Senior Specialist, Technology Training & Enablement

Key Responsibilities

• Training Delivery & Content Development
• 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:
• 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
• Adoption & Change Management
• 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
• Onboarding & Speed to Proficiency
• 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
• Field Support & Continuous Improvement
• 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
• Cross-Functional Collaboration
• 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

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

What Success Looks Like

• 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
• Adequate adoption of new tools and updates happens smoothly and efficiently

Benefits

• 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.

Compensation

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