Senior Director, Sales Strategy and Planning (San Francisco)

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 Strategy & Planning. In this critical role, you will be a key member of the Sales leadership team driving the growth and optimization of the supply acquisition side of our marketplace. You will lead the development and execution of sales strategies, optimize sales processes, manage a team, and drive revenue growth through data-driven insights and cross-functional collaboration.

Our ideal candidate is a self-starter, independent thinker, deeply analytical and detail-oriented individual with deep expertise in Sales Strategy and Planning. 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 Everyday

• Sales Strategy Development and Execution: Serve as the Sales strategy lead. Partner with Sales leadership to identify, evaluate, and operationalize strategic levers to drive growth across the organization. Provide insights that help the organization evaluate, prioritize and implement new initiatives and programs. Develop long-range plans, annual and quarterly strategic roadmaps, and oversee project management to deliver on strategic priorities.

• Workflow and Process Improvement: Implement best practices and new solutions to enhance sales efficiency and effectiveness. Lead initiatives to identify pain points, streamline sales processes, reduce friction, and improve the overall sales experience for the Sales team. Partner closely with Product and Sales Revenue Technology to implement improvements in Salesforce and other key Sales systems.

• Performance Analytics and Reporting: Maintain a robust sales performance reporting framework to track progress against targets and identify areas for improvement, including new/repeat clients, client segmentation, pipeline funnel metrics, and rep performance. Provide actionable insights and recommendations based on data analysis to drive sales productivity and effectiveness. Partner with analytics functions to develop relevant new reporting to drive new insights.

• Planning and P&L Management: Collaborate with senior executives, Finance, Sales, Marketing, Merchandising and Operations to develop budgets and forecasts to drive headcount, quota capacity, and expense management for Sales. Track performance against pipeline and revenue targets and provide accurate and timely reporting, trends, and areas for improvement. Ensure alignment of territories/divisions/regions and maximize the effectiveness of the salesforce and ROIs on investment.

• Talent planning and support: Partner Sales and Sales Operations leaders to design and administer compensation and incentive programs, and conduct planning for headcount, territories, and quotas in line with planned and updated business goals.

• Cross-Functional Collaboration: Collaborate with Sales, Finance, Marketing, Merchandising, Product, Operations, and Sales Operations teams to ensure seamless coordination and alignment of strategies and objectives. Act as a trusted advisor to Sales leadership, providing insights and recommendations to drive business growth, operational efficiency, and profitability.

• Leadership and Team Management: Lead and grow a high-performing Sales Strategy and Planning team. Provide mentorship, coaching, and professional development opportunities to team members across several sub-functions. Foster a collaborative and inclusive team culture that encourages continuous learning, growth, and engagement.

• Executive support: Support Sales Leadership in key meetings such as Board presentations, management updates related to revenue.

What You Bring To The Role

Minimum Requirements:

• Demonstrable track record of developing people and managing a team, focused on driving success.

• 10+ years Sales Operations, FP&A, Business Planning and Analytics, in a high growth, fast-paced environment.

• Demonstrable analytical skills, strategic thinking and problem solving ability.

• Demonstrable project management and structuring ability.

• Comfortable dealing with ambiguity and ability to adapt to changing environment and needs.

• Excellent written and verbal communication skills and strong executive presence.

• Highly motivated, with a sense of urgency and ability to deliver multiple tasks under pressure.

• Experience with Salesforce and BI tools such as Looker or Tableau.

• Ability to Travel 10%.

Preferred Requirements:

• Education in Business Analytics, Economics, or related field; MBA a plus.

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).

• Find out more about our Benefits here.

The expected salary range for this role is $209,400-$250,000. 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.