Head of Vacation Rental Ops & AI Automation

Florida Vacation Collection; Tampa (FL); On-site; USD 75,000 - 85,000; Full time

Job summary

Florida Vacation Collection seeks an experienced operations leader to run vacation rental operations with technology and AI. You will coordinate maintenance, manage vendors and cleaners, and ensure each property has the people, processes, and systems it needs to run smoothly.

This hands-on leadership role requires you to manage people, make decisions, and drive improvements. You will implement AI and automation, build preventive maintenance schedules, monitor performance and costs, and resolve

Qualifications

• Experience leading operations in vacation rentals, hospitality, or property management.
• Proven ability to manage multi-property teams and vendors across properties.
• Strong working knowledge of AI tools, agentic platforms, automation software, and PM systems.
• Experience building automated workflows with measurable results including efficiency gains.
• Ability to learn software quickly, configure workflows, and troubleshoot problems.

Responsibilities

• Coordinate maintenance; prioritize issues, assign vendors, track repairs, and confirm completion.
• Manage cleaners, handymen, HVAC technicians, plumbers, electricians, pool services and other providers; set pricing, responsiveness, and quality expectations.
• Oversee cleaning and turnover; ensure inspections, stocked supplies, and readiness before guest arrivals.
• Set up property operations with assigned vendors, cleaning instructions, access procedures, maintenance schedules, and task ownership.
• Build preventive maintenance schedules including deep cleans and routine inspections to reduce problems.
• Improve systems and workflows by documenting procedures and ensuring adherence.
• Implement AI and automation to reduce manual follow-up, organize property data, improve reporting, and catch missed tasks.
• Manage accountability with team leads; address overdue work or recurring performance issues.
• Handle operational escalations to resolve urgent property and guest issues and coordinate responses.
• Track performance and costs across properties including maintenance response times and vendor spend.

Skills

Leadership

Vendor management

Team management

Process improvement

Communication

Tools

AI tools

Automation software

Property management systems

Task management tools

Job description

Florida Vacation Collection seeks an experienced operations leader to run vacation rental operations with technology and AI. You will coordinate maintenance, manage vendors and cleaners, and ensure each property has the people, processes, and systems it needs to run smoothly.

This hands-on leadership role requires you to manage people, make decisions, and drive improvements. You will implement AI and automation, build preventive maintenance schedules, monitor performance and costs, and resolve