Owner Experience & Success Manager

Better Talent; Siesta Key (FL); On-site; USD 50,000 - 70,000; Full time

Benefits offered by this job

Health insurance

Paid time off

Bonuses

Job summary

The Cottages on the Key, a luxury vacation rental manager in Siesta Key, seeks an Owner Experience Manager to own homeowner relationships and drive retention. You will spend substantial time in direct conversations with owners, offering candid, well-advised guidance and proactive solutions to keep properties and accounts healthy.

The role blends office duties with regular property visits, coordinating across Marketing, Sales, Revenue, and Operations to ensure owners’ needs and preferences are

Qualifications

• 2+ years of experience in account management, short-term rentals, hospitality, property management, or similar client-facing role.
• Strong written and verbal communication skills.
• Excellent organization and attention to detail; clear record-keeping.
• Proactive approach to service with initiative to anticipate needs.
• Willingness to travel to properties around Siesta Key.

Responsibilities

• Listen closely to owners, give sound and honest advice, and manage each account strategically for retention.
• Lead difficult conversations about rental income, charges, and property needs.
• Serve as the account manager and primary contact for assigned homeowners.
• Build and maintain relationships that support homeowner satisfaction and long-term retention.
• Be familiar with the owner portfolio details, preferences, and priorities.
• Coordinate owner meetings across Marketing, Sales, and Revenue.
• Lead owner communications about property inspections and seasonal prep.
• Manage the owner gift program and delivery.
• Visit properties in the field and coordinate follow-ups with teams.
• Schedule and conduct property visits with homeowners.
• Coordinate maintenance, housekeeping, and vendor services.
• Review Breezeway work orders daily and follow up.
• Coordinate owner stays, access, and cleaning arrangements.
• Onboard new properties and guide owners through initial steps.
• Collect, track, and communicate required paperwork.
• Support ownership changes and transitions with agents.
• Maintain owner hotlist and track open requests.
• Escalate unresolved issues and propose workflow improvements.
• Familiarize with property management software and owner portals.

Skills

Account management

Communication

Organization

Proactivity

Travel

Tools

Google Workspace

Spreadsheets

Breezeway

Job description

The Cottages on the Key, a luxury vacation rental manager in Siesta Key, seeks an Owner Experience Manager to own homeowner relationships and drive retention. You will spend substantial time in direct conversations with owners, offering candid, well-advised guidance and proactive solutions to keep properties and accounts healthy.

The role blends office duties with regular property visits, coordinating across Marketing, Sales, Revenue, and Operations to ensure owners’ needs and preferences are