Director of Training and Development at OneWall Communities LLC – Stamford, Connecticut

OneWall Communities® is a vertically integrated real estate company focused on transit- and lifestyle-oriented workforce housing across multiple U.S. markets. Our continued growth is driven by a commitment to operational excellence, thoughtful innovation, and creating a worry-free environment for our residents, communities, and investors.

We are fueled by an entrepreneurial spirit that challenges us to think differently, move quickly, and continuously improve how we operate. We offer a collaborative, fast-paced culture that values accountability, growth, and balance.

We are seeking a Director of Training & Development to lead company-wide training initiatives across a rapidly expanding, multi-state property management portfolio. This role will play a critical part in scaling the organization by ensuring teams are confident, capable, and fully equipped to execute operational standards and adopt new technologies.

The ideal candidate is a strong operational partner who is technology-savvy, execution-focused, and experienced in training, implementation, and adoption of property management systems and proptech platforms.

• Develop and lead a comprehensive training and development strategy supporting a multi-state, growing multifamily portfolio
  
  

• Design and deliver structured onboarding, role-based, and ongoing training programs for on-site, regional, and corporate teams
  
  

• Lead training efforts for property management systems and proptech platforms, ensuring effective implementation and adoption
  
  

• Partner with Operations, IT, Finance, HR, and external vendors during system rollouts, enhancements, and process changes
  
  

• Support new acquisitions, transitions, and market expansions with tailored training plans and on-site or virtual support
  
  

• Conduct training needs assessments and collaborate with leadership to address performance gaps and operational opportunities
  
  

• Develop and maintain training materials, SOPs, playbooks, and digital learning resources
  
  

• Monitor training effectiveness, system adoption, and performance outcomes; adjust programs as needed
  
  

• Provide hands-on support to underperforming or transitioning properties when required
  
  

• Stay current on industry trends, proptech advancements, and best practices in multifamily operations and training
  
  

• Participate in cross-functional meetings, planning initiatives, and operational reviews
  
  

• Complete required OneWall University training programs on schedule
  
  

• Bachelor’s degree and 7+ years of related experience in multifamily operations, training, or operational leadership, or equivalent combination
  
  

• Proven experience leading training initiatives across multi-state or large-scale portfolios
  
  

• Strong background in proptech training, system implementation, and adoption
  
  

• Deep understanding of property management operations, workflows, and performance drivers
  
  

• Excellent communication and presentation skills with the ability to engage audiences at all levels
  
  

• Strong organizational and project management skills with the ability to manage multiple initiatives simultaneously
  
  

• Proficiency in Microsoft Office Suite and Google Workspace; experience with property management systems and learning platforms
  
  

• Ability to lift up to 25 lbs occasionally
  
  

• Regular standing, walking, and presenting during training sessions
  
  

• Moderate office noise levels with occasional exposure to outdoor conditions during property visits
  
  

Approximately 40% travel required, including overnight visits as needed across assigned markets