Executive Assistant (CEO Support | AI Tools Proficient)

UpworkUSNot specifiedexpertScore: 57
Executive SupportAdministrative SupportEmail CommunicationCommunicationsVirtual AssistanceAI Agent Development
We are hiring an experienced Executive Assistant to support a high-accountability executive in a fast-paced, demanding environment. This role requires someone who has done this before and who actively uses AI tools to operate faster, smarter, and with greater leverage. This is not a task-processing or entry-level role. The right person operates with sound judgment, anticipates needs, and independently removes friction. What You’ll Do • Act as an extension of the executive, managing priorities, logistics, and follow-through • Independently plan and manage complex schedules, travel, and itineraries end-to-end • Anticipate needs, flag risks early, and resolve issues without waiting for direction • Manage inboxes, meetings, and information flow with discretion and clarity • Coordinate with internal and external stakeholders confidently and efficiently • Leverage AI tools to increase speed, accuracy, and quality of execution (e.g., drafting, summarization, research, prioritization) • Continuously simplify workflows and reduce cognitive load for the executive Who This Role Is For • 7+ years as an Executive Assistant supporting senior leaders or CEOs • Prior experience in demanding, fast-moving environments • Strong working knowledge of AI tools (e.g., ChatGPT or similar) used in daily workflows • Demonstrated ability to use AI to draft, summarize, prioritize, and problem-solve independently • Comfortable making judgment calls with limited guidance • Highly organized, calm under pressure, and adaptable to change • Trusted with sensitive information and confidential matters Who This Role Is Not For • Entry-level or junior EAs • Task-only or process-driven support roles • Candidates who rely on constant direction or heavy training • Candidates unfamiliar with using AI as a daily productivity tool
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Spent: $337,844.63Rating: 5.0Verified
Executive Assistant (CEO Support | AI Tools Proficient) — Sift