Senior Director, GTM 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 and operations team supporting the New Verticals business, with expectation to grow the function as the verticals scale. Key Qualifications • 10+ years of experience in GTM strategy, revenue operations, strategy consulting, and/or business operations preferred; 5+ years minimum experience in a revenue leadership role • Proven ability to build GTM strategy and operational infrastructure in a greenfield or early-stage business context — not just optimizing what exists, but creating from scratch. • Strong analytical expertise with the ability to pull clear, actionable insights from incomplete or early-stage data. • Deep understanding of sales processes, pipeline dynamics, and revenue forecasting best practices, with the ability to adapt frameworks across different business models and buyer types. • Exceptional communication skills with the ability to influence executive stakeholders and cross-functional teams across multiple business lines simultaneously. • Comfortable operating in ambiguity — able to make good decisions with limited information and build structure around unstructured problems. • Capable of operating at both a strategic and execution level as the situation demands; willing to roll up sleeves in an early-stage environment. • Experience building processes and frameworks from the ground up. • FinTech, marketplace, or network-based business experience is a strong plus; experience operating across multiple business lines or verticals simultaneously is equally valued. Compensation Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 (NYC/Bay Area) markets, the base salary pay range for this role is below. Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the cities listed below, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location. Tier 1 (NYC/Bay Area) $265,000—$315,000 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