CEO Right-Hand / Property Operations VA — Assertive, Proactive, Full-Time

I run a fast-moving property management business in Chicago. I need a full-time right-hand operator who can handle tenant follow-up, vendor coordination, admin tasks, scheduling, documentation, and executive support.

This is not a passive “wait for instructions” VA role. Your job is to buy back the CEO’s time, solve problems, communicate directly, and keep the business moving.



I am hiring a full-time CEO Right-Hand / Property Operations Virtual Assistant for my property management company.

We manage rental properties in Chicago, including SRO-style housing, long-term tenants, maintenance issues, rent collection, vendor coordination, paperwork, scheduling, and day-to-day operational fires.

This role is for someone who wants to become the CEO’s operational backbone.

Your job is simple:

Protect my time. Keep the business moving. Close loops.

That may include business tasks, property management tasks, tenant follow-up, vendor coordination, finance/admin work, scheduling, document organization, or executive/personal admin tasks that free up my time.

This is not a narrow job-description role where you say, “That’s not my task.”

If it is legal, professional, ethical, and it helps buy back the CEO’s time, you should be willing to help handle it.

------------------What You Will Do------------------

You will help with:
• Tenant follow-up and rent/payment coordination
• Calling or messaging tenants who are late, confused, upset, or avoiding response
• Scheduling maintenance and following up with contractors/vendors
• Tracking open issues until they are fully resolved
• Updating spreadsheets, trackers, Trello cards, Google Drive files, and internal systems
• Managing invoices, payment reminders, and admin records
• Reviewing training videos and SOPs independently
• Preparing summaries, updates, and next-step recommendations
• Helping with scheduling, travel, personal logistics, calendar coordination, and other executive-support tasks
• Taking work off my plate without needing to be spoon-fed every step

------------------Who This Role Is For------------------
This role is for you if:
• You are assertive, not timid
• You are comfortable making calls
• You can speak directly to tenants, vendors, and contractors
• You do not freeze when someone is upset
• You can self-train using videos, SOPs, and written instructions
• You like solving messy real-world problems
• You ask good questions
• You can work with a direct, demanding CEO
• You are comfortable receiving blunt feedback
• You care about getting better
• You want to become a high-trust, long-term operator inside a growing company

------------------Who Should Not Apply------------------
Do not apply if:
• You are shy on the phone
• You avoid confrontation
• You need step-by-step instructions for every task
• You only want easy admin work
• You rely on ChatGPT/AI to think for you
• You disappear when confused
• You say “done” when a task is only partially done
• You dislike direct feedback
• You are uncomfortable helping with executive/personal admin tasks
• You are looking for a low-pressure role
• You cannot work during agreed hours consistently
• You already have too many other clients or jobs

AI tools are allowed. But AI cannot replace your judgment, voice, confidence, or ownership.

------------------Required Skills------------------
You must be strong in:
• Spoken English
• Written English
• Phone communication
• Tenant/customer service
• Direct follow-up
• Google Sheets or Excel
• Gmail
• Google Drive
• Trello or similar task-management tools
• Calendar/scheduling
• Documentation
• Self-learning
• Prioritization
• Problem-solving

Property management, collections, dispatch, call center, executive assistant, legal admin, or operations experience is a major plus.

------------------Work Schedule------------------
This is a full-time role.

Expected schedule:
• 40+ hours per week
• Monday–Friday
• Must be able to work during Chicago business hours or a meaningful overlap with Chicago time.

Some weekend or urgent support may occasionally be needed, especially for tenant, maintenance, or scheduling issues.

------------------Compensation------------------

Please include your requested hourly rate in your application.

I pay for performance, reliability, ownership, and long-term value.

There will be a trial/probation period. Strong performers can earn more responsibility and better compensation over time.

------------------What Success Looks Like------------------
You are successful in this role if:
• I spend less time chasing people
• Tenants and vendors receive timely follow-up
• Open issues are tracked until closed
• Payments, invoices, and admin items do not fall through the cracks
• You proactively surface problems before they become fires
• You communicate clearly every day
• You learn the business without needing constant hand-holding
• You become someone I can trust with increasingly important work

------------------Application Instructions------------------
To apply, reply with the subject line:

RIGHT HAND OPERATOR

Then answer the following questions.
Do not send a generic cover letter. Generic applications will be ignored.


1. Direct Communication Test

A tenant is late on rent and says:

“I’m not paying the late fee. I had a hard month, and it’s unfair. Remove it.”

Write exactly what you would say back to the tenant.

Keep it short. Do not be rude. Do not be weak.


2. Judgment Test

It is Monday morning. Three things happen at the same time:

A tenant says there is no heat.
A contractor missed a scheduled repair.
A tenant is late on rent and avoiding payment.

What do you handle first, second, and third? Explain why.


3. CEO Time-Buyback Test

I tell you:

“I am traveling tomorrow. I have a meeting, a workout plan, a meal schedule, a car issue, and several business tasks open. I need you to make tomorrow easier for me.”

What steps would you take to help?

Be specific.


4. Self-Training Test

Tell me about a time you had to learn a new system, tool, or process without someone teaching you live.

What did you do?


5. Phone Confidence

Are you comfortable making outbound calls to tenants, contractors, vendors, and leads?

Answer clearly: Yes or No.

Then explain your experience.


6. Availability

What hours can you work in Chicago time?

Are you available full-time?

Do you currently have other jobs or clients?


7. Voice Sample

Record a short 60–90 second voice note answering this:

“Why would you be a strong right-hand operator for a direct, fast-moving CEO?”

Include the link in your application.