Senior Specialist, Technology Training & Enablement

Experience Senior Living

11h•$90,000 - $95,000•Remote

About The Position

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 not on owning systems, but 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.

Requirements

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

Responsibilities

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