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PayLease Hires Real Estate Technology Veteran, Stephen Baker, as Its Chief Product Officer

PayLease today announced that Stephen Baker has joined the Company as its Chief Product Officer. Baker will lead the Product organization and will continue to drive innovation across PayLease’s cloud-based platform, which streamlines payments, billing, and utility management for more than 5,700 property management companies. Baker will be based in PayLease’s Chicago office and directly report to CEO, Dirk Wakeham.

Stephen Baker, Chief Product Officer

Baker joins PayLease with an extensive background in the enterprise software and real estate technology sectors. Most recently, he was Senior Vice President of Corporate Development and Strategic Partnerships at insightsoftware, a worldwide ERP software provider. He also spent several years at real estate software giant, MRI, serving as VP of Global and Strategic Markets and VP of Product Management. Baker also co-founded ShortTrack, a software startup driving automation and workflow software for title companies and real estate professionals. 

“Stephen’s background in software and real estate technology will be invaluable as we further enhance our product offering and build out capabilities that will add additional value to our client base,” said PayLease CEO, Dirk Wakeham. “I am delighted he has joined our team and I look forward to working with him on producing PayLease’s next generation of products,” he added.

Baker commented on his new role at PayLease saying, “PayLease is a fantastic company with a great foundation of products helping property management companies succeed. I am excited to lead the evolution of this platform to drive further value and innovation across the market.”

About PayLease

PayLease provides online payments, billing, and utility expense management tools to HOAs and property management companies. Property managers use PayLease to improve their business’ operational efficiencies and boost net operating income. Our solutions are easy to use and are bolstered by the highest levels of security and customer support. Since our inception in 2003, PayLease has grown to serve thousands of property management companies nationwide and is now among the fastest growing technology companies in the United States. For more information, please visit

Media Contact
Jennifer Stahlman
Phone: 303.697.8370

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