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

What We’re Looking For

• 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 one of the largest travel wholesalers in the United States, specializing in vacation travel to the Hawaiian Islands, Caribbean, Central America, Europe, Mexico, Middle East, South Pacific (Australia, Cook Islands, Fiji, New Caledonia, New Zealand & Tahiti), Japan, the United States & Canada, and cruise vacations worldwide. Pleasant Holidays is a subsidiary of the Automobile Club of Southern California, a diversified insurance, roadside assistance, financial services and travel organization serving more than 18 million AAA members across 24 states.

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 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 one of the largest travel wholesalers in the United States, specializing in vacation travel to the Hawaiian Islands, Caribbean, Central America, Europe, Mexico, Middle East, South Pacific (Australia, Cook Islands, Fiji, New Caledonia, New Zealand & Tahiti), Japan, the United States & Canada, and cruise vacations worldwide. Pleasant Holidays is a subsidiary of the Automobile Club of Southern California, a diversified insurance, roadside assistance, financial services and travel organization serving more than 18 million AAA members across 24 states.

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