Jay McKee

In May 2023, Jay McKee’s Lessen acquired SMS Assist for $950 million. It remains one of the largest proptech acquisitions dollar-wise in the sector’s history. 

Scottsdale, Ariz.-based Lessen plays at that level, with more than 30,000 vendors using its 6-year-old property services and facilities maintenance platform. As of 2024, a year after buying up competitor SMS Assist, Lessen was processing 4 million work orders annually. 

Its offerings include an AI chatbot known as Lessen Copilot, which helps residential and commercial tenants place work orders by describing in plain language an issue they are having and letting the software handle the rest, and the Lessen Advantage Marketplace, a channel for vendors to obtain materials, insurance and financing at a discounted rate.

Lessen last year was named the fastest-growing private software company in the U.S. by Inc. magazine and was No. 2 among companies in all categories of the list.

“We’ve invested a ton of money into a lot of the different areas of our tech, including data management and AI,” McKee told Commercial Observer at the time. “We can extrapolate the data to our customers and talk about it. Some customers are managing their own people on our platform. And then we’re managing the secondary supplemental vendors, and we can compare.”

Lessen has grown exponentially in the short time that it’s been around, reaching a $1.1 billion valuation just two years after its founding and beaming McKee up to a level of affluence that provided him with the confidence to reportedly joke about buying SMS Assist to that company’s founder, Mike Rothman, at a party he hosted in his Scottsdale home at the time.

Rothman laughed off McKee’s comment about buying SMS Assist since his firm was “10 times” the size of Lessen. The merged product would be valued at $2 billion