Virtual Executive Assistant / CEO Time & Calendar Strategist

I am a business owner and CEO looking for an experienced Virtual Executive Assistant who has previously supported CEOs, founders, or senior executives.

This is NOT simply a calendar-management or administrative position.

I am looking for someone who can help me redesign how I manage my time and ultimately create more freedom in my life.

What I Need Help With

My initial priorities include:

Audit and clean up my Google Calendar

Help redesign my ideal weekly schedule

Review and improve my current booking rules

Create better boundaries around who can access my time

Establish meeting rules, buffers, availability, and protected time

Identify meetings and commitments that can be eliminated, shortened, delegated, or handled asynchronously

Help determine what should require my involvement — and what should not

Create systems for managing personal and business commitments

Help document a clear set of rules/SOPs for managing my calendar going forward

Protect time for family, health, personal priorities, strategic thinking, and life outside of work

What I'm Really Looking For

I don't just want you to follow my current system.

I want you to challenge it and show me better ways you've seen executives manage their time.

If you have supported several CEOs and have seen great systems for calendar management, executive productivity, delegation, meeting management, or protecting an executive's time, I want you to bring those ideas to me.

I want someone comfortable saying:

"Here's what I've seen work with other CEOs. I think you should consider doing this differently."

The Goal

The goal is not to make me more productive so I can cram more work into my calendar.

The goal is to help me become less needed.

I want fewer unnecessary meetings, fewer interruptions, better delegation, more white space, and more time for the things that are important to me outside of running my company.

Ideal Candidate

You may be a great fit if you:

Have significant experience supporting CEOs/founders

Have managed complex executive calendars

Are highly experienced with Google Calendar

Understand executive time management and delegation

Are comfortable challenging an executive's existing habits

Are proactive rather than waiting for assignments

Can turn ideas and conversations into systems and SOPs

Have excellent judgment and discretion

Think strategically about an executive's time

Can work independently without requiring significant management

This could begin as a focused 30-day project and potentially develop into an ongoing Executive Assistant relationship if we are a great fit.

When Applying

Please answer these questions:

How many CEOs/founders have you directly supported?

Tell me about one executive whose calendar/time-management system you significantly improved. What did you change?

What are 2–3 common mistakes you see CEOs make with their calendars?

If I gave you access to a very busy Google Calendar, what would you do during your first week?

How do you determine what should remain on a CEO's calendar versus what should be delegated, eliminated, or handled asynchronously?

What systems, tools, or booking platforms have you used in addition to Google Calendar?

What would you need from me during the first 30 days to help me become less needed by my business?

Please begin your application with the words "TIME FREEDOM" so I know you read the entire posting.

Thank you!