Senior Director of GTM Strategy & Operations

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 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 Benefits Medical, Dental & Vision: Your healthcare will be available from Day 1— giving you immediate peace of mind — with best in class coverage and options. Parental Leave: Step away with paid time off to focus on family and life’s newest chapter. NYC HQ: Collaborate in our lively New York headquarters, with new office space on the way! 401(k) Retirement Savings: Plan ahead with our 401(k) program to grow your future. And starting early 2026, employees will be eligible for a company match! Flex Giving: Flex Giving empowers employees to support local nonprofits advancing housing stability in the communities we call home. Employee Assistance Fund: Confidential financial support to teammates facing unexpected hardships or emergencies. Hybrid Work Policy: Work flexibly from home, with in-person collaboration and events that matter. Unlimited PTO + Holidays: Take the time you need— whether that’s a vacation, recharge, or simply a long weekend Free Flex Subscription: As a Flex employee, you’ll have full access to our services without charge. GrubHub Credit: Enjoy meal credits while in the office, so you’re fueled for the workday ahead. FinTech, marketplace, or network-based business experience is a strong plus; experience operating across multiple business lines or verticals simultaneously is equally valued10+ years of experience in GTM strategy, revenue operations, strategy consulting, and/or business operations preferred; 5+ years minimum experience in a revenue leadership roleComfortable operating in ambiguity — able to make good decisions with limited information and build structure around unstructured problemsCapable of operating at both a strategic and execution level as the situation demands; willing to roll up sleeves in an early-stage environmentStrong analytical expertise with the ability to pull clear, actionable insights from incomplete or early-stage dataExceptional communication skills with the ability to influence executive stakeholders and cross-functional teams across multiple business lines simultaneouslyExperience building processes and frameworks from the ground upProven ability to build GTM strategy and operational infrastructure in a greenfield or early-stage business context — not just optimizing what exists, but creating from scratchDeep understanding of sales processes, pipeline dynamics, and revenue forecasting best practices, with the ability to adapt frameworks across different business models and buyer types #J-18808-Ljbffr Flex