About This Job

This role requires strong communication and handy-person skills. You will be called upon to do anything from changing a light bulb, to helping a guest figure out how to light a gas fireplace over the phone, to walking an owner through their monthly statement. Additionally, you will support in leading and developing a team of employees.

Compensation

• $55000 - $65000 / year. Actual pay will vary based on a candidate's skill, experience, education and/or location.
• Up to $150 per month car allowance for eligible employees.
• More benefits and company perks information below.

Essential Job Functions

• Lead and develop a team of employees 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.
• Oversee daily operations and workflow management of assigned portfolio of properties to optimize team productivity and meet departmental objectives. Identify areas for improvement, and implement process enhancements to drive efficiency and quality outcomes.
• Provide cross-coverage for your team and management when necessary.
• Conduct regular inspections prior to guest and owner arrivals.
• Support your team with escalated guest and homeowner concerns by responding to emails, calls and tickets.
• Develop and grow a relationship with the owners of the properties by proactively communicating and becoming the subject matter expert of those properties ensuring they are clean, maintained and well cared for.
• Meet and maintain company standards and metrics such as NPS, standard unit appearance, and efficiency.
• Support the budget for your portfolio adhering to set annual costs, with the ability to perform a cost-benefit analysis. 
• Partner and assist your Onboarding team when new units join the portfolio.
• Ability to perform light home maintenance (light bulbs, fix door hinges, unclog a toilet, etc).
• 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. 
• Establish and maintain open, collaborative relationships with fellow regional team members and upper management team
• 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 experience working in operational support roles;  housekeeping and maintenance highly preferred. . 
• Prior experience in supervisory or management level positions in a similar industry is highly preferred.
• Technical computer skills required on all forms of hardware - laptops, tablets and mobile devices
• This role involves frequent travel between worksites, so reliable personal transportation is essential.
• 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

• Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
• 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.
• Hybrid work environment with in-person local office worktime required.
• Reliable transportation required.
• Regular travel within the locally assigned market and / or region.
• 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 fifty (50) 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 offering

About This Job

This role requires strong communication and handy-person skills. You will be called upon to do anything from changing a light bulb, to helping a guest figure out how to light a gas fireplace over the phone, to walking an owner through their monthly statement. Additionally, you will support in leading and developing a team of employees.

Compensation

• $60000 - $62000 / year. Actual pay will vary based on a candidate's skill, experience, education and/or location.
• $500 Sign-on bonus paid out after 30 days of employment. Must apply on or before 5/15 to be eligible.
• Up to $150 per month car allowance for eligible employees.
• More benefits and company perks information below.

Essential Job Functions

• Lead and develop a team of employees 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.
• Oversee daily operations and workflow management of assigned portfolio of properties to optimize team productivity and meet departmental objectives. Identify areas for improvement, and implement process enhancements to drive efficiency and quality outcomes.
• Provide cross-coverage for your team and management when necessary.
• Conduct regular inspections prior to guest and owner arrivals.
• Support your team with escalated guest and homeowner concerns by responding to emails, calls and tickets.
• Develop and grow a relationship with the owners of the properties by proactively communicating and becoming the subject matter expert of those properties ensuring they are clean, maintained and well cared for.
• Meet and maintain company standards and metrics such as NPS, standard unit appearance, and efficiency.
• Support the budget for your portfolio adhering to set annual costs, with the ability to perform a cost-benefit analysis. 
• Partner and assist your Onboarding team when new units join the portfolio.
• Ability to perform light home maintenance (light bulbs, fix door hinges, unclog a toilet, etc).
• 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. 
• Establish and maintain open, collaborative relationships with fellow regional team members and upper management team
• 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 experience working in operational support roles;  housekeeping and maintenance highly preferred. . 
• Prior experience in supervisory or management level positions in a similar industry is highly preferred.
• Technical computer skills required on all forms of hardware - laptops, tablets and mobile devices
• This role involves frequent travel between worksites, so reliable personal transportation is essential.
• 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

• Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
• 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.
• Hybrid work environment with in-person local office worktime required.
• Reliable transportation required.
• Regular travel within the locally assigned market and / or region.
• 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 fifty (50) 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 offering

About This Job

This role requires strong communication and handy-person skills. You will be called upon to do anything from changing a light bulb, to helping a guest figure out how to light a gas fireplace over the phone, to walking an owner through their monthly statement. Additionally, you will support in leading and developing a team of employees.

