Director, Sales Strategy & Planning

Director, 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 RealReal'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. The ideal candidate is a strategic leader with deep expertise in sales best practices, sales planning and insights, and is capable of aligning people, processes, and technology to achieve business objectives in a high-growth sales environment. You possess great leadership qualities, thrive in dealing with ambiguity, and are capable of creating the structure to succeed in a dynamic environment.

What You Get To Do Every Day

1. 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.
2. 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. Collaborate with technical teams to pilot and implement innovative solutions that drive efficiency and competitive advantage.
3. 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 (a separate team), and continuous improvement initiatives.
4. 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.
5. Insights Delivery: Deliver actionable insights through advanced analytics, including pipeline performance (e.g., conversion rates, deal progression), business hindsighting (e.g., performance driver analysis), and client experience metrics (e.g., NPS drivers and next steps). 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.
6. 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.
7. 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.

What You Bring To The Role

• 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%

• Bachelor's degree in Business, Finance, Economics, or related field.
• MBA or advanced degree preferred.
• Experience at a management consulting firm strongly preferred.
• Proficiency in Salesforce strongly preferred.
• Familiarity with sales compensation, territory, and quota design strongly preferred.
• Previous experience with Sales enablement and training a plus.
• Experience in high growth, B2C or small company B2B sales-oriented companies preferred.
• Experience in e-commerce, retail, or luxury goods industries.

Compensation, Benefits, + Perks

• Employee Stock Purchase Plan
• 401K with Company Match
• Medical, Dental & Vision Insurance
• Paid Parental Leave
• 9 Paid Company Holidays
• Flexible Time Off (With Manager Approval)
• The expected salary range for this role is $180,000-$210,000. To determine starting pay we carefully consider a variety of factors, including primary work location and an evaluation of a candidate's skills, experience, market demands, and internal parity. Additionally, salary is just one component of TRR's total rewards package. Depending on role, employees may also be eligible for a bonus program, incentive pay and benefits.

The RealReal is the world's largest online marketplace for authenticated, resale luxury goods, with 37 million members. With a rigorous authentication process overseen by experts, The RealReal provides a safe and reliable platform for consumers to buy and sell their luxury items. We have hundreds of in-house gemologists, horologists, and brand authenticators who inspect thousands of items each day. As a sustainable company, we give new life to pieces by thousands of brands across numerous categories—including women's and men's fashion, fine jewelry and watches, art, and home—in support of the circular economy. We make selling effortless with free virtual appointments, in-home pickup, drop-off, and direct shipping. We handle all of the work for consignors, including authenticating, using AI and machine learning to determine optimal pricing, photographing and listing their items, as well as shipping and customer service.

The RealReal is committed to providing an equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or Veteran status. We will consider qualified applicants for a position regardless of arrest or conviction records. At TRR, People Come First. That's why diversity and inclusion are vital to our priorities as an equal opportunity employer. You can read about our Diversity Equity and Inclusion program here. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The employee is regularly required to sit; use hands to finger, handle, or feel and talk or hear. The employee is occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell. The employee must occasionally lift and/or move up to 10 pounds. Specific vision abilities required by this job include close vision. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.