Senior Director, Chief of Staff

The RealReal•San Francisco, CA
•$260,000 - $280,000

About The Position

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 that the company’s top priorities become coordinated action by shaping executive decision-making, holding the enterprise accountable to commitments, and connecting work across functions. The role proactively identifies issues, emerging risks, and cross-team friction, develops a clear perspective, and ensures the appropriate leaders address them. It drives consistent execution of executive decisions with clear accountability. This role is suited to a strategic operator who can frame difficult trade-offs for the CEO and build the processes and systems needed to carry decisions through. Responsibilities span strategic planning, the executive operating cadence, enterprise initiatives, Board materials, external relations support, market analysis, organizational effectiveness, confidential stakeholder coordination, and leadership support. The role also uses AI and automation to reduce manual reporting and improve information flow across the Office of the CEO and executive leadership team.

Requirements

  • 12+ years of operating experience across management consulting, BizOps, or executive operations.
  • Previous Chief of Staff experience for an executive team and experience supporting Board of Directors deliverables are required.
  • Expertise in moving between strategic thinking and execution, including translating ideas into scalable processes in complex, fast-growing environments.
  • Demonstrated ability to use modern AI platforms and workflow automation to track complex projects and generate executive summaries.
  • High willingness to work across both strategic framing and hands-on governance mechanics without administrative friction.
  • Strong track record of holding senior leaders accountable to commitments without formal reporting lines.
  • Exceptional project management skills and ability to drive complex, cross-functional initiatives from concept to completion.
  • Outstanding written and verbal communication skills, including the ability to craft clear, compelling, concise executive-level presentations and narratives.
  • Strategic mindset and proactive approach to problem-solving and decision-making in a fast-paced, dynamic environment.

Responsibilities

  • Own and drive annual and long-range planning cycles, including building frameworks, pressure-testing inputs, and producing high-quality outputs from cross-functional stakeholders.
  • Drive cross-functional alignment on annual operating plans and long-range strategy.
  • Monitor enterprise KPIs, financial performance, and strategic initiatives; track and escalate risks affecting performance.
  • Design and drive the Executive Team’s weekly, monthly, and quarterly operating cadence, including agendas, pre-reads, action-item follow-up, and meeting recaps.
  • Facilitate strategic planning sessions and offsites to support alignment and decisive action.
  • Serve as a strategic thought partner to executive leaders by challenging thinking, framing business decisions, evaluating trade-offs, and aligning leadership priorities.
  • Provide rigorous project management, track progress toward company goals and KPIs, surface risks, and lead selected high-priority CEO Office initiatives.
  • Lead enterprise-wide special projects, including M&A integration, restructuring, and transformation programs.
  • Be the single point of accountability for Board of Directors agendas and materials; coordinate content collection, draft final decks, and ensure clear, compelling narratives.
  • Track Board action items and follow-ups.
  • Assist, as needed, with preparation for earnings, shareholder communications, analyst meetings, investor days, roadshows, and external events in partnership with Investor Relations and PR.
  • Conduct and present market research, competitive intelligence, and trend analyses and recommendations to inform decisions and identify opportunities.
  • Identify and implement improvements to the operating model and collaboration methods for the Executive Team and broader organization.
  • Handle confidential and sensitive matters with discretion and serve as a neutral bridge between the Board, CEO, Executive Team, and the rest of the company.
  • Support organizational priorities, including onboarding key leaders and planning executive leadership offsites.
  • Use AI and automated tracking to reduce manual reporting and accelerate information flow across the Office of the CEO and executive leadership team.

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)
  • Depending on role, employees may also be eligible for a bonus program, incentive pay and benefits.
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