Owner Experience Manager

Owner Experience Manager

The Cottages on the Key | Siesta Key, Florida

Full-Time | On-Site | Tuesday–Saturday

Company Overview

The Cottages on the Key is a luxury vacation rental management company in Siesta Key, Florida. We are dedicated to providing exceptional hospitality and sharing the best experiences in the area with guests from around the world.

We also offer comprehensive property management services for vacation rental owners. Our personalized "white glove" services are tailored to the financial goals and unique qualities of each property, which has driven our success and continued growth.

We prioritize our culture. We foster a supportive and inclusive environment where everyone is valued, and our team is united and collaborative, which allows us to maintain an excellent work-life balance.

Position Summary

This is an account management role. The Cottages on the Key is seeking an Owner Experience Manager to own the relationship with the homeowners in our vacation rental management portfolio, and you will spend a significant part of each day in direct conversation with them. The goal is owner retention: owners who feel heard, well advised, and confident in the care of their homes.

The work is equal parts listening, advising, and strategy. You will hear what an owner is really asking for, give them honest and well-reasoned advice, and think ahead about what each account needs to stay healthy. Difficult conversations come with the job, whether about what a home is earning, charges on a statement, or the condition and needs of the house itself, and you will be expected to lead them with candor and tact.

The role sits within Operations and serves as the owner's spokesperson inside the company. You will represent each owner's interests through daily cross-departmental communication with Marketing, Sales, and Revenue, and within Operations by working closely with our maintenance supervisor, housekeeping, and quality control team. You will also support new-owner onboarding and know each home and each owner's preferences in detail. The role combines office work with regular property visits in the field.

The ideal candidate takes initiative, anticipates homeowner needs, and addresses concerns before they escalate. Strong organization is essential to track conversations, open requests, deadlines, and follow-ups across multiple properties in a fast-paced environment.

Responsibilities

Owner relationships and communication

- Listen closely to owners, give sound and honest advice, and manage each account strategically with retention in mind.
- Lead difficult conversations about rental income, charges, and the condition or needs of an owner's home.
- Serve as the account manager and primary point of contact for assigned homeowners, spending a significant part of each day in direct conversation with them.
- Build and maintain relationships that support homeowner satisfaction, trust, and long-term retention.
- Become thoroughly familiar with the assigned owner portfolio, including property details, preferences, and priorities.
- Act as the owner's spokesperson across departments, including Marketing, Sales, and Revenue, anticipating concerns and following up before issues escalate.
- Coordinate owner meetings and check-ins to keep relationships strong.
- Lead owner communications about property inspections, preventive maintenance, seasonal preparation, damage incidents, and severe weather.
- Manage the owner gift program, including preparation and delivery to in-house owners.

Property visits and coordination

- Visit properties in the field to stay familiar with their condition, document observations, and coordinate follow-up with the appropriate teams.
- Schedule and conduct property visits with homeowners to review property condition, ongoing work, and service needs.
- Coordinate maintenance requests, housekeeping concerns, vendor services, and other operational matters with internal departments.
- Review Breezeway work orders daily and follow up on open or recurring issues. • Coordinate owner stays and property access, including reservation blocks, arrival preparation, and cleaning arrangements.
- Coordinate requests involving furnishings, amenities, property improvements, and listing information, documenting preferences and required approvals.

Onboarding and transitions

- Manage the internal process of onboarding new properties, including documentation, property setup, and follow-through.
- Guide new homeowners through their initial steps and help them get comfortable with how we work.
- Collect, track, and communicate required paperwork and onboarding information across departments.
- Support ownership changes and management transitions, coordinating with owners, real estate agents, and external property managers.

Records and follow-through

- Maintain an owner "hotlist" of open requests, responsible departments, deadlines, preferences, and special considerations.
- Track issues through completion and communicate outcomes to homeowners.
- Maintain accurate homeowner contact information, property records, and communication histories.
- Assist owners with routine owner portal navigation.

Financial inquiries

- Review monthly owner statements so you can answer routine homeowner questions about expenses and charges.
- Coordinate with the Finance Department on inquiries about maintenance charges, invoices, distributions, credits, and related financial matters.

Escalation and improvement

- Escalate unresolved issues appropriately.
- Recommend improvements to homeowner communication and operational workflows.

Required Qualifications

- 2+ years of experience in account management, short-term rentals, hospitality, property management, or a similar client-facing role.
- Strong written and verbal communication skills, with the ability to manage frequent homeowner and internal communication.
- Excellent organization and attention to detail, including clear record-keeping so that no request is overlooked.
- A proactive approach to service, with the initiative to anticipate needs and follow up without repeated prompting.
- Composure in a fast-paced, ever-changing environment, with the ability to prioritize competing demands and follow through on commitments.
- Confidence on the phone and in difficult conversations, including ones about money and an owner's home, with the ability to listen well and advise honestly.
- Practical problem-solving skills, sound judgment, and the ability to work both independently and collaboratively.
- Comfort with Google Workspace, spreadsheets, and task management systems, and a willingness to learn property management software.
- Discretion when handling confidential homeowner and property information.
- Ability to travel to properties on and around Siesta Key.

Preferred Qualifications

- Experience in homeowner relations, account management, or client relationship management.
- Experience coordinating property services, conducting property visits, or supporting onboarding and administrative processes.
- Familiarity with property management systems, owner portals, or CRM tools such as Streamline and Breezeway.
- Knowledge of the Siesta Key area.

Compensation and Benefits

Annual Compensation: $ 50,000–$70,000, including performance-based bonuses.

Bonus: Paid for each new home that is signed and successfully onboarded by its deadline.

Benefits:

- Paid time off, including vacation and sick days
- Health insurance
- Workplace perks such as recreation activities, food and coffee, and flexible work schedules

If you enjoy building relationships, taking initiative, and staying involved in the care of vacation rental properties, we welcome your interest in joining The Cottages on the Key.