Chief Executive Assistant

Squared Away

1d • $24 - $36 • Remote

About The Position

Squared Away supports founders, executives, and leadership teams operating at a high level of complexity and pace. Our assistants are not task-takers. They are trusted, strategic partners who bring structure, clarity, and follow-through to demanding environments. We exist to give people their most valuable resource back: time. That work requires judgment, discretion, and consistency, every single day. Squared Away maintains a rolling application for our Executive Assistant position. This posting is for Q3 2026 (July - September). As a Chief Executive Assistant at Squared Away, you will support senior executives who expect proactive thinking, excellent communication, and dependable execution. You will manage competing priorities, anticipate needs before they are voiced, and operate with a level of ownership that mirrors in-house executive support. This is an independent contractor role designed for experienced professionals who want flexibility without sacrificing standards.

Requirements

• Applicants must maintain a permanent U.S. address in one of the following states: Alabama, Alaska, Arizona, California, Colorado, Florida, Georgia, Hawaii, Illinois, Indiana, Iowa, Kentucky, Louisiana, Maryland, Michigan, Missouri, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas, Virginia, Washington
• Military spouses living overseas on active orders are welcome to apply, provided they maintain a permanent address in one of the states listed above and can reliably support clients during U.S. business hours.
• Must be available during normal business hours Monday–Friday, 9 AM–5 PM (in your time zone) for regular client communication
• This role cannot be combined with another job that limits availability during these hours
• Ability to commit a minimum of 20 hours per week, with flexibility to take on additional hours
• Administrative experience supporting senior leaders is required
• Reliable home office setup, including: Mac or PC computer with webcam, High-speed internet, Smartphone with email capabilities, A designated, quiet workspace suitable for professional work
• Strong written and verbal communication skills, able to clearly and concisely communicate in a variety of contexts
• Proficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook, with familiarity using project management tools
• Experience managing schedules, communication, and priorities across time zones
• Understanding of cross-cultural communication in a global working environment
• Exceptional organization and attention to detail
• High emotional intelligence and situational awareness
• Comfortable working independently without constant direction
• Tech-savvy and quick to learn new systems and tools
• Proactive mindset that anticipates needs rather than reacts

Nice To Haves

• experience supporting executive-level roles is strongly preferred
• Experience working remotely is strongly preferred

Responsibilities

• Manage and optimize complex executive calendars across time zones
• Anticipate conflicts and proactively resolve scheduling issues
• Protect executive focus by enforcing priorities and boundaries
• Manage executive inboxes with discretion and sound judgment
• Draft, respond to, and triage correspondence on behalf of executives
• Ensure urgent matters are surfaced promptly and appropriately
• Coordinate domestic and international travel end-to-end
• Prepare detailed itineraries and anticipate changes or disruptions
• Prepare meeting materials, agendas, presentations, and reports
• Track action items, deadlines, and follow-through across initiatives
• Create, document, and refine workflows to improve efficiency
• Identify tools and processes that reduce friction and increase clarity
• Conduct research on competitors, tools, vendors, and market trends
• Provide concise summaries to support executive decision-making
• Handle sensitive and confidential information with absolute integrity

Benefits

• This is a fully remote 1099 independent contractor position.
• Contractors are paid for billable hours worked, with hourly rates determined by experience and tier level: Tier 1: $24/hour, Tier 2: $30/hour, Tier 3: $36/hour
• Contractors submit time through Harvest Time Tracking for billable work completed during each client plan period, and payments are issued twice monthly.
• Most contractors support 2–4 clients at a time. Client opportunities are offered based on business needs, and contractors decide which opportunities to accept, allowing them to build a workload that aligns with their availability and business goals.
• Squared Away handles client acquisition, client contracts, billing, and invoicing so you can focus on providing exceptional executive support.
• You'll work with a vetted client base across a wide range of industries, including venture capital, consulting, finance, marketing, nonprofit, real estate, technology, and more.
• This is a fully remote role with the flexibility to build a client portfolio that fits your schedule.

What This Job Offers

• Job Type: Part-time
• Career Level: Senior
• Education Level: No Education Listed