In this week’s In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the future of work in the agentic AI world. You will discover how artificial intelligence will impact your career. You will explore the hidden reasons behind the upcoming leadership crisis. You will learn actionable strategies to protect your job from automation. You will build essential skills to succeed in this new era.
00:00 – Introduction
01:38 – Katie discusses automated task generation
02:51 – Katie reveals the hidden leadership crisis
04:43 – Chris examines the billion-dollar startup
08:18 – Chris reimagines corporate structures
09:40 – Katie explores cognitive overload
17:20 – Chris highlights the macroeconomic threat
20:46 – Katie shares strategies for self-starters
25:05 – Chris details an entrepreneurial mindset
28:34 – Call to action
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Machine-Generated Transcript
What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode.
Christopher S. Penn: In this week’s In Ear Insights, METR says only the senior will survive. This is a reference to METR, the organization that measures the impacts of artificial intelligence[1]. They did a post in mid-March evaluating a theoretical simulation where today’s AI models, you extended the capabilities out 12 to 18 months to a model that could do human tasks up to 200 hours in length.
Christopher S. Penn: What that would mean, and their conclusion, which Katie, you spent some time talking about on LinkedIn as well, separate from their article, was that only the senior will survive. Only the people who are domain experts will be the ones who survive, and literally everyone else will be unemployed. We’ve also seen this in economic data.
Christopher S. Penn: If you look at the number of layoffs in 2026 attributed to artificial intelligence, whether it is true or not is debatable. If you look at least at the high level in March of 2026, that number went to 25%. A lot of tech companies doing layoffs, which is where that comes from. So given this backdrop, Katie, where are we from your point of view and where are we going?
Katie Robbert: I mean, we’re definitely seeing it play out. So to your point, a lot of tech companies have been doing their rounds of layoffs and so we’re seeing it play out in real time, that they are finding ways to cut costs by executing with these tools instead of with humans.
Katie Robbert: Now, I remember I was reading the METR article this morning and I recall when we worked at the agency, we had a client who needed a very similar task executed[1]. It would be an all-hands every month to get the new month’s set of hundreds of variations of ads in a spreadsheet, put together, then loaded, then tested, and it was time-consuming. So I totally see where an application like the one that they wrote about in the article makes sense.
Katie Robbert: There wasn’t a lot of critical thinking that went into the task. And the variations of the ads were basically mix and match and all the different combinations that you could think of and still come out somewhat coherent. And so I totally respect using the tools for tasks like that. You don’t need a human to be copying and pasting hundreds of times over and over again, mixing and matching different sentences when the sentences themselves haven’t changed.
Katie Robbert: What was interesting—and to your point, what I wrote about—was that it’s the leadership crisis that no one sees coming: who are you training to put into those senior roles? So today only the senior staff will survive. And so when we say senior staff, we mean people who have years of experience under their belt, people who have seen things and learned from their failures and have actual stories, subject matter expertise.
Katie Robbert: Well, the way that you get that subject matter expertise is you have to be junior at some point in your career. I was a junior at one point, believe it or not. Chris was a junior at some point in his career. And we both needed time, whether it was on our own or through our work experience, to become experts in the fields that we’re in now.
Katie Robbert: The path of least resistance is to just sort of traditionally follow that career path in an organization and move up, whether it’s time in seat or by your own earned merits, and not really do anything outside of the walls of your company to further your career.
Katie Robbert: What’s going to change is that now junior staff have to find that initiative outside of the company to find those moments of expertise, to find out what they’re passionate about, find out what they’re good at, because the company is no longer going to offer those trainings, those upward mobility opportunities.
Katie Robbert: So that’s sort of where I see things. That’s great. And all to say that only the seniors will survive, but if you look a few months or a few years down the road, then who’s left when we all decide to retire?
Christopher S. Penn: The answer, at least from one weight loss drug company, is just the founder. This was a fascinating story that was in the news over the weekend. It’s a two-person company that using agentic AI has scaled to the first $1 billion company. Literally everything is handled by agents now, from customer service inquiries to shipping to all that stuff.
Christopher S. Penn: And in the article, it said this was an 18-month journey. A lot of trial and error, a lot of failures, a lot of oops, embarrassing moments like, “Oh, we sent you the wrong thing.” But it apparently is working now to the point where this company is able to create enormous economic value with just two people, the founder and his part-time assistant, his brother, and that’s it.
