Executive Operations Director ( Future Director of Operations / COO ) - Real Estate Investment & Property Management

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: TYPE OF WORK

Full Time

: SALARY

$1250/month + Performance Bonuses

: HOURS PER WEEK

40

: DATE UPDATED

Jul 13, 2026

JOB OVERVIEW

We’re not looking for someone to simply complete tasks—we’re looking for someone who can eventually help run the company.

Executive Operations Director to the CEO ( Future Director of Operation / COO )

Real Estate Investment | Property Management | Construction | Business Operations

This is NOT a typical Virtual Assistant position.

We’re looking for someone who wants to build a long-term career with a fast-growing U.S. real estate investment company.

You’ll work directly with the Founder & CEO, helping organize, improve, and eventually operate multiple businesses.

If you’re someone who enjoys solving problems, building systems, taking ownership, and making organizations run better, we want to meet you.

About Us

We own and manage 100+ residential and commercial units throughout Massachusetts, USA.

Our businesses include:

• Real Estate Investment

• Property Management

• Commercial Leasing

• Construction & Development

• Sober Living Operations

• Title & Escrow Services

We are actively growing and building systems that will allow us to continue expanding for many years.

Your Mission

Become the CEO’s trusted right hand.

Your mission is simple:

Increase the CEO’s effectiveness by organizing people, projects, communication, systems, and priorities.

You’ll solve problems before they become problems.

You’ll build systems that allow the company to scale.

You’ll eventually become one of the most trusted people in the organization.

Responsibilities

Manage the CEO’s calendar and email
Coordinate contractors, maintenance staff, and vendors
Follow up with tenants regarding rent, maintenance, and lease issues
Communicate with attorneys, lenders, municipalities, utility companies, and vendors
Build and improve Standard Operating Procedures (SOPs)
Track construction and renovation projects
Prepare executive reports and dashboards
Organize digital files and company documentation
Conduct business and market research
Use AI tools (ChatGPT, etc.) to improve productivity
Help recruit, train, and manage future Virtual Assistants
Continuously improve company operations and identify inefficiencies

Required Skills

? Excellent written and spoken English

? Exceptional organizational skills

? Strong attention to detail

? Excellent follow-up

? Professional communication

? Critical thinking

? Problem-solving ability

? Google Workspace

? Microsoft Office

? ChatGPT or other AI tools

? Reliable high-speed internet

? Quiet home office

? Ability to work independently

Preferred Skills

? Property Management

? Real Estate

? Construction Coordination

? Buildium

? AppFolio

? QuickBooks

? Project Management Software

? Process Documentation

? Executive Assistant Experience

? Spanish (Highly Preferred)

Many of our tenants are Spanish-speaking. Being able to communicate in both English and Spanish is a significant advantage and will receive priority consideration.

What Success Looks Like

Within your first year:

The CEO spends less time on daily operations.
Projects move faster.
Tenants receive better service.
Contractors are held accountable.
Communication becomes organized.
Systems replace chaos.
The company becomes easier to scale.

Growth Opportunity

This is a long-term career opportunity.

Potential future roles include:

Senior Operations Manager
Director of Operations
Chief Operating Officer (COO)
We strongly believe in promoting from within.

Compensation

Competitive compensation based on experience, skills, and performance.

Regular performance reviews, raises, and bonuses are available for exceptional performance.

Application Questions

Please answer each question thoughtfully.

Tell us about yourself.
Why are you interested in this position?
What makes you different from other applicants?
Describe the most difficult project you’ve managed.
Tell us about a time you solved a problem before your manager knew it existed.
What AI tools do you use regularly?
What project management software have you used?
Tell us about a process you improved at a previous company.
Where do you see yourself in five years?
If hired today, what would be the first three things you would do during your first 30 days to improve our company?

Video Introduction (Required)

Please submit a 2–3 minute video introducing yourself.

Tell us:

Who you are
Your work experience
Why you’re interested in this opportunity
Why you’d be a great fit
Bonus: If you speak Spanish, include a 30-second introduction in Spanish.

IMPORTANT

To confirm you’ve carefully read this entire posting, begin your application with the exact words:

I build systems.

Applications that do not begin with these words may not be reviewed.

Why You’ll Love Working Here

You’ll work directly with the CEO instead of being buried inside a large corporation.

You’ll see how real estate investing, construction, business acquisitions, and property management operate behind the scenes.

Your ideas will matter.

If you’re ambitious and perform well, your responsibilities, compensation, and leadership opportunities will continue to grow.

SKILL REQUIREMENT

Property Management Project Management Executive Assistance

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Executive Operations Director ( Future Director of Operations / COO ) - Real Estate Investment & Property Management

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

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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