Greenhouse CEO Daniel Chait on how AI is changing human resources and weaning his company off venture funding via private equity

I *think* Daniel and I met at a VC happy hour many years ago. But outside of the history, he’s one of my favorite people to chat about the roller coasters of company building. He’s founder and CEO of Greenhouse, a ‘hiring operating system’ for companies which spans recruiting and onboarding tools for enterprises and SMEs. Originally backed by venture capital, in 2021 Daniel worked with TPG, a large private equity firm, to make them the majority investor. This means the company is predominantly owned by the management/team and TPG. It might ‘exit’ again at a later point (anything from a sale to an IPO), but it’s no long dependent on VC funding. There’s a ton of writing out there about getting *on* the venture curve, but not a lot about getting *off,* so Daniel’s advice below is especially important.

Hunter Walk: Before we dive into your company Greenhouse, give me one story from your childhood that foretold you were going to end up a startup founder.

Daniel Chait: Oh man, I have a ton of these! Looking back it was pretty obvious where I’d end up in my professional life. I was the kind of kid that (a) didn’t really buy into authority figures, and (b) loved solving problems and building stuff. I was also very fortunate to come from an entrepreneurial family; both my parents ran their own businesses. My dad had a medical practice and my mom founded an HR company at the kitchen table and grew it into a global powerhouse in their industry.

To pick just one representative story… I was sent to the principal’s office one day in high school, probably for goofing off in class. I never did much that was all that bad, but at the same time, I was bored in school and often thought it all felt pretty pointless vs doing “real work” which I loved. So anyway, I was waiting in a little area outside the principal’s office for him to call me in. As I sat there I was overhearing the secretaries complain about this new computer program they had (WordPerfect, my guess is it was 5.1 for DOS), which they were struggling to use.

Well, as it happened I was pretty much an expert WordPerfect user. Pretty weird hobby for a 15 year old kid but I had used it at my…