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Company Overview

At Roelens Vacations, we believe exceptional guest experiences begin with exceptional operations. As one of Southwest Florida's leading vacation rental management companies, we proudly manage more than 600 professionally maintained vacation homes across Cape Coral, Fort Myers Beach, Sarasota, and Siesta Key.

Our success is built on a commitment to outstanding service, operational excellence, and a team-first culture where collaboration, accountability, and continuous improvement drive everything we do. We invest in our people, embrace technology and innovation, and empower our leaders to make meaningful improvements that enhance the experience for both homeowners and guests.

If you're looking for an opportunity to lead high-performing teams, influence company-wide operations, and play a key role in the continued growth of an established vacation rental company, we'd love to meet you.

Position Summary

Roelens Vacations is seeking an experienced Director of Operations to lead and elevate our Housekeeping, Maintenance, and Property Inspection departments. This is a highly visible leadership role responsible for ensuring operational excellence across a portfolio of more than 600 vacation homes while delivering exceptional experiences for homeowners and guests.

Reporting to executive leadership, you'll oversee departmental managers, develop scalable operational systems, improve team performance, implement technology and AI-driven efficiencies, and create processes that support continued company growth. This role is ideal for a strategic, hands-on leader who enjoys solving complex operational challenges, coaching teams, and building systems that produce consistent results.

What You'll Do

• Lead the daily operations of the Housekeeping, Maintenance, and Property Inspection teams.

• Hire, coach, develop, and evaluate department leaders and operational staff.

• Build a culture of accountability, collaboration, and continuous improvement.

• Develop and refine standard operating procedures that improve efficiency and scalability.

• Monitor operational performance using KPIs and implement improvements where needed.

• Ensure properties consistently meet company quality, cleanliness, and safety standards.

• Coordinate property inspections and proactively identify maintenance opportunities.

• Partner with cross-functional teams to improve communication and operational workflows.

• Implement and optimize technology, automation, and AI tools to improve scheduling, reporting, communication, and operational performance.

• Oversee recurring maintenance schedules and preventative maintenance programs.

• Respond to operational challenges quickly while balancing guest satisfaction and homeowner expectations.

• Resolve escalated operational issues and implement long-term solutions.

• Identify opportunities to improve efficiency, reduce costs, and enhance the overall guest experience.

• Contribute to strategic planning and operational initiatives that support company growth.

Required Qualifications

• 3-5+ years of senior-level operations leadership experience within the vacation rental, hospitality, hotel, or property management industry is required.

• Proven experience leading multiple operational departments and managing leaders.

• Strong leadership, coaching, and team development skills.

• Demonstrated success improving operational efficiency and implementing scalable systems.

• Experience developing and documenting standard operating procedures (SOPs).

• Comfortable leveraging modern software platforms, automation tools, and AI solutions to improve operations.

• Proficiency with Microsoft Office, including Excel and Word.

• Excellent written and verbal communication skills.

• Exceptional organizational, planning, and time management abilities.

• Strong analytical thinking and problem-solving skills with the ability to make sound decisions under pressure.

• Ability to prioritize multiple projects while maintaining attention to detail.

• Self-motivated with the ability to work independently and collaboratively.

• Weekend availability as business needs require.

Preferred Qualifications

• Bachelor's degree in Business, Hospitality Management, Operations Management, or a related field (equivalent leadership experience will also be considered).

• Experience managing large-scale vacation rental or hotel operations.

• Experience implementing operational technology, workflow automation, or AI-driven business solutions.

• Multi-property hospitality management experience.

Compensation, Benefits & More

Compensation

• $80,000 annually

Bonus

• Performance bonus opportunities available.

Benefits

• Health Insurance

• Dental Insurance

• Vision Insurance

• Life Insurance

• Paid Time Off (PTO)

• Retirement Plan

• Workplace perks and team-focused culture

Job Type

• Full-Time, Vacation Rental Operations

Location

• Cape Coral, Florida (On-site)