Bookkeeping & Operations Assistant (Short-Term Rental Business)

Position Overview
We’re looking for a long-term tea ---------- mber to support our growing short-term rental business.
Your main role will be bookkeeping and data entry, keeping our financials clean and organized. If you can also handle guest communication and daily operations, this can grow into a full-time position.

Responsibilities

Primary Tasks — Bookkeeping & Data Entry:

Project: Bookkeeping Backlog up to date.
Keep Financial sheets and QuickBooks accurate and up to date
Import and categorize transactions
Update Weekly Financial snapshots and reports
Follow systems carefully
Create & Improve simple workflows/systems
Communicates progress and reconcile accounts on time
Communicates updates and flags issues fast

(Bonus)
Create better reporting templates or dashboards
Build automations or AI tools to reduce manual work

Secondary Tasks (Opportunity For Full Time Position) - Guest Communication & Daily Ops

Learn our Short Term Rental Softwares
Reply to guest messages in seconds with a friendly, professional Tone
Closes every loop — no open conversations left
Help with daily operations and scheduling
Support reporting and admin follow-ups
Help improve efficiency and automations
Double-checks all details before sending
Escalates issues (damage, refunds, complaints)



Requirements:

Detail-oriented with numbers and spreadsheets
Great written English and communication skills
Tech-savvy (Google Sheets, QuickBooks, Gmail, Drive)
Reliable internet and consistent work schedule
Loyal, self-driven, and eager to learn


Looking for Prior Experience In:

Knowledge of Accounting systems or Bookkeeping Systems
Experience in short-term rentals, hospitality, or property management
Basic automation tools (Zapier, Make, AI prompts, etc.)

Growth Path & Compensation Plan :

1. Trial Period
2. Project Period (Full-Time) ? Ongoing Part-Time (Bookkeeping)
3. Rockstar (Full-Time Role)
Trial Period: $4/hr (paid test phase)
Short trial focused on confirming competency, accuracy, and reliability.
The goal is to ensure you can manage bookkeeping and data entry confidently before moving into a longer-term role.


Project Period: $5/hr — Full-Time Until Project Completion into an ongoing part-time bookkeeping position.

After passing the trial, you’ll begin a project-based full-time phase focused on completing our current bookkeeping backlog.


This stage is to prove consistency and ownership of the anchor responsibilities (bookkeeping + data entry).


Ongoing Part Time Position - Keeping up to date with daily book keeping tasks, weekly reports ect.


Full-Time “Rockstar” Level: Full-Time Role Tea ---------- mbers who excel at bookkeeping and also handle operations-related tasks (guest communication, daily ops, automation projects) will be promoted to a full-time, long-term position with growth potential, and leadership opportunities.


Application Instructions
Subject line: “VA8272 – [Your Name]”
Please answer these short questions in your application:
1. What part of this role do you think you’d excel at, and what past experience or skills make you confident in that?
2. What specific tools have you used for bookkeeping or tracking data? Describe your experience with the tools.
3. Share a time you solved a problem or improved a process without being told to. What was the result?
4. Write a short 3-sentence reply to this guest message:
“Hi, the Wi-Fi isn’t working, can you help?”
5. Based on our Growth & Compensation Plan, what position would you like to achieve in the next 6 - 12 months and Why?

6. Also include:
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