Compensation

• $60000 / year. Actual pay will vary based on a candidate's skill, experience, education and/or location. 
• Up to $150 per month car allowance for eligible employees.
• More benefits and company perks information below.

Essential Job Functions

• Lead and develop a team of employees 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.
• Oversee daily operations and workflow management of assigned portfolio of properties to optimize team productivity and meet departmental objectives. Identify areas for improvement, and implement process enhancements to drive efficiency and quality outcomes.
• Provide cross-coverage for your team and management when necessary.
• Conduct regular inspections prior to guest and owner arrivals.
• Support your team with escalated guest and homeowner concerns by responding to emails, calls and tickets.
• Develop and grow a relationship with the owners of the properties by proactively communicating and becoming the subject matter expert of those properties ensuring they are clean, maintained and well cared for.
• Meet and maintain company standards and metrics such as NPS, standard unit appearance, and efficiency.
• Support the budget for your portfolio adhering to set annual costs, with the ability to perform a cost-benefit analysis. 
• Partner and assist your Onboarding team when new units join the portfolio.
• Ability to perform light home maintenance (light bulbs, fix door hinges, unclog a toilet, etc).
• 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. 
• Establish and maintain open, collaborative relationships with fellow regional team members and upper management team
• 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 experience working in operational support roles;  housekeeping and maintenance highly preferred. . 
• Prior experience in supervisory or management level positions in a similar industry is highly preferred.
• Technical computer skills required on all forms of hardware - laptops, tablets and mobile devices
• This role involves frequent travel between worksites, so reliable personal transportation is essential.
• 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

• Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
• 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.
• Hybrid work environment with in-person local office worktime required.
• Reliable transportation required.
• Regular travel within the locally assigned market and / or region.
• 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 fifty (50) 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 offering

About this Job

The Property Caretaker supports an assigned portfolio of vacation rental properties with responsibilities including all aspects of property management, including owner and guest relations, maintenance, and housekeeping. Supports cross-functionally across the team.

Compensation

• $23 / hour. Actual pay will vary based on a candidate's skill, experience, education and/or location. 
• Up to $100 per month car allowance for eligible employees.
• More benefits and company perks information below.

Essential Job Functions

• Assists in the daily operations of the assigned portfolio of homes. Identify areas for improvement, assisting managers in process enhancements to drive efficiency and quality outcomes.
• Support the team with escalated guest and homeowner concerns by responding to emails, calls and tickets.
• Perform light home maintenance (light bulbs, fix door hinges, unclog a toilet, etc).
• Conduct regular inspections prior to guest and owner arrivals.
• Works to resolve guest and homeowner concerns by responding to emails, calls and tickets. Partners with the management team on escalated issues. 
• Partners and assists your Business Development Representative and management team when new units join the portfolio.
• Supports cross-functionally across the team as needed.
• 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.
• Minimum 1 year experience in housekeeping, maintenance or similar role. 
• Excellent time management skills with the ability to change activity frequently and cope with interruptions.
• Strong attention to detail.
• Tech-savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.
• This role involves frequent travel between worksites, so reliable personal transportation is essential.
• 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

• Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
• 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.
• Reliable transportation required.
• Regular travel within the locally assigned market and / or region.
• 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 fifty (50) 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 Vacation & Sick Time
• Employee Assistance Program (EAP)
• Employee Discounts
• Please visit our careers page to review our full benefits offerings

The Experience Specialist (Guest Services) On-Call is a key ambassador of the Sensei guest journey, responsible for delivering seamless, personalized service from pre-arrival through departure. This role manages daily guest flow, welcomes and checks in guests, supports itinerary building, and executes real-time changes with precision and care. Working cross-functionally with all departments, the Experience Specialist (Guest Services) On-Call ensures accurate scheduling, clear communication, and proactive problem-solving to create a smooth and elevated experience for every guest. By anticipating needs and supporting both guests and internal teams, this position plays a vital role in creating a smooth, thoughtful, and elevated wellness experience for every guest.

