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Executive Assistant to Chief Executive Officer

Vermilion Development
Chicago, IL Other
POSTED ON 4/3/2026
AVAILABLE BEFORE 5/1/2026

We are seeking an elite Executive Assistant who operates as the CEO’s control tower—anticipating needs before they arise, protecting time and attention, and eliminating friction across both business and personal life.


This is not a reactive administrative role. It is a high-trust, high-autonomy position for an A operator whose primary objective is to reduce worry, increase clarity, and ensure nothing falls through the cracks.


You will stay ahead of the CEO—seeing around corners, proactively solving problems, and ensuring the day, week, and month run with precision.

What Success Looks Like

  • The CEO’s time is optimized against true priorities—not dictated by inbound requests
  • Scheduling happens proactively with minimal back-and-forth or last-minute changes
  • The CEO’s inbox is controlled, organized, and actionable—not overwhelming
  • Travel, meetings, and logistics are seamless and fully prepared in advance
  • There are no dropped balls—issues are anticipated and resolved before they escalate
  • Internal and external stakeholders experience the Executive Assistant as a direct extension of the CEO—highly responsive, impeccably organized, and consistently professional in every interaction
  • The CEO experiences materially less mental load because you are consistently ahead

Core Responsibilities

Calendar & Time Optimization (Strategic Ownership)

  • Own the CEO’s calendar end-to-end, ensuring it reflects priorities, not requests
  • Proactively plan and sequence meetings with appropriate buffers, prep time, and travel considerations
  • Continuously audit upcoming schedules to identify conflicts, inefficiencies, or risks—and resolve them in advance
  • Independently prioritize and make scheduling decisions on behalf of the CEO

Inbox Management & Communication Control

  • Serve as the primary manager of the CEO’s inbox—triaging, organizing, and driving responses
  • Proactively handle inbound scheduling requests by coordinating directly with internal and external stakeholders
  • Draft, prioritize, and respond to emails where appropriate; ensure timely follow-up and closed loops
  • Surface only what requires the CEO’s attention, while resolving or routing the rest independently
  • Maintain a zero-backlog, highly organized inbox system that reduces noise and increases clarity

Meetings & Executive Readiness

  • Coordinate all virtual and in-person meetings with precision and professionalism
  • Ensure agendas, materials, participants, and logistics are fully prepared in advance
  • Prepare meeting environments to a “white-glove” standard, including food, beverage, and room readiness
  • Drive follow-up and ensure next steps are executed—no loose ends

Travel & Logistics (Contingency-First)

  • Plan and manage all travel end-to-end, including flights, accommodations, transportation, and itineraries
  • Anticipate disruptions and proactively manage contingencies
  • Maintain and refine detailed preferences to ensure consistency and efficiency

Personal & Family Support

  • Manage personal logistics, errands, and family-related needs with discretion and efficiency
  • Anticipate and manage routine personal maintenance (e.g., car care, grooming appointments, wardrobe upkeep) so these needs are handled seamlessly and never surface as a demand on the CEO’s time or attention
  • Reduce day-to-day friction in the CEO’s personal life while maintaining absolute confidentiality

Operating Principles (Non-Negotiable)

  • Anticipation over reaction: You solve problems before they exist
  • Near-perfection mindset: You build systems and checks to avoid mistakes
  • No surprises: Risks are surfaced early with proposed solutions
  • Extreme ownership: Nothing falls through the cracks—ever
  • Speed with accuracy: You operate quickly without sacrificing detail

Qualifications

  • Minimum of 5-7 years supporting a CEO in a fast-paced, high-performance environment
  • Bachelor's Degree required
  • Demonstrated ability to manage and prioritize a high-volume inbox and scheduling flow
  • Exceptional judgment and decision-making ability
  • Elite organizational skills and follow-through
  • Strong written and verbal communication skills
  • High attention to detail and commitment to excellence
  • Ability to operate independently with minimal direction
  • Absolute discretion and professionalism
  • Valid driver’s license with strong driving record
  • Proficiency with Microsoft Office (Outlook, Word, Excel, PowerPoint


Availability & Responsiveness

This role requires a high degree of responsiveness and flexibility, including outside normal business hours when necessary.


The expectation is not constant chaos—but reliable, thoughtful coverage. The Executive Assistant is expected to build systems that reduce after-hours emergencies over time, while remaining available for truly time-sensitive matters.


EOE

Hourly Wage Estimation for Executive Assistant to Chief Executive Officer in Chicago, IL
$39.00 to $48.00
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