Chief of Staff Director Executive Assistant AI
About The Position
Chief of Staff job opening USA based remotely, to CEO Founder who has a proven COO and CMO on their team to also support. I’m leading a confidential executive search on behalf of a Founder/CEO of a >$100MM+ high-growth D2C digital marketplace company with aim to be a $0.5B in the next few years! You can operate at both strategic and tactical levels — acting as a trusted partner, gatekeeper, and confidant. With a proven COO already in place, this role is focused on optimizing the CEO’s time, priorities, and confidential initiatives, and SLT operations management. You're also tech savvy, innovative, and in ChatGTP/AI, every day at a medium to advanced super user level.
Requirements
- 7–12+ years’ experience supporting CEOs/Founders in entrepreneurial, fast-scaling small and medium size, award winning companies
- Worked for a 100-300 staff company during their growth curve ideally twice, for 3-5+ years (candidates)
- Comfortable managing and facilitating executive director board-level meetings, notes, materials, investors, VVIPs, and confidential projects, while also handling calendar, travel
- Deep business understanding of D2C/eCommerce/digital marketing/digital marketplace models/online training courses/digital coaching apps
- Passionate about one or more sports, health, wellness, fitness, supplements, at an advanced level like a biohacker
- Based in remote USA
Responsibilities
- Strategic Alignment: Translate CEO/Board vision into clear company priorities, OKRs, and execution plans.
- Operational Excellence: Drive cross-functional initiatives, process improvements, and systems that support growth.
- Leadership Enablement: Prepare CEO for board, investor, and client engagements; manage executive meetings and follow-ups.
- Decision Support: Provide research, data, and analysis to inform strategic decisions.
- Communication Hub: Act as liaison between CEO, leadership team, and wider organization.
- Special Projects: Lead high-impact initiatives (new market entry, acquisitions, organizational scaling).
- Running and facilitating executive leadership meetings, ensuring follow-through.
- Tracking key metrics, projects, and accountability against company goals.
- Drafting CEO communications (internal and external).
- Coordinating investor and board materials.
- Identifying bottlenecks and resolving cross-departmental issues.
- Driving “CEO-only” projects to completion without constant oversight.
- Serving as an early warning system for risks or gaps in execution
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
