Outbound Planner Jobs (NOW HIRING)

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 Sales Supervisor at Windstar Cruises, you will be responsible for overseeing a team of Outbound sales agents in a call center environment. Your primary objective is to ensure that the Outbound Personal Vacation Planners have support in hitting all sales targets month after month. For complete success within the role, it’s important to optimize the sales team through coaching, mentorship, training, and performance management, supported by AI-driven coaching tools and performance insights. As the Outbound Sales Supervisor, additional responsibilities include reinforcement of the Windstar Sales Academy, management of the CRM platform, and adhering to the Outbound Consumer Sales Rules to ensure that the team is successfully performing to hit monthly targets. You will champion the adoption of advanced AI tools across the team, helping planners increase productivity, streamline administrative tasks, and personalize guest outreach based on data-driven insights.

Full-time position available to work in a hybrid-model from Miami metro area, or remotely as long as you live in one of these states:

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

• Supervise employees to ensure all guests requests are handled efficiently and within the Windstar Cruises standard.
• Coach, Develop, and motivate the staff to ensure we deliver the highest level of customer service to enhance the guest experience.
• Monitor calls, CRM systems, and all correspondence emails that are agents facing communications with guests to ensure we’re delivering a 180 from ordinary experience with our guests, leveraging AI-powered call insights and quality analytics to identify trends and coaching opportunities.
• Monitor all areas of individual staff performance to ensure standards are met, including but not limited to: Call monitoring, test calls, weekly one-on-one’s, attendance, adherence, manned time, release time, etc.
• Conduct 1 on 1s, performance reviews, and sending out corresponding communications to streamline corrective actions as needed with valid documentation.
• Utilizing the Windstar Sales Academy Training alongside AI-driven coaching and call insights to effectively coach the agents on selling cruises, land packages, shore excursions, air, transfers, and hotels that are correlated to that vacation.
• Provide constructive feedback to the team with open and honest communication to ensure that goals/standards are met.
• Work with the Consumer Sales Management Team to develop better business practices and improve overall department performance.
• Work with the Consumer Sales Management Team to assist in creating promotional strategies and campaigns to drive further revenue to the brand.
• Collaborate with the Training team to reinforce and assist in training modules and programs of Windstar Cruises to provide appropriate advice and recommendations that support agents to help our guest receive a 180 from Ordinary experience, ensuring we always exceed guest expectations.
• Oversee the CRM system to ensure proper usage by agents and AI-supported features such as lead prioritization and next best actions, to prevent inaccurate data entries.
• Coach the team to meet or exceed established sales goals and performance metrics.
• Use Microsoft Office 365, enhanced by AI email drafting, follow-up suggestions, and tone optimization, to communicate with the team and provide relevant information and updates.
• Complete ad-hoc trouble shooting to assist agents with IT issues as needed.
• Provide and own initiatives on non-phone related projects and tasks.
• Oversee and participate in hiring, training, scheduling, payroll, and other departments that may further assistance with agent support.
• Own and handle agent escalations with guests as needed.
• Build and maintain strong relationships with agents, to ensure and drive positive behaviors to extend their careers at Windstar Careers.
• Adhere to company policy and procedures, including maintaining call standards and processing of booking.
• Communicating effectively with colleagues and Leadership to uphold a positive work culture within a remote working environment.
• Provide support to other teams of the Vacation Planning department as needed.
• Handle day-to-day lead tasks, such as handling booking adjustments and MyWindstar inquiries.
• Work with the Leadership team to produce better ways for our call centers to flourish in improving efficiencies, driving revenue, and increasing brand awareness.
• Perform other duties and responsibilities effectively assigned by Leadership.
• Monthly performance-based incentive.
• Champion the adoption of AI tools across the team, training and guiding agents on responsible use to increase productivity, streamline administrative tasks, and personalize guest outreach.
• Use AI dashboards and performance insights to monitor conversion trends, identify opportunities, and support data-driven coaching and performance management.
• Other duties as assigned.

• Minimum of 3-5 years of sales experience, preferably within the luxury space.
• At least 2 years of call center experience with direct customer interaction.
• Demonstrated outbound sales abilities.
• Preferred experience in Hospitality and Tourism (Cruise, Airline, Travel, Hotel Related Sales/Service).                                                                                               
• Strong communication skills, both written and verbal, with professionalism and confidence.
• Ability to de-escalate guest situations appropriately.
• Ability to present information positively and convincingly.
• Positive and enthusiastic approach to responsibilities.
• Proficient in data analysis and reporting.
• Comfortable adopting and coaching others on AI-supported tools, with a willingness to adapt to evolving technologies and digital workflows.
• Strong belief in personalized, effective customer service from pre-cruise to post-cruise interactions.
• Capable of handling multiple tasks and projects simultaneously.
• Ability to meet deadlines and provide innovative solutions.
• Supervisors 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.
• Supervisors must be flexible when needed to support the Vacation Planning Team to assist as needed based on business needs.
• Based on business needs, Supervisor must be willing to support agents as needed which can run into nights and weekends as well.
• Based in a call center environment with occasional evening or weekend shifts as needed.
• Possible occasional travel for training or conferences.
• 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.

• Minimum of 3-5 years of sales experience, preferably within the luxury space.
• At least 2 years of call center experience with direct customer interaction.
• Demonstrated outbound sales abilities.
• Preferred experience in Hospitality and Tourism (Cruise, Airline, Travel, Hotel Related Sales/Service).                                                                                               
• Strong communication skills, both written and verbal, with professionalism and confidence.
• Ability to de-escalate guest situations appropriately.
• Ability to present information positively and convincingly.
• Positive and enthusiastic approach to responsibilities.
• Proficient in data analysis and reporting.
• Comfortable adopting and coaching others on AI-supported tools, with a willingness to adapt to evolving technologies and digital workflows.
• Strong belief in personalized, effective customer service from pre-cruise to post-cruise interactions.
• Capable of handling multiple tasks and projects simultaneously.
• Ability to meet deadlines and provide innovative solutions.
• Supervisors 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.
• Supervisors must be flexible when needed to support the Vacation Planning Team to assist as needed based on business needs.
• Based on business needs, Supervisor must be willing to support agents as needed which can run into nights and weekends as well.
• Based in a call center environment with occasional evening or weekend shifts as needed.
• Possible occasional travel for training or conferences.
• 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.