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Senior Director, GTM Strategy & Operations

New York, New York, United States

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 2025 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 for the core part of our business. Flex GTM is one of the fastest-growing, high-performing, and mission-driven orgs in FinTech. We have driven 10x revenue growth every 2 years since inception and plan to do it again over the next 2 years. We are looking for a leader who can operationalize revenue initiatives and empower the front-line with world-class insights and process to 2x the growth of the core business year over year. We are looking for a driven and data-centric leader who is ruthlessly focused on practical implementation lead the strategy and operations team for this line of business.

This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters or 2 days per week in our San Francisco hub. For candidates outside of the NY/NJ/SF area, you may be eligible for our relocation assistance program.

What you’ll do

  • GTM Strategy & Annual Planning: Own annual and quarterly planning for the core business unit, and partner closely with Sales, Product and Analytics to develop and execute clear, data-driven go-to-market strategies
  • Revenue Forecasting, Insights & Analytics: Own lead forecasting, pacing, and KPI reporting for the core GTM organization; Identify trends, risks, and opportunities across pipeline, funnel efficiency, and revenue performance
  • Operational Excellence & Process Optimization: Develop and continuously refine sales processes, pipeline frameworks, sales territories and operating mechanisms to improve efficiency and consistency; partner with RevOps to ensure optimal execution within our Rev. systems environment
  • Cross-Functional Leadership & Execution: Serve as the operational hub connecting Sales, Product, Marketing, Finance, Risk, and RevOps; bring structure and clarity to ambiguous problems; build repeatable systems from the ground up.
  • Revenue Insights & Business Case Development: Conduct competitive analysis, market sizing, segmentation, and TAM analysis to inform GTM strategy; build business cases supporting new programs, product bets, investment decisions, and resource allocation.
  • Lead the team: Develop and lead a revenue strategy and operations team of 3-4 in supporting the core business.

Key qualifications

  • 10+ years of experience in GTM strategy, revenue operations, strategy consulting, and/or business operations; 5+ years minimum experience in a revenue leadership role preferred
  • Proven ability to lead strategic planning, forecasting, and operational programs in a high-growth B2B or multi-stakeholder environment.
  • Deep analytical expertise to pull clear insights from complex data
  • Strong understanding of sales processes, pipeline dynamics, and revenue forecasting best practices.
  • Exceptional communication skills with the ability to influence executive stakeholders and cross-functional teams.
  • Experience managing or leading complex cross-functional initiatives with significant business impact.
  • Capable of operating both at a ‘30,000 foot’ strategic level, and getting into execution details, as the situation requires
  • Experience in building processes and frameworks from the ground up.
  • FinTech, marketplace, or network-based business experience is a strong plus.

The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. For working locations in NY/NJ/CA, the base salary pay range will be $235,000 - $254,000. 

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.

We offer many employee benefits & perks. For full-time U.S based positions we offer:

  • Competitive medical, dental, and vision available from Day 1
  • Company equity
  • 401(k) plan with company match (our company match kicks off at the beginning of 2026)
  • Unlimited paid time off + 13 company paid holidays
  • Parental leave 
  • Flex Cares Program
  • Free Flex subscription

 For full time non-US employees, we offer

  • Competitive compensation + company equity
  • Unlimited PTO

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