Senior Director, Chief of Staff

The RealReal • San Francisco, CA

7d

About The Position

The Senior Director, Chief of Staff is a core member of the Office of the CEO and a trusted thought partner to the President & CEO and executive leaders. The role ensures company priorities become coordinated action by shaping executive decision-making, holding the enterprise accountable to its commitments, and connecting work across functions. It proactively identifies important issues, emerging risks, and cross-team friction, develops a clear perspective, and ensures appropriate leaders address them. It also drives timely, consistent execution of executive decisions with clear accountability.

This strategic operator leads annual and long-range planning, aligns cross-functional operating plans and strategy, and monitors enterprise KPIs, financial performance, and strategic initiatives. The role designs the Executive Team’s operating cadence, supports executive decision-making, manages high-priority initiatives, and oversees Board agendas and materials. It may also support investor and external relations, provide market and competitive insights, improve organizational effectiveness, handle sensitive matters discreetly, support leadership priorities, and use AI and automation to reduce manual reporting and accelerate 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 experience supporting Board of Directors deliverables.
• Ability to move between strategic thinking and execution and translate ideas into scalable processes in complex, fast-growing environments.
• Demonstrated fluency with modern AI platforms and workflow automations for tracking complex projects and generating executive summaries.
• High willingness to work across strategic framing and hands-on governance mechanics.
• 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 create clear, compelling, concise executive 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 developing frameworks, pressure-testing inputs, and delivering 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 manage 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.
• Advise executive leaders, challenge their thinking, frame business decisions, evaluate tradeoffs, and align leadership priorities.
• Provide project management leadership, 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.
• Own Board of Directors agendas and materials, coordinate content collection, draft final presentations, and ensure clear, compelling narratives.
• Track Board action items and follow-ups.
• Assist 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.
• Identify and implement improvements to the Executive Team’s and broader organization’s operating model and collaboration methods.
• Handle confidential and sensitive matters with discretion and serve as a bridge between the Board, CEO, Executive Team, and company.
• Support organizational priorities, including onboarding key leaders and planning executive leadership offsites.
• Use AI and workflow automation to reduce manual reporting and speed information flow across the Office of the CEO and executive leadership team.

Benefits

• Employee Stock Purchase Plan
• 401(k) with company match
• Medical, dental, and vision insurance
• Paid parental leave
• 9 paid company holidays
• Flexible time off with manager approval
• Depending on role, eligibility for a bonus program and incentive pay

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed