EP 376: Can AI Replace a CEO? Our answer might surprise you.
2 Jan 2026 · 30 min
Greg Shove, CEO of Section, argues AI works best as a thought partner for executives, not a replacement. He shares how Claude matched human board feedback 90-93% in a real experiment, and how Section enrolled 14,000 students in 12 months using AI for strategy and tactical work.
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Can AI do your CEO's job? Maybe not yet, but if you're a CEO and you aren't taking AI seriously, you need to. And you need to really take note of today's conversation and the guests that we have on today, because I think that AI can almost do your CEO's job. All right, I'm excited for today's show. What's going on, y'? All? Welcome to Everyday AI. My name is Jordan Wilson and I'm the host. And this Everyday AI thing, well, it's for you. It's your daily livestream podcast and free daily newsletter helping us all learn what's happening and what's going on in the world of generative AI and how we can all use that to grow our companies and to grow our careers.
So.
So if you're new here, thank you for tuning in. As always, make sure to check your podcast show notes for related episodes and to go to our website. The link is in there at your everyday AI.com because each and every day we recap our expert interview in our daily newsletter, written by a human for humans. Let's talk a little bit about if AI can do your job as a CEO. Right? Do you have to be worried about. Right. Are we going to have AI CEOs? There's a couple companies have done some publicity stunts around that. And should every CEO be using AI? Well, I've got a lot of takes on this, but I'm excited for my guests. So let's go ahead and bring our guests onto the show. There we go. We have Greg Shove, the Section CEO.
And the founder of Machine and Partners.
Greg, thank you so much for joining the Everyday AI Show.
Thank you, Jordan. Good to be here.
All right, I'm excited for today's show and for those that aren't aware, tell everyone a little bit about what you all do at Section.
Yes, Section's a business school for the age of AI. We're an online school and we make great business education and great AI education. Radically more accessible, affordable, and just good for anybody who wants to learn online with us. And we do it through live and live cohort, learning and on demand, of course. So we, you know, we make courses and we deliver great outcomes for, for students, employees who want to kind of, you know, get ready particularly for this age of AI. So how do they do their job? How they augment themselves in this moment, which is an AI moment, obviously. And then that machine and partners is an innovation lab. And AI Innovation lab, we build AI apps and prototypes for enterprise customers. So we also have our hands on, or I have my hands on, trying to actually build this stuff besides just talking about it.
Yeah. So before we get into the kind of the guts of today's conversation, I'm curious, as someone that runs in a large online learning center in section, what has the demand been like, Right. Are you guys just getting bombarded with CEOs being like, hey, we've been hearing this AI thing is pretty important, we need to learn it? What, what specifically from CEOs? What has that demand been like from CEOs?
I'd say muted, not so much. I mean, they want it for their employees. I think CEOs are talking about AI as, you know, I think mentions of AI in analyst calls, Wall street analyst calls, has gone up right. The last year. Every CEO wants to look like they're AI savvy and that they're making their organizations kind of AI, AI ready. Which, by the way, is code for saying we're going to be more efficient. Right? We're going to, we're going to save money. Which is also code for saying we're going to lay some people off. So I think that's what the CEO and CFO are trying to communicate. Having said that, I don't think many executives actually have their hands on AI and are not, you know, they're not really using it. I think they want their organizations to be AI ready. And so our demand for AI classes has gone through the roof. Went from zero to over 14,000 students in the last 12 months. So that's great. That's mostly those small business that's, you know, people with, you know, solopreneurs, side hustlers, people who need an edge. If you think about AI, it's an edge, right? It's a productivity and cognitive edge. And people who need that are students, you know, high school or college kids, Right. And then people who work in small business work for themselves, you know, kind of neat. Don't have all the resources of a big company. Right. Don't have, don't have an ability to call it or call the data, you know, the data analyst team or, you know, whatever, right. Can't call a copywriter to write the copy. So those are the people I think came to AI first. And that's why GPT, I think OpenAI had such incredible growth. They tapped into that sort of unserved market which is people that need a little bit of help. Right. And a little bit of a productivity boost. And that's, that's not typically a VP of marketing in a big company. Right. They have all the, they have all the resources they need. Listen, I want to go back to your first question, which is can AI, you know, be the CEO? I've done six startups, one bootstrap, the other five including section, backed by venture capitalists. They can take my job if AI want. If AI wants it, wants the job, AI can have it. It's not, it's not, it's not easy being a CEO, as I'm sure a lot of your audience knows. And as you know, right. Building a, building a small business is not easy. So some days I'm like, hey dude, aiu, Claude, you want my job, it's all yours.
