Personal Vacation Planner

Windstar Cruises•Miami, FL

7h•Remote

About The Position

As an Outbound Personal Vacation Planner at Windstar Cruises, you will help drive revenue growth by proactively contacting potential and existing clients, identifying sales opportunities, and converting leads into bookings. You will use AI tools to improve productivity, streamline administrative work, and personalize outreach using data-driven insights. The role also involves building lasting client relationships, guiding guests through the booking journey, and providing a seamless vacation-planning experience. You will collaborate with cross-functional teams and use AI-powered resources to stay current on products, promotions, and guest preferences so you can provide tailored recommendations and exceed expectations. This is a full-time remote position available to applicants who live in Arkansas, Arizona, Florida, Louisiana, Minnesota, Texas, or Wisconsin.

Requirements

At least 1 year of sales experience with strong service attributes; luxury-sector experience is preferred.
At least 1 year of call center experience involving phone-based customer interaction.
Demonstrated outbound sales abilities.
Professional, credible, and confident written and verbal communication skills.
Ability to present information positively and convincingly.
Commitment to personalized, effective customer service from pre-cruise through post-cruise interactions.
Enthusiastic, professional, and positive approach to responsibilities.
Ability to handle multiple tasks simultaneously.
Creative problem-solving ability and a guest-first mindset.
Willingness to comply responsibly with company policies and procedures.
Must live in one of the listed states: AR, AZ, FL, LA, MN, TX, or WI.

Nice To Haves

Hospitality and tourism experience, including cruise, airline, travel, or hotel-related sales or service.
Experience working in the luxury space.

Responsibilities

Use Windstar Sales Academy Training and AI-driven coaching and call insights to sell cruises, land packages, shore excursions, airfare, transfers, and related hotels.
Build and maintain relationships with prospective and existing customers through outbound campaigns, using AI to prioritize leads, personalize outreach, and suggest next actions.
Coordinate with the OCC Leadership Team to nurture relationships with guests who recently completed a Windstar Cruises voyage.
Maintain strong product knowledge and use AI-assisted tools to access itineraries, policies, promotions, and talking points.
Manage and follow up on leads in the Windstar Cruises CRM system, accurately recording activities, tasks, reminders, and follow-ups.
Advise Leadership promptly about potential escalations or emergencies and provide detailed history to support resolution.
Meet or exceed sales goals and performance metrics, using AI dashboards and insights to monitor productivity, conversion trends, and opportunities.
Meet or exceed call standards and use real-time AI coaching, post-call feedback, quality insights, and coaching recommendations for continuous improvement.
Engage with high-value guests through multiple channels using Microsoft Office 365 and AI-assisted email drafting, follow-up suggestions, and tone optimization.
Enter accurate information into the booking engine and CRM platform and keep client information up to date.
Adapt to changing technologies, system enhancements, digital workflows, and AI-supported features.
Multitask across multiple software systems while maintaining a high-quality guest experience.
Collaborate with other Windstar Cruises departments to develop and support promotional strategies and revenue-driving campaigns.
Communicate effectively with colleagues and Leadership to support a positive remote work culture.
Follow company policies and procedures, including call standards and booking processing requirements.
Provide support to other Vacation Planning department teams or Leadership as needed.