Personal Vacation Planner

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

Overview (Text Only)

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. Our Mission: Enriching Lives Through Travel Our Values: Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible. Job Summary: 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. Full-time position available to work remotely as long as you live in one of these states: AR, AZ, FL, LA, MN, TX, and WI.

Responsibilities (Text Only)

• 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 streamline outbound sales effectiveness.
• Multitask efficiently across multiple software systems while maintaining high quality guest experience.
• Collaborate with other departments of Windstar Cruises to develop and support promotional strategies and campaigns to drive further revenue to the brand.
• Communicating effectively with colleagues and Leadership to uphold a positive work culture within a remote working environment.
• Adherent to company policy and procedures, including maintaining call standards and processing of booking - Provide support to other teams of the Vacation Planning department or Leadership as needed.

Qualifications (Text Only)

• 1 year of sales experience, with high level service attributes, preferably working within the luxury space.
• 1 year of call center experience, being on the phone and interacting with customers.
• Demonstrated outbound sales abilities.
• Hospitality and Tourism experience preferred, included but not limited to: Cruise, Airline, Travel, Hotel Related Sales/Service.
• Must be able to communicate in writing and verbally with professionalism, credibility and confidence.
• The ability to present information in a positive, convincing manner.
• Strong belief in personalized, effective customer service from pre-cruise to post cruise interactions.
• Must demonstrate an enthusiastic and professional, positive approach to all responsibilities.
• Able to handle multiple tasks simultaneously.
• Being able to think outside the box on solutions for various issues that may arise to always have a “What is best for the Guest” mindset.
• Willing to accept and act responsibly in compliance with policy and procedure.

Benefits

• Medical, Dental & Vision
• HSA & FSA
• Life & Disability
• Accident, Hospital & Critical Illness
• Pet Insurance
• Vacation, Sick Time and paid Holidays
• 401(k) with Company Match
• Employee Assistance Plan
• Education Assistance and Employee Discounts & Travel Deals

EEO: Windstar is committed to a diverse and inclusive workplace. We are an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, pregnancy, genetic information, protected veteran status, or any other legally protected status.