Senior Specialist, Technology Training – Enablement

Experience Senior Living

Senior Specialist responsible for training ESL team members on technology platforms. Collaborating with operations leadership to enhance user experience and accelerate training effectiveness.

Posted 6/30/2026full-timeRemote • Colorado, Florida, Maryland, Ohio, Virginia • 🇺🇸 United StatesSenior💰 $90,000 - $95,000 per yearWebsite

About the role

Key responsibilities & impact

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
Track training effectiveness and adoption trends; adjust approach to improve outcomes
Partner closely with COO and Operations Leadership, Training & Development / People Team, IT / Technology Teams

Requirements

What you’ll need

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

Benefits

Comp & perks

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.

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

Training Program DesignContent CreationWorkflow TranslationChange ManagementTraining Effectiveness Tracking

Soft Skills

Engaging Presentation SkillsCollaborationTrust BuildingExecution Mindset