Head of Operations & Business Management

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. 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.

Roelens Vacations is seeking an experienced Director of Operations to lead and elevate our Housekeeping, Maintenance, and Property Inspection departments. 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.

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

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

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.

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

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

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.

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.

Exceptional organizational, planning, and time management abilities.

Ability to prioritize multiple projects while maintaining attention to detail.

Weekend availability as business needs require.

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.

Bonus
Performance bonus opportunities available.

Health Insurance

Dental Insurance

Life Insurance

Retirement Plan

Full-Time, Vacation Rental Operations

Cape Coral, Florida (On-site)

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