Chief Technology Officer

“I think that one of the hardest decisions is the fact accepting that the guy that was with you or gal on day one is not likely to be that SVP of sales or even CTO that you might need to scale your company as you hit thirty million users.”

“Our hardest role to hire for was the CTO position, without a doubt. We're an enterprise software company based in lower Manhattan of all places. There's not a lot of people who have built a multi-billion dollar enterprise software company and virtually all of …”

“When I see both as an A plus and any traction at all, like any traction at all, I feel like I literally cannot lose money on that combination.”

“Overall, I would say, 80% of the time, the CEO is better than the CTO, especially at the seed or early seed stage”

“In the old days, I would do it late in the process. I would get to know the CO would talk to the customers, right? I would go deep and then at the very end, I'd be like, okay, I gotta talk to your CTO Harry to make sure that this is real. Now I immediately ski…”

“Asking the CTO what they, what frustrates them and their product is very telling. The great CTOs will answer in 60 seconds.”

“The CTO or the IT folks are actually the people that know the least about the business. The people that, that actually understand how to use AI in a business context are those that are closest to the business.”

“If you go and talk to a CIO or a CTO of a large enterprise today, they're furiously seeking out ways to apply AI to their business. And the reason for that is because their CEO and their board told them, you're going to get fired because the entire fate of our…”

“I just don't subscribe to that theory. If I'm gonna sell a CIO, a CTO, some C-level executive a solution for millions of dollars, and if that solution fails, he's gonna lose his job, and so are a bunch of other people, and it's gonna have a very serious negati…”

“The CTO at some point up to 50 people, you're golden. And then at some point you go, actually we could bring in better, better technical skills. And if you've got a good co-founding CTO, that person becomes like a Swiss army knife and is deployed in different …”

“The CEO being a good salesperson and being a real entrepreneur is actually more important because the CTO role can be fungible depending on how complicated it is.”