Rich sits down with Chris Cunningham - Entrepreneur, Business Executive, and Head of Social Marketing of Clickup, a productivity and project management software company he was on the founding team of in 2017. Before founding ClickUp, Cunningham worked as a sales manager at Cvent. He was there as the company went public. Once he reached his ceiling there, he moved on to run FastFollowerz with Zeb Evans. Chris went on to do over 50 million in sales there. 

He continued on with Zeb to help start ClickUp, a platform that simplifies and streamlines project management for businesses and individuals. He was the companies first sales rep, closing the first big deals in company history from Home Depot, Randstad, and many more.

Under Cunningham’s leadership, ClickUp has grown rapidly, attracting over 200,000 users within its first year and expanding to over one million users within its second year. ClickUp has been recognized as a top productivity app by numerous publications and has received funding from notable investors including Craft, Tiger, and AZ16. ClickUp has raised upwards of $400 Million in investor capital and a $4 billion valuation.

Rich and Chris start off by discussing an overview of ClickUp, different ClickUp competitors, how ClickUp got it’s start, ClickUp’s first big deals, ClickUp’s biggest challenges, comparative price points, and breakthrough moments.

They then reflect on building companies, Home Depot and Randstad, faking it ’til you make it, advertising in San Diego, being a household name, how it get’s easier with every deal, and being a $1 Billion company. 

Lastly, Rich and Chris talk about the return profile of tech companies, selling companies or going public, where to raise capital, Brad Rice, the types of investors that Chris and ClickUp finds, the next steps for ClickUp, the advantages of project management, comparing CRMs, the Padres and the MLB, and living in South America. 

 Connect with Chris on Instagram: @cunningham

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