Business Development Representative

Company Overview 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, protecting and enhancing our homeowners’ investments. Position Summary 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. You will 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 will manage the entire sales cycle—from prospecting and networking to closing deals and ensuring successful onboarding. Responsibilities Business Development & Lead Generation 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 Sales & Closing 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 Market Expertise 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 Relationship Management & Onboarding 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 Pipeline & Reporting 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 Required Qualifications 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 Preferred Qualifications Existing network in Anna Maria Island and Bradenton Familiarity with platforms like Airbnb and VRBO Compensation and Benefits Annual Salary: $55,000 - $65,000 Bonus and OTE: Commission per deal signed & bonuses for number of properties signed. Target OTE $130,000 Benefits 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 #J-18808-Ljbffr