Property Manager - Short Term Rental (with Leadership Exp | WFH)

About Us:
OPTIMAL is a property management support company that works with real estate investors and property managers across North America, helping them achieve Time, Financial, and Location freedom through the implementation of remote property management techniques with back-office management and fulfilment.

Our Leadership Team is made up of Ex-Big 4 Accounting and Consulting professionals as well as property managers who have experience managing commercial and residential portfolios for the likes of Blackstone and Prologis as well as your local property management firm.


About the Role

As a Virtual Property Manager (VPM) specializing in Short-Term Rentals (STR), you will oversee daily property operations, coordinate with U.S.-based clients, and ensure exceptional guest experiences, operational efficiency, and property performance.


You will serve as the primary point of contact for assigned clients, overseeing property management activities, coordinating internal teams and vendors, and ensuring consistent adherence to client standards and operational procedures.



Key Responsibilities

Short-Term Rental Operations

• Oversee daily operations of STR properties, ensuring listings, reservations, calendars, pricing, and property information remain accurate and up to date.
• Monitor booking activity, occupancy, guest inquiries, and reservation changes to ensure smooth operations.
• Coordinate property readiness, including cleaning schedules, inspections, turnovers, and guest check-ins/check-outs.
• Ensure properties are consistently prepared and maintained to meet client standards and guest expectations.

Guest Experience & Customer Service

• Oversee guest communications throughout the reservation lifecycle, ensuring timely, professional, and personalized responses.
• Manage guest concerns, complaints, special requests, and escalations while maintaining high satisfaction levels.
• Coordinate resolutions for booking issues, access concerns, maintenance requests, and other guest-related matters.
• Support the team in maintaining excellent guest reviews and overall property ratings.

Maintenance & Vendor Coordination

• Supervise maintenance requests, work orders, and vendor coordination to ensure timely resolution of property issues.
• Coordinate with housekeeping, maintenance, and other service providers to maintain property standards.
• Monitor vendor performance, service completion, and associated costs.
• Escalate urgent maintenance concerns and ensure properties remain safe, functional, and guest-ready.

Client Management

• Serve as the primary point of contact for assigned U.S.-based clients, providing operational updates and addressing property-related concerns.
• Manage client expectations and ensure service delivery aligns with agreed standards and priorities.
• Communicate property performance, operational concerns, and recommendations for improvement.
• Support clients in implementing and optimizing STR property management platforms such as Guesty, Hostaway, and other related systems.

Team Leadership & Development

• Provide guidance, coaching, and support to Virtual Property Managers and STR operations team members.
• Monitor team performance, service quality, productivity, and adherence to client-specific procedures.
• Assist in onboarding and training team members on STR processes, systems, and communication standards.
• Promote accountability, collaboration, and continuous improvement within the team.

Process Improvement & Operational Excellence

• Develop, maintain, and improve STR workflows, standard operating procedures (SOPs), and operational guidelines.
• Identify inefficiencies and recommend solutions to improve response times, guest experience, and property operations.
• Ensure accurate documentation, reporting, and consistent use of property management systems.
• Identify operational risks and escalate issues requiring client or management intervention.

Qualifications

• 3+ years of experience in U.S. Short-Term Rental (STR) property management or vacation rental operations.
• Strong working knowledge of STR platforms such as Guesty, Hostaway, Hospitable, OwnerRez, Breezeway, or similar systems.
• Experience in guest communication, reservation management, housekeeping coordination, property turnovers, and maintenance oversight.
• 2+ years of leadership or supervisory experience, preferably managing remote teams or STR operations.
• Strong client-facing communication skills, with the ability to manage expectations and handle escalations professionally.
• Demonstrated ability to oversee daily operations, prioritize urgent concerns, and manage multiple properties efficiently.
• Highly organized, detail-oriented, proactive, and capable of working independently with minimal supervision.
• Experience in coaching, mentoring, and supporting team performance.
• Strong problem-solving skills and a commitment to exceptional guest experiences and operational excellence.