CIO

“Will a handful of CIOs get very publicly flogged and fired in the next year because they accidentally didn't understand this and just did an API deal because they wanted to feel popular and leaked data into these models? Guaranteed.”

“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…”

“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…”

“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.”

“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.”

“When we talk to the CIO, they know that their engineering teams are using cloud code and codex and cursor, and they're seeing the productivity gains come out of those teams.”

“I think the tone is actually remarkably optimistic and excited and positive as opposed to, you know, there's a sort of, You know, typical trough of disillusionment, you know, from Gartner and the hype cycle or whatnot.”

“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…”

“One CIO that was a very smart guy, but a bottleneck. And it wasn't a scalable model.”

“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.”

“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.”

“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.”

“Their fear is, like, unleashing, not just the agents themselves, but humans to do integration. Because you put, People creating new integrations. And you just say, please break my system of record.”

“This is going to be, like, the new big question that every CFO, CIO, et cetera, is running around trying to, with their hair on fire, trying to figure out.”

“If you are the CIO organization in a Fortune hundred company, and you are thinking about an SAP or an Oracle migration, well, call one 800 Tessera, because if you are looking to drive a major, you know, system of record migration without exploring What, you kn…”

“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…”

“What we tell people is that I think the winners are yet to be identified and so experiment with more vendors, do shorter term contracts.”

“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 …”

“Today, our customer is the CIO. I think over time, our customer becomes a partnership with the CIO and the CFO.”

“There has to be top-down alignment. That's what we found, is that there has to be alignment from senior leaders that this has to be done. Because as you get into larger organizations, the actual folks doing the implementation, it can be a very large team. And …”

“With AI, what happens is because these AI chatbots or agents that you create are non-deterministic and can really go access any system, I think a lot of CIOs, CTOs are kind of nervous because there is so much of their internal infrastructure that may not be pr…”

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

“If you are there, every buyer, every, especially the enterprise, every CIO has AI budget today. We can talk about whether it's discretionary or budgeted or where it's coming from. Everyone has budget for AI. So more money's going out at the CIO's office at the…”

“It's not useful for me to have a meeting with the CIO. The CIO does not care about his time series database. I mean, he should maybe, but he doesn't.”

“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…”

“18 to 24 months back when I used to speak to a lot of CIOs, one thing people which came out which very common was... Okay, I want to know what you guys are doing in AI... But do not roll out. If you roll out, I'm switching off your software today because they …”

“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…”

“Increasingly what is happening is that the most progressive of the CIOs and the chief data officers What they want is independence with respect to vendors, including Snowflake. So they want their storage, their data to be stored in vendor-neutral formats, in o…”

“All these CMIOs and CIOs are on WhatsApp groups every single day and talking to each other. And if you screw up with one of those health systems, maybe two of those health systems, you're kind of done for like a couple years, probably. You don't get another sh…”

“It's almost primarily a developer led motion in pretty much every environment. CIOs have to be accountable and responsible, but they're learning, they're being taught by their developers, the things that they've been distant from for quite a while.”

“Giving them that language as a CIO to partner with their peers is a really important part of the value we bring, and we do that behind the scenes with them and educate them on, it's not just about what language they want to use, it's about the language they ne…”

“Yeah, he put in the controlling trust document the fact that he wanted the trustees to delegate investment authority to the CIO and CEO of the foundation. That's unusual. We do not have an investment committee.”

“Career risk aversion drives a lot of behavior, and Bill felt to the extent you could put some distance between the asset allocator and the oversight or governance group, you had a shot at allowing the CIO to be more bold, because Bill always said, boldness is …”

“It's not easy because there can be screaming opportunities and China might be perfect example today where intellectually a lot of CIOs know these valuations are getting unjustifiably cheap. But back to career risk. They don't want to walk in, in front of their…”

“There's this whole sort of thesis of bottom up enterprise software sales that you don't need to sell to the CIO. You make this amazing cool tool and the users will discover it and use it. And what actually happens is that most that that always works for like t…”

“On the investment side, most CIOs will embrace the opportunity to wait and see which managers Yale supports in size. They're happy to outsource wading through large fields of chaff and see if Yale finds wheat.”

