Description

Exciting Career Opportunity at VTrips

Are you ready to take on a leadership role that keeps operations running smoothly and efficiently across multiple vacation rental markets? VTrips, a premier vacation rental company based in Ponte Vedra, FL, is looking for an organized, proactive, and field-savvy Operations Support Specialist (OSS) to join our dynamic team. If you thrive in a fast-paced environment and have a passion for operational excellence and team development, we want to hear from you!

The OSS serves as a critical support leader within the Operations team, working closely with the Director of Operations (DOO) to ensure consistency in service delivery and operational execution. This role provides leadership to Property Care Managers and Maintenance Technicians by offering hands-on training, reinforcing best practices, and supporting compliance with operational standards and KPIs.

Daily Responsibilities:

Collaborate with the DOO to resolve operational issues across assigned regions.
Assist Property Care Managers through field training, shadowing, and coaching.
Conduct joint quality control inspections with managers and technicians.
Monitor the completion and timeliness of work orders and property care tasks.
Support administrative reporting and documentation as directed.
Step into operational roles when needed to maintain service continuity.

Weekly Responsibilities:

Lead operational reviews and one-on-one touchpoints with field teams.
Provide on-the-ground support for COP (Clean, Operable, Presentable) and GOP (Guest-Ready, Owner-Ready, Presentable) assignments.
Assist in the development and management of weekly team schedules.
Attend operational meetings to align priorities and convey updates from leadership.
Execute Admin Walks to identify opportunities for coaching and process improvements.

Monthly Responsibilities:

Partner with the DOO on onboarding and ongoing training for operational staff.
Track and evaluate KPI performance to support developmental conversations.
Participate in cross-departmental meetings to drive collaboration and alignment.
Promote “safety first” protocols and escalate any hazards to the DOO.
Be on-call for emergency preparedness and response support.

Benefits:

Competitive salary.
Comprehensive medical, dental, and vision insurance.
401(k) retirement plan with company match.
Paid time off and holidays.
Employee discounts on vacation rentals.
Professional development opportunities.

AAP/EEO Statement:

We are an Equal Opportunity Employer committed to the principles of Equal Employment Opportunity.

Other Duties:

Please note this job description is not exhaustive and may be subject to change. Duties, responsibilities, and activities may vary based on regional and location-specific needs of the company.

Apply now and become a vital part of the VTrips family where your career is more than just a job – it's an adventure!

Requirements

Requirements:

Proven experience in hospitality, operations management, or a similar leadership role.
Ability to travel frequently within assigned regions.
Strong interpersonal and communication skills.
Comfortable with administrative and hands-on field tasks.
Proficiency in using scheduling tools, reporting systems, and Microsoft Office Suite.
Valid driver’s license and reliable transportation.
Ability to stand, walk, lift, and work in a variety of environmental conditions.

Work Environment:

This hybrid role includes both administrative duties and frequent fieldwork, requiring adaptability, leadership presence, and hands-on engagement in property inspections and team support activities.