Regional Owner Success Lead

About the Company
We’re a vacation rental company where great people create exceptional experiences. From our humble beginnings with a simple idea, we've grown into a trusted industry leader delivering genuine hospitality to every guest. What sets us apart isn't just our advanced technology or high property standards, but our culture of doing things the right way, building trust, and supporting each other as a team. When you join Casago, you're not just taking a job—you're becoming part of a company that values your contributions, invests in your growth, and gives you the opportunity to make a real impact on the homeowners and guests we serve every day.

About This Job

The Regional Owner Success Lead will manage a team of Coordinators on our Hawaii team. The ideal candidate has the ability to lead a team of coordinators that provides exceptional customer service while balancing empathy and accountability during demanding times. This role requires effective communication, analytical thinking, and problem-solving skills along with the ability to adapt to and lead change. The role is responsible for continued education and up-to-date knowledge of our products, programs, and services.

Compensation

• $50000 - $65000 / year. Actual pay will vary based on a candidate's skill, experience, education and/or location.

• More benefits and company perks information below.

Essential Job Functions

• Oversee daily operations and workflow management to optimize team productivity and meet departmental objectives. Identify areas for improvement, and implement process enhancements to drive efficiency and quality outcomes.

• Lead and develop a team of Owner Success Coordinators through effective coaching, mentoring, and performance management. Conduct regular one-on-one meetings and annual evaluations to support professional growth and ensure alignment with company goals.

• Audit team’s work for quality of support, accuracy of information provided to owners, and delivery tone.

• Provide guidance and support to team members in handling challenging situations and resolving homeowner concerns.

• Set clear performance goals and expectations for team members, and conduct regular performance reviews.

• Conduct disciplinary action as needed, including informal and formal write-ups and corrective action plans to improve performance.

• Monitor, analyze, and evaluate trends in volume and workload against performance.

• Manage and monitor the team’s schedule.

• Understand higher-level business goals and our department’s role and impact.

• Manage staffing in relation to daily contacts in a multi-channel in- and outbound contact center, focusing on meeting performance metrics and exceeding customer expectations.

• Ensure employee adherence to company values, quality, accuracy, schedule, and other expectations in a fast-paced environment.

• Build and maintain business relationships and open lines of communication with other internal support teams.

• Foster a collaborative work environment that promotes open communication, innovation, and employee engagement. Address team conflicts constructively and in a timely manner as they arise.

• Assist the recruiting process with interviewing, selection and onboarding new team members while ensuring compliance with company policies and employment regulations.

• Other duties as assigned because every day is different in hospitality!

Skills + Qualifications

• Experience working in hotel, hospitality, vacation or similar industry is highly preferred.

• 1-2 years of experience in a direct supervisory or management level position in a similar industry.

• 3-5 years of customer service/call center experience.

• Tech-savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.

• Experience managing day-to-day team operations, providing guidance and support, and fostering a positive, productive team culture focused on collaboration, accountability, and growth.

• Demonstrated ability to:

• Multi-task, prioritize, and remain organized in a fast-paced and constantly changing work environment.

• Embrace and lead change.

• Problem solve with limited direction and support, implementing innovative solutions.

• Review and analyze information to identify trends and propose solutions

• Dependable 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.

• Must be dependable, self-motivated, and able to work independently while contributing positively to a collaborative team environment.

• Comfortable talking to people—online or in person—and being able to share information in a way that’s clear, thoughtful, and represents the company in a positive way always.

Workplace Environment + Physical Requirements

• Fully remote work environment with reliable internet connection.

• Speed test required: please use this link to run the internet speed test. The internet speed must be at least 100.0 download/10.0 upload. If your internet does not meet these requirements, you will need to upgrade prior to applying.

• We’re in hospitality 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.

• Typically a Monday - Friday workweek with expectations to be flexible to support the needs of the business.

• You’ll be working in your home office setting. This position requires frequent, repetitive use of a computer, phone, and office equipment. This position requires patient, professional communication with prospective clients, and the ability to build confidence with prospects.

• Ability to move freely (balancing, climbing, crawling, driving, squatting, standing, stooping, walking, bending, pushing, pulling, reaching, and repetitive hand/finger motions) and lift up to a maximum of twenty-five (25) pounds without assistance.

Benefits + Perks

• Health/dental/vision insurance based on hours worked

• Employer Sponsored & Voluntary Supplemental Benefits based on hours worked

• 401K retirement savings plan with immediate 100% company match on the first 4% you contribute

• Health & Dependent Care Flexible Spending Accounts based on hours worked

• Paid Flex Time Off

• Employee Assistance Program (EAP)

• Employee Discounts

• Please visit our careers page to review our full benefits offerings

Casago is an equal opportunity employer committed to fostering a diverse and inclusive workplace. We do not discriminate against applicants based upon race, color, religion, sex (including pregnancy, gender identity, and sexual orientation), national origin, age, disability, genetic information, or other classes protected by applicable law. Veterans are encouraged. Casago is committed to maintaining a safe and productive work environment. Possession, use, or being under the influence of alcohol or illegal drugs in the workplace is prohibited.

Some positions may require that you drive a personal vehicle and/or company vehicle for work purposes. Employees who are required to drive a personal vehicle must have reliable transportation, a valid driver’s license, and be at least 18 years of age. Employees who are required to drive a company vehicle must have a valid driver’s license, be at least 21 years of age, and have been a licensed driver for no less than 3 years.

An offer of employment for this role will be contingent upon the successful completion of a background check and / or an OFAC screening, country dependent.