Senior Director Jobs in Boca Raton, FL (NOW HIRING)

Senior Director, Training & Learning, Owner Experiences

Join Vacatia and Build the Training Experience Behind Exceptional Owner Experiences

Vacatia is an innovative hospitality company reinventing the vacation rental and ownership experience across discovery, booking, and stay. Were building the next generation of travel lifestyle products, blending technology, hospitality, and design to create smarter, more connected experiences for guests, owners, and partners.

Were looking for a Senior Director, Training & Learning, Owner Experiences to build and lead the training strategy for the teams that support Vacatia owners. This leader will create the programs, coaching, tools, and learning experiences that help employees move beyond transactional service and deliver confident, thoughtful, relationship-driven experiences across Owner Care, Owner Success, Club Vacatia, onboarding, retention and save, escalations, multilingual support, chat, and other Owner Experience functions.

This is not a role focused on simply delivering more training. Youll work directly with Owner Experience leaders to define what great looks like, identify where employee capability is affecting performance, and build practical solutions that change behaviors and improve results. From new hire readiness and service excellence to coaching, leadership development, systems training, and performance improvement, youll help create the capabilities behind an exceptional owner experience.

If you love building training programs from the ground up, staying close to the operation, and seeing your work translate into better employee and customer outcomes, this is an opportunity to make a meaningful impact at Vacatia.

Why Youll Love Working at Vacatia

• Build the Future: Shape the Training & Learning strategy for an evolving Owner Experiences organization and build programs that can scale as the business grows.
• Impact That Matters: Connect training directly to owner satisfaction, quality, retention, first-contact resolution, employee readiness, and operational performance.
• Go Beyond Traditional Training: Build capability in communication, influence, empathy, confidence, relationship building, problem-solving, de-escalation, and service recovery, not just systems and processes.
• Autonomy and Ownership: Own the training strategy from new hire onboarding and role readiness through ongoing development, coaching, leadership capability, and measurement.
• Stay Close to the Business: Use real calls, chats, cases, owner feedback, quality results, and operational performance to understand where employees need support and build learning around what is actually happening.

Your Impact

• Build and lead the Training & Learning strategy for Vacatias Owner Experiences organization.
• Create structured new hire learning journeys that take employees from onboarding through role readiness, proficiency, and ongoing development.
• Develop service excellence training that strengthens communication, active listening, empathy, confidence, influence, relationship building, problem-solving, de-escalation, and service recovery.
• Build training that helps employees understand the difference between simply resolving a transaction and creating long-term value and trust with an owner.
• Partner with Owner Experience leaders and subject matter experts to translate operational requirements, policies, programs, systems, and owner needs into practical learning experiences.
• Create consistent coaching frameworks and equip managers with the tools to reinforce expectations, coach behaviors, and improve employee performance.
• Develop manager and leadership capability across coaching, feedback, accountability, performance management, communication, employee engagement, and team development.
• Use quality results, owner feedback, calls, chats, cases, surveys, and performance data to identify capability gaps and continuously improve training.
• Establish clear measures of training effectiveness that connect learning to employee readiness, behavior change, quality, owner satisfaction, retention, productivity, and operational performance.

What You Bring

• 10+ years of progressive experience in Training, Learning & Development, Customer Experience Training, Contact Center Training, or a related field.
• 5+ years of experience leading training teams or functions.
• Demonstrated experience building, scaling, or transforming training programs in customer service, customer success, contact center, hospitality, or another high-volume service environment.
• Strong experience designing new hire, operational, systems, service excellence, coaching, and leadership training.
• Expertise in instructional design, adult learning, facilitation, performance consulting, coaching, and learning measurement.
• Experience using call monitoring, quality results, customer feedback, and operational data to identify performance and capability gaps.
• Strong understanding of customer service or contact center operations, including quality, productivity, escalations, retention, and performance management.
• Experience with Learning Management Systems, digital learning platforms, knowledge management tools, and modern learning technologies.
• Strong facilitation and communication skills with the ability to connect with frontline employees while building credibility with managers and senior leaders.
• A builder mindset with the ability to create structure, establish standards, and scale programs in a fast-moving and evolving environment.
• Experience in hospitality, vacation ownership, travel, membership, customer success, or another complex consumer environment is strongly preferred.
• Experience supporting multilingual or geographically dispersed teams is a plus.

Join Us

Join us at the start of something big. If youre ready to build training that goes beyond the classroom and changes how employees show up for owners every day, wed love to hear from you.