CIO

“If you're budget additive to a company, you probably want to be bottoms up selling motion and a small unit value. These new CIO or CFO is going to wake up saying, I need your new widget. So you have to be a small unit value and kind of bottoms up and that's in…”

“Remember, they're introducing you to CIOs and VP-level people. That's not what you need in the first two years.”

“Pure tops down sale. I will never be able to go into a CIO's office and show them a really spiffy deck and give them a customer reference and get a deal, right?”

“Do you know the average CIO is like a Five year tenure. I did, I actually thought there were like, 15 years. But no, a friend of mine was like, oh no, it's three to five years.”

“It won't stop because the venture guys will be mature. It won't stop because the founders will kind of be more careful. It won't even stop because the LPs will stop. It will stop because the LP's bosses, the overall CIOs will stop allocating capital to venture…”

“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 had spent my entire life Doing the soul crushing exercises of selling to CIOs, and it's just a soul crushing work.”

“The way you see it is, you're, you see those CIO surveys where they rank their priorities. And what happens is, you know, as AI has gone up the zeitgeist, it's gone up the priority list, and just something that was number three goes to number six, and then it …”

“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…”

“I think you have to be unwaveringly aggressive now on BD and sales, because I think you have an 18 to 24 month period where CIOs, CISOs are like, hey, we have to have it, we have to have a message for it. That won't last forever.”

“All the enterprise stuff is still in some sense rogue today. So much of it is rogue. It is out of budget. It is out of band, and as that changes, it will change which vendor we buy from.”

“Salesforce, Shopify Datadog, Databricks, they, if they can execute faster than they've executed the last 20 years or eight years, however they are, of course, CIOs want to buy from Salesforce.”

“What has not changed is if you have the guts to pick up the call, the phone, call me, leave a voicemail, text me, email me, call me again, that there's nothing, nothing replacing that because dude, like all these CIOs are getting inundated, inundated with AI p…”

“Every CIO I speak to is really keenly aware of, we cannot, you know, throw our lot in with just one model provider. We're gonna need to be agnostic.”

“I think going into 20, 27, CIOs and others are gonna be like, okay, just show me the F and ROI. We're not gonna, not just gonna ration tokens based on who we like the most in the company and who makes the best PowerPoint pitch. Show me the ROI.”

“When the pressure on spend is out there, the sentence you said that really resonated with me is every company is going to have an internal tiering. They might all buy it from OpenAI or Anthropic, but every company with a CIO who's half awake It's going to have…”

“Next year is going to be very explicit budgets for everybody on AI and exactly. I mean, it's captain obvious to say, this is one of the areas in venture and everything where everything's up. Everything's great. Everything's great. I mean, Not, not the pre-AI c…”