Chief Technology Officer

“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.”

“His name is he's our lovely CTO. We met working in engineering company previously. He's 19 years old managing 40 people now.”

“Don't chase the title when your personality is not suited to the title”

“When you build something, you typically build with the CTO in mind, thinking I'm going to build this and I'm going to go and sell to the CTO. The CTO is where you sell, but then you actually get a check from CFO, where it's used by the CAO. So all of that mapp…”

“From CEO to CTO, like, the way I think about it is your CEO needs to be able to sell anything your CTO can build. Your CTO needs to be able to build anything your CEO can sell. And as long as those two things are true, there's a really good match, and you can …”

“I think the highest turnover job of any executive at Silicon Valley might be the CMO. I don't know for sure, but like, you know, you don't see a lot of turnover CFOs. You don't see a lot of turnover CTOs”

“If I had a company that required super, super deep technical expertise, I think that would be the case where I would be much more skeptical of having a single Person that has it all. And I would want a separate technology officer versus not.”

“My advice generally is don't try to optimize. Don't try to cost cut at the beginning. Start by just giving engineers as many tokens as possible.”

“I think chat GPT would probably be. The worst CTO because it's such a people pleaser and it's so sycophantic”

“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 has got to marshal the resources of the whole company to get what he needs to get the job done. And if you go to like a junior person, you're like five levels below you and make her cry. You know, you're probably right, but like, you're never going to …”

“CTOs tend to be skeptics. They're, they love facts. They seek knowledge. They want depth of awareness and understanding, and they also like to be self-sufficient. This is a total generalization, but I've seen this pattern over and over again. The CEO is the pe…”

“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…”

“How do we tell our story to a non-technical buyer? Because it moved a lot from the CTO to the chief compliance officer at that certain point. And that, you know, went up to the CFO when there was audit pieces.”

“There is a conflict between the CPO and the CTO that actually drives innovation in my opinion, because one person is trying to optimize the resourcing, the fixed, right? While another person is actually trying to field opportunities and figure out how to wait …”

“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…”

“What I started to learn pretty early on is that people don't like to talk about their struggles shipping. Especially, you know, CPOs and CTOs don't like to go on a public forum and say, our company isn't shipping, or our engineering team is stuck, or our team …”

“We actually landed a unicorn. He was a former bike cop that decided to ditch Law enforcement and go data scientists and machine learning.”

“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.”

“The real risk is having a CTO that you don't know that well is usually a disaster. You can't trust them in the same way that you can somebody you've worked any amount of time with.”

“And across hundreds of CTOs, the answer has been zero. No one thinks it's actually going to replace.”

“Did you know the team, the CTO, is also their sales leader? Not a business leader. Their sales leader is also the CTO.”

“So CMO to CMO connects. CTO to CTO connects so that they can discuss challenges and goals. That in and of itself is delivering a differentiated experience because you're offering strategy in a way that maybe your peers aren't able to do, particularly not at sc…”

“If your CTO by today, isn't sure how to, doesn't, isn't sure how to integrate AI into your product. Ask yourself if you need a new CTO. It doesn't mean get rid of them, but your competitiveness, I think is going to continue to decay and accelerate.”

“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.”

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

“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.”

“Chief architects and CTOs are pretty inefficient in terms of Actually getting enough context in their heads to make a good decision on any given, given point.”

“Typically when a CEO of a 500 person company feels their CTO is, is struggling, they're probably running into like one of two different things. Either the individual CTO is like causing friction with other people on the team. For some reason, like their peers,…”

“Which, what CTO wants to talk to the CMO of DevSecOps? Like my platform, but they definitely want to talk to somebody that is working on understanding their needs. That was a former customer and that wants to come back with a team and understand, are we strate…”

“Going forward many companies will bring on AI architects that might even be at the same level or report directly to a CTO to think about what are the models that we're going to use and what are the boundaries of AI and how can we build reproducible AI and thin…”

“In today's world, almost in everything that we're doing, we need a technologist, right? ... You can be a CEO material, but you need a CTO in today's world. In whatever you're building.”

“The number one reason I see these failures happen is when the CEO's like pretty good, they're committed, they'll do it for 10 years, they'll run up the hill, they'll, they'll hustle, they'll get the sales, but the CTO isn't that good.”

“Keep your identity, like your personal identity, small and flexible and agile. And the reason I say that is if you attach your identity to any specific aspect of your job or you get, you know, self-esteem from, You know, writing code well, or writing a certain…”

“We need actually properly done experiments that measure what kind of impact interacting with these systems over the course of months will have on people's psychology, and we need actual institutional review boards overviewing the ethics of these experiments, r…”

“I view the CEO as the proxy for sales and marketing. Like if the CEO is great with some help, maybe you and I can, we're working on a search together day. We can help you find a sales and marketing leader. But I don't really care who you have at a hundred K in…”

“While I have no doubt that there are some CTOs out there that can also build a business, but I am a firm believer that a CTO is a great product technology partner, but the business is built by the CEO.”

“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.”

“It's very rare that you find someone who's going to be a great CTO. Who's also willing to like go build the first application and be the lead engineer and do everything from scratch”

“I think it's important for the product organization, even though it's very small, to report directly to the founder CEO. Sometimes I see it tucked Under the CTO, and obviously that can work too, but I feel like it's a better way for the founder to stay involve…”

“By this point, you're absolutely going to need a VP of engineering. This is somebody who helps the CTO with the actual managing of the organization. You know, it's pretty commonly the case that the co-founder or CTO is chosen because of their technical chops a…”

“So I strongly believe company cannot live without CEO. That's for sure. Most companies cannot live without head of sales and CMOS. But probably you can leave without, you know, a CTO. You can hire a CTO.”

“CTOs do a very specific job. They run technical organizations and the skills required to do that are very different than somebody that's building out the first version of an app.”

“We were targeting at that point in the beginning, it was like founders you know, CEO, CTO. It is mostly that. And then as we sort of continue to grow and scale and expand you know, we went into the HR job title, the idea admins and so on.”

“When you're talking about not having a technical co-founder, what I'm actually implying is in this scenario, I wouldn't advise going out and finding a CTO or technical co-founder. And I don't think Tyler is saying that's what they want to do, but what you're d…”

“Yeah. Yeah. It's crazy. That's insane. Yeah. Yeah. Yeah. And sometimes it's even like Word documents stored on on their hard drive or stuff like this.”

“So the CTO does, our CTO I've offered equity to the developers. They weren't real excited about that. I mean, they wanted, it's a personal choice. Most of the people on our team do have equity but the developers don't.”

“So many open source companies have died because they transact around the edges with like director level or technician level with, for support. And they never got to the CTO, the CIO and true strategic account control like the big players had.”

“Community development's really important, but if you just develop a little community, and it doesn't change a CIO, a CTO, anyone that's writing as serious as checks priorities, like by definition, you didn't build a software company that had an opportunity to …”

“The VP of engineering every morning wakes up thinking, do I have the absolute best team? Is my team in the best position to deliver what they need to deliver? It's a people person. Yeah, I'm really thinking about making sure that your engineer's in the righ…”

“Yeah, it was both. And we didn't agree on, on, you know, how to make it happen.”

“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 …”

“I think when you get to a hundred customers, you just have to do that, right? If you're a SaaS B to B, of course. Before that, you could compromise depending how deep the founder and the CTOs are in the product.”

“When you have a CTO separate from a CPO, it creates this natural tension where you have one person whose job is to kind of be driving the business, driving the strategy, and then the CTO is more focused on how it's done and also making sure that You know, I ca…”

“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.”