Enterprise Account Executive

Flex Factor is the first AI-powered platform that identifies and intercepts false payment declines in real time, preventing checkout from ever failing for cardholders. Backed by Bessemer Venture Partners, Flex Factor is reengineering how merchants reverse the negative economic impacts of false declines – including lost revenue, reduced LTV, and wasted CAC.

As a Series A startup, Flex Factor's fast-pace enviroment is best suited for those looking to join a rocket ship early. We work hard, work fast, and have fun!

Flex Factor prevents false payment declines in real time, helping businesses protect revenue, improve authorization rates, and deliver better customer experiences at checkout.

We are hiring an Enterprise Account Executive to lead complex sales cycles within strategic organizations. This role focuses on understanding operational and financial impact, building consensus across stakeholders, and driving deals from discovery through close.

You will work opportunities generated by Enterprise BDRs and also originate your own pipeline within target accounts. Success in this role comes from strong discovery, business acumen, and the ability to translate payment performance challenges into measurable ROI for executive buyers.

You will partner with solutions, product, and leadership teams to guide prospects through evaluation, align technical and business stakeholders, and create buying momentum across finance, payments, and risk organizations.

• Run full enterprise sales cycles from discovery through close
• Lead multi-stakeholder conversations across finance, payments, risk, and executive leadership
• Quantify business impact and build ROI-driven business cases
• Navigate procurement, security, and technical validation processes
• Develop and execute account strategies with BDRs and leadership
• Expand opportunities through multi-threading and internal champions
• Maintain accurate pipeline forecasting and deal strategy in CRM
• Collaborate with product and implementation teams to ensure successful handoff
• Generate additional pipeline within target accounts when needed

• 5+ years of closing experience in B2B SaaS, fintech, or payments environments
• Proven track record closing complex mid-market or enterprise deals
• Experience selling into finance, payments, fraud, or operational stakeholders
• Strong discovery and business case development skills
• Comfortable navigating long sales cycles and multiple decision-makers
• Ability to manage pipeline, forecast accurately, and prioritize effectively
• High ownership mindset and strong communication skills

• Payments ecosystem experience (processor, gateway, orchestration, fraud, risk, or issuing)
• Experience selling ROI-driven solutions to CFO or finance leadership
• Familiarity with Hubspot and modern sales engagement tools

• Closed-Won Revenue – Achievement of quarterly and annual quota
• Pipeline Conversion Rate – Progression of qualified opportunities to close
• Forecast Accuracy – Reliable deal management and predictability

• Competitive base salary plus commission
• Competitive base salary plus uncapped commission
• Equity participation in a high-growth fintech company
• Strategic deal exposure and executive visibility
• Health, dental, and vision insurance
• Flexible paid time off and company holidays
• Remote-friendly work environment and home office support
• Access to modern sales and data tools
• Ongoing training and career development opportunities