STR Bookkeeper

DO NOT APPLY IF YOU HAVEN'T BEEN A BOOKKEEPER AT A SHORT TERM RENTAL/VACATION RENTAL COMPANY

Role: Bookkeeper
We are a fast-growing vacation rental management company looking to add a Bookkeeping Admin to our team for the long term. As we scale, clean books are what keep our owners confident, our vendors reliable, and our business compliant. This role supports our financial back office: keeping expenses clean and categorized, validating and scheduling vendor payments, helping file occupancy taxes on time, and helping make sure owner statements are accurate before they go out. You also support supply ordering and other items the team and properties need. You support the bookkeeping before it reaches our accountant, so accuracy and follow-through matter here more than almost anywhere else in the company. This is a detail role for someone who has done this in short-term rentals before and understands owner statements, trust accounting, pass-through expenses, and occupancy tax.
Responsibilities
Review, code, and categorize all expenses and daily transactions, including reservation adjustments for discounts, altered stays, and refunds
Validate vendor payments before release, matching them to Breezeway work orders and approvals and confirming the work, amount, and rate are correct
Schedule and process vendor payments so nothing goes past due, and keep vendor records current
Prepare and file transient occupancy tax (TOT) returns and ready financial data for tax filings, keeping us compliant in every jurisdiction
Confirm the right occupancy tax rates and charge amounts are set across OTAs and direct bookings, and flag any gaps
Support the ordering of supplies and other items, tracking purchases against the right accounts
Support the owner statement review each cycle, checking for accuracy before statements go out
Reconcile all company and owner accounts in QBO and tie balances out to your PMS
Catch and resolve duplicate charges, missing receipts, and miscoded items, and keep clean documentation for every transaction
Support month-end close and the owner statement run
Results
Owner statements reviewed and ready by the 10th of each month
Owner-reported statement errors: 0 per cycle
Vendor payments past due or released with the wrong amount: 0 per month
TOT returns filed by their due date: 0 late filings
Uncategorized or unreconciled transactions at month-end close: 0
Requirements
Prior bookkeeping or AP experience inside vacation rental or short-term rental property management, non-negotiable
Experience with TopKey, or with expense tracking for a larger vacation rental management company
Hands-on QuickBooks Online (QBO) experience
Proficient in Google Workspace, including Sheets for data analysis and reporting
Experience in a short-term rental PMS, Streamline or Guesty required
Familiar with Breezeway work orders, and Notion for documentation
Experience preparing and filing TOT or lodging taxes, and familiar with how OTAs collect and remit occupancy tax
Understands owner statements, trust accounting, and the difference between owner-billable, company, and pass-through expenses
High attention to detail and able to self-check before anything leaves your desk
Organized and consistent with documentation
Comfortable building your own checklists and SOPs to work more efficiently and to guide others
What Success Looks Like in 90 Days
30 days: comfortable handling and categorizing all transactions, and paying some vendors
60 days: supporting owner statement reviews and understanding the TOT filing calendar
90 days: helping with month-end categorization and catching missing items, and ensuring owner statements are ready by the 10th

Hours: M-F 8-5 PST - 45 hours per week

Pay: $1,365 per month paid out on the 15th and 30th of the month
Wifi and VPN Stipend of $30 per month paid out as $15 on each paycheck

13th month awarded based on performance and hours worked throughout the year.

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