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Supervisor, Outbound Reservations

We Put the World on Vacation

Travel + Leisure Co. is the world’s leading vacation ownership and travel membership company, with a dynamic and growing portfolio of resort, travel club, and lifestyle travel brands. Our dedicated associates help the company achieve its mission to put the world on vacation. Innovation and growth keep our work interesting and fun. Every day is a chance to learn something new and turn vacation inspiration into exceptional experiences for millions of travelers worldwide.

Overview

Responsible for leading, guiding, and developing a team of Vacation Planning Counselors specializing in servicing outbound calls to Club Wyndham and Worldmark Owners. This role requires driving team productivity, achieving service objectives, and focusing on sales performance. The ideal candidate will bring innovative ideas and a strategic mindset to enhance outbound performance and team success. This position is pivotal in creating a high-performing outbound calling team, emphasizing consultative selling techniques, objection handling, and closing strategies to maximize conversions and revenue growth.

Start Date: Friday, May 9th, 2025

Training Schedule (5 weeks):

Monday - Friday: 9:00am to 6pm EST

Post Training Schedule:

Set schedule will be provided towards the end of training. Hours of Operation:

Tuesday - Friday: 9:00am to 8:00pm EST

Saturday: 9:00am to 6:00pm EST

Off: Sunday & Monday

Responsibilities

Employee Development

  • Track and analyze individual agent performance data to identify trends and opportunities.
  • Create tailored development plans with positive, innovative strategies to improve performance.
  • Coach Counselors on advanced sales techniques and customer engagement strategies.
  • Ensure Counselors apply knowledge gained during training to achieve sales and service goals.
  • Conduct informal training sessions to reinforce sales and service best practices.
  • Serve as a mentor for Counselors, focusing on professional growth and sales success.

Sales Leadership

  • Drive a sales-focused team environment, prioritizing outbound call success and achieving conversion targets.
  • Develop innovative campaigns and strategies to boost outbound sales results.
  • Utilize data analytics to identify high-value opportunities and tailor team efforts accordingly.

Team Management

  • Effectively communicate sales targets, progress, and performance expectations at team and individual levels.
  • Conduct regular team meetings to share updates, motivate, and inspire the team.
  • Maintain a high-energy environment where excellence in sales and personal development is recognized and rewarded.
  • Foster a collaborative and competitive sales culture.
  • Implement recognition programs to celebrate individual and team sales achievements.

Performance Management

  • Set clear sales goals and expectations in line with department and company objectives.
  • Monitor and enforce adherence to department policies, procedures, and sales standards.
  • Measure and improve productivity, sales performance, and quality expectations.
  • Document performance conversations and implement corrective actions when necessary.
  • Provide timely feedback and support to help associates exceed sales objectives.

Program and Product Administration

  • Ensure agents effectively communicate the value of Club Wyndham and WorldMark products and services.
  • Oversee the resolution of escalated servicing and sales-related issues.
  • Handle supervisor-level calls and ensure timely resolution.

Administrative Duties

  • Collaborate with other departments (e.g., RPM, Training, Human Resources) to drive team performance.
  • Participate in the recruitment process by conducting interviews and selecting top talent.
  • Provide frontline technical support (passwords, computer/phone issues) to agents as needed.

Personal Learning and Self-Improvement

  • Stay updated on industry trends, sales strategies, and outbound best practices.
  • Create and execute a personal development plan with immediate leadership guidance.
  • Actively participate in coaching sessions to refine leadership and sales strategies.

Qualifications

  • Proven experience in a sales-driven leadership role, preferably in a contact center environment.
  • Strong analytical skills to track performance metrics and identify improvement opportunities.
  • Exceptional coaching and mentoring abilities to develop high-performing sales teams.
  • Ability to foster a positive, motivating environment that encourages individual and team excellence.
  • Excellent verbal and written communication skills to convey expectations and provide feedback effectively.
  • Innovative mindset with a proven track record of implementing successful sales strategies.
  • Strong conflict resolution skills and ability to handle escalated calls with professionalism.

Preferred Skills

  • Experience with outbound calling campaigns and high-performance sales teams.
  • Expertise in sales training and techniques, including objection handling and closing strategies.
  • Proficiency in CRM systems and sales analytics tools is a plus.

How You'll Be Rewarded:

We offer a diverse range of comprehensive health and welfare benefits to associates who work 30 or more hours per week to meet your needs and support you throughout your career with us. Travel + Leisure Co. benefits include:

Note: Temporary and/or seasonal associates are ineligible for Paid Time Off.

  • Medical
  • Dental
  • Vision
  • Flexible spending accounts
  • Life and accident coverage
  • Disability
  • Depending on position, paid time off, parental leave and holidays (speak to your recruiter for additional information)
  • Wish day paid time to volunteer at an approved organization of your choice
  • 401k with employer match (subject to eligibility requirements, including tenure - speak to your recruiter for additional information)
  • Legal and identify theft plan
  • Voluntary income protection benefits
  • Wellness program (subject to provider availability)
  • Employee Assistance Program

Where Memories Start with You

Hospitality is at the heart of all we do at Travel + Leisure Co. Here, you’ll find an inclusive environment where we deliver excellence and take time to have fun, celebrate together, and support one another. We're always looking ahead to what’s next and how we can strengthen our business, its neighboring communities, and the customer experience. Join our global team and build a career where memories start with you.

