Outbound Consumer Sales Supervisor

Job Summary

As an Outbound Sales Supervisor at Windstar Cruises, you will oversee a team of Outbound Personal Vacation Planners in a call center environment. Your primary objective is to ensure the team hits all sales targets month after month. You will also optimize the sales team through coaching, mentorship, training, and performance management, supported by AI-driven coaching tools and performance insights.

Responsibilities

• Supervise employees to ensure all guests' requests are handled efficiently and within Windstar Cruises' standard.
• Coach, develop, and motivate the staff to ensure they deliver the highest level of customer service to enhance the guest experience.
• Monitor calls, CRM systems, and all correspondence emails with guests to ensure a 180-degree experience, 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 call monitoring, test calls, weekly one-on-one meetings, attendance, adherence, manned time, release time, etc.
• Conduct 1-on-1s, performance reviews, and send corresponding communications to streamline corrective actions as needed with valid documentation.
• Utilize 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 goals/standards are met.
• Work with the Consumer Sales Management Team to develop better business practices and improve overall department performance.
• 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 guests receive a 180-degree 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 assist 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.
• Adhere to company policy and procedures, including maintaining call standards and processing of bookings.
• Communicate 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.
• 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.

Qualifications

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

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 Statement

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.