Pennrose · 1 day ago
Director of Systems Enablement & Training
United States
Full-time
Remote
Director/Executive
7+ years expPennrose is focused on ensuring technology investments translate into consistent adoption and measurable results. The Director of Systems Enablement & Training serves as a bridge between IT and Operations, owning system readiness, functional training, and adoption outcomes while leveraging deep expertise in Yardi within the affordable housing environment.
ConstructionProfessional ServicesProperty DevelopmentProperty ManagementReal Estate
Responsibilities
Ensure technology investments translate into consistent adoption and measurable results
Serve as the business-facing bridge between IT and Operations, owning system readiness, functional training, and adoption outcomes
Act as the functional authority across Yardi platforms and other enterprise tools, translating system capability into clear, effective training
Build a scalable train-the-trainer model, establish enablement standards, and support the responsible use of emerging technologies to drive sustained operational impact
Own the design and execution of functional systems training across enterprise platforms
Partner closely with IT on release timing and with Operations on readiness, adoption, and business use measurement
Co-design and execute a scalable train-the-trainer model that builds internal capability and ensures consistent deployment of functional training
Support the organization’s thoughtful adoption of emerging technologies, including AI-enabled tools, by developing training and guidance that promotes confidence, responsible use, and alignment to business needs
Establish standards, curriculum, and measurement approaches that support continuous improvement and scalable systems enablement across the enterprise
Qualification
Required
7-10 years of hands-on Yardi experience in the affordable housing industry (required), including platforms such as Voyager and Aspire
Demonstrated experience designing and delivering functional training or enablement programs
Ability to rapidly learn new systems and translate technical capability into operational training and adoption strategies
Strong leadership, communication, and stakeholder-management skills, with the ability to work across business functions
Comfort operating in a fast-paced, evolving, technology-driven environment with enterprise-level accountability
Company
Pennrose
Pennrose is a property development and management company.
201-500 employees
Funding
Current Stage
Growth StageLeadership Team
Geoff Milz
Regional Vice President
Recent News
2026-01-03
Hartford Business Journal
2025-12-02
Company data provided by crunchbase