You know, like, well let's, let's even talk. Yeah. Because you know, I, and we'll get into even a little bit of your personal usage. Right? I'm a small business CEO. I use AI all the time. But even maybe for those, you know, those CEOs may be listening right now who might still be on the fence, right?
Or they're like, okay, yeah, I'm pretty.
Sure we need to start using AI. Let's just address it for, for those people. Can AI do their job?
Yeah, listen, I can do. I think one thing that is critical to all of us, I think the best leaders, best individual contributors who want to be leaders, and the best leaders have this quality that I call high low. They can think and, and act high low. And high low means you can be strategic when you need to be, right. You can think about what's our product strategy, how do we price this product, who's the best customer for the product, how do we find product market fit? That's thinking high, thinking low and doing low is I gotta write the press release or I have to write the sales outreach email and stuff like that. And this idea of going from sort of on the ground to 10,000ft and moving between those two modes. High Low are basically operating modes for individuals and for companies or for teams. And you got to go up and down between those two modes all day long, all week long, all year long. So high low to me is sort of a key requirement to be a leader. I think in any size business and I think most of us, it's not natural to us to be good at both. We're typically, you know, often we're good at being operators or we're good at Being thinkers, not usually both and not kind of at the same time. I think we all have strengths and weaknesses. We all have blind spots. Right. We all have strong muscles and weaker muscles. And that to me is kind of the power of AI. When we think about sort of approaching any decision, we should apply this kind of high, low end lens. Right. How to be, again, how to be strategic, how to be tactical. And if, if you're not really good at that, then use AI is, is my point of view. Use AI as a thought partner. I think AI currently is undervalued as a thought partner.
Yeah, absolutely. And you know, speaking of that, we did a whole episode 310 on that exact one. So if you want to go check that out, let's do that. But I want to get to even how CEOs Greg. Think and view, you know, large. Think and view about large language models. So, you know, as an example, I think I'll work with CEOs all the time and they're flabbergasted, right? When I can say, oh, here we can take your transcript of your last meeting and all of a sudden, you know, put your own data in there, run some prompts and all of a sudden you have an email to shareholders, you have a PowerPoint deck and it's all built within chat GPT and you don't have to leave. I think people are amazed. Do you think that there's maybe a, a huge disconnect between this kind of topical awareness that CEOs have of large language models and them actually fully understanding the business capabilities?
Yeah, for sure. Listen, I think CEOs are like the rest of us. They're getting a lot of their AI news from the media. Not media like yours. Right. But kind of mainstream media. And that's mostly misinformation or disinformation. It's just, it's hypergloom. That's the first thing. Second thing you think about certainly a larger company CEO. They're getting their, their AI sort of updates. So they're kind of, maybe they're even, they're kind of, they're, they're, they're learning about AI from their head of technology, typically the cio, cto, then maybe their engineer. And those guys, I think are a little more skeptical and I think they're a little more concerned about it because the hype has been, you know, use AI and you'll be way more productive as an engineer. You're not, you're not going to need as many engineers. I think most CTOs and CIOs are those kinds of people, like, yeah, you know, it's helpful, but it's not a game changer, right? They're not yet hearing from business people. The CEOs not yet hearing business people, like, hey, it made my team that much more productive or that, you know, or we're producing better quality output. So they need to get more stories kind of from their organization around. This is really working. And, you know, this is the benefit we're getting. It took a while. Our company's small section has 30 employees, right? And so it took us a while, right? I was like the evangelist initially. And then, you know, I kind of got what everybody else gets. I think organization a little bit of resistance, a little bit like, oh, here's the CEO, you know, off on a new adventure, you know, talking about AI all the time. And then people start to play with it. And then you know what happens? People bounce off AI, right? They try it. It hallucinates and no, no, no one knows how to prompt. Like, what's prompting, right? That's a weird thing. So people start to play with it, don't get a lot of good outcomes right away. And then they kind of bounce off, right? And you got to push through that. And a CEO does too. You know, his organization, his or her organization has to push through that. And then they have to individually, they, they go try AI, right? And nothing, you know, they're not blown away, right? And in part because what's a CEO do all day? The CEO sits in meetings and tries to make decisions. That's why I think this idea of AI as thought partner is kind of an analog for CEOs to realize that if you can use AI as someone to kind of, you know, talk to someone, something to talk to, right? And load your own data. I don't, I don't think CEOs get this. You can share safely. And again, remember, CEOs are hearing, oh, the data is not safe. They're going to steal your data, train their models on your data again, that's just nuts. It doesn't work that way, right? You can have private AI or secure AI, you know, individually or as an organization. But this idea of loading your business plan into AI, or loading your product roadmap, or, you know, information that's important to you, and then have a conversation with your AI about it and expose your blind spots, expose some things you haven't thought about, right? Unintended consequences, unforeseen risks. These are things CEOs need to think about. That's called high Low and use AI to do that.
