COMPANY OVERVIEW:
Trust First Management - Why Join Us? (This isn’t your average job ad.)
We’re not looking for someone to just fill a role.
We’re looking for A-Players who want to be part of something big — something that’s moving fast, breaking records, and rewriting what “great” looks like in the short-term rental industry.
We manage 30+ high-performing vacation rentals with an average guest rating of 4.93+ (translation: we don’t do “average”). Our mission: deliver exceptional guest and owner experiences every single time — and scale smart to hit $5 million in total booking revenue in the next 6 months.
Here’s what you’re really signing up for:
A Front-Row Seat to Hypergrowth: You’ll be part of a team that’s scaling aggressively — and winning. You’ll see firsthand how to build a market-dominating business.
Work With High Standards & High Performers: No dead weight. No clock-punchers. Just a small, elite team that executes fast and cares deeply about results.
Make a Tangible Impact: You won’t be “just a number” here. The work you do will directly move revenue, reviews, and company growth.
Be in a Company That Invests in You: We use cutting-edge tools, AI, and proven business systems to make your work more effective and your career path faster.
Growth Path Built In: As we scale, leadership and specialized roles open up — and we promote from within. If you perform, you’ll move up quickly.
Pride in the Product: You’ll represent high-quality properties and a brand that owners and guests genuinely love.
Who We’re For:
People who want more responsibility, faster.
People who hate “average” and thrive when the bar is high.
People who want their work to matter — and want to see the results of it, fast.
This isn’t a corporate ladder. It’s a rocket ship. If you’re the kind of person who sees opportunity and moves on it, you’ll fit right in here.
POSITION SUMMARY:
We are seeking a detail-oriented Vacation Rental Operations & Finance Administrative to support our short-term rental operations during overnight hours. This is an operations-first, finance-support role with overnight guest coverage responsibilities. The position works five 12-hour shifts (overnight in the USA) per week (60 hours total) and reports to the Operations Lead. Prior short-term rental experience is required and book keeping or accounting experience with familiarity with Quickbooks is preferred.
During quieter overnight periods, the role focuses heavily on administrative and finance support, including maintaining accurate reservation records, documenting overnight issues, categorizing invoices, and coding expenses. You will also provide low-volume overnight guest coverage, responding to standard short-term rental inquiries and operational issues with professional, brand-aligned communication while working independently overnight.
RESPONSIBILITIES:
Maintain accurate reservation data, notes, and overnight logs in Guesty
Document overnight issues and handoffs for the daytime team with clear specifics
Manage internal trackers, checklists, and task boards; flag gaps or inconsistencies
Follow standard operating procedures consistently and identify recurring issues or process breakdowns
Submit and coordinate property inventory orders as needed
Provide administrative support to operations, finance, and other departments
Review, categorize, and prepare invoices and receipts in TopKey for approval
Ensure expenses are properly coded, matched to properties or work orders, and synced to QuickBooks
Flag discrepancies, missing documentation, or unusual charges and assist with month-end support
Monitor and respond to overnight guest messages, handling standard STR issues and escalating true emergencies per established processes while maintaining calm, brand-aligned communication
QUALIFICATIONS:
1-2 years Prior short-term rental, property management, co hosting experience required
Experience with guest communication and issue triage
Experience with invoicing, expense tracking, or bookkeeping support
Familiarity with tools like Guesty, TopKey, and/or QuickBooks
Must have written and spoken fluency in English
Strong attention to detail
Comfortable working independently overnight
COMPENSATION & BENEFITS:
Hourly Rate: $5.00 - $7.00 based on experience
Bonus
Quarterly bonus incentive offered.
Benefits
Paid time off such as PTO, sick days, and vacation days
Schedule
Wednesday: 10pm to 10am EST
Thursday: 10pm to 10am EST
Friday: 10pm to 10am EST
Saturday: 10pm to 10am EST
Sunday: 10pm to 10am EST