Description
COMPANY OVERVIEW:
Vaaraway is a marketing and reservations management company built by homeowners for homeowners. We help property owners maximize the value of their vacation rentals by handling marketing, booking management, and technology integration.
Our focus is on getting homes seen and booked at the best possible rates while making the ownership experience as hands-off as possible. We do not provide on-site guest services. Instead, we take care of listing strategy, pricing optimization, booking logistics, and owner reporting so that owners have a clear picture of their property’s performance with less work on their end.
Along with our parter company, The Cottages on The Key, Vaaraway is located in Siesta Key, Florida and we are dedicated to providing exceptional hospitality and sharing the best experiences in the area with guests from around the world.
At Vaaraway, we prioritize our culture. We foster a supportive and inclusive environment where everyone is valued. Our team is united and collaborative, allowing us to maintain an excellent work-life balance.
POSITION SUMMARY:
As an Operations Manager at Vaaraway, you will play a pivotal role in ensuring exceptional guest experiences and seamless property management across our luxury vacation rentals in Siesta Key, FL. You’ll be the connection point between homeowners, House Managers, and the Vaaraway team—keeping property onboarding organized, ensuring owner statements are accurate, and maintaining strong, proactive communication with owners about how their homes are performing. You will also act as the primary liaison for homeowners, promptly addressing requests and concerns to build trust and long-lasting relationships.
This is a relationship-focused role that also requires strong operational management and attention to detail. You’ll guide and mentor our House Managers to uphold the highest standards of hospitality and property care, while also monitoring Monday.com boards to ensure new listings are progressing on schedule. Your leadership skills, operational expertise, and ability to thrive in a fast-paced environment will directly contribute to owner satisfaction, team success, and the continued growth of Vaaraway.
RESPONSIBILITIES:
- Provide proactive updates on property performance, guest feedback, and revenue projections.
- Deliver bi-monthly revenue communications and maintain open, consistent dialogue.
- Meet with local owners in person during their stays.
- Oversee House Managers, ensuring proper guest care and property upkeep.
- Participate in training, onboarding, and coaching House Managers on operational and hospitality excellence.
- Support House Managers with booking questions and guest communication.
- Oversee onboarding tasks: property intake forms, financial documentation (W9/ACH), vendor coordination, photoshoots, and reservation transitions.
- Ensure mastery of key systems (Breezeway, Point Central, Avalara).
- Conduct audits of owner statements and resolve discrepancies.
- Oversee arrival reports and manage owner-initiated requests (OIRs).
- Work with the revenue team to analyze occupancy, rates, and demand trends.
- Provide coaching to owners and House Managers on operational performance.
- Contribute to updating SOPs for sales, guest management, and property care.
QUALIFICATIONS:
- 3 years of leadership experience
- 1-2 years of vacation rental, property management or hospitality experience
- Exceptional interpersonal skills — polished, professional, and relationship-driven.
- Strong operational and organizational abilities with attention to detail.
- Ability to manage multiple priorities in a dynamic, hospitality-driven environment.
- Experience in luxury property management, vacation rentals, or hospitality preferred.
- Tech-savvy with experience in platforms such as Breezeway, Point Central, or similar.
- Comfortable with flexible schedules and 24/7 on-call availability when needed.
COMPENSATION & BENEFITS:
Annual Salary: $80,000 - $100,000
Bonus
Performance-based override
Benefits
- Paid time off such as PTO, sick days, and vacation days
- Employee recognition programs
- Wellness programs
- Commuting/travel assistance
- Workplace perks such as recreation activities, food and coffee, and flexible work schedules
Schedule
Monday - Friday with some on call availability and flexibility required