Senior Operations Manager and Right Hand to Owner: Short & Long Term Rentals

POSITION OVERVIEW
We are a growing property management firm managing luxury STRs in Tennessee and an LTR portfolio in Minnesota. We are not looking for a task-doer. We are looking for the owner's right hand: a proactive, system-minded leader who can run our evenings and weekends like they own them, help lead new projects and initiatives with the owner, and develop and improve the internal systems we run on.

WHY THIS ROLE:
We're looking for a tea ---------- mber who will take ownership, think creatively, and contribute to refining our systems as we grow. We're excited to build a lasting relationship with someone in this role, ensuring you feel supported, trusted, and empowered to make decisions. This isn't a role for a task-doer or someone who is most comfortable in a role that primarily involves following a checklist. This is a role for a creative problem-solver with a high EQ and excellent communication skills and follow-through.

Real Authority: You'll have real authority to resolve issues, including a spending limit. When something breaks at 9PM, you are the decision-maker, not a message-forwarder. The owner should hear about most problems after they've been solved. This is a high-trust position, and that trust will be earned: your authority grows as you demonstrate judgment.

A Seat That Grows: This role is built to grow into an overall management position across the business, on evidence, not promises. You'll work directly with the owner and act as the connective layer for our small team.

Growth-Minded & Solutions-Focused: We don't dwell on problems; we find solutions. We want people who are hungry to learn, grow, and improve our systems every day.

Positive Energy: Property management and guest hospitality involve surprise challenges. Pipes burst, guests lock themselves out. We approach our work with a positive attitude and a "can-do" spirit.

A Relationship, Not a Transaction: We want a years-long partnership. Impact over activity: you won't be micromanaged; you'll be given clear goals, real trust, and the freedom to execute.

This role is approximately 40 hours per week. Your compensation will reflect your experience, initiative, growth, and contribution to the business's success.

Schedule (this is the heart of the role, please read carefully):
Friday and Saturday 3:00PM to 12:00 midnight, and Sunday through Tuesday 3:00PM to 11:00PM, US Eastern time. Wednesday and Thursday off.
These hours are when our guests check in, our team is offline, and our owner needs full coverage. Reliable presence during this exact window is a hard requirement.

YOUR CORE MISSION

Evenings & Weekend Command (about half your time):
During your shift, you are the front line and the d ---------- for the whole business. Guest messages and check-in issues at our Tennessee cabins. Urgent tenant and contractor issues in Minnesota. The surprise problems that don't respect business hours. Your job is to resolve them with judgment and calm, using your authority and our established playbooks, so the owner's evening stays quiet. Success is measured by how rarely problems need to reach him, and how completely they're handled when he reads about them the next morning.

Operations & Loop-Closing (about a third):
The "Loop-Closer": when a task comes in, you manage the communication, the schedule, and the reporting in ---------- and in daily report-outs to the team. You make sure work moves from "reported" to "fully completed," and that everyone involved has what they need. You coordinate repairs and vendors, maintain inventory across properties, oversee move-in/move-out procedures, document interactions, and identify potential issues before they become problems. You work alongside our STR specialist and our LTR property manager as the connective layer between them and the owner.

Special Projects & Marketing (the remainder):
You take on the owner's next-most-important thing: marketing pushes (email campaigns, social, listing platforms), process building, research, and whatever the business needs next. This is where the role grows.

ESSENTIAL REQUIREMENTS:
3+ years working in a US-based business with operations responsibility.

High C2 fluency in English: Confident in multi-person meetings, initiating phone calls, and in non-scripted situations in English.
Proven judgment: You have made real decisions with real stakes, without waiting for permission, and you can tell us about them specifically.
The "Loop-Closer" DNA: You live by the 24-hour no-update rule. If a project is open, you provide an update before we have to ask.
Highly detail-oriented and organized: Able to track tasks across multiple properties, prioritize by urgency and importance, and follow up on outstanding issues.
A positive growth mindset, and proactive communication: you don't wait to be asked for updates, and you're receptive to feedback.
Availability for the exact schedule above, reliably, long-term.

The Tech Stack: We use OwnerRez, ---------- , and Google Workspace. We value your operations judgment over your specific software experience; if you've run comparable tools, we can train you on our stack.

MUST HAVE reliable internet connection with backup.
Proficiency with Google Drive, WhatsApp, and ability to quickly learn ---------- .

HOW TO APPLY:

To verify your attention to detail, please follow these steps exactly:

Subject Line: Include the name of the original bass player for the Grateful Dead.

Cover Letter (Paragraph 3): Include the phrase "closing the loop."

In your response, confirm you are available for the exact days and times described above.

1) Describe a specific time you solved an urgent problem without waiting for direction. How did it start, what steps did you take, what did it cost, and how was it resolved?

2) Describe a time you spent your employer's money (or made a binding decision) on your own authority to fix a problem. What was the situation, what did you d ---------- , and how did your boss react?

3) At any ---------- nt you'll have multiple open items running: say a repair waiting on a contractor, an unhappy guest, and a supply order all live at once. Two things: (1) What system do you personally use to track these so nothing slips and everyone gets an update before they have to ask? (2) When you can't get to everything, how do you d ---------- what comes first? Give a real example showing both.

Please include a resume or summary of your background. If you have professional recommendations from previous US-based employers, we strongly encourage you to include them.

4) Tell us how your previous experience sets you up to excel in this role. We're especially interested in where you've led or developed people, built or improved systems, and operated with real autonomy.

A note on AI: We use it too, so use whatever tools help you. That said, we receive many applications with virtually identical answers to our application questions, which are obviously written by AI.
We'd much prefer to read about your real experience, in detail, in your own words. However you use AI, we ask one thing in return: be straight about what you've actually done and how you actually communicate. And tell us two things: how you used AI to put this application together, and how you'd use it in the day-to-day of this role.