September 11, 2023
Orlando, Florida
Job Type
Annual Salary: $85,000 - $110,000 based on achievement and experience 



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!


Are you ready to use your skills to help drive a company’s financial success?

We’re looking for a Finance Manager who will work closely with our COO, managing the company's financial health to promote success and growth while maintaining exemplary financial practices.

As both an operational and financial position, this role will be ideally suited for you if you prefer working outside the status quo. Your primary duties will include financial planning and analysis to help guide our strategic growth, creating strategic business plans, reports, and advising our COO and executive management on important financial decisions.

In turn, you’ll benefit from the stability of our brand coupled with the excitement of our merger as we move to increase our footprint and establish a global vacation rental presence.

If you’ve got the skills and are excited to make a significant impact and be rewarded for your hard work, connect with us today. We’d love to work together.


  • Perform financial management duties, including generating financial data, compiling and submitting reports, analyzing industry trends, and assessing the company's financial health.
  • Oversee the operations and development of the company’s finance departments, including creating and reviewing policies, budgeting, recruiting, training, and conducting regular assessments of financial procedures.
  • Supervise the preparation of quarterly and annual account reconciliations, monitor and enforce compliance with tax and financial reporting standards, and assist with cash flow forecasting.
  • Advise the COO and executive management on decisions related to the company’s finances.
  • Supervise the documentation of the company’s financial status and forecasts.
  • Mediate between the organization, employees, stakeholders, shareholders, and investors on financial issues for an amicable resolution of differences.
  • Create strategic business plans based on the analysis of the company’s status and financial forecasts.


  • 5+ years of professional work experience as a Finance Manager, Accountant or in a similar role is required, preferably in the vacation rental industry.
  • Proven knowledge of financial analysis and strategy.
  • In-depth understanding of financial reporting standards, tax regulations, and industry legislation.
  • Excellent analytical skills and attention to detail.
  • Excellent verbal and written communication and presentation skills.
  • Proven negotiation skills.
  • Familiarity with Track and QuickBooks preferred.


Annual Salary: $85,000 - $110,000 based on achievement and experience


  • Paid time off, such as PTO, sick days, and vacation days
  • Health insurance
  • Life insurance
  • Dental insurance
  • Vision insurance