2022 HW Vanguard: Court Cunningham


As co-founder and CEO of Orchard, Court Cunningham sets the company vision and strategy that propelled Orchard to 850 employees in five years. Under Cunningham’s leadership, Orchard achieved triple-digit growth in 2021 and will more than double its growth this year. Orchard’s explosive growth is a testament to Cunningham’s commitment to delivering value to homebuyers and the real estate professionals who serve them.

Cunningham inspires and empowers the entire company. Through transparent town halls and regular communication, Cunningham helps everyone to feel ownership over the work they do. Orchard’s spring 2022 anonymous engagement survey for employees revealed over 90% confidence in Orchard’s leadership, with 100% of employees sharing that the leaders at Orchard keep them informed about what is happening, both within the organization and within the larger industry. 

What has been the secret to your success?

Success begins with the people you hire. As a CEO, you should build a team around you that is empowered to take risks, own them and find a way to try new things. 


Court Cunningham



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3d rendering of a row of luxury townhouses along a street

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