Role Overview
This is a dynamic, hands-on role at the intersection of guest experience and operations within a boutique hospitality brand. While theCounty Curated is based in Toronto, the properties are in Prince Edward County, and this role supports both remote operations and on-site needs. You will be deeply involved in everything from managing guest interactions to supporting day-to-day operations, playing a key role in ensuring the portfolio runs smoothly and performs at a high level. The role offers a mix of remote work and on-site involvement, ideal for someone who enjoys variety, ownership, and being close to the action.
This is an opportunity to join an established and growing hospitality business operating in Prince Edward County, while working closely with a Toronto-based team. You will work directly with ownership, gain exposure to all aspects of the business, and contribute to the continued growth and performance of a multi-property portfolio.
Key Responsibilities
Guest Experience & Communication
- Manage and optimize booking platforms (Airbnb, VRBO, Website) to drive occupancy and revenue
- Develop and manage property listings to ensure accuracy and alignment with brand standards
- Manage guest communications ensuring timely, professional, and brand-aligned responses
- Prepare and issue tailored booking quotes to maximize conversion and guest satisfaction
- Proactively manage the guest journey from inquiry to post-stay follow-up
- Resolve guest issues efficiently and manage escalations with a solutions-first approach
- Request, track, and respond to guest reviews to maintain high ratings and strengthen brand reputation
Operations & Administration
- Lead weekly team check-ins to review priorities, issues, and upcoming bookings
- Assist in coordinating and scheduling property tasks, including cleaning, repairs, and maintenance, through scheduling software to ensure all work is completed on time and to established standards
- Support the preparation of financial statements and internal reporting
Marketing & Brand Support
- Assist in developing and maintaining a social media content calendar aligned with seasonal demand and brand strategy
- Support execution of marketing initiatives, promotions, and campaigns
- Contribute to ongoing optimization of property listings to improve visibility and conversion
Executive & Personal Support
- Provide administrative support to the partners, including calendar management, scheduling, and coordination of meetings
- Assist with select personal and business-related tasks and errands, as required
- Support special projects and ad hoc requests to ensure overall operational efficiency
Success in This Role Looks Like
- Timely, professional, and brand-aligned communication across guest and internal touchpoints
- Proactive problem-solving and the ability to anticipate needs and resolve issues
- Smooth and well-coordinated property operations completed on time and to standard
- Strong organization and follow-through across scheduling, documentation, and day-to-day operations
- Effective coordination and communication with internal team members and external service providers
- Accurate and up-to-date operational and financial records, supporting reliable reporting
- Reliable administrative and executive support, ensuring calendars, priorities, and requests are managed efficiently
Ideal Candidate
- Highly organized and detail-oriented
- Strong communicator with a hospitality-first mindset
- Comfortable managing multiple priorities in a fast-paced environment
- Proactive, resourceful, and solution-oriented
- Interested in both operations and guest experience within a growing business
- Tech-savvy, with the ability to quickly learn new systems if required
Additional Requirements
- Ability to travel to Prince Edward County on a regular basis to support on-site operations across the property portfolio
- Valid driver’s license and access to a reliable vehicle required
Experience & Qualifications
Required
- Strong administrative and organizational experience, with the ability to manage multiple priorities
- Experience coordinating schedules, vendors, or service providers
- Experience supporting a small team or working in a fast-paced, entrepreneurial environment
- Proficiency in standard office and productivity tools, including Microsoft Office (Word, Excel) and Google Workspace (Docs, Sheets, Drive)
Assets
- Experience in hospitality, property management, operations, or a similar role
- Experience managing guest communications and delivering high-quality customer or client service
- Familiarity with booking platforms such as Airbnb, VRBO, or similar reservation systems
- Exposure to social media or marketing support
- Basic financial coordination experience, including tracking expenses or supporting reporting
Pay: $42,000.00-$55,000.00 per year
Benefits:
- Mileage reimbursement
- Paid time off
Application question(s):
- Do you have access to a vehicle?
Licence/Certification:
- Driving Licence (required)
Location:
- Toronto, ON M5V 3B1 (preferred)
Willingness to travel:
Work Location: Hybrid remote in Toronto, ON M5V 3B1
