Chief Executive Assistant - Global Opportunity

What We're Looking For

Squared Away is seeking a highly skilled and motivated Chief Executive Assistant to join our dynamic team in the staffing and recruiting industry. As an integral part of our organization, you will provide exceptional support to senior executives, ensuring that their daily operations run smoothly and efficiently.

This role presents a unique global opportunity, allowing you to work with top-tier clients and professionals across various markets. You will be tasked with managing complex schedules, coordinating international travel, and liaising with stakeholders to facilitate effective communication.

In this fast-paced environment, we are looking for someone who is proactive, detail-oriented, and able to anticipate the needs of our executives. Working closely with our clients, you will contribute to strategic initiatives and utilize your organizational skills to help drive business success. This position offers a chance to grow your career within a thriving company that values innovation and excellence. If you have a passion for providing outstanding support and are ready to take on new challenges, we invite you to apply for this exciting opportunity.

Squared Away maintains a rolling application for our Executive Assistant position. This posting is for Q3 2025 (July - September)

What You'll Be Doing

• Manage and maintain complex calendars for executives, ensuring efficient time management and prioritization of meetings.
• Coordinate international and domestic travel arrangements, including flights, accommodations, and itineraries for high-profile clients.
• Serve as a liaison between executives and internal/external stakeholders, ensuring clear and effective communication.
• Prepare and organize materials for meetings, including agendas, presentations, and reports, ensuring that executives are well-prepared.
• Handle confidential information with discretion and maintain the highest level of confidentiality in all communications and transactions.
• Assist in project management tasks by tracking deadlines, deliverables, and providing status updates to executives.
• Conduct research and gather information on industry trends, competitors, and market opportunities to support executive decision-making.

Requirements

What You'll Bring to the Table

• Proven experience as an executive assistant or in a similar role supporting C-level executives in a fast-paced environment.
• Exceptional organizational and multitasking skills, with a keen attention to detail and the ability to prioritize tasks effectively.
• Strong written and verbal communication skills, able to articulate ideas clearly and concisely in various contexts.
• Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook) and familiarity with project management tools.
• Ability to work autonomously with limited supervision while also collaborating effectively with team members.
• Previous experience in a global setting, with an understanding of cross-cultural communication and time zone management.
• A proactive mindset with a problem-solving approach, demonstrating initiative and flexibility in handling unexpected challenges.
• U.S.-based time zones (EST, CST, MST, PST); all states except New York

Benefits

Compensation

• Independent Contractor Split: Client payments are distributed with a 60/40 split, where 60% of the payments go directly to the assistant. This structure demonstrates our dedication to recognizing skill and commitment. Assistants have the flexibility to support as many client hours as they wish.

Authentic, not Artificial

TLDR: Do not use ChatGPT or any other AI tool to draft your responses. We can tell, and it will disqualify your application. We value authentic, original answers that reflect your own experience and perspective.

We're eager to get to know you and what you can bring to the table. While we support using AI to enhance our day-to-day, we kindly ask that you refrain from using it during the application process. Your responses should be your own original work and reflect your personal experience, voice, and perspective. We’re excited about your unique skills and experiences, authentically and without AI in the mix.

Reapplying?

If you’ve previously applied and were not selected, we encourage you to reapply! We release an updated version of this application each quarter to give returning candidates another opportunity to be considered. You’re welcome to submit a new application when the next version becomes available.