Director of Training & Development

Vacatia; Kissimmee (FL); On-site; USD 120,000 - 180,000; Full time

Job summary

Vacatia seeks a Director of Training & Development – Sales to lead strategy, design, and execution of training programs for the sales organization. This role partners with sales to develop talent, strengthen performance, and foster a culture of continuous learning and professional growth.

The ideal candidate has 5+ years in training and development and 3+ years in leadership, with expertise in instructional design, LMS, and CRM tools.

Qualifications

• 5+ years in training and development, preferably within vacation ownership, hospitality, or sales.
• 3+ years of leadership or management experience within training and development.
• Bachelor's degree in Business, Education, Organizational Development, HR, or related field preferred.
• Proven experience designing and delivering sales and leadership development programs.
• Strong knowledge of adult learning principles, instructional design, facilitation, and e-learning.

Responsibilities

• Develop and oversee comprehensive training programs for sales professionals, sales leaders, and key roles throughout the organization.
• Build innovative learning strategies that support sales performance, productivity, revenue growth, and business objectives.
• Design workshops, classroom training, role-playing, coaching sessions, and continuing education programs.
• Develop programs focused on sales techniques, communication, objection handling, closing skills, customer engagement, and ethical sales practices.
• Create and improve onboarding experiences and structured learning paths that reinforce culture, product knowledge, and compliance.

Skills

Training & development

Sales training

Instructional design

Adult learning

Coaching & mentoring

Education

Bachelor's degree

Tools

CRM platforms

LMS

Digital learning tools

Job description

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Vacatia is a rapidly growing hospitality and vacation ownership company committed to delivering exceptional resort experiences and creating successful owners.

We are looking for an experienced, dynamic, and innovative Director of Training & Development – Sales to lead the strategy, design, and execution of training and professional development programs for our sales organization.

This is an opportunity for a training leader who understands that great sales organizations are built through great people. You will partner directly with sales to develop talent, strengthen sales performance, build future leaders, and create a culture of continuous learning and professional growth.

What You'll Do

• Develop and oversee comprehensive training programs for sales professionals, sales leaders, and key roles throughout the organization.
• Build innovative learning strategies that directly support sales performance, productivity, revenue growth, and business objectives.
• Design engaging workshops, classroom training, role-playing exercises, coaching sessions, and continuing education programs.
• Develop programs focused on sales techniques, communication, objection handling, closing skills, customer engagement, and ethical sales practices.

Build a High-Impact Onboarding Experience

• Create and continuously improve sales onboarding programs that accelerate new-hire productivity.
• Establish structured learning paths that reinforce company culture, sales methodologies, product knowledge, compliance, and performance expectations.
• Partner with sales leaders to ensure new team members receive the training, coaching, and resources needed to succeed.
• Create and facilitate leadership development programs for current and emerging sales leaders.
• Identify high-potential talent and create development opportunities that prepare employees for increased responsibility.
• Serve as a mentor and coach to sales professionals and leaders at all levels.
• Help establish a strong internal talent pipeline and succession planning strategy.

Measure What Matters

• Establish training metrics and performance indicators to evaluate the effectiveness and business impact of learning initiatives.
• Analyze sales performance, productivity, employee feedback, and other data to identify training opportunities.
• Continuously refine training programs based on measurable results and organizational needs.
• Partner with sales leadership to identify knowledge gaps, performance opportunities, and emerging development needs.

Build a Modern Learning Environment

• Develop and maintain a comprehensive library of training resources, including manuals, digital learning content, videos, facilitator guides, and other learning tools.
• Leverage adult learning principles, instructional design, technology, and e-learning to create engaging learning experiences.
• Stay current on sales training trends, leadership development practices, adult learning methodologies, and vacation ownership industry trends.
• Partner with Human Resources to align training with employee engagement, talent development, succession planning, and organizational priorities.

Champion Compliance & Ethical Sales

• Ensure training programs reinforce company policies, regulatory requirements, compliance standards, and ethical sales practices.
• Partner with appropriate internal stakeholders to ensure training content remains accurate, current, and compliant.
• Promote a culture focused on delivering exceptional customer experiences while maintaining the highest standards of professionalism and integrity.

What We're Looking For

• 5+ years of experience in training and development, preferably within the vacation ownership, timeshare, hospitality, or sales industry.
• 3+ years of leadership or management experience within training and development.
• Bachelor's degree in Business, Education, Organizational Development, Human Resources, or a related field preferred.
• Proven experience designing and delivering sales and leadership development programs.
• Strong knowledge of adult learning principles, instructional design, facilitation, and e-learning.
• Demonstrated ability to coach, mentor, and develop sales professionals and leaders.
• Exceptional presentation and facilitation skills with the ability to engage audiences at all levels.
• Strong understanding of sales processes, performance management, compliance, and ethical sales practices.
• Ability to use data and performance metrics to measure training effectiveness and identify opportunities.
• Experience with Learning Management Systems (LMS), CRM platforms, and digital learning tools preferred.
• Strong organizational skills with the ability to manage multiple priorities and initiatives in a fast-paced environment.
• A passion for developing people and creating high-performing teams.

Why Vacatia

At Vacatia, we’re redefining the vacation ownership experience through innovation, operational excellence, and a guest-first mindset. We offer a collaborative culture, growth opportunities, and the chance to make a meaningful impact across our resort operations.

Vacatia, Inc. is an Equal Opportunity Employer M/F/D/V and values diversity in the workplace.