Senior Director, Sales Compensation & Effectiveness

About The Role

We are seeking a hands-on, strategic, analytical and results-driven leader to join our team as the Sr. Director of Sales Compensation & Effectiveness. In this critical role, you will lead the design, implementation, and management of sales compensation plans, territory alignments, and quota-setting processes to drive revenue growth and operational efficiency. This role will partner closely with Sales, Finance, HR, and Executive Leadership to create rewards and territory strategies that align with The Real Real’s business objectives, incentivize high performance, and ensure scalability.

The ideal candidate is a strategic thinker with deep expertise in sales compensation, territory and quota planning, and performance analytics. You possess great leadership qualities, thrive in dealing with ambiguity, and are capable of creating the structure to succeed in a dynamic environment.

• Sales Compensation Strategy & Design:
  Develop and implement competitive, equitable, and motivating sales compensation plans that align with company goals and industry benchmarks. Analyze compensation structures to ensure they drive desired sales behaviors, support retention, and maximize ROI. Oversee regular reviews and updates to compensation plans to adapt to market trends, business needs, and performance data.

• Territory & Quota Management:
  Design and optimize sales territory alignments to maximize coverage, efficiency, and revenue potential. Establish fair, achievable, and data-driven quotas that align with company growth objectives and market realities. Leverage data analytics to assess territory performance and adjust strategies as needed. Design sales rep books of business, assess productivity, and oversee the book of business adjustment SOPs and adjustment execution.

• Sales Performance Analytics:
  Build and maintain robust reporting systems to track sales performance, compensation effectiveness, quota attainment and territory productivity. Provide actionable insights to Sales Leadership and Finance to inform strategic decisions. Identify trends, risks, and opportunities through advanced data analysis and forecasting models.

• Operational Excellence:
  Streamline processes for compensation administration, territory management, and quota setting to enhance efficiency and scalability. Implement tools and technologies (e.g., CRM, compensation software) to support data-driven decision-making and operational workflows. Ensure compliance with legal, regulatory, and internal policies related to compensation and sales operations.

• Cross-Functional Collaboration:
  
  Partner with Sales Operations Strategy & Planning and Finance to align compensation and headcount budgets with financial goals and drive forecast accuracy. Work with People Team to ensure compensation plans support talent acquisition and retention strategies. Collaborate with Sales Leadership to align strategies with field execution and goals. Partner with Sales technology teams to design and implement new technological capabilities to enhance rep productivity and client experience related to quotas, territories and books.

• Leadership & Team Development:
  Lead, mentor, and develop a high-performing team responsible for sales compensation, territory planning, quota management and rep performance operations. Foster a culture of accountability, collaboration, and continuous improvement.

Minimum Requirements:

• 10+ years of experience in sales operations, sales compensation, or related fields, with at least 5 years in a leadership role.

• Proven track record of designing and implementing successful sales compensation plans and territory/quota strategies in a high-growth environment.

• Strong analytical skills with expertise in data modeling, forecasting, and performance metrics.

• Proficiency in CRM systems (e.g., Salesforce) and compensation management tools (e.g., Xactly).

• Exceptional communication and stakeholder management skills, with the ability to influence and align cross-functional teams.

• Ability to thrive in a fast-paced, dynamic environment and manage multiple priorities.

• Comfortable dealing with ambiguity and ability…