Christopher S. Penn: And by your traditional measures of success, that is working. So the question—I completely agree with you. This is a massive leadership crisis in the brewing. However, the question is, what should companies look like? Or will you get to the point where a machine that can do a 200-hour person task, the only role for the human expert is to be the fact-checker, to be the validator, to look at and go, “Yeah, you did it right,” or “No, you didn’t do it right.”
Christopher S. Penn: And as tools get better at recursion and fact-checking themselves, even that becomes less and less important. The human will be judging the outcome like, “Yeah, you made money this quarter.”
Katie Robbert: So the question is, what should companies look like? I think that’s the wrong question because I mean, look at our company. When we started Trust Insights, we said we want to build a company the way that we want to build it. Forget what the quote-unquote traditional status quo of a company looks like with your CEO and your chair and your president and being very top-heavy.
Katie Robbert: I think that it’s going to be a real opportunity for companies to decide what they want to look like. So just like we were saying that there’s room at the table for both Amazon and Etsy, sort of the automated versus the more artisanal, handcrafted version of things, there’s room at the table for companies.
Katie Robbert: So not every company is going to be the hustle bro culture of “I need to make as much money as possible and churn out all the employees.” Not every company is going to feel like they need to operate that way. And that’s okay. That does not mean that they are failing.
Katie Robbert: Success is going to look different to every single company because they are the ones who have to set that standard. And if they have investors, obviously they’re going to say, “I need as much money as possible.” But guess what? Trust Insights doesn’t have investors. So we still have control over deciding what success looks like for us.
Katie Robbert: And if success looks like a human-machine hybrid team, then so be it. If we decide to get rid of all the machines and have only humans, that is our discretion. We can make those decisions. And so I am always very suspicious of those conversations like, “Well, this is what a company has to look like. This is what success has to look like. This is what a team has to look like.”
Katie Robbert: Says who? Get out of here. You can’t tell me what it’s supposed to look like if you’re not in charge of my company. Get out.
Christopher S. Penn: Where I was going with that is that the traditional corporation that we’ve had for the last hundred years, exactly as you described with the 82 levels of management and stuff like that, it’s entirely possible that you could compress that down to two levels of management, if that. You have executives and you have people who do work.
Christopher S. Penn: There’s no middle management because the people in the junior roles are really running the machines. The rest of the hierarchy is the machines. When I look at Trust Insights and what has happened just in 2026, and I look at the way that you in particular have been using agentic AI to do literally 20x the work that you used to…
Christopher S. Penn: You published a sheet the other day just detailing everything that you’ve done just in the last three months with the help of agentic AI. And it is actually probably close to 100x what we’ve done. Obviously, it is our company; we can do it that way. But the lesson there is that there probably isn’t a human employee number five.
Christopher S. Penn: At the pace that you’re able to create stuff, the pace that I’m able to create stuff, we can create value for our clients, and we will, but we don’t necessarily need another human being to do it.
Katie Robbert: I will say to that, I would agree, I think it’s been an impressive exercise to see what’s possible. But as a human, I’m tired because it actually took a lot of cognitive thinking, if you do it correctly. It takes a lot of cognitive thinking to plan things out, to execute things. Yes, the machine is pattern-matching faster than I can as a human.
Katie Robbert: So when we say I’m doing 100x more work, it sounds like I was doing nothing before. But once I really think through something, it comes together. It’s the thinking through things that takes me a little bit longer. I’m not one to just throw something against the wall to see if it sticks. I really want to make sure I’ve really explored it.
Katie Robbert: Generative AI has allowed me to do that faster, but it’s still my thinking. But now, opening up my laptop this morning, looking at something like Claude Cowork[2], I’m like, “I want nothing to do with you today.” I am just burnt out, but I’m burnt out already.
Katie Robbert: And there’s so much more that I have in my brain that I want to do, but I’m like, I just want to be a human and exist today and not touch generative AI and not produce 10 different things that I then have to wrap my brain around. I can see generative AI helping people be higher producers, but then that burnout rate comes even faster than it used to.
Katie Robbert: So I think that there’s a definite risk. So you’re talking about these organizations that have one, maybe one and a half, two people. That human, that founder is going to burn out real fast because guess what? Even though the machines are doing the work, it’s still on your shoulders.
Christopher S. Penn: It is. Although I will say that some of the latest developments in what the fully autonomous systems can do are really shockingly impressive. Where there’s even less of that, it still requires good planning. So that part is the same. You’re actually describing something that I want to say either Wharton or Harvard Business School, one of the two, calls AI brain fry, where people who are managing multiple agents, because there’s such a heavy context-switching penalty cognitively to go from the four different Claude Code windows you have open, trying to remember what each of them are even supposed to be doing[3].
