Dirk Wakeham

Dirk Wakeham is a veteran technology and SaaS executive with more than three decades of leadership experience concentrated in PropTech, FinTech, and the multifamily-housing sector. He holds a Bachelor of Science in Business Administration from California State University, Fullerton. Over his career he has founded or led six technology and real-estate software companies — Zego, Kibo, Lanyon, storEDGE, LeasingDesk, and RealPage.

His track record is tightly intertwined with RealPage. He founded LeasingDesk (circa 2000), a renters-insurance and risk-mitigation business for the multifamily industry, which RealPage acquired in 2007. He then served as President of RealPage from roughly 2009 to 2021, a period in which he helped scale revenue from approximately $140 million to $320 million and helped guide the company through its 2010 IPO, expanding its resident-screening, insurance, and revenue-management businesses.

He subsequently became CEO of PayLease (rebranded Zego), a fintech/payments platform for property management and HOAs backed by Vista Equity Partners. Under his leadership Zego scaled to serve thousands of property managers and millions of residential units, and in 2020 he led its sale to Global Payments in an all-cash deal valued at about $925 million. Most recently he served as a Managing Director at Vista Equity Partners, advising and leading growth strategies for enterprise-software portfolio companies.

On November 11, 2025, RealPage appointed Wakeham as President & CEO (and a board member), succeeding Dana Jones. He framed the move as "coming home." He has also held board or advisory roles at Critical Start, StarRez, Leonardo247, Kibo, Lanyon, Parcel Pending, and Rentlytics.

• Invests and advises primarily at the seed / early stage, putting personal capital and operating expertise into companies in PropTech, FinTech, and B2B/SaaS business-productivity software.
• Gravitates to real-estate and multifamily-adjacent technology — payments, screening, analytics, resident experience — domains where his operating background (LeasingDesk, RealPage, Zego) gives him direct conviction and useful networks.
• Tends to engage as an investor-advisor / board member rather than a passive check-writer, leaning on his experience "building high-performing teams, fostering trusted partnerships, and guiding organizations through transformation and growth."
• Bias toward companies with a credible path to scale and acquisition — several of his bets (Rentlytics, Parcel Pending, Zego) ended in exits to strategic acquirers.