This elite position is not for the faint of heart. It demands unmatched dedication, resilience, and an unwavering commitment to excellence. Every day presents new challenges that require you to perform at the highest level and support clients who are leaders at the top of their fields. Mediocrity has no place here—this role is for those who thrive on pushing boundaries and delivering exceptional results.

Squared Away is seeking top-tier professionals to join us asChief Executive Assistantsin a fully-remoteindependent contractor (1099)capacity. This is not a "side hustle" or a gig—it’s an opportunity to collaborate with some of the most influential business leaders globally. To succeed, you must bring a mindset of excellence, adaptability, and the drive to exceed the high expectations of our elite clients.

This role is for those who excel in fast-paced, high-stakes environments, thrive on solving complex challenges, and are passionate about providing unparalleled service.

Our work is guided by four core pillars:over-communication, extreme attention to detail, thinking outside the box, and being a team player.

Role Specifics

Position:Chief Executive Assistant
Location:U.S.-based time zones (EST, CST, MST, PST); all states except New York
Hours:Must be available to work 9:00 am - 5:00 pm in U.S. time zones
Commitment:Must support clients for a minimum of 25 hours per month

Responsibilities

Proactive Client Support:Anticipate client needs and deliver strategic solutions, managing complex scheduling, project oversight, event coordination, and daily operations
Relationship Building:Establish and maintain professional relationships rooted in trust, reliability, and excellence in communication
Email Management:Efficiently handle and prioritize high-volume client email communications
Scheduling:Seamlessly coordinate meetings across time zones, ensuring precision and availability
Executive-Level Support:Execute critical tasks, including travel arrangements, expense reporting, and strategic support for business development, fundraising, and lead generation

Requirements

Experience:Minimum of 1 year in high-level administrative roles, with demonstrated expertise in managing calendars, planning travel, and providing exceptional support to fast-paced, high-performing clients and businesses across diverse industries. Only candidates with proven ability to deliver top-tier results will be considered
Technology Proficiency:Advanced experience with tools such as Slack, Google Drive, Microsoft Excel, Salesforce, Canva, CRM platforms, and QuickBooks
Education:A high school diploma is required; an Associate’s degree or higher is preferred
Skills:Uncompromising attention to detail, exceptional organizational and communication abilities, and the capability to operate independently in demanding environments
Technology Needs:Must have a fully functional mobile phone and computer (not a Chromebook or tablet) capable of handling advanced client platforms

Compensation

Independent Contractor Split:Client plans are split 60/40, with 60% of client payments directly allocated to the assistant. This model reflects our commitment to rewarding expertise and dedication

Overseas Applicants

We welcome candidates stationed overseas, including Japan, provided they can work U.S.-based business hours (9:00 am - 5:00 pm). Response times must align with U.S.-based client expectations to ensure consistency.

About Squared Away

Squared Away is a premier virtual executive assistant agency committed to empowering military spouses with meaningful, flexible careers while delivering world-class support to top-tier clients. Our elite clients include leaders in Fortune 500 companies, venture capital firms, and high-level executives across the globe.

This role demands the highest level of commitment, a relentless pursuit of excellence, and the ability to thrive under pressure. If you’re ready to take on the challenges of working with the most influential leaders worldwide and uphold Squared Away’s elite standards, we encourage you to apply.

Cheers to the future!

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