“It's largely not an investment job. I think people kind of know that, but I'd take it maybe a degree further. There are many functions that make an investment organization work well, and they are all important. Some of them are important because if you step on…”

“Around us, CIOs were leaving their jobs without a transition, and the teams below them would leave In anticipation of a new boss coming in over them, and they wanted to take matters into their own hands rather than just wait for fate to dictate what would happ…”

“And I think that's another thing that's really important as a CIO is to give your team members the opportunities to grow professionally without dropping problems in their lap, being incremental about it.”

“First of all, I wasn't given a choice, but second of all, I think ideally that would be the best way to do it because it gives the successor the opportunity to get his or her sea legs under them without necessarily the scrutiny of sitting there in front of you…”

“Let, I think, eight percent of CIOs have a budget increase over 10%. So, 92% don't. So, think fixed, you know, near fixed budget, but 85% of them say they're aggressively increasing their spend on AI.”

“There's less of an emphasis on end user experience, I think in the enterprise space, because once you're kind of over the line where the CIO says, okay, that's on the checklist of things that your software does, anything above that doesn't really matter very m…”

“When a CIO departure occurs, the growing manager will have more options to continue a productive working relationship with the new CIO.”

“A CIO can't manage another CIO's portfolio because you really do gravitate to your strengths.”

“I knew that one of the big problems with CIOs is they stay too long. And I do think portfolios need refresh.”

“And so our team is really good at politely declining to engage, right? Not just because the use case doesn't fit or it's not ICP, but we qualify the champion out, even if it's a CIO.”

“The edge that they had was eventually the route to the CIO, the CTO to then just, all right, let's just Deploy this across the whole organization. That path is very short. Whereas for many PLG companies like us on the distance was really long.”

“I have a tremendous amount of respect for people who do the CIO job because every day you're relearning things that you thought that you had figured out about a manager disappointing you, manager surprising you, things you missed”

“A CIO doesn't make that many decisions a year. You're not running a pod for .72. The ability to move a highly illiquid portfolio is not easy.”

“Managing people and managing investments are not the same side of your brain. There's no a priori reason that someone should be skilled at both. And maybe there's, in fact, the opposite. If you're an analytical, quiet person, you actually don't want to manage …”

“Usually that hunger dissipates after success, and you probably want to be off manager before that hunger dissipates, but it takes an incredible amount of fortitude to say, To someone across the table, hey, I know you're getting rich, sloppy, and lazy. You're n…”

“And I think one of the great challenges on the CIO side is your job is to figure out systems input hunger, the soul of these people pitching you, but you're seeing them in very controlled context for the most part.”

“How I dealt with it in the novel was to think about the pressure of the CIO, a line that I often repeat to CIOs, which is like, it's three percent of the portfolio, but 97% of our headaches.”

“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.”

“I think there's a pretty reasonable chance that there's some falter in the next 12 to 18 months where there's a crisis of confidence among investors where at some point something will come out Where we all observe, oh, maybe GPTs aren't as useful as we thought…”

“THERE ARE HUNDREDS, MAYBE THOUSANDS OF CIOs THAT ARE TELLING THEIR WHOLE ORGANIZATION NOT TO USE CHATGPT.”

“I want to have a larger number of team captains who are people who have been here for a long time, who we've seen their work product, we trust their work product, and those people can be empowered to make decisions on individual investments because those peopl…”

“I do think when you serve on an IC, you have to remember that you're a coach and not a player in that regard. I have the benefit of seeing ICs from multiple angles, not just serving on them, but also we obviously have a lot of ICs that we present to here as we…”

“Specifically in our category, when it's not a clearly budget line item defined, you always don't start from CIO. You start for the business functions. You end up talking to head of operations or head of sales or someone, and they would, Try to buy Whatfix for …”

“That was the stuff that no one was actually really interested in, but it was the vast amount of effort, and it was where the vast amount of money was, and for that, you didn't spend time with the business, and you didn't talk about innovation. You spent time w…”