Director, Sales Planning

Flex is a growth‑stage, NYC headquartered Fin Tech company creating the best rent payment experience. It’s hard to believe 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 while building unprecedented investor support and a vibrant 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 for the core part of our business. Flex GTM is one of the fastest‑growing, high‑performing, and mission‑driven orgs in Fin Tech. We have driven 10× 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 2× 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 to 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.

• 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 Rev Ops 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 Rev Ops; 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.

• 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.
• Fin Tech, 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.…