
Job Overview
Employment Type
Full-time
Work Schedule
Day Shifts
Fixed Shifts
Benefits
Health Insurance
Dental Insurance
Paid Time Off
401(k)
Parental leave
Commuter Benefits
Professional development opportunities
Job Description
project44 is a leading technology company headquartered in Chicago, IL, with a second headquarters in Bengaluru, India. The company is revolutionizing global supply chains through its advanced Decision Intelligence Platform called Movement. This platform transforms fragmented logistics data into real-time, AI-powered insights that allow companies to connect instantly, make clearer decisions, and automate processes intelligently. project44 serves a diverse global customer base and is committed to fostering innovation, urgency, and purpose in tackling complex logistics challenges. The company believes that a better supply chain is not only possible but essential for improving businesses and making a positive impact on the world.
The role offered is for two Executive Support Associates in the Office of the CEO, providing dedicated and high-availability support to the Founder and CEO of project44. This is a full-time, on-site position located in Chicago, requiring office attendance five days a week. The position operates through staggered shifts to ensure seamless coverage across the full day to support the CEO’s extensive professional and personal schedule. Under the direct guidance of the Senior Director of Executive Operations, this role demands a high degree of trust, discretion, and professionalism.
Unlike traditional administrative jobs, this is a high-trust, high-discretion role perfect for someone who excels in a fast-moving and dynamic environment where no two days are alike. The Executive Support Associate will handle complex logistics, personal coordination, and executive support concurrently with attention to detail and ownership of execution. The ideal candidate will be resourceful, calm under pressure, anticipatory of needs, proactive in problem-solving, and a trusted operator who ensures smooth operation both personally and professionally for the CEO.
Key responsibilities include managing personal logistics such as schedules, appointments, reservations, deliveries, and household tasks. The associate acts as a reliable point of contact during their assigned shifts, which may include early mornings, evenings, and occasional weekends. Travel and itinerary management is a significant part of the role, requiring the booking and coordinating of complex domestic and international travel arrangements, maintaining real-time itineraries, and quickly adapting to changes.
In addition to travel coordination, managing the CEO’s calendar, prioritizing scheduling requests, ensuring preparation for meetings, and managing expenses using platforms like Concur and Expensify are essential duties. The associate will also execute special projects, conduct research, coordinate events, and support personal errands. Operational improvements within the Office of the CEO are encouraged, reflecting a commitment to continuous improvement.
This position requires AI fluency, with an expectation that the candidate actively uses AI tools like Claude and ChatGPT to enhance efficiency in planning, communication, and problem-solving. Candidates who demonstrate curiosity and openness to AI integration will be prioritized. This role also demands absolute discretion, confidentiality, and impeccable professional judgment.
project44 is committed to diversity, equity, and inclusion, striving to build teams that reflect the communities they serve. The company values authentic self-expression and fosters a workplace where all team members feel a sense of belonging. project44 is an equal opportunity employer that welcomes applicants from all backgrounds and experiences. Candidates are encouraged to apply even if they meet only 50% of the qualifications. This opportunity is ideal for motivated individuals passionate about making an impact and working within a high-performance team environment.
The role offered is for two Executive Support Associates in the Office of the CEO, providing dedicated and high-availability support to the Founder and CEO of project44. This is a full-time, on-site position located in Chicago, requiring office attendance five days a week. The position operates through staggered shifts to ensure seamless coverage across the full day to support the CEO’s extensive professional and personal schedule. Under the direct guidance of the Senior Director of Executive Operations, this role demands a high degree of trust, discretion, and professionalism.
Unlike traditional administrative jobs, this is a high-trust, high-discretion role perfect for someone who excels in a fast-moving and dynamic environment where no two days are alike. The Executive Support Associate will handle complex logistics, personal coordination, and executive support concurrently with attention to detail and ownership of execution. The ideal candidate will be resourceful, calm under pressure, anticipatory of needs, proactive in problem-solving, and a trusted operator who ensures smooth operation both personally and professionally for the CEO.
Key responsibilities include managing personal logistics such as schedules, appointments, reservations, deliveries, and household tasks. The associate acts as a reliable point of contact during their assigned shifts, which may include early mornings, evenings, and occasional weekends. Travel and itinerary management is a significant part of the role, requiring the booking and coordinating of complex domestic and international travel arrangements, maintaining real-time itineraries, and quickly adapting to changes.
In addition to travel coordination, managing the CEO’s calendar, prioritizing scheduling requests, ensuring preparation for meetings, and managing expenses using platforms like Concur and Expensify are essential duties. The associate will also execute special projects, conduct research, coordinate events, and support personal errands. Operational improvements within the Office of the CEO are encouraged, reflecting a commitment to continuous improvement.
This position requires AI fluency, with an expectation that the candidate actively uses AI tools like Claude and ChatGPT to enhance efficiency in planning, communication, and problem-solving. Candidates who demonstrate curiosity and openness to AI integration will be prioritized. This role also demands absolute discretion, confidentiality, and impeccable professional judgment.
project44 is committed to diversity, equity, and inclusion, striving to build teams that reflect the communities they serve. The company values authentic self-expression and fosters a workplace where all team members feel a sense of belonging. project44 is an equal opportunity employer that welcomes applicants from all backgrounds and experiences. Candidates are encouraged to apply even if they meet only 50% of the qualifications. This opportunity is ideal for motivated individuals passionate about making an impact and working within a high-performance team environment.
Job Requirements
- Based in Chicago
- In-office five days per week
- Shift-based scheduling with two Associates covering staggered shifts for full-day availability
- Availability required outside standard business hours as CEO’s schedule demands
- Highest standards of discretion, confidentiality, and professional judgment
- Ability to manage complex logistics and multitask under pressure
- Strong interpersonal skills for liaising with vendors, contacts, and internal teams
Job Qualifications
- 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 ability to manage competing priorities with composure
- Strong written and verbal communication skills that are clear, concise, and professional
- Proficiency with expense tools such as Concur and Expensify, travel booking platforms, and Microsoft Office or Google Workspace
- AI fluency with active use of tools like Claude and ChatGPT for research, planning logistics, drafting communications, and problem solving
- Resourceful problem-solver with a bias toward action and a service-first mindset
- Absolute discretion and confidentiality at all times
Job Duties
- Provide comprehensive day-to-day support to the CEO across professional and personal priorities as directed
- 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 shifts including early mornings, evenings, and occasional weekends
- 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 including flights, accommodations, and ground transportation
- 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 Senior Director, Executive Operations
- Prioritize and triage scheduling requests, flag 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
Job Criteria
Experience
Mid Level (3-7 years)
Job Location
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