Director, GTM Sales Strategy & Planning

We are seeking a hands-on, strategic, analytical and innovative leader to join our team as the Director, Sales Strategy & Planning. In this role, you will lead the development and execution of The Real Real’s sales strategy, driving long-term revenue growth and operational excellence. This role oversees strategic planning, budgeting, forecasting, and insights delivery while optimizing sales processes, tools, and governance.

This role partners closely with Sales leadership, the Sales Ops org, Finance, Product & Tech, and other cross-functional partners such as Merchandising and Marketing.

• Sales Strategy Development & Execution:
  Develop and drive the long-term sales strategy and roadmap, aligning with company goals and market opportunities in the luxury consignment sector. Lead cross-functional initiatives to enhance sales capabilities, integrating people, processes, and tools for scalable growth. Partner with Sales and Marketing Leadership to ensure strategic alignment and execution of revenue-driving initiatives.
• Driving Innovation:
  Spearhead innovation in sales by conducting external benchmarking to identify best-in-class capabilities and industry trends. Collaborate with technical teams to research and integrate emerging technologies (e.g., AI-driven analytics, automation tools) to enhance sales processes and customer engagement. Pilot and implement innovative solutions that drive efficiency and competitive advantage.
• Driving Operational Excellence:
  Lead efforts to optimize sales and sales operations processes to achieve superior efficiency, scalability, and performance. Establish best-in-class sales workflows, leveraging industry benchmarks and innovative practices to enhance operational effectiveness. Drive adoption of optimized processes through change management, training, and continuous improvement initiatives.
• Budgeting, Planning & Forecasting:
  Oversee the creation and management of sales budgets, ensuring alignment with financial objectives. Develop accurate revenue and cost forecasts, utilizing advanced financial modeling and market analysis. Collaborate with Finance to integrate sales forecasts into company-wide financial plans.
• Insights Delivery:
  Deliver actionable insights through advanced analytics, including pipeline performance, business hindcasting, and client experience metrics. Build and maintain dashboards and reports to provide Sales Leadership with real-time visibility into performance trends and opportunities. Leverage predictive analytics to anticipate market shifts and inform strategic decisions.
• Project Management:
  Lead high-impact sales strategy and operations projects, ensuring timely delivery and alignment with business priorities. Manage cross-functional teams and stakeholders to drive project outcomes, utilizing structured methodologies (e.g., Agile, PMP). Track and report on project progress, risks, and outcomes to senior leadership.
• Governance for Sales & Sales Operations:
  Establish and enforce governance frameworks for sales and sales operations, ensuring compliance with policies and alignment with strategic goals. Oversee data integrity, process adherence, and accountability across sales systems and teams. Facilitate regular governance reviews to assess performance and drive continuous improvement.

• 10+ years of experience in sales strategy, sales operations, or related fields, with at least 5 years in a leadership role.
• Proven expertise in sales analytics, planning/forecasting, and strategic roadmap development in a high-growth environment.
• Strong project management skills, with experience leading complex, cross-functional initiatives.
• Deep understanding of sales processes and best-in-class capabilities, with a track record of improving people, processes, and tools.
• Exceptional analytical skills, with experience in financial modeling, pipeline analytics, and client experience metrics.
• Excellent communication and stakeholder management skills, with the ability to influence senior leadership.
• Ability to thrive in a fast-paced, dynamic environment and manage multiple priorities.
• Ability to travel 10%.