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About the Role

As Senior Director, Chief of Staff, you will be a core member of the Office of the CEO and a trusted thought partner to the President & CEO and executive leaders. You will ensure the company’s top priorities translate into coordinated action by shaping executive decision-making, holding the enterprise accountable, and fostering cross-functional collaboration. This role requires a strategic operator comfortable with framing trade-offs and establishing processes to execute them.

Responsibilities

Own and drive the process for annual and long-range planning cycles, including building frameworks, pressure-testing inputs, and delivering high-quality outputs.
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.
Design and drive the Executive Team's operating cadence, including meetings, agendas, pre-reads, action-item follow-up, and post-meeting recaps.
Facilitate strategic planning sessions and offsites to ensure alignment and decisive action.
Serve as a strategic thought partner to executive leaders, challenging thinking, framing key business decisions, evaluating tradeoffs, and aligning priorities.
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 such as M&A integration, restructuring, and transformation programs.
Serve as the single point of accountability for all Board of Directors agendas and materials, orchestrating content collection, drafting final decks, and ensuring crisp, compelling narratives.
Track board action items and follow-ups.
Assist in preparation for earnings, shareholder communications, analyst meetings, investor days, roadshows, and external events.
Conduct and present market research, competitive intelligence, and trend analyses and recommendations.
Identify and implement improvements to the operating model and collaboration methods for the Executive Team and the broader organization.
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.
Support key organizational priorities, including onboarding of key leaders and planning for executive leadership offsites.
Automate work using AI and automated tracking to reduce manual reporting and speed information flow.

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 translating ideas into scalable processes in complex, fast-growing environments.
Proven skill in leveraging modern AI platforms and workflow automations to track complex projects and generate executive summaries.
High willingness to operate across both strategic framing and hands-on governance mechanics.
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, with the ability to craft clear, compelling, and concise executive-level presentations and narratives.
Strategic mindset with a proactive approach to problem-solving and decision-making in a fast-paced, dynamic environment.
Ability to handle confidential and sensitive matters with absolute discretion.
Regularly required to sit; use hands to finger, handle, or feel and talk or hear.
Occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell.
Must occasionally lift and/or move up to 10 pounds.
Specific vision abilities required include close vision.

Skills

Strategic Planning
Execution
Cross-functional Alignment
KPI Monitoring
Risk Management
Executive Operating Cadence Design
Meeting Facilitation
Strategic Thought Partnership
Project Management
Board Content Preparation
Investor Relations Support
Market Research
Competitive Intelligence
Organizational Effectiveness
Confidentiality Management
AI Fluency
Workflow Automation
Written Communication
Verbal Communication
Problem-Solving
Decision-Making

Location

Primary work location (details not specified)

Work Type

Full-time

Experience Level

Senior Director
12+ years of operating experience

Salary/Compensations

$260,000-$280,000

Benefits

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)
Potential for bonus program and incentive pay

About the Company

The RealReal is the world’s largest online marketplace for authenticated, resale luxury goods, with 40 million members.
Operates with a rigorous authentication process overseen by experts.
Provides a safe and reliable platform for consumers to buy and sell luxury items.
Employs hundreds of in-house gemologists, horologists, and brand authenticators.
A sustainable company that gives new life to pieces across numerous categories, supporting the circular economy.
Offers effortless selling services including virtual appointments, in-home pickup, drop-off, and direct shipping.
Utilizes AI and machine learning for optimal pricing, photography, listing, shipping, and customer service.

Equal Opportunity

The RealReal is committed to providing 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.
Will consider qualified applicants for a position regardless of arrest or conviction records.
Diversity and inclusion are vital priorities as an equal opportunity employer.
Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.