Personal Vacation Planner

Awarded World’s Best Small Ship Cruise line, Windstar Cruises is known for intimate yacht style experience and unique voyages to the world’s best small ports and hidden harbors. Its three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the world. Our mission is to imagine and deliver personalized and immersive experiences 180 degrees from ordinary.

We enrich people’s perspective through inspired travel.

Enriching Lives Through Travel

Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible.

As an Outbound Personal Vacation Planner at Windstar Cruises, you will play a key role in driving revenue growth by proactively reaching out to potential and existing clients, identifying new sales opportunities, and converting leads into bookings. In this position, you will utilize advanced AI tools to increase your productivity, streamline daily administrative tasks, and personalize your outreach based on data-driven insights.

Your commitment to exceptional customer service will be demonstrated through building and nurturing lasting client relationships, guiding guests through every stage of their booking journey, and ensuring a seamless and memorable vacation planning experience. Additionally, you will collaborate closely with cross-functional teams and leverage AI-powered resources to stay informed about the latest products, promotions, and guest preferences, enabling you to deliver tailored recommendations and exceed customer expectations.

AR, AZ, FL, LA, MN, TX, and WI.

• Utilizing the Windstar Sales Academy Training alongside AI-driven coaching and call insights to effectively sell cruises, land packages, shore excursions, airfare, transfers, and hotels that are correlated to that vacation.
• Build and maintain strong relationships with prospective and existing customers through outbound campaigns (request a call, request a quote, brochure requests, booking journey touchpoints), using AI to prioritize leads, personalize outreach, and suggest next best actions.
• Coordinate with OCC Leadership Team to nurture relationships with guests who’ve completed their recent voyage with Windstar Cruises.
• Demonstrate strong product knowledge of Windstar Cruises while using AI-assisted knowledge tools to quickly access itineraries, policies, promotions, and talking points to ensure consistent and positive guest experience.
• Manage and follow up on leads within the Windstar Cruises CRM system, accurately logging activities, tasks, reminders, follow-ups, and leveraging AI to support planners in focusing on their guests.
• Advise Leadership of all potential escalations or emergency situations in a timely manner, being sure to include detailed history to formalize a resolution.
• Meet or exceed established sales goals and performance metrics, using AI dashboards and performance insights to self-manage productivity, conversion trends, and opportunities.
• Meet or exceed call standards on every guest interaction while adhering to AI real-time coaching, or even post call feedback, quality insights, and coaching recommendations for continuous improvement.
• Engage with high-value guests across multiple channels within Microsoft Office 365, enhanced by AI email drafting, follow-up suggestions, and tone optimization to ensure professionalism and personalization.
• Entering accurate information into booking engine, CRM platform, and to keep client information up to date as needed.
• Adapt to evolving technologies, system enhancements, digital workflows, and AI-supported features that…