You know what, Greg? I do have to call out the hypocrisy because I hear this all the time of companies not even wanting to use large language models for that reason for data security and data privacy. And I always ask them, right, like if we're doing consults with people, I'm like, okay, where do you store your files? Oh, you store them in a cloud system. Guess what?
That same provider is already has this.
Quote, unquote, access to the data. So, you know, I always scratch my head about that one, but that's beside the point.
Yeah, I think that's a general mistrust of big tech. Honestly. I think that's, you know, at the CEO level or any level, I think that's a, that's probably of some, some perception that later they're going to find a way to take our data and either monetize it, you know, or create some advantage from it. And they'll change their, even like they'll change their terms and conditions, which is hap does happen all the time. Right. And the social networks have done that. So I think frankly, the social networks, the big, big tech social has sort of left this pretty, pretty significant layer of mistrust around kind of our data. Right. Again, I don't think people understand how these models really work. Right. They're trained. And then, you know, again, you can work with your own data with these models pretty safely from my perspective. And by the way, my, my point of view on this is my, my data is a drop of data in the ocean of data. And so, you know, this idea that my board deck is, you know, is so, I don't know, so special or so proprietary that, you know, they, they want this data. They don't listen. If I was the CFO of a Fortune 500 company, I'm not loading my board deck or business plan into, you know, into GPT. I'm getting a private version of GPT or I'm getting GPT Enterprise or I'm getting Microsoft Copilot, which are private and segregated, you know, instances. But you know, for a small business, you just manage your privacy controls, right? GPT teams, you know, turn your privacy on.
Right, exactly, exactly. Yeah. And, and hey, as a reminder to our live stream audience, thanks for tuning in. If you do have any questions, make sure to get them in now. But Greg, I do want to hit rewind just a little bit here and talk a little bit more about this concept of using AI as a thought partner. Right. The way that we tell People, you know, we've done, yeah. Thousands of live trainings as well. We tell people to turn ChatGPT into a consultant before you ever ask for any output. Right. How have you even done this personally? How have you. Or you know, in your company maybe. But how have you used AI as a thought partner?
