Senior Specialist, Technology Training & Enablement

The Senior Specialist, Technology Training & Enablement is responsible for ensuring ESL team members are quickly and effectively able to use core technology platforms to execute their work.

This role sits within Training & Development and focuses on training, adoption, and change management through hands‑on content creation, live facilitation, and field support. The emphasis is on ensuring they are understood, adopted, and consistently used to drive operational performance.

This role partners closely with the COO and Operations leadership to align training priorities, support system rollouts, improve user experience, and accelerate speed to proficiency across communities.

• Design and deliver role‑based training programs (in‑person and virtual) across all core systems (e.g., Yardi, Sherpa, UKG)
• Create and maintain training content and materials, including:
  • Playbooks
  • Job aids
  • Quick‑reference guides
  • Absorb courses
• Ensure training is practical, workflow‑based, and aligned to how work is performed in the field
• Facilitate both onboarding sessions and ongoing training for existing team members

• Support technology adoption efforts tied to new system implementations, enhancements, and updates
• Execute structured change management plans, ensuring users understand what is changing and how to apply it in their daily work
• Reinforce usage expectations through ongoing training, communication, and coaching
• Gather user feedback and identify friction points to improve both training and system usability

• Partner with the People team to support new hire onboarding, ensuring early and effective system training
• Define and deliver training that enables employees to become proficient quickly and confidently
• Continuously refine onboarding training based on observed gaps and user needs

• Partner with community and regional teams to identify challenges in system usage and address them through training or process reinforcement
• Observe how systems are used in the field and adjust training to close execution gaps
• Track training effectiveness and adoption trends; adjust approach to improve outcomes
• Support consistency across communities while allowing for practical, real‑world application

• Partner closely with:
  • COO + Operations Leadership (priorities, rollout alignment)
  • Training & Development / People Team (learning strategy, onboarding)
  • IT / Technology Teams (system updates, implementation timing)
• Act as the connector between system functionality and real‑world execution

• Experience in training, enablement, or operations support in a multi‑site environment (senior living, healthcare, hospitality, or similar)
• Strong ability to deliver engaging in‑person and virtual training
• Proven experience creating practical, user‑friendly training content
• Experience supporting technology adoption or system implementations
• Ability to translate systems into simple, clear workflows and instructions
• Highly collaborative with the ability to build trust with field teams
• Strong execution mindset with a focus on clarity, consistency, and speed

• New hires reach proficiency in core systems quickly following onboarding
• Training programs are consistent, scalable, and easy to access
• Technology is used across communities with clarity and minimal friction
• Field teams demonstrate confidence and consistency in system usage
• Adoption of new tools and updates happens smoothly and efficiently

This position is remote with routine travel to communities across Florida, Colorado, Virginia, Maryland, Indiana, and Ohio. Travel is required.

We offer a full benefits package that includes medical, dental, vision, STD/LTD, life and voluntary life, 401k with employer matching, paid holidays, and up to 20 days PTO in the first three years.

Employment is contingent upon successful completion of background screening in accordance with Florida law and company policy. Certain positions may require fingerprinting and Level 1 or Level 2 background screening. Applicants can review Florida care provider background screening requirements here:

$90,000 - $95,000, with 15% annual bonus target