role


Flex enables businesses to accept HSA/FSA payments, unlocking the $120B sitting in these accounts. We’re an early stage startup backed by Y-Combinator, SV Angel, Liquid2, and Precursor Ventures, with angels from Stripe, Shippo, Unit21, and OpenAI.

We ascribe to Netflix’s “Dream Team” culture and strive for every team member to be exceptional in their role and as teammates. Our team is remote across US time zones with quarterly in person meetups. Given this, the ability to operate autonomously is an absolute must.

The role

We’re looking for the rare account executive who is both a star seller but a builder at heart. This is a unique role offering the opportunity to collaborate with the CEO on defining our sales strategy and own the execution.

While a traditional AE role is primarily focused on running a pre-existing playbook, we’re looking for a seller who wants to write the playbook. We think 3 traits will drive success for a seller in this role:

  • Owner Mindset - Is deeply curious and challenges how things are done. They have a strong bias for action and drive fast experimentation.
  • Sales IQ - Has a track record of excellence in tech sales. Minimum of 1+ years of closing experience w/deal sizes in the $10-50K ACV range.
  • Ambitious -Wants an opportunity to prove themselves while working closely with the founders as we learn and apply quickly.

This is an exciting opportunity for an account executive who wants to be on the ground floor of building an early stage startup. As our founding account executive, your responsibilities will span beyond a traditional sales role. You’ll be involved in positioning, pricing, product feedback, and more.

To start, you’ll inherit our outbound pipeline and process. As we continue to grow, you’ll also be responsible for our inbound pipeline.


Hard requirements:

  • Closing Experience 1+ years of quota carrying, tech sales closing experience
  • Strong track record of success. We will do reference checks on your attainment history.

Nice to have:

  • Business Development 1+ year of BDR experience at a SaaS company
  • Previous startup experience ideally, at a seed through series B startup


Low Ego - You’re not above any task. You readily accept feedback and view it as an opportunity for growth. Collaborative - You thrive in team settings, naturally working across functions to drive the best outcomes for our customers. Hustler - You put in the effort required to make things happen. Organized - You know your pipeline like the back of your hand and your CRM is always up to date with deal details. Self starter - You know how to teach yourself new tools, skills etc.


  • Equity compensation
  • Medical, dental and vision plans
  • Unlimited PTO and sick days
  • Parental leave

Flex is an equal opportunity employer and encourages all applicants from every background and life experience. We celebrate diversity and do not discriminate based upon race, religion, color, national origin, sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.

About Flex

Flex enables businesses to accept HSA/FSA payments, unlocking the $120B sitting in these accounts. We're on a mission to make health more accessible.

Team Size:2
Sam O'Keefe
Sam O'Keefe
Miguel Toledo
Miguel Toledo