Chief Executive Assistant

About Squared Away

Squared Away partners with founders, executives, and leadership teams who operate in demanding, fast-moving environments. The assistants here are expected to be more than task handlers; they serve as dependable strategic partners who add order, clarity, and consistent follow-through.

The company’s purpose is to return time to the people who need it most. Achieving that requires sound judgment, confidentiality, and steady execution every day.

Squared Away keeps a rolling intake for its Executive Assistant role. This posting is intended for Q3 2026, covering July through September.

Role Overview

This is a senior-level position, not an entry-level or occasional assignment. As a Chief Executive Assistant, you will support senior executives who rely on proactive thinking, strong communication, and dependable delivery. You’ll manage shifting priorities, identify needs ahead of time, and work with the level of ownership expected from an in-house executive support professional.

This opportunity is structured as an independent contractor role for experienced professionals who want flexibility while maintaining high standards.

What Success Looks Like

People who do well in this environment usually communicate clearly, stay calm when priorities change, and take initiative without needing constant direction. They are comfortable with variety, prefer solving problems over repeating the same tasks, and can remain responsive during weekday business hours. They also organize their day into focused work blocks in the morning and afternoon so they can stay available, communicate promptly, and complete work efficiently.

Key Responsibilities

You will be expected to manage executive support with a high degree of discretion, structure, and follow-through. Core responsibilities include calendar coordination across time zones, inbox management, travel planning, meeting preparation, workflow refinement, research support, and handling sensitive information with care.

Executive Operations and Time Management

• Organize and optimize demanding executive calendars across multiple time zones.
• Spot scheduling conflicts early and resolve them before they become issues.
• Safeguard executive focus by reinforcing priorities and boundaries.

Communication Support

• Oversee executive inboxes carefully and with good judgment.
• Draft, reply to, and sort correspondence on behalf of executives.
• Escalate urgent matters quickly and appropriately.

Travel and Logistics

• Arrange domestic and international travel from start to finish.
• Create detailed itineraries and plan ahead for changes or disruptions.

Preparation and Execution

• Prepare agendas, presentation materials, reports, and meeting documents.
• Track action items, deadlines, and follow-ups across multiple initiatives.

Systems and Process Improvement

• Build, document, and improve workflows that increase efficiency.
• Recommend tools and processes that reduce friction and improve clarity.

Research and Strategic Support

• Research competitors, vendors, tools, and market developments.
• Summarize findings in a concise way that supports decision-making.

Discretion and Trust

• Protect confidential and sensitive information with complete integrity.

Requirements

Applicants must have a permanent U.S. address in one of these 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, or Washington.

Military spouses living abroad on active orders may also apply, as long as they keep a permanent address in one of the listed states and can support clients reliably during U.S. business hours.

Availability during regular business hours, Monday through Friday from 9 AM to 5 PM in your own time zone, is required for client communication. This role cannot be paired with another job that restricts availability during those hours.

Candidates must be able to commit at least 20 hours per week, with flexibility to take on more hours if needed. Administrative experience supporting senior leaders is required, and executive-level support experience is strongly preferred. Prior remote work experience is also strongly preferred.

A reliable home office is required, including a Mac or PC with a webcam, high-speed internet, a smartphone with email access, and a quiet dedicated workspace suitable for professional work.

Skills and Attributes

Successful candidates typically bring strong communication ability, advanced organization, and a high level of emotional intelligence. They are comfortable using Microsoft Office tools, project management systems, and modern digital tools. They should be able to manage schedules and priorities across time zones, work independently, adapt quickly to new systems, and handle cross-cultural communication in a global environment.

Compensation and Contractor Terms

This is a fully remote 1099 independent contractor position. Pay is based on billable hours and depends on experience tier:

• Tier 1: $24 per hour
• Tier 2: $30 per hour
• Tier 3: $36 per hour

Contractors log billable time in Harvest Time Tracking during each client plan period, and payments are made twice a month. Most contractors support 2 to 4 clients at once. Client opportunities are shared according to business needs, and contractors choose which ones to accept, allowing them to shape a workload that fits their availability and goals.

Squared Away manages client sourcing, client agreements, billing, and invoicing so contractors can focus on delivering strong executive support. Contractors work with a vetted client base across industries such as venture capital, consulting, finance, marketing, nonprofit, real estate, technology, and more.

Application Expectations

The company values clear thinking, good judgment, and authentic communication. AI tools may be used thoughtfully and responsibly, but application responses should reflect the candidate’s own voice, experience, and decision-making. Fully AI-generated answers without personal input may affect consideration.

If selected to move ahead, candidates will be evaluated on how they think, communicate under pressure, and make decisions. The focus is on clarity, ownership, and professionalism rather than perfection.

Reapplication and Privacy

Applicants who have applied before and were not chosen are encouraged to try again. The application is refreshed each quarter to reflect changing needs and to give returning candidates another opportunity.

By submitting an application, candidates agree to the Candidate Privacy Notice.