Senior Director, New Verticals Sales (Insurance)

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 Flex is on a mission to give consumers control over their most significant recurring expenses — and auto insurance premiums sit squarely in that category. For most drivers, auto insurance is a non-negotiable monthly commitment, yet the payment experience has remained rigid and unforgiving. Flex changes that. As Director or Senior Director, New Vertical Sales (Auto Insurance), you will own Flex’s go-to-market strategy and commercial execution for the auto insurance vertical, building the enterprise partnerships that establish Flex as the embedded payment flexibility layer for carriers, agencies, and their policyholders. Reporting to the VP of Strategic Partnerships (New Verticals), you will define the approach, build the pipeline, and close the deals that put this vertical on the map for Flex. This is a true zero-to-one charter — you will identify the right partners across personal lines carriers, independent agencies, and auto insurtechs, develop those relationships at the executive level, and drive deals from initial conversation through signed agreement and go-live. You will work hand-in-hand with Product, Engineering, Marketing, and Finance to shape Flex’s offering for the insurance market and ensure every partnership delivers real, measurable value. This is a remote role is for an individual contributor who thrives in ambiguity, sets the agenda rather than waiting for one, and has the market credibility and executive presence to open doors and close deals in the auto insurance space. Success looks like a scaled, repeatable partner acquisition motion, a growing book of live carrier and agency partnerships, and a clear point of view on where Flex should go next in insurance. What You'll Do Build Flex’s go-to-market strategy for the auto insurance vertical — identifying the highest-value partner segments across personal lines carriers, independent agencies, and insurtechs, and building the pipeline to pursue them Lead enterprise sales development end-to-end, from prospecting and executive relationship-building through term sheet negotiation, contract execution, and go-live Serve as a credible, trusted advisor to C-level and senior decision-makers at target organizations, deeply understanding their strategic priorities and articulating exactly how Flex creates value for their policyholders and their business Close deals by owning complex, multi-stakeholder deal negotiations — structuring partnership economics that work for both parties while navigating legal, compliance, and procurement processes with urgency Shepherd each partnership from signed agreement through technical deployment and go-live, working closely with Product and Engineering to ensure strong execution and early performance metrics Translate partner feedback and competitive dynamics in the auto insurance market into actionable input for Product, Marketing, and Pricing — continuously sharpening Flex’s positioning and offering Build the auto insurance sales playbook — documenting learnings, establishing scalable processes, and developing the repeatable partner acquisition motion that enables efficient growth beyond initial market entry Leverage AI-assisted sales tools to drive pipeline efficiency, inform competitive strategy, and accelerate ... (truncated, view full listing at source)