SkyRun Vacation Rentals – Anna Maria Island is a high-growth short-term rental management company dedicated to delivering exceptional guest experiences and maximizing homeowner value.
We manage a portfolio of high-end vacation homes across Anna Maria Island and operate with a hospitality-first mindset. Our team combines operational excellence, clear communication, and strong local expertise to create memorable stays for guests while protecting and enhancing our homeowners’ investments.
We believe in:
High standards and accountability
Clear processes and strong team communication
Ownership mentality at every level
Continuous improvement
Taking pride in delivering 5-star experiences
If you thrive in an environment where details matter, standards are high, and your work directly impacts guest satisfaction and company reputation, you will fit in well here.
We're looking for a driven Business Development professional to expand our portfolio of premium vacation rental properties in the Anna Maria Island and Bradenton area. In this role, you'll be the face of SkyRun Vacation Rentals, building relationships with property owners, real estate professionals, and community partners to grow our presence in one of Florida's most desirable vacation destinations. You'll combine your sales expertise with market knowledge to help property owners unlock the full potential of their investments while achieving significant personal earning potential through a competitive commission structure.
As our Business Development representative, you'll take ownership of the entire sales cycle—from initial prospecting and networking to closing deals and ensuring successful onboarding. This is a unique opportunity for someone who thrives on building connections, enjoys the challenge of consultative selling, and wants to be part of a growing team in the thriving short-term rental industry. If you're energetic, persuasive, and motivated by results, this role offers unlimited growth potential in a dynamic market.
Conduct discovery calls and in-person property walkthroughs
Analyze property potential and present revenue projections to owners
Pitch SkyRun's management services and value proposition
Negotiate and close management agreements
Consistently meet or exceed monthly and quarterly growth targets
Build and maintain long-term relationships with:
Serve as the primary point of contact during onboarding of new locations
Ensure smooth transition from signed agreement to active listing
Maintain an active and organized sales pipeline (CRM)
Track outreach, meetings, and conversion metrics
Provide regular reporting on:
2+ years of experience in sales, business development for short term rentals
Proven ability to generate leads and close deals
Strong interpersonal and communication skills
Self-starter with a high level of accountability and drive
Comfortable working both independently and in a team
$55,000 - $65,000
Paid time off such as PTO, sick days, and vacation days
Health, Dental, and Vision insurance
Dental insurance
Employee recognition programs
Workplace perks such as recreation activities, food and coffee, and flexible work schedules
