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

Go Home, LLC
CEO Right-Hand / Property Operations VA
Full-Time, Assertive, Proactive Operator

Type of Work: Full Time
Starting Rate: $3.00/hour
Hours: 40 hours per week
Schedule: 5 working days per week within a Monday through Saturday operating window. Sundays are always off.
Time Zone: Meaningful overlap with Chicago business hours required.

I run a fast-moving property management business in Chicago. I need a full-time right-hand operator to help with tenant follow-up, vendor coordination, scheduling, documentation, admin work, and executive support.

This is not a passive “wait for instructions” VA role.

Your job is simple:

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

We manage rental properties in Chicago, including tenant issues, maintenance, 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, not someone looking for easy admin work.

------------------Compensation Notice------------------

This role starts at $3.00/hour.

The starting rate is fixed and not negotiable during the interview process.

Do not apply with the idea that you will interview, impress me, and then ask for a higher starting rate.

However, good people should not feel stuck. Strong performers can earn more responsibility and better compensation over time.

Performance reviews may happen after 30 days and 90 days based on reliability, communication, ownership, judgment, attendance, throughput, and ability to close loops.

If $3.00/hour is not acceptable as the starting rate, do not apply.

If you are only looking for temporary work while searching for something better, do not apply.

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

You will help with:
• Tenant follow-up and rent/payment coordination
• Calling or messaging tenants, vendors, and contractors
• Scheduling maintenance and following up until work is done
• Tracking open issues until they are fully closed
• Updating spreadsheets, Trello cards, Google Drive files, and internal systems
• Managing invoices, reminders, admin records, and documentation
• Reviewing training videos and SOPs independently
• Preparing summaries, updates, and next-step recommendations
• Helping with scheduling, logistics, calendar coordination, and executive-support tasks

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

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

------------------Who This Role Is For------------------

This role is for you if:
• You are assertive, not timid
• You are comfortable making outbound 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, screenshots, and written instructions
• You ask good questions
• You communicate clearly when something is unclear
• You can handle direct feedback
• You want to become a high-trust, long-term operator

------------------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 disappear when confused
• You say “done” when a task is only partially done
• You dislike direct feedback
• You cannot work consistently during agreed hours
• You already have too many other clients or jobs
• You plan to ask for more than $3.00/hour before proving yourself

If you d ---------- the role is not for you, I expect professional communication and a clean handoff. Disappearing without notice is not acceptable.

------------------AI Tools and Throughput------------------

AI tools, including ChatGPT, are allowed.

I care about throughput, judgment, and completed work.

AI should help you move faster, organize better, summarize clearly, document work, and produce cleaner output.

AI should not be used to avoid thinking, avoid phone calls, avoid decisions, avoid accountability, or send generic answers.

If AI makes your work faster and more accurate, good.

If AI makes you passive, vague, dependent, or generic, this role is not for you.

------------------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
• 5 working days per week
• Workdays may fall between Monday and Saturday
• Sundays are always off
• Must have meaningful overlap with Chicago business hours

------------------Application Instructions------------------

To apply, use this subject line:

RIGHT HAND OPERATOR - $3 FIXED RATE

Do not send a generic cover letter. Generic applications will be ignored.

Answer every question below. ---------- . Rate Confirmation------------------

This role starts at $3.00/hour.

Do you understand and accept that this is the fixed starting rate?

Answer clearly:

Yes, I accept the $3.00/hour fixed starting rate. ---------- . 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. ---------- . 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. ---------- . 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. ---------- . Phone Confidence------------------

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

Answer clearly: Yes or No.

Then explain your experience. ---------- . AI Judgment Test------------------

How do you use AI or ChatGPT to get more work done?

Give one example.

Also explain one situation where you should not rely on AI and should use your own judgment instead. ---------- . Availability------------------

What hours can you work in Chicago time?

Are you available full-time?

Do you currently have other jobs or clients?

If yes, explain your current workload. ---------- . Long-Term Fit------------------

Are you looking for a long-term role or a temporary role?

If you were offered a higher-paying opportunity after a few weeks or months, how would you handle that professionally? ---------- . Voice Sample------------------

Record a short 60 to 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.

Applications without a voice sample may be ignored.

------------------Final Note------------------

I am not looking for someone who only interviews well.

I am looking for someone who can work, communicate, follow up, learn quickly, and become useful fast.

If you are reliable, assertive, direct, organized, and serious about growing into a long-term operator role, apply.

If you want an easy role, vague expectations, flexible excuses, or a higher starting rate, do not apply.