Squared Away Partners, LLC
About Squared Away
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
Q1 2026
(January - March)
What We're Looking For This is not an entry-level role, and it is not a side role.
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.
What Tends to Work Well in This Role Our work is fast-paced, collaborative, and built on trust. Assistants who thrive here typically:
Have established experience supporting senior executives
Enjoy variety and problem-solving over repetitive task work
Are available and responsive during weekday business hours
Take a proactive approach and anticipate needs rather than waiting for direction
Stay effective when priorities change or when not everything is fully defined
Treat confidentiality and discretion as non-negotiable
Structure their day with dedicated work blocks in the morning and afternoon, allowing for consistent availability, focused work time, and timely communication with executives
If you see yourself in this list, you’re likely a great match for how we work at Squared Away.
What You’ll Be Responsible For Executive Operations & Time Management
Manage and optimize complex executive calendars across time zones
Anticipate conflicts and proactively resolve scheduling issues
Protect executive focus by enforcing priorities and boundaries
Executive Communication
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
Travel & Logistics
Coordinate domestic and international travel end-to-end
Prepare detailed itineraries and anticipate changes or disruptions
Preparation & Execution
Prepare meeting materials, agendas, presentations, and reports
Track action items, deadlines, and follow-through across initiatives
Systems & Process Improvement
Create, document, and refine workflows to improve efficiency
Identify tools and processes that reduce friction and increase clarity
Research & Strategic Support
Conduct research on competitors, tools, vendors, and market trends
Provide concise summaries to support executive decision‑making
Discretion & Trust
Handle sensitive and confidential information with absolute integrity
What Success Looks Like in the First 90 Days In the first 90 days, successful Chief Executive Assistants at Squared Away typically:
Actively take on client work and build momentum by supporting assigned clients successfully
Build trust and rapport with their executive(s) through consistent communication and follow-through
Develop a strong understanding of executive priorities, preferences, and working style
Take ownership of calendar and inbox management, proactively anticipating needs and resolving issues before escalation
Establish reliable systems for tracking tasks, deadlines, and follow‑ups
Communicate clearly and confidently, even when priorities shift or information is incomplete
Maintain discretion and professionalism while handling sensitive information
Structure their workday to balance availability, focused work time, and responsiveness
This is not about perfection. It’s about progress, ownership, and building momentum.
Minimum Qualifications (Required)
Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
Must be based in a U.S. time zone (EST, CST, MST, or PST); applicants must reside in the United States,
excluding New York
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
Experience working remotely is strongly preferred
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
Skills & Attributes We Look For
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
Compensation & Contractor Details
Independent contractor (1099) role
Client payments are distributed on a
60/40 split , with
60% paid directly to the assistant
Assistants choose how many client hours they take on
Squared Away manages client acquisition, billing, and invoicing
Access to a vetted client base across industries including consulting, marketing, nonprofit, finance, real estate, and more
100% remote with flexibility in client load
Earnings vary based on client plans, hours worked, and availability; assistants have control over their client load and overall monthly earnings.
Authentic, not Artificial We value clear thinking, sound judgment, and authentic communication.
While we support the thoughtful use of AI tools in day-to-day work, we do not allow AI-generated responses during the application process. Applications that rely on AI-generated answers will be disqualified.
If you move forward in the process, it’s because we want to hear your voice, perspective, and experience. We’re not looking for perfection. We’re looking for honesty, clarity, and professionalism.
Reapplying? If you’ve applied previously and were not selected, we encourage you to reapply. We release updated versions of this application each quarter to reflect evolving needs and give returning candidates another opportunity to be considered.
#J-18808-Ljbffr
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
Q1 2026
(January - March)
What We're Looking For This is not an entry-level role, and it is not a side role.
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.
What Tends to Work Well in This Role Our work is fast-paced, collaborative, and built on trust. Assistants who thrive here typically:
Have established experience supporting senior executives
Enjoy variety and problem-solving over repetitive task work
Are available and responsive during weekday business hours
Take a proactive approach and anticipate needs rather than waiting for direction
Stay effective when priorities change or when not everything is fully defined
Treat confidentiality and discretion as non-negotiable
Structure their day with dedicated work blocks in the morning and afternoon, allowing for consistent availability, focused work time, and timely communication with executives
If you see yourself in this list, you’re likely a great match for how we work at Squared Away.
What You’ll Be Responsible For Executive Operations & Time Management
Manage and optimize complex executive calendars across time zones
Anticipate conflicts and proactively resolve scheduling issues
Protect executive focus by enforcing priorities and boundaries
Executive Communication
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
Travel & Logistics
Coordinate domestic and international travel end-to-end
Prepare detailed itineraries and anticipate changes or disruptions
Preparation & Execution
Prepare meeting materials, agendas, presentations, and reports
Track action items, deadlines, and follow-through across initiatives
Systems & Process Improvement
Create, document, and refine workflows to improve efficiency
Identify tools and processes that reduce friction and increase clarity
Research & Strategic Support
Conduct research on competitors, tools, vendors, and market trends
Provide concise summaries to support executive decision‑making
Discretion & Trust
Handle sensitive and confidential information with absolute integrity
What Success Looks Like in the First 90 Days In the first 90 days, successful Chief Executive Assistants at Squared Away typically:
Actively take on client work and build momentum by supporting assigned clients successfully
Build trust and rapport with their executive(s) through consistent communication and follow-through
Develop a strong understanding of executive priorities, preferences, and working style
Take ownership of calendar and inbox management, proactively anticipating needs and resolving issues before escalation
Establish reliable systems for tracking tasks, deadlines, and follow‑ups
Communicate clearly and confidently, even when priorities shift or information is incomplete
Maintain discretion and professionalism while handling sensitive information
Structure their workday to balance availability, focused work time, and responsiveness
This is not about perfection. It’s about progress, ownership, and building momentum.
Minimum Qualifications (Required)
Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
Must be based in a U.S. time zone (EST, CST, MST, or PST); applicants must reside in the United States,
excluding New York
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
Experience working remotely is strongly preferred
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
Skills & Attributes We Look For
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
Compensation & Contractor Details
Independent contractor (1099) role
Client payments are distributed on a
60/40 split , with
60% paid directly to the assistant
Assistants choose how many client hours they take on
Squared Away manages client acquisition, billing, and invoicing
Access to a vetted client base across industries including consulting, marketing, nonprofit, finance, real estate, and more
100% remote with flexibility in client load
Earnings vary based on client plans, hours worked, and availability; assistants have control over their client load and overall monthly earnings.
Authentic, not Artificial We value clear thinking, sound judgment, and authentic communication.
While we support the thoughtful use of AI tools in day-to-day work, we do not allow AI-generated responses during the application process. Applications that rely on AI-generated answers will be disqualified.
If you move forward in the process, it’s because we want to hear your voice, perspective, and experience. We’re not looking for perfection. We’re looking for honesty, clarity, and professionalism.
Reapplying? If you’ve applied previously and were not selected, we encourage you to reapply. We release updated versions of this application each quarter to reflect evolving needs and give returning candidates another opportunity to be considered.
#J-18808-Ljbffr