ESSENTIAL DUTIES AND RESPONSIBILITIES include the following:

On Property Guest Support 

• Primary On-Property Guest Contact – Serves as the dedicated point of contact for guests throughout their stay, delivering warm, personalized service from check-in to departure. Manages real-time itinerary adjustments, fulfills special requests, and provides thoughtful recommendations on dining, activities, and resort offerings. Receives guest handoff from the Pre-Arrival Team 72 hours prior to arrival to ensure a seamless experience and proactively resolves issues to uphold the highest standards of service.
• Guest Welcome & Check-In – Welcome guests with warmth and professionalism, executing seamless check-in and check-out of appointments in accordance with established protocols and standards.
• Itinerary Management – Build, update, and fine-tune guest itineraries throughout their stay, ensuring alignment with their state intentions, preferences, and adherence to established protocols and standards.

Room Only & External Wellness Requests

• Room Only Booking Requests (LEP) – Manage wellness service booking requests from Four Seasons Lāna’i Experiences Planners (LEP) for Sensei room-only guests. Monitor the LEP inbox and ensure requests are answered within 24 hours and the inbox is cleared by noon and 3:00pm daily. Follow all established scheduling procedures and booking protocols.
• Manele VIP Booking Requests – Manage wellness service booking requests from Four Seasons Executive Assistants for Four Seasons Manele Beach Resort VIP guests. Monitor the LEP inbox and ensure requests are answered within 24 hours and the inbox is cleared by noon and 3:00pm daily. Follow all established scheduling procedures and booking protocols.
• Island Club Booking Requests – Manage wellness service booking requests from Island Club Members. Monitor the LEP inbox and ensure requests are answered within 24 hours and the inbox is cleared by noon and 3:00pm daily. Follow all established scheduling procedures and booking protocols.
• Internal Space Reservation Requests – Manage internal wellness space reservation requests. Confirm bookings are handled promptly and in compliance with established scheduling protocols.

Guest Experience Support

• Sensei Knowledge Resource – Serve as a trusted source of information, confidently responding to guest questions and requests across a wide range of topics including, but not limited to: The Sensei Way, Sensei Wellness Packages, The Weekly Activity Calendar, Guide, Spa and Wellness Services and confidently speak to various Guide and Practitioner specialties and modalities, Sensei by Nobu menu and In Room Dining Menu, Four Seasons, Love Lāna’i and Island Activities, local directions, shopping, on and off property dining, local entertainment, hotel services, and safety.
• Service Recovery & Empowerment – Proactively resolve guest issues and empowered in turning around any guest opportunities that may arise; taking ownership to troubleshoot and resolve issues, while upholding the highest level of service.
• Billing & Reporting: Ensure accurate guest service charges, billing, and reporting, addressing transaction disputes as needed.
• Interdepartmental Collaboration: Manages interdepartmental communication between Sensei Pre-Arrival Specialists (PAS), the Sensei Property Pre-Arrival Experience Specialist, Sensei Leadership Team, Four Seasons Reservations, Four Seasons Retreat Hosts, Four Seasons Lāna’i Experience Planners (LEP) to inform, update and follow-up on guest needs.
• Brand Representation – Serve as a brand ambassador for Sensei’s philosophy and uphold Sensei values in daily practices.
• Professional & Welcoming Demeanor – Demonstrates warmth, sincerity, and professionalism in all verbal and nonverbal guest interactions.
• Professional Appearance – Maintain impeccable grooming, hygiene, and wear uniform and proper footwear as directed.
• Guest Privacy & Safety – Maintain confidentiality and security of all guest information and follow all safety procedures and policies.
• Workspace Organization – Maintain a clean, organized, and professional workspace at all times.
• Administrative Tasks – Complete clerical tasks such as filing, mailing, photocopying, and supply organization as needed.
• Facilities & Maintenance Reporting – Immediately report equipment malfunctions, safety hazards, supply needs, and injuries to a supervisor.
• Training & Compliance – Successfully complete all required training and certifications. Adhere to all company and departmental policies.
• Leadership – Maintain a positive, upbeat role, promote and exemplify Company values and represents departmental objectives and interests to internal and external customers.
• Customer Service – Follow up on complaints, questions, and concerns; respond to internal/external customer needs in a friendly, timely and efficient manner.
• Teamwork – Develop and promote teamwork and cooperation among co-workers
• Safety – Comply with established safe work practices and attend to all safety-related training provided or made available by the Company.
• Other Duties as Assigned – Support supervisors and operations as needed.

