Exective Assitant to Real Estate Entrepreneur

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: TYPE OF WORK

Full Time

: SALARY

12 per hour

: HOURS PER WEEK

40

: DATE UPDATED

Jul 11, 2026

JOB OVERVIEW

Executive Assistant / Chief of Staff to Real Estate Entrepreneur

This is a fairly long job post requiring careful reading, and there are many questions to answer as part of this process. It may take some time but it could very well be worth it because we are urgently hiring an awesome person to join our excellent team immediately! We offer excellent compensation for the right people.

We are a growing real estate investment, property management, and title company organization based in Miami, Florida.
Our companies own and manage over 100 residential rental units, including multifamily, single-family rentals, Section 8 housing, and short-term rental properties. We also operate a successful title company and are actively acquiring additional properties.
We are looking for an exceptional Executive Assistant / Chief of Staff who can become a long-term strategic partner to the founder.

This is not an entry-level assistant position. You will help organize, manage, and improve operations across multiple businesses while helping the founder stay focused on the highest-value activities. We are looking for someone who enjoys solving problems, taking ownership, creating systems, and making things happen without constant supervision.

The Right Person is:

Extremely organized
Highly intelligent
Detail-oriented
Resourceful
Trustworthy
Proactive
Comfortable figuring things out independently
Excellent at written and verbal communication
Calm under pressure
Able to manage many projects simultaneously
You don't wait for instructions.
You identify problems and bring solutions.
You follow through relentlessly until tasks are completed.
You double-check your work before submitting it.
You think like an owner.

Responsibilities:

Executive Support
Calendar management
Meeting coordination
Travel planning
Event coordination
Inbox management
Follow-up management
Vendor coordination
Personal scheduling
Real Estate Operations
Track acquisitions and due diligence
Coordinate inspections
Software implementation
Track contract deadlines
Coordinate lenders, attorneys, brokers, title companies, and other real estate vendors
Maintain deal pipeline reports
Assist with underwriting and research
Prepare meeting materials
Property Management Support
Monitor property management KPIs
Track vacancies
Track leasing performance
Coordinate maintenance vendors
Follow up on tenant issues
Improve operating procedures
Help build and document systems
Project Management
Assistance with health and wellness matters
Manage special projects from start to finish
Track deliverables and deadlines
Create accountability systems
Build SOPs and workflows
Market research
Vendor research
Property research
Competitive analysis
AI tools and automation research
Problem-solving assignments
Draft emails
Prepare reports
Communicate with vendors
Coordinate internal teams
Follow up until completion

Required Skills:

Exceptional written English
Strong business communication skills
Excellent organizational ability
Advanced Google Workspace skills
Strong Microsoft Office skills
Project management experience
Ability to learn new software quickly
Strong internet research skills

Bonus Qualifications:

Experience with:

Real estate investing
Property management
Section 8 housing
Multifamily operations
Airbnb / short-term rentals
Title companies
----------
ClickUp
Asana
Airtable
Notion
ChatGPT and AI tools
EOS operating system

What Success Looks Like
Within 90 days:

Founder inbox under control
Calendars fully organized
Critical tasks never missed
Project tracking system implemented
Weekly executive dashboard created
Follow-up system running consistently
SOP library started
Team accountability improved

Within 12 months:

Become one of the founder's trusted inner circle individuals
Manage major projects independently
Help scale operations
Reduce founder workload significantly
Improve execution across all companies

Compensation:

Based on experience and capability.
We are willing to pay significantly more for exceptional talent who can truly own outcomes and become a long-term partner.

Application Questions:

To be considered for this position, please answer all of the following questions in corresponding numbered answers and in detail. Generic or AI-generated answers will not be considered. Important: To confirm that you carefully read this entire job posting, begin your application with the words "Blue Mango."

1. Employment History
How many employers have you worked for during the last 10 years?
For each employer, please provide:
Company name
Job title
Employment dates
Reason for leaving
What was the longest position you have ever held?

2. Executive Support Experience
Describe the most demanding executive, entrepreneur, or business owner you have ever supported.
Please include:
Industry
Company size
Number of employees
Number of projects managed simultaneously
What made the role challenging

3. Problem-Solving
Tell us about a major problem you identified before your manager, executive, or business owner became aware of it.
What was the problem?
What actions did you take?
What was the outcome?

4. Last 3 Positions
Why did you leave your last three positions?
If you were terminated why? And if you resigned what could those employers have done to keep you longer?

5.. High-Pressure Work Environment
Describe the busiest period of your career.
Approximately how many projects, clients, properties, tea ---------- mbers, or deadlines were you responsible for simultaneously?
How did you stay organized?

6. Technology & Software Experience
List every major software platform you have used professionally during the last three years.
For each platform, rate your proficiency from 1–10.

7. Artificial Intelligence Experience
How do you currently use AI tools in your work?
Please provide at least three specific examples.

8.. Real Estate Experience
Describe any experience you have with:
Real estate investing
Property management
Multifamily housing
Section 8 housing
Construction or renovations
Real estate acquisitions
Lending
Title companies
Airbnb and short term rental properties
Real estate law
Please provide specific examples.

9.. Difficult People
Describe the most difficult person you have ever had to work with.
How did you handle the situation?
What was the outcome?

10. Career Goals
Where do you see yourself in three years?
Where do you see yourself in five years?
What would make you stay with one company for 10+ years?

11. Ownership Mentality
Tell us about a situation where you inherited something that was disorganized, broken, inefficient, or failing.
What specifically did you do to improve it?
What measurable results did you achieve?

12. Compensation
What annual compensation are you seeking?
What compensation range would make you excited to stay with a company long term?

13. Availability
How many hours per week are you currently available?
What is your time zone?
Are you willing to work U.S. Eastern Time business hours?

14. Inbox Management Test
How many unread emails are currently in your inbox? What system do you personally use to ensure important items never fall through the cracks?

15. Data
Have you ever had access to company bank accounts, financial information, confidential legal matters, passwords, payroll data, or sensitive business information? If so, describe your responsibilities.

16. Describe a time you built a process or system that significantly improved operations.

17. Why are you interested in a long-term position rather than freelancing?

18. What direct experience have you had as an Executive Assistant?

SKILL REQUIREMENT

Property Management Executive Assistance

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Exective Assitant to Real Estate Entrepreneur

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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