Director of Training and Support

Director of Learning & Operational Enablement
Location: Tampa/St. Pete with extensive travel to different locations
Compensation: $125,000–$150,000 base salary + comprehensive benefits

About the Opportunity
We are seeking a strategic and innovative learning leader to build, execute, and continuously improve training, development, and operational enablement programs across a large multi-location service organization.
The successful candidate will design scalable learning experiences, drive operational readiness, accelerate adoption of key initiatives, and help improve business performance through effective training systems and support resources.Key Responsibilities
Learning Strategy & Organizational Development

• Develop and execute the organization''s learning and development strategy.
• Create scalable training solutions that support rapid growth and operational excellence.
• Design leadership development programs focused on management, coaching, customer experience, performance, culture, and profitability.
• Establish learning frameworks and career development pathways for frontline employees, managers, and emerging leaders.

Training Program Development

• Lead the design, delivery, and continuous improvement of onboarding, leadership, and operational training programs.
• Create engaging learning experiences using blended learning methodologies, including instructor-led training, microlearning, video-based learning, coaching, and self-paced programs.
• Ensure learning programs are easy to adopt, practical, and aligned with real-world operational needs.

Content Creation & Learning Resources

• Oversee the development of modern learning materials, including:
  • Training videos
  • E-learning content
  • Playbooks
  • Facilitator guides
  • Job aids
  • Presentations
  • Knowledge base resources
• Utilize storytelling, visual design, and interactive learning techniques to increase engagement and adoption.

Learning Technology & AI Innovation

• Evaluate, implement, and optimize learning technologies and digital learning platforms.
• Leverage AI tools to improve content creation, coaching, performance support, and training efficiency.
• Manage and optimize Learning Management Systems (LMS) and knowledge repositories.
• Monitor learning analytics and business performance metrics to measure effectiveness and drive continuous improvement.

Facilitation & Large-Scale Learning Events

• Lead workshops, leadership forums, annual meetings, and company-wide learning events.
• Serve as a visible champion for learning, leadership development, and performance improvement.
• Facilitate high-impact training sessions for leaders and frontline teams.

Stakeholder Partnership & Influence

• Partner with operational leaders, department heads, and cross-functional teams to identify capability gaps and implement training solutions.
• Influence stakeholders at all levels of the organization through strong communication, coaching, and relationship-building skills.
• Balance strategic priorities with operational realities to deliver scalable and sustainable learning solutions.

Team Leadership

• Lead, coach, and develop Learning & Development team members.
• Establish goals, KPIs, and performance standards for the training function.
• Foster a culture of innovation, accountability, collaboration, and continuous improvement.

Qualifications
Required

• Bachelor''s degree or equivalent professional experience.
• 7+ years of progressive experience in Learning & Development, Training, Organizational Development, Leadership Development, or a related field.
• Strong knowledge of adult learning principles, instructional design methodologies, and organizational development practices.
• Experience developing training curricula, e-learning content, videos, and modern learning experiences.
• Hands-on experience with LMS platforms, digital learning technologies, learning analytics, and AI-enabled productivity tools.
• Excellent facilitation, presentation, coaching, and communication skills.
• Strong project management, change management, and stakeholder management capabilities.

Preferred

• Experience supporting multi-site, field-based, franchise, retail, hospitality, logistics, transportation, or service-oriented organizations.
• Experience implementing scalable learning programs in high-growth environments.
• Knowledge of performance measurement, operational KPIs, and business-impact analysis.
• Experience leading large-scale training events, leadership conferences, or learning summits.
• Experience leveraging AI and emerging technologies to accelerate content development and improve learner engagement.

Determining compensation for this role (and others) at Vaco/Highspring depends upon a wide array of factors including but not limited to the individual’s skill sets, experience and training, licensure and certifications, office location and other geographic considerations, as well as other business and organizational needs. With that said, as required by local law in geographies that require salary range disclosure, Vaco/Highspring notes the salary range for the role is noted in this job posting. The individual may also be eligible for discretionary bonuses, and can participate in medical, dental, and vision benefits as well as the company’s 401(k) retirement plan. Additional disclaimer: Unless otherwise noted in the job description, the position Vaco/Highspring is filing for is occupied. Please note, however, that Vaco/Highspring is regularly asked to provide talent to other organizations. By submitting to this position, you are agreeing to be included in our talent pool for future hiring for similarly qualified positions. Submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. Further assessment of candidates beyond this initial phase within Vaco/Highspring will be otherwise assessed by recruiters and hiring managers. Vaco/Highspring does not have knowledge of the tools used by its clients in making final hiring decisions and cannot opine on their use of AI products.