Robert Dell’Osso and Cheryl Dell’Osso bring a powerful combination of real estate expertise, operational leadership, and technology-driven innovation to PM Systems Conference.

Robert Dell’Osso has spent most of his life in real estate and property management, giving him a deep understanding of both property owners’ and managers’ perspectives. As the founder and Broker-in-Charge of MasterKey Property Management in North Carolina’s Raleigh-Durham Triangle area, he has successfully grown the business while becoming a knowledgeable resource on investment properties. Robert holds the Residential Management Professional (RMP) designation and serves in several leadership roles within the National Association of Residential Property Managers (NARPM), including 2026 National Government Affairs Committee Chair and President of the Triangle NARPM Chapter.

Cheryl Dell’Osso, Co-Owner and Chief Operating Officer of MasterKey Property Management, brings nearly a decade of experience in technology marketing and leadership. She oversees daily operations, business strategy, and team development, leading the company’s adoption of technology, automation, and artificial intelligence to improve efficiency and customer experience. As a licensed North Carolina real estate broker, Cheryl focuses on sustainable growth, operational excellence, and exceptional service.

Together, Robert and Cheryl combine hands-on property management experience with strategic leadership and innovative technology to share practical insights on building efficient systems, scaling operations, and growing a successful property management business.