Premier tech-enabled real estate property services platform is building a best-in-class executive team as it enters its next phase of growth.

SCOTTSDALE, Ariz.–(BUSINESS WIRE)–Lessen, the premier tech-enabled, end-to-end solution for outsourced real estate property services, announced today the appointment of Joshua Swift as president, residential sector, and Michael Krumwiede as chief strategy officer. The addition of Swift and Krumwiede, real estate and technology veterans formerly with Zillow and Colony Starwood Homes, underscores the company’s commitment to building a best-in-class leadership team as it enters its next phase of growth.

These strategic hires come on the heels of Lessen’s acquisition of SMS Assist, the largest private-to-private PropTech M&A deal to date, creating the leading tech-enabled real estate services company in the U.S. serving approximately 250,000 residential and commercial properties and facilitating about 2.5 million repair and maintenance orders annually.

In his new role, Swift will lead the business execution, strategy and growth for Lessen’s residential platform. This includes offering broader services to the existing customer base, expanding to new markets and customers and building strategic partnerships. Swift’s teams are focused on operational excellence and elevating the client experience across the entire residential lifecycle to deliver exceptional results and cost savings for Lessen’s clients.

As chief strategy officer, Krumwiede will drive the creation of sustainable and scalable strategic plans for the business and the goals to execute Lessen’s vision. He will also evaluate and lead expansion opportunities, such as partnerships and new business lines, as well as capital markets activities to fuel growth.

“Josh and Michael bring a wealth of knowledge and deep experience in the real estate and technology sectors, having developed and led growth of early-stage companies to large-scale national enterprises,” said Jay McKee, CEO of Lessen. “Their expertise will be invaluable in shaping and executing our strategic vision as we scale to provide a world-class service offering to our customers.”

Swift brings 20 years of experience in leadership and executive roles focused on operations, product, asset management and investment management. As SVP of Zillow Offers, Swift was a key senior executive leading Zillow’s transition from the digital to the physical world. He oversaw the creation of the iBuying division and the expansion of the business to 25 markets within the first 24 months of operations while leading a team of over 1,500 people. Before Zillow Group, he served in various executive leadership roles in the single-family rental REIT sector with Colony Starwood Homes and predecessor companies. Swift has a proven track record in the growth of start-up companies to create large private and public platforms.

“Lessen is strategically positioned to be a market leader in both the residential and commercial services space,” said Swift. “We have a great product that is in high demand. I am very excited about bringing together the talented people across the organization and combining them with our best-in-class technology to deliver an outstanding customer experience.”

Krumwiede brings over a decade of experience leading teams in corporate strategy, capital markets and finance in the real estate and technology industries, ranging from early-stage to public companies. He served as vice president of capital markets & strategy at Zillow, vice president of capital markets & corporate development at Colony Starwood Homes and held senior positions at Invitation Homes, the largest public single-family rental REIT in the U.S. Previously, he worked in investment banking with Moelis & Company. Throughout his career, Krumwiede has orchestrated over $45 billion in mergers & acquisitions and capital formation, creating two large-scale national real estate platforms.

“Lesson’s enterprise solution tackles age-old property services pain points in one of the largest asset classes in the world,” said Krumwiede. “I’m thrilled to join the talented team at Lessen, build on its strong foundation and help drive our next growth phase.”

About Lessen

Lessen is the premier provider of tech-enabled, end-to-end renovation, turn, and maintenance services for the residential real estate rental industry. Powered by our proprietary technology suite, our local field project managers deploy and oversee a network of vetted service professionals in 40+ markets delivering consistency, quality and speed, at scale. Lessen enables our clients to overcome labor shortages, reduce headcount and overhead, grow and scale their business and benefit from our supply chain and buying power to secure project materials – Lessening burden, saving our clients time and money.

Lessen Inc. is a venture-backed, privately held company headquartered in Scottsdale, Arizona. To learn more, please visit

About SMS Assist

SMS Assist, a Lessen company, is redefining the way service providers and property owners work together by delivering unprecedented transparency and control within the facilities maintenance industry. Retail stores, banks, restaurants, rental homes, and more make up the over 200,000 properties that rely every day on our technology platform, in-house subject matter experts and 24/7 support. We leverage our network of 20,000 skilled providers across more than 55 trades to deliver an exceptional maintenance experience to the communities where we live and work.

SMS Assist has offices in Chicago, IL and Phoenix, AZ. To learn more, visit


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