Director, Sales Planning & Incentive Compensation

Flex • San Francisco, CA

6d • $235,000 - $254,000 • Hybrid

About The Position

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.

Requirements

• 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.

Nice To Haves

• FinTech, marketplace, or network-based business experience is a strong plus.

Responsibilities

• 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.

Benefits

• 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
• Competitive compensation + company equity
• Unlimited PTO

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 251-500 employees