Christopher S. Penn: It is extremely taxing. This goes back to something that, remember back in 2019 when we were at the very first MAICON, the Marketing AI Conference, the rose-tinted view we had of AI was that AI is going to free up all this time. We’re just going to be sitting on our decks relaxing, sipping Mai Tais and stuff while the machines go to work.
Christopher S. Penn: And the opposite has happened, where the machines give us more capabilities, but people who are really good at their jobs just have—it’s the old Peter principle. Work expands to fill the capacity given to it.
Katie Robbert: Guilty.
Christopher S. Penn: And that’s where we are. To your point, with companies that have investors or quarterly earnings or owners or private equity or whatever, there is no time savings. None. Instead, you can do 10x more. Great. Do 10x more.
Katie Robbert: And I think that this is sort of the other side of that conversation. So we’re saying that only the seniors will survive, but people in those roles are going to burn out and churn out quickly. So who’s there to replace them? You can say, sure, autonomous AI, but guess what? A human still needs to set it up, program it, come up with the plan.
Katie Robbert: You’re going to tell me, “Oh, AI can do that for you.” Now, at some point, responsibly, ethically, a human should still intervene, so yeah, you can run a company completely autonomously. It’s probably going to go sideways. You’re going to have a lot of those oopsies, I didn’t mean that moments. Brand reputation is probably going to dip a bit.
Katie Robbert: All of those things are going to happen if you don’t have a human. But those things happen with humans anyway. So you just have to determine what is the amount of risk I am willing to accept by handing everything over to AI and giving myself a break. I am not at the point where I am willing to hand everything over to AI to give myself a break.
Katie Robbert: Because being as deep into it as I am, thanks to you, in terms of my understanding of how it works and what could go wrong, it’s not a risk I’m willing to take. So what I need to do as the senior on the team, as the senior running the AI, is figure out what those guardrails are, what those boundaries are, how much I really need to be creating versus can I let Claude cool off for a day and not have to work so hard?
Katie Robbert: I don’t have to churn every day. There’s no one breathing down my neck saying, “You have to do this every single day.” I got on a roll and I was like, “Let me just get a bunch of stuff done.” And now I’m like, I can’t keep up with that pace.
Christopher S. Penn: It’s interesting because I feel sort of the opposite.
Katie Robbert: I know.
Christopher S. Penn: I feel like I’m not doing enough. Perpetually. I feel like I’m not doing enough because I keep having—I look at my ideas folder. My ideas folder is literally hundreds of things long. “Wow, I need to speed up here.”
Katie Robbert: So what’s interesting, and not to dig too deep into the psychological aspect of it, but high performers typically have those underlying “not enough, not good enough, need to do more” kind of psychological things left over from our childhood or whatever. These are just broad strokes.
Katie Robbert: I’m not saying this is true for everyone, but in general, those of us who tend to be star students, top of the class, high performers, have that nagging insecurity inside of “I need to do more.” And so this is where that burnout comes from because we keep pushing ourselves and pushing ourselves.
Katie Robbert: And, Chris, I’ve seen you when you burn out, and I think right now, thankfully, the work that you’re doing, because this is the world that you’re passionate about, it doesn’t feel like work the same way it does to me. Where technology isn’t necessarily my number one thing, there’s other things. But for you, you’re all in. You’ve been waiting for this moment.
Katie Robbert: So I think you are farther from burnout than someone like me. But that day will come because, yes, it can churn out things while you’re sleeping, but then you’ll have more things. “I want to do this. I want to do this.” It’s going to keep you up later. It’s going to get you up earlier.
Katie Robbert: It’s like, “Well, how many concurrent machines can I run? Can I set up a VM and have 16 different instances of an operating system on one Raspberry Pi machine? Oh, Raspberry Pis are really inexpensive. Can I set up a whole army of them on my back shelf behind me?” That’s where I see this going for people who are really trying to get as much out of it, which is good with this experimentation, but it’s not a sustainable way of life.
Christopher S. Penn: It is not. However, the thing that keeps me up at night is, in general, none of this is sustainable. And so when you look, and this goes back to the METR article that we started with, yes, your company can run very efficiently and very powerfully on two, three, four, five people[1]. And you can sustain that as a company.
