Founded in 2015, My Perfect Stays is the largest vacation rental management company on the island of Maui, managing over 400 luxury vacation homes and condos with a team of more than 50 local hospitality professionals.
Our mission is simple: provide the perfect stay for every guest and complete peace of mind for every homeowner.
We believe exceptional hospitality comes from great people. Our team works together to deliver thoughtful service, clear communication, and consistently high standards for every property we manage.
My Perfect Stays is seeking a dynamic General Manager to lead our operations on the beautiful island of Maui. This is a pivotal leadership role where you'll take charge of all aspects of our property portfolio, driving both operational excellence and strategic growth. As the primary leader on the ground, you'll build and inspire a talented team while maintaining our commitment to exceptional guest experiences and strong financial performance. You'll work closely with property owners, oversee day-to-day operations, and collaborate with executive leadership to execute ambitious growth initiatives. This role is perfect for a results-driven leader who thrives on taking ownership, making decisive calls, and creating sustainable systems that deliver measurable impact in the fast-paced hospitality industry.
Oversee and manage all daily operations of the company's properties and staff in Lahaina and Kihei on the island of Maui
Lead, recruit, train, and develop a high-performing team
Ensure exceptional guest satisfaction and manage escalated guest issues
Develop and implement operational policies, procedures, and best practices
Drive revenue performance, manage budgets, and report on key financial metrics
Build and maintain relationships with property owners, vendors, and partners
Ensure compliance with all applicable local, state, and federal regulations
Collaborate with executive leadership at Monarch Collective Holdings on strategy and growth initiatives
Monitor property standards and coordinate maintenance and housekeeping
Identify and lead continuous improvement initiatives across operations
5+ years of progressive leadership experience in vacation rental management, hospitality, or property management with demonstrated P&L ownership
Proven operator who can manage multiple departments simultaneously without losing visibility into any of them
Financially literate and data-driven — comfortable owning a budget and presenting variance analysis to leadership
Exceptional communicator with strong owner and guest relationship skills
Track record of building and retaining strong local teams in a service-intensive environment
Calm under pressure, decisive, and solutions-oriented
Authorization to work in the United States
Ability to work on-site in Lahaina and Kihei, Hawaii
Experience with Breezeway a plus
Experience with Streamline a plus
Annual discretionary bonus is based on individual and company performance during the calendar year.
Paid time off such as PTO, sick days, and vacation days
Health insurance, Dental, and Vision insurance
Life insurance
Retirement benefits or accounts
Healthcare spending or reimbursement accounts, such as HSAs, FSAs, and HRAs