Director of Training & Development – Sales

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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 5+ years of experience in training and development, preferably within the vacation ownership, timeshare,…