Yeah, I mean, one of the ways, and this kind of. We started a year ago and we still do it every quarter because we have a board meeting every quarter and I've got a great board. I have a world class board at Section, a former CEO, Time Warner and Akamai, and great investors. And so what we do is we basically ask AI to pretend to be board members before the board meeting. So when we send our board deck, which is the pre read board deck, to the human board, we also share it with AI. And these days we focus on GPT and Claw just because it's easy to upload PDFs to those two LLMs. And so when we do that with the AI and then after the board meeting, we take great kind of notes in terms of all the feedback we got from the human board. We have five people on a human board. We compare the human board to the AI and for the last year, Claude has basically scored 90 to 93% every time. In terms of the advice or insights we get from Claude, almost match, right? Not quite 100, what the human board told us. And GPT is close behind, right? Usually around 89 to 90%. So that, that's just a great use case. Right. I'm using AI and I'm asking AI to adopt a Persona, so. And several Personas. So, you know, be an aggressive board member that wants growth. Be a more conservative board member that wants to kind of drive to break even or profitability faster. Right. Things like that. Right. Be a board member that's more focused on developing technology value versus sales value. Things like that. Ask your AI to adopt a Persona and basically play a role with you. So that means I'm better prepared for the board meeting, Right. Doesn't mean I don't need the board. Not yet. Not just yet. And it probably means the board still still needs me. You know, we'll pay the salary, but. And by the way, I asked the board to do the same thing though. When I said send the board the deck to read, I say, listen, here's the prompts you should use. Kind of, you know, asking AI to play the role of the CEO. Right. And kind of really I think that means we can come to that meeting a little more prepared and A little faster to get to the more kind of the meaty subjects or that, you know, get to the real issues we want to talk about. Right. And I think we can do that with any kind of meeting we have or any kind of significant decision we have coming up. Ask AI to kind of be your thought partner. Ask AI to think about it as you would think about it and then think about someone who's not like you. So if you're detail oriented, ask AI to be ambitious and aggressive. Right. And sort of, you know, blue sky thinker. If you're a blue sky guy thinker. Right. If you're always an optimist, like I am as an entrepreneur, you probably are, then ask AI to adopt a different Persona, right. To be more risk oriented and to be more concerned around what could go wrong or do both. Right. I just think that, again, this is an underutilized use case for most of us. And it. I think it's most powerful when we share some of our information with AI. A plan, you know, a design, you know, anything, Right. You know, a product roadmap. And then ask AI to kind of talk to us about it. I use it for medical stuff all the time. I've got a busted ankle, I need surgery. And I've now got. I've done. I've got five different doctors as you know. You know what doctors are like, right? You know, kind of overconfident and don't talk a lot because they want you out of their office in about five minutes unless you agree to do the procedure with them. So I got five doctors, five different opinions. These are all top, you know, top doctors at Stanford and so on around here in the, you know, where I live in Palo Alto. And I'm getting kind of confused, right? You know, and again, I'm not going to have AI tell me which one to do, which, you know, which procedure, which doctor. But AI does a great job. When I load up my scans and load up my MRI report, AI does a pretty good job of summarizing the different options that are available, and then you can talk to AI about it. Give me the ones like rank the rank, the options that get me playing soccer faster, like with the shortest rehab, right. Give me the options that have the least amount of risk, the least invasive. AI can do that. It's hard to have that conversation with, you know, with docs, they just don't have the time and I think, frankly, the patience to do it. So I just think that, again, we're not going to have AI make these decisions Yet. So the AI is probably not doing my job yet, but I think it can tee up, I think the options and give us a good, kind of good roadmap to make a decision.
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I want to talk a little bit more about this kind of internal case study that you've had of asking your board members, you know, some heavy hitters there, you know, to essentially use AI, you know, as part of their day to day, using it as a thought partner. A year in, I think, what have you learned? I mean you gave us some great stats there. I love that. In terms of, you know, 93. I think you said 90. So what have you learned and how have even these people's mindsets on AI and large language models to be a high level thinking partner. How has that changed after a year?
Yeah, I don't know. You know, I don't know how my board thinks about it specifically. It's a great question how I think about it and I think it in general, I think what happens is we go through this sort of, you know, this shift from yeah, is this useful or is it going to hallucinate or does it really work to. Oh, it's actually, first of all, I think we get to this point where we realize it's pretty easy to interact with AI and it's getting easier with voice and you know, and sort of talking to AI. I think that is another unlock by the way. Get, get, you know, get, get AI on your phone and start, you know, obviously GPT4, the iOS apps got, you know, talk conversations with AI or talk to AI. That's another kind of breakthrough because it feels more natural for people to talk to AI particular when you think about partner use case. But I think we go through this kind of like transition of, oh, it's, it's kind of, it's pretty easy to. And kind of natural to interact with it. And then this idea of I can add my data, so now we're talking about my stuff, right. In conjunction with the AI. And then I think we realize, oh, there's a moment where I got some pretty good advice. It did summarize that document well, and it not just summarized it well, but highlighted a couple things that I didn't think about. And I think that's the moment we all have to get to where we know it can summarize, we know it can draft, we know it can kind of do it, you know, do a good job with language based tasks. But how about language based thinking? And when you see it sort of identify something you hadn't thought about or highlight a risk or you know, call out a number that is maybe you. Again, a metric that you hadn't considered, things like that, then you. I think that's kind of the unlock where you realize, okay, there's something here for me. Yeah, you know, I'm a human, I know my shit, but, you know, I don't know it. All right? And maybe this AI can just be this sort of, yeah, this companion, kind of COVID my bases. Because in those kinds of conversations, those kinds of meetings, you know, you're meeting with an investor, you're meeting with your bank or whatever, you're trying to get a loan. You know, ask, ask your, ask your AI to pretend to be a, you know, the loan officer at the bank kind of idea and the kind of questions that person's going to ask. So I just think it's, again, we all have blind spots and the faster we expose those blind spots and move through them and make better decisions. You know, I think that, you know, we're all better off. So, yeah, it can take a while. But when you get that first insight, when you see AI tell you something you hadn't thought of, I think you're like, okay, you know, it's kind of a light bulb moment.
