Onboarding Specialist

• Onboarding Specialist
• Hollywood, FL - Onsite
• $50,000 - 55,000/year

About StaySouth

StaySouth Vacation Homes is a locally owned vacation rental management company serving Southeast Florida and part of the Casago network. We combine local hospitality expertise, professional management systems, and personalized homeowner service.

The Role

As our portfolio grows, the Property Onboarding Specialist owns every newly signed home’s path from executed management agreement to live, bookable listing and handoff to our Local Operations team. You’ll coordinate Operations, Revenue Management, Marketing, Compliance, Accounting, and outside vendors so that every property launches fully configured, compliant, and guest-ready.

What You’ll Do

• Manage the onboarding pipeline for each new property: build the onboarding plan, set go-live dates, assign task owners, and track milestones through launch
• Collect and verify owner information and documents, including access details, house rules, HOA/condo requirements, emergency contacts, and payout setup with Accounting
• Configure new properties in Guesty: specs, occupancy, amenities, check-in/checkout rules, fees, taxes, calendars, and reservation restrictions
• Launch and verify listings on Airbnb, Vrbo, Booking.com, and our direct booking site, coordinating professional photography, listing content with Marketing, and channel sync
• Implement approved pricing from Revenue Management in Wheelhouse and confirm rates, fees, and availability sync correctly
• Coordinate physical and operational readiness: inspections, cleaning, linens, repairs, smart-lock setup, guest access instructions, and Breezeway cleaning and inspection workflows
• Track permits, licenses, and registrations with our Compliance Manager and document clearance before any property goes live
• Keep homeowners updated at every milestone, run the final go-live readiness review, and complete a structured handoff to Operations, Owner Relations, and Guest Experience

What We’re Looking For (Required)

• 2+ years in property onboarding, property management, vacation rental or hospitality operations, implementation, or project coordination
• Experience managing multiple concurrent projects or launches with deadlines and cross-department dependencies
• Hands-on experience with a property management system, CRM, or project-management tool
• Experience collecting and maintaining owner or client documentation accurately
• Clear written and verbal communication with homeowners, vendors, and internal teams
• Nice to Have
• Vacation rental or short-term rental onboarding experience, including Airbnb, Vrbo, or Booking.com listing setup
• Experience with Guesty, Breezeway, Wheelhouse, or similar STR platforms
• Knowledge of South Florida short-term rental regulations and permitting
• Bilingual English and Spanish