Senior Director, Chief of Staff

About The Role As Senior Director, Chief of Staff, you’ll be a core member of the Office of the CEO and a trusted thought partner to our President & CEO and executive leaders. You’ll make sure the company’s top priorities turn into coordinated action: shaping how the executive leadership team makes decisions, holding the enterprise accountable to its commitments, and connecting work across functions so we move as one team. You will proactively spot key issues, emerging risks, and cross-team friction, establish a clear perspective, and make sure the appropriate leaders resolve them. Additionally, you will drive swift, consistent execution of executive decisions with distinct accountability. This role suits a strategic operator who is as comfortable framing a hard trade-off for the CEO and building the process and systems that see it through.

What You Get To Do Every Day

Strategic Planning & Execution: Own and drive the process for annual and long-range planning cycles, including building frameworks, pressure-testing inputs, and delivering high-quality outputs from cross-functional stakeholders. Drive cross-functional alignment on annual operating plans and long-range strategy. Monitor progress against enterprise KPIs, financial performance, and strategic initiatives. Track and escalate risks impacting performance.

Executive Operating Rhythm: Design and drive the Executive Team's operating cadence (weekly, monthly, quarterly meetings), meeting agendas, pre-reads, action-item follow-up, and post-meeting recaps; facilitate strategic planning sessions including offsites to ensure alignment and decisive action.

Executive Thought Partnership: Serve as a strategic thought partner to executive leaders. Challenge the thinking while helping frame key business decisions, evaluate tradeoffs, and align leadership priorities.

Project Management: Provide rigorous project management leadership, tracking progress towards company goals/KPIs, surfacing risks, and leading select high-priority CEO office initiatives. Lead enterprise-wide special projects (M&A integration, restructuring, transformation programs).

Board Content: Serve as the single point of accountability for all Board of Directors agendas, materials, orchestrating content collection, drafting final decks, and ensuring crisp, compelling narratives. Track board action items and follow-ups.

Investor & External Relations: Assist as needed in preparation for earnings, shareholder communications, analyst meetings, investor days, roadshows and external events (in partnership with Investor Relations and PR).

Market & Industry Insights: Conduct and present market research, competitive intelligence, and trend analyses and recommendations to inform decision-making and identify new opportunities.

Organizational Effectiveness: Identify and implement improvements to the operating model and collaboration methods for the Executive Team and the broader organization.

Confidentiality & Stakeholder Bridge: Handle confidential and sensitive matters with absolute discretion, serving as a neutral and respected bridge between the Board, CEO, Executive Team and the rest of the company.

Leadership Support: Support key organizational priorities, including onboarding of key leaders, and planning for executive leadership offsites.

Automate the work. Use AI and automated tracking to cut manual reporting and speed the flow of information across the Office of the CEO and executive leadership team.

What You Bring To The Role

Minimum Requirements:

12+ years of operating experience across management consulting, BizOps, or executive operations. Previous Chief of Staff experience for an executive team and supporting Board of Directors deliverables is a must.

Expertise in moving between strategic thinking & execution: You’ve translated ideas into scalable processes in complex, fast growing environments.

Demonstrated AI Fluency: Proven skill in leveraging modern AI platforms and workflow automations to track complex projects and generate executive summaries.

Exceptional Operational Stamina: High willingness to operate across both strategic framing and hands-on governance mechanics without administrative friction.

High Influence & Diplomatic Backbone: Strong track record holding senior leaders accountable to commitments without formal reporting lines.

Exceptional project management skills: with the ability to drive complex, cross-functional initiatives from concept to completion

Outstanding written and verbal communication skills: You craft executive-level presentations and narratives that are clear, compelling, and concise

Strategic mindset with a proactive approach to problem-solving and decision-making in a fast-paced, dynamic environment.

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 $260,000-$280,000. 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 40 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.