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Executive Assistant to the CEO - A192
Executive Assistant to the CEO - A192Pearl • Chicago, IL, US
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Executive Assistant to the CEO - A192

Executive Assistant to the CEO - A192

Pearl • Chicago, IL, US
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Executive Assistant To Support The CEO

A managed mobility services company that supports small and medium-sized businesses with all aspects of telecommunications fleet management. The company is scaling rapidly and requires strong operational and administrative support at the executive level.

We are seeking a high-caliber Executive Assistant to support the CEO in managing and scaling the company's operations. This role goes beyond typical administrative work and blends executive support, operational follow-through, and light project coordination. You will act as a force-multiplier to the CEO by protecting their time, maintaining clear priorities, and ensuring operational and administrative tasks are handled accurately and consistently.

The scope is approximately 90% business-related support and 10% personal logistics. This role requires someone proactive, analytical, highly organized, and capable of maintaining tight control over details, deadlines, and follow-through.

Your Impact :

  • Enable the CEO to focus more on strategy, leadership, and external relationships by reducing time spent on administrative tasks.
  • Bring structure, clarity, and organization to the CEO's daily operations.
  • Improve internal coordination and operational consistency through reliable follow-up and task management.
  • Contribute to smoother project execution by coordinating information, owners, and next steps.
  • Ensure commitments, deadlines, and operational routines stay on track.
  • Build repeatable systems that the CEO can rely on long-term.

Core Responsibilities :

Executive & Administrative Support :

  • Own and manage the CEO's calendar, including internal meetings, external calls, and priority-based scheduling.
  • Coordinate and book travel arrangements (flights, hotels, transportation) and create detailed itineraries.
  • Handle inbox triage : flag urgent messages, draft replies, file emails, and ensure no important items slip through.
  • Prepare correspondence and communicate with internal teams, vendors, and partners as needed.
  • Support legal and administrative documentation (routing forms, collecting signatures, tracking deadlines).

    • Meetings & Coordination :

  • Prepare agendas, key points, notes, and action items for CEO-requested meetings.
  • Track follow-ups and ensure owners meet commitments and deadlines.
  • Coordinate with internal team members to move initiatives forward based on CEO direction.

    • Operations & Light Project Coordination :

  • Support ad hoc projects by conducting online research, gathering information, and organizing next steps.
  • Maintain and update the CRM (ConnectWise) with accurate information (training provided if needed).
  • Assist with expense reports, receipt tracking, and light bookkeeping coordination.
  • Keep task lists or project tracking tools updated and organized.

    • Personal Support (Approx. 10%) :

  • Schedule personal appointments, reservations, gifts, and occasional household / vendor coordination as needed.
  • Protect the CEO's personal time by managing schedule conflicts and ensuring adequate breathing room.
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