Mid Market Account Executive

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 Mid Market Account Executive to join our growing team and own a portfolio of strategic named accounts. This is a high-impact, quota-carrying role for a senior seller with a track record of landing and expanding enterprise relationships, preferably in payments and/or ecommerce.

You’ll be responsible for prospecting, building pipeline, and leading complex consultative sales cycles with key accounts. This role is perfect for someone who thrives in a fast-paced environment, enjoys strategic selling, and wants to shape the future of Flex’s go-to-market motion.

What You’ll Do

• Own and grow a portfolio of strategic named accounts, focusing on both net-new wins and expansion opportunities.

• Develop and execute account plans for top targets, identifying key stakeholders, business needs, and value creation opportunities.

• Proactively generate pipeline through outbound prospecting, conference networking, and targeted event engagement.

• Lead complex, consultative sales cycles from discovery to close, leveraging proven sales methodologies such as MEDDICC.

• Collaborate cross-functionally with Marketing, Partnerships, and Product to deliver tailored solutions that solve customer challenges.

• Serve as a senior contributor on the sales team—mentoring peers, sharing best practices, and influencing strategy.

• Accurately forecast and report on pipeline and deal progression using CRM best practices.

• Represent Flex at industry conferences, prospect events, and partner summits to drive brand visibility and customer engagement.

• Participate in company-wide offsites held a few times per year to align, collaborate, and celebrate wins.

Who You Are

• 2–3+ years of mid-market sales experience with a proven record of exceeding quota.

• Demonstrated success selling into strategic accounts with multi-stakeholder, long-cycle deals.

• Industry experience in payments and/or ecommerce strongly preferred.

• Proficiency in a structured sales methodology (MEDDICC, Challenger, SPIN, etc.) and disciplined forecasting.

• Strong ability to prospect and self-generate pipeline while leveraging internal resources.

• Executive presence and excellent communication skills, capable of influencing C-suite buyers.

• Willingness to travel for conferences, events, and client meetings (~25%).

Mindset

• Low ego — open to feedback and growth.

• Collaborative — thrive in cross-functional team settings.

• Hustler — put in the effort required to make things happen.

• Self-starter — quick to learn new technologies and skills.

Why Join Flex

• Backed by Y Combinator, First Round Capital, Core Innovation Capital, and SV Angel.

• Competitive compensation, equity, and unlimited PTO.

• Health, dental, and vision insurance for employees.

• Opportunity to work alongside a hard-working, high-performance team that celebrates wins together.

• Company offsites a few times per year to build relationships and shape strategy.

• Direct impact on revenue and strategic partnerships.

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.