Awards

2020 HW Tech Trendsetter: Court Cunningham

Orchard, Cofounder and CEO

Court-Cunningham
Court Cunningham, Cofounder and CEO, Orchard

Court Cunningham’s vision for real estate is to provide a fully-integrated, one-stop-shop for homebuyers and sellers. Through the founding of Orchard, Cunningham pioneered the “buy before you sell” model for the company, which solved the conundrum that plagues the majority of homebuyers: having to sell their home before buying a new one. Under Cunningham’s leadership, Orchard is fundamentally transforming the home-buying process from online home search, to managing listings and showings online, to an all-digital closing, similar to what Amazon has done for retail, or what Carvana has done for car buying. Orchard’s customer-first model means every development Cunningham leads has been to directly help homebuyers and sellers. Orchard’s customers receive the benefit of having access to Orchard’s advanced technology and an experienced licensed agent, all for the same fee as a traditional broker. Some specific examples of how Cunningham’s vision has helped Orchard, and therefore its customers, include: Cunningham’s leadership in the decision to recruit from a diverse set of backgrounds has led to a diversity of thought which helps to deliver the best possible customer experience, Cunningham’s “startup within a startup” mentality, and his emphasis on a customer-centric culture that understands that the customer experience can make or break a business. 

Most Popular Articles

Smith Douglas Homes Doubles Down On Pace And Growth

While many homebuilders, such as D.R. Horton and Tri Pointe Homes, significantly reduced the number of new home starts over the last quarter amid sluggish homebuyer demand, Smith Douglas Homes Corp. is taking a different approach, akin to that of Lennar. Pace over price.  The builder’s strategy reflects a commitment to affordability and serving the […]

Mar 18, 2026 By

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HousingWire on Tuesday announced the launch of the HousingWire Mortgage Rankings, a new performance intelligence product designed to provide a clear, data-driven view of mortgage origination activity across the U.S. The rankings benchmark mortgage originators based on observed production, offering a standardized view of performance across geographies, loan types and channels. Historically, the mortgage industry has lacked […]

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