1-3 years of experience in sales and/or customer service (preferred)
Background in tourism, hospitality, or travel (highly preferred)
Passion for delivering exceptional customer experiences and helping others
Knowledge of the Hawaiian Islands (or eagerness to learn!)
Ability to personalize recommendations based on guest needs
Comfortable working independently, multitasking, and thriving in a fast-paced environment
Strong verbal and written communication skills
Basic computer skills; POS experience is a plus (training provided)
Fluency in English (required)
Fluency in Japanese (preferred)
Join Our ʻOhana
If you're passionate about travel, love connecting with people from all cultures, and want a role where your work truly makes a difference, we encourage you to apply today.
Come be part of a team that celebrates Aloha, supports your growth, and rewards your success. 🌺
Benefits to working at Pleasant Holidays:
Medical (with prescription)
Vision
Dental
Flexible Spending Accounts
Paid Time Off for Holidays, Vacation, and Illness
Company paid Life Insurance
Long Term Disability
401(k) Plan
AFLAC Plans
Travel Discounts on all Pleasant Holidays packages, Hotel Rooms, Car Rentals, Tours & Activities. Discounts apply to family members and friends too!
Pleasant Holidays is an Equal Opportunity Employer
Our organization participates in E-Verify
Pleasant Holidays will consider for employment all qualified applicants, including those with criminal histories, in a manner consistent with the requirements of applicable federal, state and local laws
💰 Pay & Bonuses
$16/hour starting pay
Commission eligible upon hire
Uncapped commission potential -earn more as you sell
Benefits
Dental insuranceVision insurance401(k)Paid time offRemote work optionsFlexible schedulePerformance bonus
Additional Information
Hotel Concierge Sales Agent (Maui)
Share the Spirit of Aloha And Build a Career You'll Love
Do you love helping people create unforgettable experiences? Are you energized by connecting with guests from around the world and sharing the beauty of Hawaiʻi? If so, Pleasant Holidays would love to meet you.
Pleasant Holidays is looking for enthusiastic, people‑focused Concierge Sales Agents to serve as true Ambassadors of Aloha on the Island of Kaua'i. In this role, you'll work one-on-one with guests at hotel concierge desks, helping them plan and book memorable tours and activities-both on the island and throughout the neighbor islands-so their vacation becomes the trip of a lifetime. This is more than a job-it's a chance to be the friendly face of Aloha while earning strong pay, commission, and unbeatable travel perks.
Why You'll Love Working With Us
✈️ Incredible Travel Perks
Two (2) roundtrip airline tickets every year after one year of employment. Valued at $650 per ticket - fly anywhere in the world!
Eligibility to apply for an IATAN card after one year. Industry discounts worldwide!
Up to 20% off Pleasant Holidays vacation packages
Up to 20% off tours and activities booked in advance
Special partner discounts and occasional complimentary stays
Family & Friends discounts available
*Terms and restrictions apply. Benefit eligibility varies based on position status. Details provided upon hire.
Position Details
Location: Island of Maui (Kaanapali)
On-Island Residency Required - must currently live on the island to be considered
Schedule: Full Time (38-40 hours per week) positions available *Weekend availability required
Work Sites: Hotel Concierge Desks (You may be assigned to multiple hotel concierge desks; locations determined by management)
Training & On-boarding
Remote new hire on-boarding and POS training
Additional hands-on training takes place at a hotel concierge desk
Computer/laptop with internet is preferred but not required
Ace · Lahaina, HI