Anna Maria Island Jobs (NOW HIRING)

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.

• Prospect and generate new leads through:

  • Networking with real estate agents, brokers, and investors

  • Local outreach and community engagement

  • Cold calling, email campaigns, and in-person meetings

• Identify high-quality vacation rental opportunities aligned with company standards

• 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

• Develop deep knowledge of:

  • Anna Maria Island and Bradenton STR markets

  • Pricing trends, seasonality, and demand drivers

  • Local regulations and compliance requirements

• Advise property owners on:

  • Revenue optimization

  • Property upgrades to maximize ROI

• Build and maintain long-term relationships with:

  • Property owners

  • Realtors and brokers

  • Local partners and vendors

• 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:

  • Lead flow

  • Conversion rates

  • Market feedback and opportunities

• 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

• Existing network in Anna Maria Island and Bradenton

• Familiarity with platforms like Airbnb and VRBO

$55,000 - $65,000

• Commission per deal signed & Bonuses for number of properties signed. Target OTE $130,000

• 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