Chief of Staff / Executive Operations Manager — Real Estate & Short-Term Rentals

READ THIS FIRST

I am looking for someone who can eventually become my right hand across the entire business.

This is NOT an Executive Assistant position.

I don’t need someone to manage my calendar, take notes, remind me about tasks, or wait for instructions.

I need an absolute execution monster who can take the hundreds of moving pieces in my business, organize them, drive people to completion, solve problems independently, and dramatically reduce how much I personally have to manage.

My businesses involve:

* 20+ short-term rentals
* Property management
* Large renovation and construction projects
* Real estate acquisitions
* Direct-to-seller marketing
* Contractors and maintenance teams
* Cleaners and vendors
* Claims and damage recovery
* Financing and lenders
* New property launches
* Large acreage/development projects
* VAs and remote employees
* AI/automation implementation

There are constantly dozens of projects and hundreds of follow-ups happening simultaneously.

Your job is to make sure nothing gets dropped.

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YOUR JOB IS TO CREATE LEVERAGE FOR ME

If I tell you:

“Get me three HVAC quotes for this property, figure out why the septic contractor hasn’t responded, make sure the lender has the revised scope, get an answer from the excavator, find out why this Airbnb claim hasn’t been paid, and make sure the new listing launches Friday.”

I should not need to ask about those things again.

You figure out:

Who needs contacted → what information is missing → who owns it → what the deadline is → what needs followed up on → what can be solved without me → and what actually requires my decision.

Then you drive everything forward.

I DON’T WANT PROBLEMS BROUGHT TO ME

Whenever possible, I want:

Problem → research → options → your recommendation → decision needed from me.

Not:

“What do you want me to do?”

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What You Will Own

You will eventually oversee and coordinate execution across the business.

That includes:

* Maintaining the master company/project priority list
* Turning my ideas and conversations into actionable projects
* Assigning responsibilities and deadlines
* Following up relentlessly until tasks are completed
* Holding employees and contractors accountable
* Coordinating VAs and department leads
* Tracking construction and renovation projects
* Tracking property launches
* Coordinating lenders, contractors, vendors and service providers
* Making sure important emails/messages receive responses
* Researching problems before bringing them to me
* Obtaining quotes and comparing options
* Preparing decisions for me
* Running weekly accountability meetings
* Tracking KPIs across departments
* Identifying bottlenecks
* Improving SOPs and company systems
* Working with our AI/automation person to eliminate unnecessary manual work
* Catching problems before I notice them
* Making sure something I mentioned three weeks ago doesn’t disappear because I stopped talking about it

Eventually, you should understand my businesses well enough to know what I am going to ask before I ask it.

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THIS POSITION WILL NOT BE EASY

I move quickly.

I have a lot happening simultaneously.

Priorities can change.

I ask a lot of questions.

I generate new ideas constantly.

I expect people to follow through.

And I have very little patience for repeatedly asking about something that should already have been handled.

If you need an extremely structured corporate environment where someone gives you five tasks every morning, this position will be miserable for you.

But if you love taking chaos and turning it into execution, you may absolutely thrive here.

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I NEED SOMEONE BETTER ORGANIZED THAN I AM

You should be the person saying:

“You mentioned this two weeks ago. Here’s where it stands.”

“We’re waiting on these three people. I’ve already followed up twice.”

“This contractor’s quote doesn’t make sense. I got two alternatives.”

“This project will miss its deadline unless we make this decision today.”

“You don’t need to handle this. I already solved it.”

That’s the level I’m looking for.

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THE GOAL

Eventually, I want the organizational structure to look something like:

Owner/CEO → Chief of Staff → Department Leads / Specialists / VAs

I don’t want to personally manage eight different employees and constantly check whether things happened.

You make sure they happen.

That means you must be comfortable holding other people accountable—even people with specialized expertise you don’t personally have.

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DO NOT APPLY IF:

* You are primarily an Executive Assistant
* You need detailed instructions for every task
* You are afraid to make decisions
* You avoid uncomfortable follow-ups
* You aren’t comfortable holding people accountable
* You regularly forget things
* You wait several days before following up
* You think updating a task-management system = getting something accomplished
* You send problems upward without first trying to solve them
* You become overwhelmed when 20 things happen simultaneously

I would rather not fill this position than hire an average person.

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PROVE YOU’RE THE PERSON

Generic applications will be ignored.

Answer ALL of these:

1. What is the most complicated business/operation you’ve personally helped run? How many employees, projects, customers, or locations were involved?

2. Tell me about an executive/founder you supported who had too many things happening simultaneously. How did you create order?

3. Give me an example where your boss gave you a vague objective instead of instructions. What did you do?

4. Tell me about something important that would have been forgotten or missed if you hadn’t caught it.

5. Give me an example where you had to hold an employee, contractor, or vendor accountable when they weren’t performing.

6. Your boss gives you 30 unrelated tasks in one conversation. Walk me through exactly what happens afterward.

7. You need an answer from a contractor today. You’ve called twice, texted, and emailed with no response. What do you do?

8. Three employees tell you their tasks are delayed because they’re waiting on other people. What do you do?

9. Tell me about a decision you made without asking your boss first. Why did you feel comfortable making it?

10. What information would you want from me during your first 30 days so you could eventually begin anticipating what I need?

11. What systems have you personally used to manage complex projects, teams, SOPs, communication, and accountability?

12. What experience do you have with real estate, construction, property management, Airbnb/STRs, hospitality, or investing?

MOST IMPORTANT QUESTION:

13. Assume I disappear for 7 days and barely respond to you. What specifically would you do to make sure the business continues moving forward without me?

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VIDEO REQUIRED

Send a 3–5 minute video.

Tell me about the most chaotic operation, company, executive, or project you’ve ever managed.

Explain:

What was happening → why it was difficult → what YOU took ownership of → systems you created → problems you solved → measurable result.

Don’t tell me you’re organized.

Show me evidence that you’ve operated at this level.

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Compensation

I am willing to pay well above typical OnlineJobs.ph compensation for an exceptional person.

I’m not looking for cheap labor.

I’m looking for leverage.

If hiring you gives me back significant hours every week, makes the rest of my team perform better, prevents expensive mistakes, and allows the company to grow without everything flowing through me, you will be extremely valuable to me.

There is substantial room for increased compensation and responsibility for someone who becomes indispensable.

If you’re the kind of person who sees 100 moving pieces and immediately wants to take control of them, I want to hear from you.