Sales Planning & Compensation Contractor

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 2026 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 Flex is looking for an experienced contractor to support our Revenue Strategy & Operations team on sales compensation. Most of the work is building our commissions capitalization approach with Accounting. You'll take the plans we have today and turn them into a defensible, repeatable capitalization schedule that holds up in an audit. You will size the price and you'll also help model new compensation plans and pick up analytics requests from Revenue leadership. The role is about 30 hours a week, and the hours can flex up or down for the right person. What you'll do Commissions capitalization • Partner with Accounting to apply ASC 340-40 to Flex's commission plans. • Build the calculations that show recoverability: link commission dollars to the units and revenue they generated, and work out the capitalizable portion when payouts exceed the related revenue. • Recommend and document amortization periods and methods, such as expected customer life or portfolio approaches. • Build a repeatable monthly or quarterly capitalization and amortization schedule that runs off the existing comp run outputs. Hand it off with documentation that a non-author can run. • Prepare audit-ready support and documentation of methodology. • Point out plan-design changes that would make more of the commission spend clearly capitalizable. New plan design support • Model proposed plan changes for the 2027 plans: quotas, pay curves, accelerators, caps and SPIFFs. • Estimate plan cost against OTE and SPIFF budgets, and run scenario analysis for leadership. • Draft plan documents and rollout materials alongside Alex. Key Qualifications • 6-8+ years in sales compensation, revenue or technical accounting, or FP&A, with direct exposure to commission plans. • Hands-on experience implementing ASC 606 / 340-40 commission capitalization, not just maintaining someone else's schedule. • Advanced Excel/Google Sheets modeling. Precise, organized and comfortable being audited. • Ability to explain accounting mechanics clearly to non-accountants and comp mechanics to Accounting. • Self-directed. Can deliver with light oversight on a part-time schedule. • SQL (or AI-assisted querying) and experience with Snowflake, Sigma and Salesforce data. • Background at a comp consultancy (Alexander Group, SBI, Simon-Kucher) or Big 4 audit or advisory. • Experience building comp plans 0 to 1 in a high-growth environment. What Success Looks Like • First 30 days: inventory of current plans with a capitalization classification for each payout type, capitalization mechanism calculated for AE and AMs • By Q4 close: capitalization and amortization schedule live and tied to comp run outputs, with documentation ready for audit. • Ongoing: plan scenario models delivered on time for 2027 planning, and analytics requests turned around within agreed SLAs. Compensation This is a contract position with an hourly rate of $125–$165 per hour, commensurate with experience and our internal leveling guidelines. Flex takes a market-based approach to pay and utilizes a geographic pay differential based on a cost of labor index; if you are located outside of our Tier 1 (NYC/Bay Area) markets, your rate will be adjusted to align with the market conditions of your specific geographic zone. There is potential for this engagement to convert to a full-time role, in which case compensation would be aligned to the full-time salary range and benefits for the level. 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. Offices Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program. Benefits For full-time U.S. employees we offer: • Competitive medical, dental, and vision • Company equity • 401(k) plan with company match • Unlimited paid time off + 13 company paid holidays • Parental leave • Free Flex subscription For full-time non-U.S. employees, we offer: • Competitive compensation + company equity • Unlimited PTO