Director, Sales Planning & Incentive Compensation

Flex • New York, NY

19d • $217,000 - $235,000 • Hybrid

About The Position

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 VP of GTM Strategy & Operations, this role will own sales planning and incentive compensation across all of our revenue teams. In this role, you will partner closely with HR Compensation, Finance, Sales Leadership, RevOps, and cross-functional stakeholders to design, implement, and manage compensation plans that drive growth, align seller behavior with business objectives, and scale with our rapidly growing organization. This is a high-impact, cross-functional role — you will help create the compensation architecture and execution cadence that ensures our sales teams are motivated, rewarded fairly, and incentivized for the right behaviors. Your work will be critical to aligning GTM execution with company goals, optimizing payout structures, and ensuring transparency, fairness, and compliance. This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters (a few blocks from Union Square) or 2 days per week in our SF Hub. For candidates outside of the NY/NJ or SF area, you may be eligible for our relocation assistance program.

Requirements

• 7–12+ years of relevant experience in sales compensation, sales planning, sales finance, or related functions — with a demonstrated track record of designing and managing incentive compensation plans across multiple seller teams
• Deep analytical skills: financial modeling, forecasting, quota-setting, payout modeling, data analysis, and reporting. Comfortable working with large data sets, complex compensation scenarios, and translating results into actionable recommendations.
• Strong business acumen and strategic thinking: ability to tie compensation structure to sales behavior, business goals, and GTM strategy.
• Excellent cross-functional collaboration, working with HR, Finance, Sales Leadership, RevOps, and senior stakeholders
• Comfortable working in a fast-paced, high-growth, high-change environment; ability to adapt plans and processes as GTM strategy evolve
• Bachelor’s in Business, Finance, Economics, HR, or related field

Responsibilities

• Compensation Plan Design & Strategy: Structure incentive compensation plans across multiple revenue organizations: determine appropriate base vs. variable pay mix, commission/bonus structures, accelerators, quota frameworks, regional/territory and role variation; collaborate with HR Compensation, Finance, and Sales Leadership to ensure plans are competitive, financially sustainable, and aligned with business strategy and go-to-market motions
• Quota Setting, Planning & Forecasting: Lead quota-setting and sales planning processes; model variable compensation costs under various scenarios to forecast payout liability and budget impact
• Compensation Administration & Execution: Own the end-to-end execution of compensation plans: administration, calculations, validation, payout, reconciliation, and audits each cycle — ensuring accuracy, transparency, fairness; manage documentation, change control, versioning, communication, and stakeholder support — ensuring compensation plans are clearly communicated to sales leadership and reps; act as primary point of contact for comp-related questions, disputes, or clarifications.
• Analytics, Reporting & Optimization: Build, maintain, and analyze dashboards and reports tracking quota attainment, payout distribution, reps’ performance, comp spend, and other compensation-related metrics. Use insights to recommend plan adjustments; Conduct periodic reviews (quarterly / annually) of compensation plan effectiveness
• Cross-Functional Leadership & Stakeholder Management: Serve as the bridge between Sales, HR, Finance, RevOps, and senior leadership for all matters related to compensation plan design, execution, and governance; Manage the compensation planning calendar: plan design cycles, quota-setting cadence, approvals, communication, implementation, and payouts across all four revenue organizations
• Build and Lead the team: Build a team of analysts to support the Sales compensation function as the organization grows

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
• Number of Employees: 251-500 employees