EA & Travel Coordinator, Office of the CEO

About the Role:

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.

Key Accountabilities:

• 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.

Requirements & Skills:

• 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.

Our interview process is designed to understand how you think, how you operate, and how you handle the unexpected. For this role, you can expect:

AI fluency is a requirement for this role. Candidates who actively use AI tools even in personal or casual contexts will be prioritized.

Diversity & Inclusion:

At project44, we're designing the future of how the world moves and is connected through trade and global supply chains. As we work to deliver a truly world-class product and experience, we are also intentionally building teams that reflect the unique communities we serve. Were focused on creating a company where all team members can bring their authentic selves to work every day.

Were building a company that every one of us at project44 is proud to work for, and our journey of becoming a more diverse, equitable and inclusive organization, where all have a sense of belonging, is shaped through the actions of our leadership, global teams and individual team members. We are resolute in our belief that each team member has an equal responsibility to mold and uphold our culture.

project44 is an equal opportunity employer seeking to enrich our work environment by creating opportunities for individuals of all backgrounds and experiences to thrive. If you share our values and our passion for helping the way the world moves, wed love to review your application!

For any accommodation needed during the hiring process, please email . Even if you dont meet 100% of the above job description you should still seriously consider applying. Studies show that you can still be considered for a role if you meet just 50% of the roles requirements.