Jobs · Administrative · Illinois

PA & Travel Coordinator, Office of the CEO

project44 · Chicago, IL · 1 mo ago
On-siteAdministrativeFull-time

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.

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.

Requirements & Skills

  • 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.

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