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.

Qualifications:

• FinTech, marketplace, or network-based business experience is a strong plus; experience operating across multiple business lines or verticals simultaneously is equally valued.
• 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.
• Comfortable operating in ambiguity — able to make good decisions with limited information and build structure around unstructured problems.
• Strong analytical expertise with the ability to pull clear, actionable insights from incomplete or early-stage data.
• Exceptional communication skills with the ability to influence executive stakeholders and cross-functional teams across multiple business lines simultaneously.
• Experience building processes and frameworks from the ground up.
• 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.
• 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.
• Capable of operating at both a strategic and execution level as the situation demands; willing to roll up sleeves in an early-stage environment.