Senior Director, GTM Strategy & Operations

Senior Director, GTM Strategy & Operations

New York, NY

Flex is a growth-stage, NYC headquartered Fin Tech 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?

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.

• 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 Rev Ops 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 Rev Ops 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.

• 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…