September 5, 2023
Orlando, Florida
Job Type
Annual Salary: $50,000 - $60,000 based on experience and achievement 



Staylah is a growing vacation rental collective that thrives on delivering exceptional stays to guests and optimal returns for owners. Our genesis, in 2022, came as a result of firsthand experience with lackluster property management and care for our portfolio of short-term rental properties. Dwindling returns, poor emphasis on quality, and unhappy guests drove us to find a better way.

This calling led to the departure from a stable, lucrative, 20-year career in risk and insurance, where one of our founders, Matt Hammer, was an integral partner in growing a startup into a public company. Now, this passion is directed toward building the preeminent vacation rental collective in the world.

Staylah has joined forces with regional leaders Juliana Boselli-Neves and Rafael Boselli of Glasstone Vacations to catapult success and bolster its value proposition in Florida. Building off nine years of success in delivering exceptional returns for owners and raving fan guests, this combined powerhouse has partnered with over 100 high-quality vacation hosts within its first year together. The fun has just begun, and we’re seeking adventurers to join our club.

More details about what drives us:


A global vacation rental collective delivering luxurious, trustworthy stays where guests can rest, roam, and revive while owners thrive.

Core Values

  • Faith – Honor God in everything. Trust and commit. Live in the moment, with the end in mind.
  • Utmost – Stewardship of our time, talent, and treasure to best fulfill our purpose, priorities, and commitments.
  • Adventure – Blaze new trails. Challenge the status quo. Engage with boldness, enthusiasm, and care.
  • Rest – Prioritize care for mind, body, and spirit to live fulfilled.
  • Fun – Laugh, play, and make the most of every opportunity. You only get one crack at life. Have fun!


As we continue to grow, we're looking for someone to fill our Bookkeeper role who is meticulous, values precision, and is ambitious about the future. If you take pride in accuracy, spot an error a mile away, and thrive in a fast-paced workplace, you’ll excel here.

This position means you’ll be at the heart of our financial operations, ensuring that every transaction is recorded correctly and that our financial statements reflect the health of our business. Your daily tasks will be diverse, from entering new transactions, posting, and creating trial balances to developing insightful spreadsheets and dashboards. We’ll look to you for your expertise in making journal entry adjustments, understanding financial statements, and closing the books.

What's in it for you?

As our Bookkeeper, you'll work alongside a team of leaders driven by integrity, values, and commitment to building a legacy. Your contributions will help directly shape the financial trajectory of Staylah and make way for growth in your career.

Are you in? Apply today! We’re looking forward to connecting.


  • Establish and maintain trust accounts.
  • Maintain records of financial transactions by posting and verifying.
  • Help create bookkeeping policies and procedures and advise on compliance.
  • Establish and maintain the chart of accounts.
  • Reconcile entries to balance subsidiary accounts.
  • Prepare a trial balance and financial reports and maintain financial dashboards to ensure compliance with federal, state, and local regulations.
  • Monitor variances from projected budgets.


  • 3+ years of bookkeeping/accounting experience in the property management/vacation rental space.
  • Experience using property management and bookkeeping software
  • Bachelor’s degree in accounting, finance or a related discipline is preferred
  • Able to work independently as well as on a team.


Annual Salary: $50,000 - $60,000 based on experience and achievement


  • Paid time off, such as PTO, sick days, and vacation days
  • Health insurance
  • Life insurance
  • Dental insurance
  • Vision insurance
  • Healthcare spending or reimbursement accounts, such as HSAs, FSAs, and HRAs
  • Short-term disability insurance