You know, one thing that I always think about and you know, I talked about a couple times on the show before is, you know, especially when it comes to like, oh, can AI do your job, your CEO's job, or can AI really do this? This task Better than someone that's been doing it for, for 20 years? Number one, the answer is yes, probably. But I think a lot of people, CEOs, C suite leaders, decision makers, think of AI as this almost technical implementation piece. I don't think that's it. I think it's actually change management. Right. Because I think historically, for decades, business leaders have been rewarded for what they do with their own knowledge, with their own domain expertise. But that's what large language models are good at. Right. So what would you say to a CEO that is, maybe they're hearing this.
And maybe they're inspired, but they're still.
Struggling because they're like, no, a large language model can't do this. I got rewarded. I'm where I'm at today as a CEO because of how smart I am. What would you say to them?
Yeah, what I'd say is, first of all, as we already talked about, get hands on yourself if you can't, you know, you can't really appreciate, I think, the opportunities or the potential unless you get hands on yourself. So get hands on yourself. That's the first thing. Second thing is, you know, assign the task to someone, you know, head of AI. The person who raises, you know, the smart kid in the office that raises, raises their hand and says, listen, I want to be the one to figure out AI. Find someone, probably not a technical person. I don't think the head of AI, by the way, should be the technologist. I think it should be a business person who understands workflows, understands tasks, kind of the business problems, and then understands enough about AI to see where the intersections are and find the two or three big specific use cases inside your company. Organization could be an organization like section where, you know, there's only 30 of us, but we've got like, there's probably 10 tasks that really are big tasks that we do all the time. For example, for us, it's creating courses, it's writing scripts. So we're a concerted effort with AI to see if AI can make that task or make that job. You know, kind of better, faster, cheaper, better quality, like pick some sort of, you know, some highlights, use cases and try to really apply AI. That's second. Third, deploy AI to the team, pay for it, you know, if. Pay for it, especially for the privacy controls, like, you know, GPT teams, for example, is 25 bucks a month, maybe, maybe do it for six months, pay for it, and, you know, get everybody kind of going. That is the hard part, though, that moment, because I think you're Right. There's resistance. It's about change management. You can train them and you have to train them so they know how to use it. And after that you've really got to kind of reward and encourage the behavior change. And the behavior change is find these little personal use cases, right? You're in marketing. Find the way AI is going to help you in marketing right now. You know, the change management, you know, kind of theory, right? You got to get past at least 10% and if not 20%, typically change management sort of theorists will tell you past 20%, that's the tipping point. And the rest of your organization kind of, kind of follows. And we're not there yet in almost every organization, right? We're not at 20% in terms of AI adoption, in terms of everyday usage. So if you are serious about this as a CEO or a leader and you want, your team, could be a five person team, you know, 10 person team. You've got to get, you know, three, four, five people in that 10 person team kind of over that hump, right? Which is they're using AI every day. You've got to make it safe. You got to encourage it. You gotta let them upload their data. You know, you gotta do a bunch of stuff, you gotta, you gotta recognize where it fails and talk about it. You gotta talk about the wins, talk about the kind of failures. You gotta get past that 20. We just did a survey, Jordan, of a thousand knowledge workers. Eight percent in our survey were what we call in the AI class. And that means two things. Attitudinally they were acceptant, you know, acceptant of AI and, and seeing its kind of power and its value. And then secondly, we tested them for their prompting proficiency. So we actually ran them through a kind of prompting exercise to see if they could really like, you know, work within it with an AI. Only 8% passed, right. And our audience is probably pretty early adopter oriented, right? So you know, that's not enough, right? It's got to be 10, 15, 20%. So we got, we got a few years to go, right? And we gotta, we gotta get through some resistance. And the resistance is anxiety. And anxiety is coming mostly from media, which is, you know, AI is coming for your job. And in some cases it is. Quite frankly, you know, 80% of call center operators, in my opinion will be those 80% of those jobs will be eliminated in the next five years in the United States. That, that's my perspective on it. So there is some real implications here. But in general, I think the anxiety is kind of hyped up media.
