Senior Director, Training & Learning

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. We’re building the next generation of travel lifestyle products, blending technology, hospitality, and design to create smarter, more connected experiences for guests, owners, and partners.

We’re 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. You’ll 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, you’ll 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 You’ll 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 Vacatia’s 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 valu