Personal Vacation Planner

See what our team members have to say about this great opportunity!

- "I appreciate the ability to work from home that many of my coworkers are well-traveled and respond quickly by phone and email. I get to be in touch with intelligent guests and agents from all over and together we craft dream trips they’ll remember for life!"

- "I really enjoy that everyone here is willing to help each other. Everyone here is beyond ordinary!"

- "The support and understanding from upper management not just in our professional life, but personal life is amazing!"

• →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.

• 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 required, 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.

Work Schedule:

• Personal Vacation Planners will average 40 hours per work week.
• Agents must be punctual and flexible within their schedule to work as early as 9:00am EST and report at any time during the opening hours of the call center; Monday - Friday 9:00am to 8:00pm EST. Saturdays 9:00am to 6:00pm EST. All Hours are Eastern Standard Time.

Work Environment:

• Remote work environment.
• Hard Wire Wi-Fi required.
• Must meet ergonomic standards for a home office with a private area to work with limited distractions.

BENEFITS: For full-time employees, Windstar offers a comprehensive benefits package including:  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.