Learning Manager, Systems & Technology

Company Overview

Headquartered in Richmond, Virginia, Capital Square is a vertically integrated national real estate firm specializing in tax‑advantaged real estate investments, including Delaware statutory trusts (DSTs) for Section 1031 exchanges, qualified opportunity zone funds for tax deferral and exclusion and a real estate investment trust (REIT). The company is also an active developer and manager of multifamily communities. Since 2012, Capital Square has completed more than $7.8 billion in transaction volume.

Capital Square’s eight most recent mixed‑used development projects total approximately 2,000 apartment units with a total development cost in excess of $590 million, and Capital Square Living, the firm’s property management division, now manages over 10,000 apartments across multiple states. Capital Square’s related entities provide a range of services – including due diligence, acquisition, loan sourcing, property/asset management and disposition – for a growing number of high‑net‑worth investors, private equity firms, family offices and institutional investors.

Recognized by Inc. 5000 as one of the fastest growing companies in the nation for seven consecutive years, and among the Top 100 Inspiring Workplaces of North America, Capital Square raises capital, builds and sets expectations. Learn more at

Capital Square and Capital Square Living are seeking an experienced, innovative, and solutions‑driven learning leader to join our unified Learning & Development team as the Learning Manager, Systems & Technology. This role will serve as an enterprise‑wide learning partner, responsible for designing, delivering, and reinforcing all learning initiatives related to systems, technology adoption, and operational excellence across both organizations. Working closely with onsite teams, corporate departments, and executive leaders, this position ensures that every team member – from front‑line service associates to corporate operations staff – has the tools, skills, and confidence to perform efficiently, consistently, and effectively.

The ideal candidate will be an expert at simplifying complex systems and processes, creating engaging learning experiences that drive adoption, operational accuracy, and measurable performance improvement.

• Develop and execute learning strategies to strengthen system proficiency, technology adoption, and operational consistency.
• Collaborate with leaders across departments to assess needs and align initiatives with company goals.
• Design and deliver engaging training through various formats including live sessions, e‑learning, and microlearning.
• Facilitate clear, hands‑on training sessions that build confidence and understanding of key platforms and processes.
• Create and maintain learning resources such as job aids, videos, and quick‑reference materials to reinforce adoption.
• Evaluate program effectiveness using data, feedback, and performance metrics to drive continuous improvement.
• Partner with IT and Operations teams to support system implementations and ensure smooth rollouts.
• Translate feedback and operational insights into strategies that enhance efficiency, accuracy, and compliance.

• Bachelor’s degree preferred; advanced degree in Business, Education, Information Systems, or Organizational Development preferred, or working equivalent.
• 5+ years of progressive experience in multifamily property management or real estate, including 3+ years in Learning & Development, Training, or Operations.
• Proven experience designing and facilitating system and process training across multi‑site organizations.
• Working knowledge of property management technologies, including Yardi Systems (Flex CRM, Voyager, Elevate, Rent Cafe), Microsoft Teams, SharePoint, and Office Suite, Smart Rent, Checkpoint , AIRM, and similar tools preferred.
• Understanding of system integrations, reporting, and data‑driven process improvement.
• Instructional design, facilitation, or process improvement certifications a plus.
• Strong ability to simplify complex systems and workflows.
• Skilled in data analysis, project management, and collaboration.
• Proficien…