Wakeham Returns to RealPage, Prioritizing Trust, Transparency and AI-Driven Growth

Dirk Wakeham has returned to RealPage, a provider of artificial intelligence (AI)-enabled software platforms for the real estate industry, to lead the firm’s next chapter of growth. Wakeham became president and CEO in November, succeeding Dana Jones who held the role since 2021.

He brings extensive proptech and fintech leadership to the role. In addition to serving as president of RealPage from 2009 to 2012, he previously served as managing director of Vista Equity Partners and founded LeasingDesk, which was acquired by RealPage. He also has led organizations such as KIBO Commerce, Lanyon, storEDGE, and Zego.

In his first months as president and CEO, Wakeham says he was deliberate in not having any preconceived notions. He took the first 90 days to embark on a listening tour, talking one-on-one with approximately 80 of RealPage’s top leaders and meeting with the company’s top customers, to formulate a value creation plan.

First and foremost for Wakeham is continuing to build customer trust and moving forward as a business after the Department of Justice settlement regarding the firm’s revenue management software. As part of the settlement, there were no penalties, no admission of guilt, and no ongoing challenges with RealPage’s products.

“This notion of trust is really job one,” he says. “We want to make sure that we're doing everything we can to ensure our customers have confidence in us and that we're doing the right things around data governance and data security.”

According to Wakeham, he heard customers share they are increasingly concerned about data security. 

“We manage a significant amount of data, and many of our customers rely on integrations with third-party providers. Given the sensitivity around tenant information, there’s a real focus on data security. We’re focused on ensuring the valuable information within our platform is properly stored, secured, and then governed, with clear controls over how access is granted. Whether it’s a third-party integration or authorized access, we want to make sure everything is done in a very managed and governed way, reducing risk and protecting that data.”

In addition to trust, Wakeham says another priority is commercial clarity and transparency when it comes to RealPage’s contracting and invoicing with an end goal to simplify the process as much as possible. With an assemblage of over 50 companies that have been acquired over the past two decades, many of the products have different ways in which they get billed and contracted, with a customer potentially having a dozen or so contracts from legacy systems. 

Fee transparency and artificial intelligence are two current industry buzzwords that also are at the forefront for RealPage, Wakeham says. 

“Fee transparency is a newer issue and one that we're helping our customers navigate through, just given the complexity of it. I think this is going to be an ongoing challenge for our industry,” he shares. “Housing is unaffordable because we're building a million less houses a year than we should be. Supply is way under the demand. We’re an industry that’s going to continue to be a political football for folks in Washington and our state houses because it’s hard for people to afford to live in the product.”

In terms of AI, the company has spent over $2 billion over the last five years on innovations and strategic acquisitions, and it announced its Lumina AI Workforce product suite last year at its user conference. 

“AI is all the rage, and we're spending a fair bit of money on that. We are activating our AI investments and helping our customers get those things rolled out. We're also thinking a lot about how we can help our customers be more productive with these tools, not just throw them out there and say ‘good luck,’” he adds.

Wakeham says RealPage believes AI needs to be embedded into the core operating system to provide a better user experience and data security. 

“We’re thinking about this as a new operating system. If you roll back three or four years, there was a lot of discussion around centralization. How do we get better efficiency by centralizing our leasing functions, our accounting functions? We believe AI is the next evolution of that,” he notes. “So how do you take that centralization concept and become more efficient with that in various use cases? We’ve got half a dozen AI agents that we've identified—from operations to leasing to resident services to procurement to financial analysis to utility analysis. We view these as massive areas of functionality that can create efficiency for our customers.”

One other area Wakeham would like to see RealPage double down on is its partnerships with customers and the ethos around understanding their pain points.

“I'd like to reinforce that customer listening and partnership,” he adds. “A lot of the great products that we have here were actually built by or innovated by our customers. They had a business need, they built it, they innovated on it, and then we ended up acquiring it or partnering with them to expand it into more markets for more customers. I want to get back to that for sure.”