Director of Training & Development – Sales

Vacatia; Kissimmee (FL); On-site; USD 110,000 - 160,000; Full time

Job summary

Vacatia is seeking a Director of Training & Development – Sales to design and execute training and professional growth for our sales organization. You will partner with sales to develop talent, strengthen performance, and foster a culture of continuous learning.

You will lead onboarding, leadership development, and measurable training programs while ensuring compliance and ethical sales practices across the organization.

Qualifications

• 5+ years of experience in training and development, preferably within vacation ownership, timeshare, hospitality, or sales.
• 3+ years of leadership or management experience within training and development.
• Proven experience designing and delivering sales and leadership development programs.
• Strong knowledge of adult learning principles and instructional design.

Responsibilities

• Develop and oversee comprehensive training programs for sales professionals, leaders, and key roles.
• Create innovative learning strategies to support sales performance and growth.
• Design workshops, coaching sessions, and continuing education programs.
• Establish onboarding programs and structured learning paths to reinforce culture and product knowledge.

Skills

Leadership

Instructional design

Facilitation

Coaching

Data-driven decision making

Education

Bachelor's degree in Business

Bachelor's degree in Education

Bachelor's degree in Organizational Development

Bachelor's degree in Human Resources

Tools

LMS

CRM platforms

Digital learning tools

Job description

Director of Training & Development

Kissimmee FL, Orlando FL

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

Lead Sales Training & Development

• 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.

Develop Future Leaders

• 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.