Enterprise Account Executive

October 23

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Flex

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Fintech • SaaS • B2B

Flex is a SaaS payments infrastructure company that enables merchants and brands to accept HSA/FSA and other health-benefit payments. Its API-first platform integrates with e-commerce platforms (Shopify, WooCommerce, etc. ) and supports complex flows like split-card payments, subscriptions, eligibility verification, automated Letters of Medical Necessity, and enterprise-scale reporting to boost conversion and average order value. Flex is aimed at health, wellness and fitness brands that want to unlock pre-tax benefit spend at checkout while staying compliant.

11 - 50 employees

Founded 2023

💳 Fintech

☁️ SaaS

🤝 B2B

📋 Description

• Own and grow a portfolio of strategic enterprise 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.

🎯 Requirements

• 2–3+ years of enterprise 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%).

🏖️ Benefits

• 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.