Property Operations and Bookeeping for Property Mgmt (short and long term)

ABOUT THE ROLE & VISION

We are a growing property management company managing luxury short-term rentals in the Tennessee Smoky Mountains and a long-term portfolio in Minnesota. We aren't looking for a task-taker; we are looking for a Controller—someone who thinks like an owner, protects our time and operations and ensures our attention to detail and excellence remain air tight as we grow.

POSITION OVERVIEW
Salary Range: ($5.00 – $8.00/hr for 20 hours/week, with the potential to go to 40 hrs)
Hours: 20 hours per week (Target: 9:00 AM – 1:00 PM US Eastern Time).

WHY JOIN DREAM CABIN GETAWAYS?
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 sometimes involves surprise challenges. Pipes burst, tenants stop paying. It is critical that we approach our work with a positive attitude. We value collaboration, open communication, and a "can-do" spirit.
A Relationship, Not a Transaction: We want a years-long partnership where you feel supported, trusted, and empowered to make decisions.

Impact Over Activity: We value outcomes. You won't be micromanaged; you will be given clear goals and the freedom to execute, along with the support to be able to succeed.


YOUR WEEKLY FOCUS
20% bookkeeping and financial administration: You handle deposit reconciliations between OwnerRez/Airbnb/Vrbo and REIhub, and audit and pay contractor invoices, ensuring billed hours match agreements. You manage purchasing for cabin supplies to keep our "jewel properties" guest-ready. With the support of our accountant, you generate professional Monthly Owner Statements for our PM clients.

60% Operations & Loop-Closing: You own operations from "Reported" to "completed and guest/tenant is happy". You enforce the 24-Hour No-Update Rule, providing proactive status updates on all open projects in ---------- without being prompted.

20% Guest and Tenant Support: You handle external comms with warmth, professionalism, and excellence. You have the people skills to make people feel heard, understood and taken care of.

Required Experience & Technical Skills

3+ Years in US-Based PM: You understand the rhythm of STRs and LTRs.
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.
Financial Rigor: Proven experience with Accounting or bookkeeping, ideally for long or short term rentals.
Highly Detail-Oriented and Organized: Able to track tasks across multiple properties and follow up on outstanding issues. Skilled at prioritizing tasks based on urgency and importance.
You have a positive growth mindset.
Strong communication skills: you are a proactive communicator who doesn’t wait to be asked for updates. You’re eager to participate in ongoing discussions about improving communication protocols and systems, and receptive to feedback.
Assertiveness: You are comfortable "chasing" contractors and tenants with a smile, and holding vendors accountable to their bids.

The Tech Stack: While we use OwnerRez, REIhub, and ---------- , we value your PM and Bookkeeping Experience over your specific software experience. If you are an expert in the industry, and familiar with competitor tools, we can train you on our specific 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 and financial expertise, 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."

The Initiative Test: Describe a specific time you solved a contractor or tenant problem without waiting for direction.

The Financial Filter: Briefly describe your past accounting/bookkeeping work. Specifically:

Which software have you used (REIhub, QBO, Xero)?
Have you ever managed Trust Accounting or Owner Statements?
In 2-3 sentences, how do you handle a situation where an Airbnb payout doesn't match the expected booking amount in your PMS (like OwnerRez)?

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