We are an equal opportunity employer, and all applications will be considered for employment without attention to their membership in any protected class. If you require any reasonable accommodation to complete your application or any part of the recruiting process, please email your request to MyCareer@travelandleisure.com, including the title and location of the position for which you are applying.

Average salary estimate

$70000 / YEARLY (est.)
min
max
$60000K
$80000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Supervisor, Outbound Reservations, Wynd

At Travel + Leisure Co., we're all about putting the world on vacation! We’re looking for a passionate Supervisor of Outbound Reservations to join our vibrant team based in sunny Florida, working from the comfort of your home! In this pivotal role, you’ll be leading and nurturing a group of Vacation Planning Counselors who connect with Club Wyndham and Worldmark Owners through outbound calls. You'll drive productivity and sales while fostering a high-energy environment that celebrates success and growth. Your innovative approach will help develop sales techniques that elevate our team's performance to a whole new level. With responsibilities ranging from coaching agents on advanced sales practices to creating tailored development plans, you'll be instrumental in turning vacation inspiration into unforgettable experiences for millions. Plus, you'll collaborate with various departments to elevate our service standards. If you have a knack for motivating teams and a passion for enhancing customer experiences, this is the perfect opportunity for you. Come be a part of a company that thrives on growth, learning, and delivering exceptional travel experiences every day!

Frequently Asked Questions (FAQs) for Supervisor, Outbound Reservations Role at Wynd
What are the main responsibilities of the Supervisor, Outbound Reservations at Travel + Leisure Co.?

As the Supervisor of Outbound Reservations at Travel + Leisure Co., you'll oversee a team of Vacation Planning Counselors, drive team productivity, and achieve service and sales goals. Your role involves coaching staff on sales techniques, developing tailored development plans, and fostering a positive team environment to enhance outbound performance.

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What qualifications do I need for the Supervisor, Outbound Reservations position at Travel + Leisure Co.?

To excel as a Supervisor of Outbound Reservations at Travel + Leisure Co., you should have proven experience in a sales-driven leadership role, preferably within a contact center environment. Strong analytical skills and the ability to motivate and coach a sales team is essential, alongside excellent communication skills and an innovative mindset.

Join Rise to see the full answer
What kind of training does Travel + Leisure Co. provide for the Supervisor, Outbound Reservations role?

Travel + Leisure Co. offers a comprehensive training schedule for the Supervisor, Outbound Reservations role that includes a five-week program from Monday to Friday, 9:00 AM to 6:00 PM EST. This training will equip you with the knowledge and skills necessary to foster a successful outbound calling team.

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How does Travel + Leisure Co. support professional development for the Supervisor, Outbound Reservations?

Travel + Leisure Co. is committed to your professional development as a Supervisor of Outbound Reservations. You'll engage in continuous learning opportunities, create personal development plans, and participate in coaching sessions to refine your leadership and sales strategies, ensuring you're always at the top of your game.

Join Rise to see the full answer
Is there room for career advancement as a Supervisor, Outbound Reservations at Travel + Leisure Co.?

Absolutely! As a Supervisor of Outbound Reservations at Travel + Leisure Co., you will have various opportunities for career advancement within the company. With our focus on employee development and a culture that promotes excellence, you can grow your career in a dynamic environment that values your contributions.

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Common Interview Questions for Supervisor, Outbound Reservations
Can you describe your experience in managing outbound sales teams?

When answering this question, focus on specific examples of your leadership roles, how you motivated your team, and any innovative strategies you implemented to increase sales. Highlight the results achieved through your efforts, showcasing your analytical skills.

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How do you approach coaching your team for better performance?

Discuss your methods for tracking performance metrics and developing tailored coaching plans. Illustration of successful mentoring experiences can reinforce your response, stressing the importance of ongoing development and constructive feedback.

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What strategies do you use to drive sales and meet conversion targets?

Share your innovative ideas and any campaigns you've successfully executed that led to increased sales. Mention techniques such as consultative selling and how you've trained your team on these approaches.

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How do you handle conflicts within a team?

It's key to mention your conflict-resolution skills and your approach to fostering a positive team environment. Provide specific examples of conflicts you've resolved, focusing on communication and collaborative resolution.

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What metrics do you believe are most important for measuring outbound sales performance?

Discuss key performance indicators like conversion rates, call quality, and customer satisfaction scores. Explain how you used these metrics to identify areas for improvement and boost team performance.

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How do you ensure that your team understands company products and services?

Talk about your strategies for ongoing product training and knowledge-sharing sessions. Emphasize how important it is for team members to feel confident in communicating the value of services to clients.

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Describe a time you had to manage an underperforming employee. What was your approach?

Provide a specific example highlighting your ability to assess performance issues, implement improvement plans, and support the employee in reaching their goals. Focus on your empathetic and coaching aspects.

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Why do you want to work for Travel + Leisure Co. as a Supervisor, Outbound Reservations?

Show your enthusiasm for the company’s mission of putting the world on vacation. Highlight your alignment with their values and how your background prepares you to make a positive impact on their outbound sales team.

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How do you stay updated on industry trends and best practices?

Share methods you use to stay informed, such as attending training sessions, following industry news, and networking. Express the importance of continual learning and improvement in your professional development.

Join Rise to see the full answer
What is your leadership style when managing a sales team?

Reflect on your leadership style, whether it be transformational, transactional, or coaching-oriented. Provide examples showing how you've adapted your approach based on team needs and situations, emphasizing results and team morale.

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TEAM SIZE
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HQ LOCATION
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EMPLOYMENT TYPE
Full-time, remote
DATE POSTED
March 29, 2025

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