Remote Luxury Cruise Vacation Planner (AI‑Driven Sales)

Windstar Cruises; Miami (FL); Remote; USD 42,000 - 64,000; Full time

Benefits offered by this job

Medical & Vision

HSA/FSA

Life & Disability

Accident & Hospital

Pet Insurance

Paid Time Off

401(k) Match

Employee Assistance

Education Assistance

Travel Discounts

Job summary

Windstar Cruises is seeking an Outbound Personal Vacation Planner to drive revenue by proactively reaching out to clients, identifying new sales opportunities, and converting leads into bookings. You will leverage advanced AI tools to boost productivity and personalize outreach while delivering exceptional customer service throughout the booking journey.

This full-time remote role is available to residents of AR, AZ, FL, LA, MN, TX, and WI, with collaboration across cross-functional teams to

Qualifications

• 1 year of sales experience or equivalent in luxury travel preferred.
• Experience in call centers or high-volume phone outreach.
• Ability to communicate professionally, credibly and confidently.
• Strong emphasis on personalized, guest-centric service from pre- to post-cruise.

Responsibilities

• Sell cruises, land packages, shore excursions, airfare, transfers, and hotels using AI-driven coaching.
• Build relationships with prospective and existing customers via outbound campaigns and CRM activity.
• Log activities, reminders, and follow-ups accurately in the CRM and booking systems.
• Provide tailored recommendations and support to ensure a seamless vacation planning journey.

Skills

Sales aptitude

Outbound calling

Customer service

Job description

Windstar Cruises is seeking an Outbound Personal Vacation Planner to drive revenue by proactively reaching out to clients, identifying new sales opportunities, and converting leads into bookings. You will leverage advanced AI tools to boost productivity and personalize outreach while delivering exceptional customer service throughout the booking journey.

This full-time remote role is available to residents of AR, AZ, FL, LA, MN, TX, and WI, with collaboration across cross-functional teams to