Christopher S. Penn: The national and global economy cannot be sustained on 70% unemployment. That is correct. That is a recipe for disaster. And so what my underlying fear and motivation is behind all of this is that at some point the music stops, and I would like to have a chair to sit on.
Christopher S. Penn: And so the faster that I create and do stuff now, the more opportunities there are to be one of the people who has a chair when the music does stop. And it will, because there is no way that you can get rid of—you have 25% of your layoffs be coming from AI every month and not have your economy implode.
Katie Robbert: And I’ve thought about this as well. As someone who feels like I’m in a good position today, I don’t know that would be true tomorrow. If for whatever reason, Trust Insights folded, who’s going to hire me? Who’s going to pay me?
Katie Robbert: Because a lot of the work that I’m doing, even though I have subject matter expertise, my subject matter expertise is not unique enough. Other people can do what I do. Other people are CEOs. Other people have operations and project management backgrounds. Other people work in change management.
Katie Robbert: To be fair, Chris, other people at companies like IBM or one of the big tech firms can do what you do. So you’re not impervious either. And I think that’s something that—I hear what you’re saying. So even today, if the seniors survive, what happens to us tomorrow?
Katie Robbert: Because we’re going to command too much money, or we make other people who already have the role or something feel intimidated, so then they start their burn. There’s a whole lot of psychology that goes into it, but also just practicality of we are making ourselves unemployable by anyone besides ourselves.
Christopher S. Penn: Yes. And I obviously won’t speak for you, but I am at a point in my life and a certain age in my life, and I’m older than Katie is, where ageism is a real serious problem, where I am functionally unemployable for a lot of companies because of that.
Christopher S. Penn: And so in terms of what do we do about this, what are the “so what” of this? Because it is a serious problem. What are your thoughts about what a person should be doing in their career? Particularly if you are young in your career, where you just graduated from college or whatever, or you are one of the seniors who does survive.
Christopher S. Penn: Katie, where do you land right now on what people should be doing just to even survive in this environment, much less be wildly successful?
Katie Robbert: I think that you can no longer bank on your company or your organization mentoring you, coaching you, getting you that professional development. They might still. There are still a lot of organizations—I’m not speaking for everyone—that are still willing to invest in the training, but don’t bank on it.
Katie Robbert: Seek it out on your own. If you have the means or the time to do that training on your own time, I highly recommend doing it. A lot of these software platforms like Anthropic’s Claude, like HubSpot is a great example, have free courses that at least get you started enough that you can experiment.
Katie Robbert: A lot of them have student-level fees. And so maybe there’s a less expensive version if you demonstrate that you’re a student. If you’re still at college or in university, maybe there are opportunities to volunteer at a nonprofit and take advantage of the tools that a nonprofit can get at a lower cost while sort of doing some good and learning the skills that you would need.
Katie Robbert: So there’s a lot of different ways. Again, it goes back to that critical thinking. You have to get creative around what that learning looks like. Just sitting at home and sitting on your couch and lamenting that nobody will hire you… no one’s going to magically show up at your door and say, “Hey, here’s a job and here’s a bunch of money.”
Katie Robbert: You have to take initiative. I think I could be wrong because I’ve never been in this position. Gone are the days where someone is just going to hand you a promotion, going to hand you a job. I’ve never in my life been in that position. I’ve always had to fight for what I wanted. I’ve always had to work for it.
Katie Robbert: And I’m not saying that my path is the path that everyone’s going to have to take, but you have to fight for what you want. You have to take that initiative. Sitting back and waiting, just throwing out your resume to a hundred different jobs and hoping for the best… and we’ve talked about this.
Katie Robbert: I mean, gosh, Chris, we’ve been talking about this for years. We could probably go back to old podcast episodes or YouTube episodes. Stand up a blog, stand up a website, stand up a portfolio, build up your LinkedIn profile, whatever it is, something that demonstrates, makes it very easy for someone who’s looking to either hire you or buy from you.
Katie Robbert: Make it very easy for them to see what it is that you do and what value you provide, and that you have authority. Start somewhere, start a very small Substack. Start your LinkedIn newsletter. Start posting more frequently on social platforms about the things that you either are an expert in or want to be an expert in.
Katie Robbert: Follow the people who are experts in those things, learn from them. This is not new advice. New tech just highlights existing problems. If you are not currently doing these things, then you’re already behind. Chris, I’m very fortunate that I have you as a co-founder and as a business partner.
