General Manager

Company Overview

At Heavenly Vacations by Casago, we believe the best vacations begin with local expertise and genuine hospitality. Proudly serving the Hawaiian Islands, our team is passionate about creating exceptional experiences for both homeowners and guests through personalized service, trusted relationships, and an unwavering commitment to excellence. As local experts, we understand that every home, every owner, and every guest is unique, and we take pride in delivering thoughtful, attentive care at every step.

Our culture is rooted in the spirit of aloha, where integrity, respect, stewardship, and service guide everything we do. We believe in treating every property as if it were our own, building lasting relationships through trust and transparency, and working together to create memorable experiences that keep guests returning year after year.

Backed by the resources of the trusted Casago network while maintaining our local ownership and personalized approach, Heavenly Vacations offers the opportunity to build a rewarding career with a team that is passionate about hospitality, community, and making a meaningful difference every day.

Position Summary

Heavenly Vacations by Casago is seeking a General Manager to lead our Kauai operations with both strategic vision and hands-on operational excellence. This is the top on-island leadership role for our Lihue-based team, with full accountability for the performance, profitability, and growth of our Kauai vacation rental portfolio. The General Manager owns the P&L, drives revenue and business growth, and directly leads the on-island team — while also building the kind of homeowner and guest relationships that reflect our Owner-Centric™ philosophy and the spirit of aloha. It's a role for a confident, hands-on leader who can set ambitious goals, hold a team accountable to them, and represent the Heavenly Vacations brand across the island.

Essential Responsibilities

• Oversee daily operations and workflow management for the Kauai vacation rental portfolio — guest services, housekeeping/turnover, and maintenance — to optimize team productivity and ensure seamless guest experiences

• Manage the operating budget for the Kauai portfolio, adhering to set annual costs and performing cost-benefit analysis as needed

• Lead, coach, and develop the on-island team — including the Property Operations & Quality Control Coordinator, Property Caretaker, and Maintenance Technicians — through regular one-on-ones, performance management, and annual evaluations

• Develop and grow relationships with homeowners by proactively communicating and becoming the subject matter expert on their properties, ensuring they are clean, maintained, and well cared for

• Meet and maintain company standards and metrics, including NPS, property appearance, and operational efficiency

• Support the team with escalated guest and homeowner concerns via email, phone, and tickets

• Conduct regular property inspections prior to guest and owner arrivals

• Foster a collaborative team environment, addressing conflicts constructively and promoting open communication and engagement

• Manage local vendor relationships (cleaning, maintenance, landscaping, and similar services) to ensure quality, reliable, and cost-effective service

• Assist with recruiting, interviewing, and onboarding new team members in compliance with company policy and employment regulations

• Collaborate with cross-functional teams and represent the Kauai market in leadership meetings, communicating decisions effectively to direct reports

• Partner with the Onboarding team as new properties join the portfolio, and provide cross-coverage for the team and Co-GM(s) as needed

• Ensure compliance with all relevant Hawaii state and Kauai County short-term rental regulations, licensing, and permitting requirements

• Portray the company’s values within and outside of the organization while performing the functions of the position.

• Positively represent our family of companies to owners, guests, our community and its business leaders.

• Play a leadership role to learn and execute all company policies and procedures.

Required Qualifications

• 3+ years of experience in operations roles within the vacation rental, hospitality, hotel or similar industry

• Prior supervisory or management-level experience in a similar industry

• Strong communication and relationship-management skills, with experience managing homeowner, client, or ownership relationships

• Working knowledge of vacation rental operations — housekeeping/turnover standards, maintenance coordination, and guest-service expectations

• Comfortable with data-driven decision-making and monitoring KPIs/operational metrics

• Based on Kauai or able to relocate; available to work on-site, including flexible hours (weekends/holidays) in a 24/7 operational environment

• Valid driver's license and reliable transportation for regular property visits across the island

• Willingness to participate and work in a learning organization.

• Must be able to perform effectively under pressure.

• Excellent communication skills, both verbal and written – in person, on the phone, and through various

  means of electronic communication.

• Responsible and prepared. Showing up on time and ready to go is key to creating great stays for

  our guests and peace of mind for our homeowners.

• Reliable personal transportation is essential as role involves frequent travel between worksites.

• We’re in the hospitality industry and our schedules can change based on guest and homeowner needs. Shifts may include early mornings, evenings, weekends, and holidays. We require flexibility to support this.

Preferred Qualifications

• Bachelor's degree in Business Administration, Hospitality Management, or a related field

• Prior experience with a vacation rental management company or another Casago-network brand

• Experience with vacation rental or property management software (e.g., Guesty, Breezeway, PMS platforms, channel managers)

• Existing familiarity with the Kauai/Kauai County short-term rental market and permitting environment

• Local ties to the Kauai community and familiarity with the island's neighborhoods and visitor patterns

• Problem-solving ability is a plus.

Compensation & Benefits

Annual Salary: $85,000 - $92,000 commensurate with experience

Benefits

• 1 Week Paid Vacation after 1 Year, 2 Weeks Paid Thereafter

• Single Payer Health insurance paid for by company

• Dental insurance

• Vision insurance

• Optional Supplemental Insurance

• 401K

• Opportunity to participate in Professional and Life Educational Seminars

• Employee recognition programs