Real Estate
Court Cunningham
Phil DeGisi
Accomplice, FirstMark Capital, Revolution Growth

Orchard, founded in 2017 by CEO Court Cunningham, Phil DeGisi and Juxtapose, takes a fully verticalized approach to help people with their most important and painful transaction: the sale of their current home and the purchase of their next one. The insight to Orchard was based on the observation of the sheer number of moving pieces in these large transactions, as well as the number of parties involved, and how all of this caused not only unnecessary complication for people but also increased the cost of the transaction. Orchard's novel technology streamlines this process by providing users with a one-stop shop for all of their needs, from finding the right new home to securing financing, selling their current home, buying title insurance and more. Orchard's best-in-class technology platform allows it to guarantee backup offers for people's current homes, helping them unlock their equity up front to make an offer on a new home without contingencies. It also uses technology to enhance the experience of buying a new home, offering personalized property recommendations as well as connecting buyers to mortgage lenders. Today, Orchard operates nationwide and is enabling billions of dollars of home sales every year.

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founding CEO

Court Cunningham

Court founded Orchard with a passion for simplifying the convoluted home buying and selling process in the US. Previously, Court was the CEO of Yodle for nearly a decade, completing its sale to Earlier in his career, Court was an SVP at DoubleClick.


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Article Title
Court Cunningham

"Buying a home is the single biggest financial decisions of most consumers' lives. I found the opportunity to make this stress-free, fair and simple while transforming a $2 trillion market incredibly exciting."

Year Founded
Real Estate
Transforming life's most stressful transactiON

We partnered with Court to build a next-generation real estate platform that transforms the way everyday Americans buy and sell homes. Today, Orchard offers consumers AI-powered home discovery, on-demand purchasing so customers can buy a new home before selling their old home, and a modern digital closing—all for the same fee as traditional brokers. Court was previously the founding CEO of Yodle, where he took the company to over $200M in revenue and over 1,200 employees.

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Court before Orchard

I was previously the CEO of Yodle for 9 years, where I and the team grew the business from inception to over $200M in revenue and sold the business to in March 2016. Yodle was a leader in local online advertising that connected small businesses to consumers simply and cost-effectively through websites, SEO, email and SEM. Prior to Yodle, I was SVP of Marketing Automation at DoubleClick, where I built an industry-leading email marketing solution that was sold to Epsilon in 2005. I received an MBA from Harvard Business School in 1997 and a BA in English from Princeton University in 1991.

Career Highlights


Met Phil DeGisi, my co-founder at Orchard, who has been the best business parter of my career with his grit, creativity and practicality.


Sold Yodle to for $342M.


Launched DartMail, one of the first email marketing platforms in the US, and scaled it to the de facto industry leader in 5 years.


Met the woman who ultimately became my wife at her high school graduation (she was 18; I was 12...)

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