Senior Director, Revenue Strategy & Operations

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 Reporting to the Head of GTM Operations & Strategy, this role will be responsible for the GTM strategy, operational support, and execution of our front-line teams across Flex's New Verticals business. As Flex expands beyond its core market into new segments, this leader will play a foundational role in building the GTM infrastructure that enables us to scale. We are looking for a builder — someone who thrives in ambiguity, moves quickly to structure the unstructured, and brings both strategic rigor and operational horsepower to a business that is early but moving fast. This is a high-visibility role that will directly shape how new lines of business grow, and will require close partnership with Sales, Product, Analytics, Finance, and the broader GTM leadership team. What You'll Do GTM Strategy & Annual Planning: Own annual and quarterly planning for the New Verticals business unit, partnering closely with Sales, Product, and Analytics to develop and execute clear, data-driven go-to-market strategies tailored to each vertical's unique dynamics. Revenue Forecasting, Insights & Analytics: Own lead forecasting, pacing, and KPI reporting for the New Verticals GTM organization; identify trends, risks, and opportunities across pipeline, funnel efficiency, and revenue performance; build the reporting infrastructure largely from scratch as new verticals mature. Operational Excellence & Process Optimization: Design and continuously refine sales processes, pipeline frameworks, territory structures, and operating mechanisms purpose-built for new verticals; partner with RevOps to ensure optimal execution within Flex's revenue systems environment. Cross-Functional Leadership & Execution: Serve as the operational hub connecting Sales, Product, Marketing, Finance, Risk, and RevOps across the New Verticals portfolio; bring structure and clarity to ambiguous, fast-moving problems; build repeatable systems that can scale with the business. Revenue Insights & Business Case Development: Conduct market sizing, segmentation, and TAM analysis for new verticals; build business cases supporting go/no-go decisions, new programs, product investments, and resource allocation across the portfolio. Lead the Team: Develop and lead a revenue strategy ...