April 8, 2023
Orlando, Florida
Job Type
Annual Salary: OTE $100,000 



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 from firsthand experience with lackluster property management and care for our portfolio of short-term rental properties in Tennessee. Dwindling returns, poor emphasis on quality, and unhappy guests drove us to find a better way. 

This calling lead to the departure from a stable, lucrative, 20-year career in risk and insurance, where our founder, 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 a regional leader in stewarding vacation rental accommodations in Florida to catapult success and bolster its value proposition. This partnership fast-tracks growth and results in the management and care of over 60 vacation rental accommodations of excellence in less than a year’s time. 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, driven go-getter to join our business development team as an Owner Guide. 

This colleague/adventurer is responsible for scouting, securing, and guiding new owner/host relationships. This is a new position for our firm. This colleague will have a unique opportunity to join as one of the founding adventurers to chart the course on this fun, exhilarating journey. 

There will be opportunities for advancement and an unprecedented mentoring/shadowing opportunity to learn from seasoned executives with success in growing companies from start-up to public. 

This is a hybrid position based in Orlando, FL. Flexibility for periodic travel to Tennessee will be necessary.


  • Scout, secure, and guide new owner relationships. 
  • Build relationships with centers of influence: real estate agents, mortgage brokers, travel agents, builders, and vacation rental communities. 
  • Create and execute marketing campaigns for new owner relationships (direct mail, phone calls, social media, drop-ins, etc.) 
  • Attend networking events to promote the Staylah brand and build relationships in the community. 
  • Attend property showings with prospective owners. 
  • Develop rental income proformas. 
  • Analyze current owner operating cost data to identify opportunities for improvement.
  • Distribute relevant and updated content throughout marketing channels, including print, digital, video, and community outreach campaigns. 
  • Work with the leadership team for content creation.


  • Previous experience generating and maintaining a pipeline of qualified leads, preferably in the vacation rental industry, real estate, insurance, or financial services space. 
  • Thrives in a competitive environment. Instinctively motivated to generate and convert new owner relationships. 
  • Experience and understanding of vacation rental management and services are preferred.
  • Ability to establish and maintain relationships with local real estate agents.
  • Able to understand and interpret the critical historical, market, and home data to determine accurate property projections. 
  • Must have excellent verbal, written, and presentation skills. Able to communicate efficiently through telephone, email, and letter-writing correspondence.
  • Proficient in PowerPoint, MS Word, Excel, Publisher, Outlook, and CRM software.


Annual Salary: OTE $100,000 

Bonus Details: Base salary + commission for new owner relationships 

Benefits & Perks: 

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