QUALIFICATIONS

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. Education and/or Experience

• Bachelor’s Degree or higher in Hospitality, Event Planning, Operations with an interest in health and wellness or comparable experience preferred.
• Experience working in the medical and/or wellness industry at a front desk or control desk, reservations, call center or hotel concierge.

Required Technical / Other Skills and Abilities

• Experience in computer, reservations, and itinerary systems. Literate in software packages such as Microsoft Office, Book4Time or other spa booking systems, Opera or other PMS software, OASIS, dining reservations systems, Asana, and Outlook.
• Ability to effectively communicate verbally and in writing with guests and co-workers.
• Strong understanding of guest experience.
• High commitment to guest satisfaction and service including maintaining a courteous and professional manner and a positive attitude, exhibiting a willingness to help, and promoting positive interactions with guests.
• Ability to proactively sell products and services.
• Good organizational skills and the ability to pay close attention to detail with minimal supervision.
• Must be able to have flexible hours and work evenings, weekends and holidays.

Required Licenses/Certifications

• None

PHYSICAL REQUIREMENTS

The physical requirements described on the attached “Physical Requirements of Position” chart are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. See attached “Physical Requirements of the Position.”

CONFIDENTIAL INFORMATION

This position has access to confidential information – (customer personal data, credit cards, medical records).

COMPANY FUNDS

This position has no access to company funds

Traits We Value 

• Commitment to a healthier living environment and embracing the Sensei Way and philosophy espoused and science identified in Dr Agus’ teachings and writings
• Collaborative mentality and the ability to recognize how to get things done as a team
• Self-confidence and composure to accept critique, process it, and apply the learnings to improve
• Resourceful and adaptable, understanding that a big idea can come from anywhere 
• Open to learning, developing new skills and professional experiences 
• Loves a good challenge  
• Resourceful and adaptable  
• A strong sense of curiosity  
• Embraces feedback and constantly seeks to improve  
• Collaborative and knows how to get things done as part of a team 

Compensation & Benefits  

• Competitive Salary 
• Robust and comprehensive Health Insurance 
  • Medical (100% paid HMO), Dental, Vision, Life, Disablity insurance and Voluntary Insurance Plans 
• Employee Assistance Program
• 401k Plan Matching 
• Tax Savings Benefits Plans 
  • Pre-tax 401l Matching Plan 
  • Healthcare Flexible Spending Account (FSA) Saving Plan
• Wellbeing Benefit - Monthly allowance for wellness/wellbeing related expenses 
• Employee Discount Program

Living and Working on the Island of Lānaʻi

Lānaʻi is the third-smallest island in the Hawaiian Islands and home to a close-knit family-orientated community of approximately 3,300 residents contributing to its strong sense of community and local pride.  98% of the island is owned by Oracle founder and Sensei Wellness co-founder Larry Ellison, who also owns both on-island Four Seasons resorts located just under 9 miles from each other and the average speed limit in the city is 20 mph.   

Lanai is home to one K-12 school, a gas station, a few owner-operated eateries and sundries stores, a two-screen movie theatre, and the newly renovated Lāna’i City Bowling Alley.

Working on Lānaʻi offers a unique opportunity to be part of a small, collaborative team in a setting where community and connection matter. This lifestyle is best suited for individuals who are excited by serene island living, no stoplights, and are intentionally seeking a slower paced lifestyle.  For those who choose it with intention, living and working on Lānaʻi can be deeply rewarding, offering meaningful work, strong relationships, and a rare sense of place.

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, sex (including gender identity or expression; pregnancy, childbirth, or related medical conditions), sexual orientation, age, religion, color, ancestry, disability (including association or relationship with an individual with a disability), marital status, National Guard obligation, genetic test results, arrest and court records, reproductive health decision, domestic or sexual violence victim status, breastfeeding requirements, assignment of income for child support obligations, or credit history or report.