September 11, 2023
Orlando, Florida
Job Type
Annual Salary: OTE of $100,000 (base + commission) 



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!


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 us as our Business Development Executive.

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 who succeed in growing companies, from start-ups to the public.


  • Work independently to drive a multi-functional recruiting program to ensure top-caliber properties are regularly onboarded with Staylah.
  • Prospect, identify, develop, and manage a pipeline of potential clients and new owners.
  • Qualify leads by working closely with key stakeholders.
  • 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, inclusive of 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 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 of $100,000 (base + commission)

Benefits & Perks: 

  • 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
  • Relocation assistance
  • Workplace perks such as recreation activities, food and coffee, and flexible work schedules