And speaking of some of these stats, right, like the 8% pass out of a thousand, that's, that's pretty shocking, but not surprising. But Ted, here bringing up a great point that I'm going to turn into a question here. So saying PwC, in their latest CEO survey found that only 30% of CEOs are actually using AI. Right. There's been a couple other studies as well that said in the mid-90s, 90% of C level executives say that AI is a top company priority, yet about 5% are actually incorporating generative AI across their organization. Greg, from your perspective, why is there such a disparity between every single C suite leader saying AI is the most important priority, but hardly no one is actually implemented?
Yeah, but that's like saying, you know, cost cutting is a priority, but the CEO is still flying on the corporate jet. Yeah. I don't know why we're surprised. You know, like CEOs say what they think is important for their organization. That doesn't mean they necessarily want to do it or need to do it. CEOs are busy. No. You know, no one sat down and showed them how to use it. CEOs are being told it's not safe. Don't load, don't load company data into the AI. I don't think for a CEO, AI is that useful unless you can talk to it about your data. Right. About your situation. So whether it be personally at home, your travel plans, your medical records, whatever it is, all those great personal use cases or at work. Right. That's it's likely for a CEO, means you want to talk to it about your company and your, your company data. Like, you know, using just what the model knows about your business is not enough. Right. The CEO is not going to get any insight from that. So the CEO needs to feel comfortable. I can load up my, you know, you know, you know, my board deck. Right. So, yeah, this is not surprising. We're early. We're a year and a half in, you know, so it's going to take, it's going to take a decade.
Yeah. Greg, we've, we've talked about a ton in today's conversation and could probably keep going for hours, but, you know, as we wrap up today's show, you know, what is maybe that one piece of advice? So maybe, you know, a CEO listening was kind of on the fence and now they're, you know, convinced and they're like, all right, I got to go all in. What is your one piece of advice or one Takeaway when it comes to, you know, this concept of AI really being able to be a thought partner to CEOs.
All right, well, only one's tough. We'll do two. Two. The first one is get AI on your phone and when you're in the car, talk to GPT4 through the conversational kind of interface as a thought partner. It won't have your data, but you'll have a conversation with it. That'll teach you, I think that AI really can, can, can be this thought partner for you. Second one is anytime anybody comes to you inside your organization, doesn't matter how, how big or small your organization is, they want money, they want requests for, you know, headcount, they want, they have a new project they want approval on, they have an idea they want to talk to you about. Ask that person, what does AI think? If you do that, your organization will learn very quickly that you are committed to being an AI enabled organization and that, that you get it. And they'll go back and next time they come to you, they will have asked AI as well. So they will have used AI as a thought partner and frankly, do that yourself. Right. If you're going to ask other employees, you know, what does AI think? Then if you're thinking about something, a decision, then ask, ask the same question and you know, go to Claude. My preference is Claude as a business thought partner. GPT a close second. But you know, I, I use it every day to, and that's the question I ask, what do you think of this?
You know, I mean, today's episode I think has been crucial for CEOs as they start to finally quote, unquote, figure out generative AI in 2024. Greg, thank you so much for coming on the Everyday AI show and sharing your insights. We really appreciate it.
Thank you. Jordan. Great to be here.
And that's a wrap for today's edition of Everyday AI. Thanks for joining us. If you enjoyed this episode, please subscribe and leave us a rating. It helps keep us going for a little more AI magic. Visit youreverydayai.com and sign up to our daily newsletter so you don't get left behind. Go break some barriers and we'll see you next time.
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