Lessen’s CEO, Jay McKee, has been named one of GlobeSt.’s Influencers in CRE Technology for 2026. Under Jay’s leadership, Lessen has grown into a national platform that brings together technology, AI, and operational excellence to transform a historically fragmented industry. Today, our solutions support real estate portfolios across more than 280,000 properties, delivering faster service, greater visibility, and more consistent outcomes. We are proud of the momentum our team continues to build and grateful to our employees whose work makes this impact possible every day. If you are interested in being part of a company shaping the future of real estate technology, we would love to connect.
Last week, we had the opportunity to celebrate Employee Appreciation Week at Lessen, recognizing the incredible people who power our success every day. From fun color-themed spirit days and swag giveaways to coffee bars, taco stands, and team photos across our offices and remote teams, it was a week full of connection and celebration. We also recognized 23 outstanding employees who exemplify Lessen’s core values and make a meaningful impact across the organization. At Lessen, we truly value our employees and are grateful for the dedication, teamwork, and pride they bring to their work each day. Their hard work is what makes our success possible, and we are proud to celebrate and thank them.
In December, our sales team gathered in Scottsdale for our FY26 Sales Kickoff—an energizing opportunity to come together, build connections, and align on what’s ahead. These moments matter: they give us space to collaborate, share ideas, and plan how we’ll support one another in the year to come. The week reinforced what makes this team special—smart, driven people working together toward shared goals. We’re heading into the new year energized and excited about what we’re building at Lessen.
2. Our founder and CEO, Jay McKee, was recently selected by Commercial Observer for their Power Proptech list — a recognition reserved for leaders driving the future of real estate technology. Jay earned that spotlight for bold moves like Lessen’s $950M acquisition of SMS Assist, one of the largest proptech deals in industry history. Today, with 30,000+ vendors and more than 4 million work orders processed annually, Lessen is transforming property services with AI innovations like Lessen Copilot and our Advantage Marketplace. It’s fast growth with real impact — and we’re just getting started.
1. Built In recently featured Richard Gray, Enterprise Sales Director in Lessen’s Commercial division, in its spotlight on enterprise sales leaders. Richard shared how his 15 years across commercial real estate, facilities management, and tech-enabled services shaped his approach to enterprise partnerships: “Selling to enterprises takes empathy, data, and a deep understanding of the customer’s world. Each deal is like solving a puzzle, and the reward is seeing your solution improve performance across hundreds or thousands of locations.” At Lessen, that philosophy drives how our team helps large, multi-site operators modernize facilities management and deliver measurable impact. https://builtin.com/articles/what-its-work-these-enterprise-sales-team#Lessen
Happy Thanksgiving from the team at Lessen! As we head into the holiday season, we want to wish our clients, vendors, and teammates a very Happy Thanksgiving. This time of year is all about gratitude. We’re especially thankful for the incredible people who make up our Lessen community. Both our Scottsdale and Chicago teams kicked off the festivities early with in-office Thanksgiving lunches filled with good food, great conversations, and a chance to pause and appreciate one another. Moments like these remind us how fortunate we are to work alongside such dedicated, collaborative, and caring teammates across all our offices. Whether you’re celebrating near or far, we hope your holiday is full of warmth, rest, and time with the people who matter most. From all of us at Lessen — Happy Thanksgiving!
Discover the Story Behind Lessen’s Growth Curious about what it’s like to build one of the fastest-growing companies in property services? Check out the September 2025 issue of Lifestyle WPC magazine, featuring an exclusive interview with our CEO, Jay McKee. Jay shares how Lessen evolved from a bold startup idea into a national leader transforming property services through technology, innovation, and teamwork. He also gives a behind-the-scenes look at our expanding suite of products—and the people driving our success. If you’re passionate about innovation, collaboration, and shaping the future of property operations, this feature is a great window into who we are and where we’re headed next. For the full story click here - https://wpcareymagazine.com/issue/autumn-2025/the-power-of-place/
Honoring Veterans Day at Lessen Today, we join the nation in recognizing Veterans Day — a time to honor the brave individuals who have served in the United States Armed Forces, remember those who made the ultimate sacrifice, and celebrate the families who have supported their loved ones through service. At Lessen, we’re proud to have team members who have served our country or who have family members currently serving. Their courage, dedication, and integrity reflect the same values that drive our work every day. We extend our deepest gratitude to all veterans for their service and sacrifice — today and always. Thank you for your service!
Lessen Named One of Arizona’s “10 Startups to Watch Heading Into 2026” We’re thrilled to share that Lessen has been named one of AZ Big Media’s “10 Arizona Startups to Watch Heading Into 2026.” This recognition is more than a milestone—it’s a reflection of the innovation, collaboration, and customer impact driving our team every day. From scaling smarter property operations to modernizing how repairs, maintenance, and capital projects get done, we’re proud to be building right here in Arizona—and growing nationwide. At Lessen, we’re reimagining what’s possible in property services through a platform that connects technology, talent, and trusted partnerships to deliver real value across every property type, at every scale. If you’re passionate about building the future of property operations, there’s never been a more exciting time to join us. https://azbigmedia.com/business/10-arizona-startups-to-watch-heading-into-2026/
Halloween at Lessen: A Spooktacular Celebration Across Our Offices! From candy and costumes to cocktails and conversation, our teams in Chicago and Scottsdale celebrated Halloween in true Lessen style! In Chicago, the 22nd-floor kitchen transformed into a festive haunt filled with treats, snacks, and plenty of laughs as the team gathered for a Halloween Happy Hour. In Scottsdale, our crew enjoyed a frightfully fun afternoon featuring great food, drinks, and music from our in-house DJ Tyler Hosley—the perfect soundtrack for a howling good time! We loved seeing everyone’s Halloween spirit—whether in person or through the photos shared of kids, pets, and family costumes. Thanks to everyone who joined in the fun and made this Halloween one to remember! Pictured: Our Scottsdale Accounts Payable team, knocking it out of the park as the Rockford Peaches from A League of Their Own!
