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Executive Support Associate, Office of the CEO

Chicago, IL

 

 

 

Why project44?   

At project44, we believe in better.   

We challenge the status quo because we know a better supply chain isn’t just possible, it’s essential. Better for our customers. Better for their business. Better for the world.   

With our Decision Intelligence Platform, Movement, we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward.   

Headquartered in Chicago, IL, with a 2nd HQ in Bengaluru, India, we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose. If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team – we should talk.  

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:  

Executive & Personal Support 

  • 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.  

Travel & Itinerary Management 

  • 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. 

Scheduling & Calendar Coordination 

  • 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.  

Expense & Receipt Management 

  • Manage receipts, expense reporting, and reimbursements using Concur and Expensify. 
  • Maintain organized digital filing systems for expense documentation and compliance.  

Special Projects & Ad Hoc Support 

  • 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. 

What You Bring 

  • Minimum of 3-5 years in executive support, personal assistant, lifestyle management, or a comparable high-trust role. 
  • Experience supporting a high-profile executive, founder, or UHNW principal strongly preferred. 
  • 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. 

 How We Hire 

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: 

  • A recruiter screen focused on your background, availability, and comfort with a shift-based, high-availability role. 
  • An AI fluency conversation — we'll ask how you use tools like Claude or ChatGPT today and where you see them being useful in a fast-moving support role. We're looking for curiosity and openness, not perfection. 
  • A practical scenario with the hiring team — you may be asked to walk through how you'd handle a real-world logistics or coordination challenge, and whether/how you'd use AI tools to solve it. 
  • Final conversations with the Sr. Director, Executive Operations and VP, People.  

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. We’re focused on creating a company where all team members can bring their authentic selves to work every day. 

We’re 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, we’d love to review your application! 

For any accommodation needed during the hiring process, please email recruiting@project44.com. Even if you don’t 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 role’s requirements. 

 

 

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