Executive Support Associate, Office of the CEO

project44•Chicago, IL

2d•Onsite

About The Position

project44 is seeking two Executive Support Associates to join the Office of the CEO, providing dedicated, high-availability support to our Founder and CEO. These roles are structured as staggered shifts across the day to ensure seamless coverage across the CEO's full day — professional and personal — and operate under the direct oversight of our Sr. Director, Executive Operations. This is a high-trust, high-discretion role for someone who thrives in a fast-moving, dynamic environment and understands that supporting a high-profile founder means no two days look alike. The right person is resourceful, calm under pressure, anticipates needs before they're voiced, and takes deep personal ownership of execution. This is not a traditional office admin role. It requires the judgment, professionalism, and personal accountability of a trusted operator — someone who can manage logistics, personal coordination, and executive support simultaneously without missing a beat.

Requirements

Based in Chicago; in-office five days per week — this is a fully on-site role.
Shift-based scheduling: two Associates cover staggered shifts to ensure full-day availability. Shift hours will be confirmed during the hiring process.
Availability required outside standard business hours as the CEO's schedule demands.
Highest standards of discretion, confidentiality, and professional judgment at all times.
Minimum of 3-5 years in executive support, personal assistant, lifestyle management, or a comparable high-trust role.
Exceptional organizational skills and the ability to manage competing priorities with composure.
Strong written and verbal communication skills — clear, concise, and professional.
Proficiency with expense tools (Concur, Expensify), travel booking platforms, and Microsoft Office / Google Workspace.
AI fluency is a requirement: you actively use tools like Claude and ChatGPT to research, plan logistics, draft communications, and solve problems faster. Genuine curiosity about how AI can make you more effective is expected.
Resourceful problem-solver with a bias toward action and a service-first mindset.
Absolute discretion — you understand that what happens in this role stays in this role.

Nice To Haves

Experience supporting a high-profile executive, founder, or UHNW principal strongly preferred.

Responsibilities

Provide comprehensive day-to-day support to the CEO across professional and personal priorities as directed by the Sr. Director, Executive Operations.
Manage and coordinate personal logistics including scheduling, appointments, reservations, deliveries, and household or lifestyle-related tasks.
Serve as a reliable, responsive point of contact during assigned shift hours — including early mornings, evenings, and occasional weekends as coverage requires.
Anticipate the CEO's needs and proactively solve problems before they surface.
Liaise with vendors, service providers, personal contacts, and internal team members on behalf of the CEO.
Book and manage complex domestic and international travel logistics — flights, accommodations, ground transportation, and contingency plans.
Build detailed, real-time itineraries and ensure all parties are aligned and informed.
Monitor travel in real time and pivot quickly when plans change.
Coordinate with executive EAs across the leadership team to align travel schedules.
Support calendar management for the CEO in coordination with the Sr. Director, Executive Operations.
Prioritize and triage scheduling requests, flagging conflicts and recommending resolutions.
Ensure the CEO is briefed, prepared, and on time for all commitments.
Manage receipts, expense reporting, and reimbursements using Concur and Expensify.
Maintain organized digital filing systems for expense documentation and compliance.
Execute special requests, research projects, event coordination, and personal errands as directed.
Support executive event logistics including dinners, private events, and VIP experiences.
Contribute to operational improvements within the Office of the CEO.