Senior Director, New Verticals 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 Senior Director, New Verticals Sales to spearhead Flex’s expansion into nascent, non-discretionary payment categories (e.g., insurance, HOAs, utilities, auto). While Flex is a rapidly scaling business, this pivotal role demands a proven leader who thrives in early-stage environments, adept at identifying and cultivating first-of-kind, company-defining enterprise partnerships where solutions are often loosely defined and require innovative approaches. Reporting directly to the VP of Strategic Partnerships (New Verticals), you will leverage a sophisticated blend of strategic business development, strong operational acumen, and a rigorous sales discipline to originate, negotiate, and close high-value, complex partnership deals for Flex’s embedded split pay offering. You will be instrumental in shaping our market entry strategy, collaborating closely with senior leadership and cross-functional teams (Product, Engineering, Marketing, Finance) to refine our GTM approach and ensure successful technical deployment and long-term partnership health. What You'll Do Pioneer New Markets: Proactively identify, engage, and secure strategic enterprise partners for Flex’s embedded Buy Now Pay Later (BNPL) offering within uncharted payment verticals, driving first-of-kind deals from inception to successful launch. Strategic Pipeline & Opportunity Management: Develop, prioritize, and rigorously manage a robust pipeline of high-value, complex opportunities with a strong sense of urgency, converting prospects into marquee accounts. Executive Relationship Building: Act as a trusted strategic advisor to C-level executives (CEOs, CPOs, Heads of Partnership/Strategy) at prospective partner organizations, deeply understanding their strategic priorities and expertly positioning Flex’s transformative solutions. Lead Complex Deal Negotiation: Negotiate and optimize legal and economic terms within term sheets and partnership agreements. Product & GTM Contribution: Collaborate with Product, Engineering, and Marketing teams to identify and incorporate critical market feedback, influencing product development, pricing strategies, and positioning to enhance our embedded GTM offering and competitive advantage. End-to-End Partnership Launch: Lead partnerships from signed agreement through technical deployment and successful go-live in partnership with product and technical teams, ensuring seamless execution and maximizing partner value. Key Qualifications 10+ years of experience , in strategic partnership and/or enterprise sales within high-growth FinTech environments, with a demonstrated focus on new market entry and zero-to-one product adoption. Proven track record of defining and executing growth strategies and new markets, consistently sourcing and closing company-defining, first-of-kind opportunities with senior decision-makers for Payments/FinTech solutions, especially those involving buy now, pay later (BNPL) programs. Demonstrated ability to close deals in new markets with new product/service offerings Expert in influencing executive-level stakeholders: Exceptional communication, influencing, and complex negotiation skills, with a demonstrated ability to operate confidently and effectively at the highest levels of partner organizations. Strategic Vision & Execution: Possess deep strategic thinking capabilities coupled with a strong bias for action, comfortable with ambiguity and rapid iteration, and adept at pivoting strategies as market dynamics evolve. Strong Financial & Legal Acumen: Extensive experience building deal models, justifying complex partnership economics, and navigating legal agreements. Leadership & Cross-Functional Collaboration: Proven ability to lead and influence both direct teams and cross-functional stakeholders (Product, Engineering, Marketing) to drive successful partnership outcomes. Comfort with Ambiguity: Thrives in a fast-paced, evolving environment, demonstrating urgency, adaptability, and the ability to build structure in loosely defined situations. Bachelor’s degree required; MBA or advanced degree strongly preferred. Flex takes a market-based approach to pay, and compensation may vary depending on your primary work location. Work locations are categorized into one of three tiers based on a cost of labor index for that geographic area. The successful candidate’s on-target earning (OTE) pay will be commensurate with their experience, qualifications, and Flex’s internal leveling guidelines and benchmarks. Senior Director, New Vertical Sales: $315,000-$375,000 OTE Director, New Vertical Sales: $270,000 - $320,000 OTE 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