- Location
- San Francisco California USA
- Employment
- Full-Time
- Seniority
- Director
- Compensation
- $260,000–280,000/year
- Department
- Executive & General Management
- Posted
- Nov 4, 2026
About The RealReal
The RealReal is a US luxury consignment marketplace founded in 2011. It sells pre-owned fashion, jewelry, watches, art and home furnishings through its website and stores. Its teams authenticate, price and photograph goods before they go on sale.
The RealReal seeks a Chief of Staff to partner with the CEO and executive leaders, translating enterprise priorities into coordinated execution across planning, governance, Board materials, cross-functional initiatives and organizational effectiveness. The role leads the executive operating cadence, supports investor and external relations, and applies AI and workflow automation to accelerate reporting and information flow. The expected annual salary range is $260,000–$280,000, with starting pay determined by factors including work location, skills, experience, market demands and internal parity.
Role & Responsibilities
- Own and drive annual and long-range planning cycles, building 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, and track and escalate risks.
- 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 ensure alignment and decisive action.
- Partner with executive leaders to frame business decisions, evaluate trade-offs and align leadership priorities, while challenging their thinking.
- 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.
- Own accountability for Board of Directors agendas and materials, coordinate content collection, draft final decks, create clear and compelling narratives, and 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, with 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, serving 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.
Qualifications
- At least 12 years of operating experience across management consulting, BizOps or executive operations.
- Previous Chief of Staff experience supporting an executive team and Board of Directors deliverables.
- Ability to move between strategic thinking and execution, translating ideas into scalable processes in complex, fast-growing environments.
- Proven ability to use modern AI platforms and workflow automations to track complex projects and generate executive summaries.
- Willingness to work across strategic framing and hands-on governance mechanics without administrative friction.
- Strong track record of holding senior leaders accountable for 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 crafting clear, compelling and concise executive-level presentations and narratives.
- Strategic mindset and proactive approach to problem-solving and decision-making in a fast-paced, dynamic environment.
Skills
Experience
At least 12 years of operating experience across management consulting, BizOps or executive operations; previous Chief of Staff experience supporting an executive team and Board of Directors deliverables is required.
Workplace
This position is based in San Francisco, California, USA.
Explore jobs in California or in the USA.
Compensation
The base compensation for this position ranges from USD 260,000 to USD 280,000 per annum.
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. Employees may also be eligible for a bonus program and incentive pay, depending on role.
Culture
A consignment passes through several hands. Authentication specialists examine the item, merchandising teams prepare the listing and client teams work with the person who consigned it.
About Cerulean
Cerulean is the definitive career portal for the global luxury industry. We match exceptional professionals with exclusive opportunities at the world's most prestigious brands. From haute couture and fine watchmaking to prestige beauty, hospitality, and boutique retail, Cerulean centralises luxury employment to help you find the career for which you were destined.
Frequently Asked Questions
The luxury industry is characterised by a diverse and nuanced nomenclature. Esteemed houses frequently employ proprietary terminology, and even within a single organisation like The RealReal, titles may vary across global markets to reflect local conventions. To ensure absolute clarity, Cerulean assigns a standardised, industry-coherent canonical title to every listing. However, it is worth noting that this role is functionally synonymous with «Senior Executive Operations Director», «Director of Executive Operations», «Executive Strategy Director», «Chief Executive Office Director», and other variations. Our sophisticated search architecture anticipates these variations, ensuring that inquiries using related terms will seamlessly yield the exact roles you desire.