General Manager

Company OverviewAt 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 SummaryHeavenly 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 ResponsibilitiesOversee 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 experiencesManage the operating budget for the Kauai portfolio, adhering to set annual costs and performing cost-benefit analysis as neededLead, 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 evaluationsDevelop 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 forMeet and maintain company standards and metrics, including NPS, property appearance, and operational efficiencySupport the team with escalated guest and homeowner concerns via email, phone, and ticketsConduct regular property inspections prior to guest and owner arrivalsFoster a collaborative team environment, addressing conflicts constructively and promoting open communication and engagementManage local vendor relationships (cleaning, maintenance, landscaping, and similar services) to ensure quality, reliable, and cost-effective serviceAssist with recruiting, interviewing, and onboarding new team members in compliance with company policy and employment regulationsCollaborate with cross-functional teams and represent the Kauai market in leadership meetings, communicating decisions effectively to direct reportsPartner with the Onboarding team as new properties join the portfolio, and provide cross-coverage for the team and Co-GM(s) as neededEnsure compliance with all relevant Hawaii state and Kauai County short-term rental regulations, licensing, and permitting requirementsPortray 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 Qualifications3+ years of experience in operations roles within the vacation rental, hospitality, hotel or similar industryPrior supervisory or management-level experience in a similar industryStrong communication and relationship-management skills, with experience managing homeowner, client, or ownership relationshipsWorking knowledge of vacation rental operations — housekeeping/turnover standards, maintenance coordination, and guest-service expectationsComfortable with data-driven decision-making and monitoring KPIs/operational metricsBased on Kauai or able to relocate; available to work on-site, including flexible hours (weekends/holidays) in a 24/7 operational environmentValid driver's license and reliable transportation for regular property visits across the islandWillingness 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 variousmeans of electronic communication.Responsible and prepared. Showing up on time and ready to go is key to creating great stays forour 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 QualificationsBachelor's degree in Business Administration, Hospitality Management, or a related fieldPrior experience with a vacation rental management company or another Casago-network brandExperience 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 environmentLocal ties to the Kauai community and familiarity with the island's neighborhoods and visitor patternsProblem-solving ability is a plus. Compensation & BenefitsAnnual Salary: $85,000 - $92,000 commensurate with experience Benefits1 Week Paid Vacation after 1 Year, 2 Weeks Paid ThereafterSingle Payer Health insurance paid for by companyDental insuranceVision insuranceOptional Supplemental Insurance401KOpportunity to participate in Professional and Life Educational SeminarsEmployee recognition programs