Senior Director, Sales Compensation

Company: Epsilon Strategy & Insights
Location: Schiller Park
Posted on: March 22, 2026

Job Description:

We are seeking a strategic, highly analytical, and hands-on leader to own market sizing, quota strategy, and growth intelligence as part of the Sales Compensation & Revenue Management organization. The Sr Director, Sales Compensation is accountable for personally building and maintaining the core TAM, SAM, and SOM models, translating market opportunity into executable quota and capacity plans, and delivering data-driven insights that directly advise executive decisions around growth, investment, and go-to-market strategy. You will lead as a player–coach, working directly alongside your team to both develop and operationalize market and quota strategies. This includes hands-on ownership of models, assumptions, analyses, and outputs—not just setting direction. You will partner closely with Sales, Finance, Marketing, Product, and Sales Compensation to ensure tight alignment between market opportunity, revenue commitments, and real-world execution. This role owns both the strategic definition and operational execution of market sizing and quota frameworks, including ongoing maintenance and refinement. What You’ll Achieve This is a highly hands-on leadership role. While you will help shape direction and influence strategy, you are expected to personally build, analyze, and maintain the core models, analyses, and outputs—working directly alongside your team. This is not an advisory-only role. Success requires deep execution, technical ownership, and day-to-day involvement in the work, not just setting strategy and delegating execution. Responsibilities: • Personally develop, implement, and maintain the enterprise-wide methodology for TAM, SAM, and SOM, building and owning the underlying models using both top-down (industry research, third-party data) and bottom-up (CRM, pipeline, historical sales performance) approaches. • Directly own and operate the ongoing refresh, validation, and governance of market models based on new data, product launches, competitive dynamics, and strategic shifts. • Build and maintain detailed market segmentation frameworks across geography, vertical, product capability, and go-to-market constraints. • Partner closely with Marketing, Product, and Sales to align on ideal customer profiles (ICP), translating qualitative inputs into quantitative, executable market models. • Individually construct and maintain financial, capacity, and forecasting models that translate market opportunity into revenue potential and quota frameworks. • Ensure TAM, SAM, and SOM insights are fully operationalized into planning, forecasting, and long-range growth assumptions—not left as standalone analyses. Quota Strategy & Planning • Own and implement the end-to-end lifecycle of quota strategy, including design, execution, rollout, and in-year maintenance. • Personally design, build, and document quota-setting methodologies, ensuring quotas are grounded in market opportunity, sales capacity, and revenue commitments. • Partner with Sales Leadership, Finance, and Sales Compensation to translate market and capacity insights into working quota models, files, and system logic. • Directly manage and produce quota allocation outputs across teams, roles, and segments, ensuring consistency, scalability, clarity, and accuracy. • Personally lead and complete annual and in-year quota updates, adjustments, and rebalancing driven by market changes or organizational shifts. • Serve as the senior issue point for sophisticated quota design, sizing, and allocation questions, actively modeling and solving issues rather than delegating execution. Qualifications : • Bachelor’s degree in Business, Finance, Economics, or a related field (or equivalent experience). • 10 years of experience across sales compensation, sales operations, finance, strategy, or market analytics. • 5 years of experience leading teams, including people managers. • Deep expertise in quota methodologies, compensation design, and incentive governance. • Strong experience with market sizing, quota methodologies, and capacity modeling. • Sophisticated financial modeling and forecasting skills. • Deep experience with CRM and analytics tools (e.g., Salesforce, Tableau, Power BI, Anaplan). • Exceptional communication skills and ability to influence across a matrixed organization.

Keywords: Epsilon Strategy & Insights, Chicago , Senior Director, Sales Compensation, IT / Software / Systems , Schiller Park, Illinois