Strategic Account Executive, Mid Market - New Vertical Sales

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team? About the Role We are seeking an entrepreneurial and highly accomplished Strategic Account Executive for our New Vertical Sales team to drive Flex's expansion into new sectors. Flex is on a mission to give consumers control over their most significant recurring expenses — and the essential bills Americans pay every month represent one of the largest, most underserved opportunities to do exactly that. They are a defining financial commitment for millions of Americans, yet the flexibility and control consumers expect from modern financial products has largely passed these categories by. As a Strategic Account Executive, you will own Flex's commercial push into this space, building the partnerships that establish Flex as the embedded payment layer for consumers. You will operate with significant independence, helping define your own territory strategy, managing a high-value pipeline, and closing complex, multi-stakeholder deals without heavy oversight. You will also serve as a strategic voice back into Flex — translating partner feedback and market dynamics into actionable input for Product, Marketing, and Pricing. Success here means building something durable: not just a closed deal, but a scalable playbook, a respected presence in the market, and partnerships that deliver measurable value for Flex’s partners and their customers. You will work cross-functionally with Product, Engineering, Finance, and Marketing — and you’ll raise the bar for how enterprise sales is done at Flex. • Build and execute a territory strategy, identifying and prioritizing the highest-value mid-market and SMB opportunities • Own the full sales cycle from prospecting to close, managing a disciplined pipeline with urgency and converting opportunities into live, revenue-generating partnerships • Develop and maintain C-level and senior decision-maker relationships at target organizations, serving as a credible advisor who deeply understands partner priorities and articulates Flex’s value with precision • Lead complex, multi-stakeholder deal negotiations end-to-end — structuring partnership economics, navigating legal and procurement processes, and maintaining deal momentum through close • Shepherd each partnership from signed agreement through technical deployment and go-live, partnering cross-functionally with Product and Engineering to ensure strong early performance • Feed competitive intelligence and partner feedback back into Flex’s GTM and product direction, helping sharpen positioning and the offering for the vertical • Build the vertical sales playbook — documenting learnings, establishing repeatable processes, and creating the partner acquisition motion that enables efficient growth beyond initial market entry • Leverage AI-assisted sales tools to drive pipeline efficiency, personalize outreach at scale, and accelerate deal progression What you’ll bring • 5+ years of experience in sales with meaningful experience selling into mid-market and SMB enterprises • A proven track record of closing complex, first-of-kind deals in new or emerging markets, ideally involving embedded financial products, consumer payments, or BNPL in high-ACV, multi-stakeholder environments • Executive presence and influence — you’ve operated confidently at the C-suite level, building trust with senior decision-makers and navigating complex organizations to drive outcomes • Strong financial and legal acumen — you can build and defend deal models, structure partnership economics, and negotiate agreements with both commercial rigor and pragmatic deal-making • High agency and comfort with ambiguity — you define your own approach in undefined spaces, bring clarity and momentum to evolving situations, and don’t wait for direction to take initiative • Experience contributing to team-level strategy — sharing market insights, advocating for AI-enabled workflows, and helping elevate sales craft across the organization • Proficiency with AI-assisted sales tools as a core part of your workflow — you actively use them to sharpen outreach, manage pipeline intelligence, and accelerate deal cycles Compensation The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. This is a commission earning role. The OTE (On Target Earnings) listed below: OTE (NYC/Bay Area, Los Angeles, Seattle) $240,000—$300,000 USD OTE (Salt Lake City, all other USA cities) $204,000—$255,000 USD Life at Flex We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace. Offices Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program. Benefits For full-time U.S. employees we offer: • Competitive medical, dental, and vision • Company equity • 401(k) plan with company match • Unlimited paid time off + 13 company paid holidays • Parental leave • Free Flex subscription For full-time non-U.S. employees, we offer: • Competitive compensation + company equity • Unlimited PTO