April 24, 2023
Orlando, Florida
Job Type
Annual Salary: Up to $200,000 base salary 



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.

To catapult success and bolster its value proposition in Florida, Staylah has joined forces with regional leaders Juliana Boselli-Neves and Rafael Boselli of Glasstone Vacations. 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!


To support the vision of establishing a global collective of luxurious, trustworthy accommodations of excellence, we are looking for a passionate, growth-minded leader to join our executive team as Chief Operating Officer.

As a leader on our executive team, the COO is responsible for executing the vision of Staylah by strategically making data-driven decisions to ensure optimal guest experiences and owner returns while achieving corporate financial goals. This role requires collaboration with leadership to understand, contribute, build teams, and implement best practices to realize success.

Even though the business has been operating profitably for nine years, there is an opportunity to strengthen the foundation to fuel further growth in the current and new territories. The COO will have fresh input in Marketing, Sales, HR, Finance, Operations, and Technology.  There will be opportunities for ownership for the right adventurer.


  • Contribute and execute Staylah’s vision.
  • Oversee daily operations, delegate, motivate, and build teams to optimize guest and owner experience.
  • Establish and manage the appropriate KPIs for business segment leaders.
  • Analyze the budget to identify cost-saving efficiencies.
  • Implement systems to ensure scalability of core business and auxiliary businesses.
  • Collaborate on brand, value proposition, and target growth markets.
  • Integrate potential acquisitions and partnerships.
  • Create and maintain thorough reporting for the leadership team.
  • Ensure training and development programs align with talent needs.
  • Coordinate business functions to work ensure they work together optimally.
  • Manage key stakeholder relationships.


  • 5+ years of proven leadership experience for high-performing teams is required. (Property Management / Vacation Rental Management preferred)
  • Adept at transitioning seamlessly from strategizing to implementation, translating into tangible results.
  • High level of computer proficiency and ability to learn and utilize various technology platforms.
  • Strong analytical, critical thinking, and interpersonal skills.
  • Able to deliver presentations and conduct meetings both in person and via video.
  • Bachelor's degree in hospitality, business administration, marketing, or related field preferred
  • Must be able to relocate to the Orlando area within six months. Relocation and housing assistance are available.


Annual Salary: Up to $200,000 base salary

Bonus Details: Bonus opportunities based on individual and company performance


  • Paid time off, such as PTO, sick days, and vacation days
  • Health insurance
  • Life insurance
  • Dental insurance
  • Vision insurance
  • Healthcare spendings or reimbursement accounts, such as HSAs, FSAs, and HRAs
  • Short-term disability insurance
  • Relocation assistance
  • Workplace perks such as recreation activities, food and coffee, and flexible work schedules