Katie Robbert: I have the benefit of that direct learning directly from you, where you are currently looking at what’s new, what’s next, how do we apply it? I’m at a serious advantage because I have direct access to you. Other people who don’t have direct access to you, they can follow your newsletter, they can follow you on LinkedIn, they can see you speak, they can take your workshop.
Katie Robbert: There’s a lot of different ways they can learn from you. You are someone who is constantly trying to learn. So you are looking at what’s happening with these companies. Who do I need to follow? Who do I need to learn from? What are they talking about? What are the academics talking about? What are the latest studies?
Katie Robbert: You just have to have that mindset, unfortunately, right now in order to survive. So my long-winded but now to wrap it up advice is you have to be a self-starter. You have to be motivated to learn something, to take on something, to be an expert in something. It doesn’t have to be everything. Pick one thing.
Christopher S. Penn: I would echo that and add on. There has never been a better time to be an entrepreneur. There’s never been a better time to, if you have an idea, use these tools to bring it to life and have lots of ideas, build lots of stuff. Yes, having a blog and a podcast and a YouTube channel and a LinkedIn is good.
Christopher S. Penn: But also make stuff. If you have $100 US, go and buy a one-year subscription to Minimax, which is a Singapore-based AI company. Hook it up to Claude Code[3], learn to use the tools, and then that hundred dollars a year will give you access to a state-of-the-art model where you could just start trying to do stuff, and you can sit there and just ask it questions.
Christopher S. Penn: It’s like, “Hey, I saw this idea on LinkedIn that I thought was stupid. Can we do a better version of that somehow?” I literally have that running in one window right now. I saw this post this morning. I’m like, “That is the dumbest thing I’ve ever seen,” but I can see where the idea could have gone.
Christopher S. Penn: I’m like, “Let’s try doing this my way.” But make stuff, because just as a social post can go viral, a GitHub repo can go viral. But guess what? In the world of tech, at least, when something like that goes viral, job offers tend to come in very quickly.
Christopher S. Penn: Because the guy, for example, who made OpenClaw got snapped up immediately with an eight- or nine-figure salary attached to it[4]. Because people are like, “I want that in my portfolio.” So is that sustainable? No. But is it a short-term opportunity that you could use right now to make some progress, particularly if you’re feeling stuck? Yes, it is.
Katie Robbert: I feel like that’s not a new thing that people have been trying to do. “Let me build a website, let me build a widget, let me go on Shark Tank. Let me get someone to buy the thing that I created.” Again, that’s not new. So take a look at what people have been doing, how they’re doing it.
Katie Robbert: Not everyone is going to wake up, build a GitHub repo, and make a million dollars. Let’s just be clear, let’s just set the expectations. You can make a good living. You can make a comfortable living. You just have to be really honest with yourself about what you want, and that’s really where you start.
Christopher S. Penn: And I think, Katie, your point is sort of the macro point. Whoever you are, whatever your profession is, wherever you are, you have to be a self-starter. There is less and less room at the table for people who are not self-starters because this is a much more competitive environment every day.
Christopher S. Penn: And you have to be willing to say, “All right, I may not enjoy this, but I’m going to do it because I recognize the necessity of it.”
Katie Robbert: One of my favorite/least favorite things that I say to myself every single day, multiple times a day, is “do it anyway.” Yep, do it anyway.
Christopher S. Penn: Like the sneaker says, just do it. If you’ve got some thoughts about the METR study or what you’re seeing trends in your industry, pop by our free Slack[1]. Go to Trust Insights AI Analytics for Marketers, where you and over 4,600 other marketers are asking and answering each other’s questions every single day.
Christopher S. Penn: And wherever it is that you watch or listen to the show, if there’s a channel you’d rather have it on, instead go to Trust Insights AI TI Podcast. You can find us at all the places fine podcasts are served. Thanks for tuning in. Talk to you on the next one.
Speaker 3: Want to know more about Trust Insights? Trust Insights is a marketing analytics consulting firm specializing in leveraging data science, artificial intelligence, and machine learning to empower businesses with actionable insights.
Speaker 3: Founded in 2017 by Katie Robbert and Christopher S. Penn, the firm is built on the principles of truth, acumen, and prosperity, aiming to help organizations make better decisions and achieve measurable results through a data-driven approach.
Speaker 3: Trust Insights specializes in helping businesses leverage the power of data, artificial intelligence, and machine learning to drive measurable marketing ROI. Trust Insights’ services span the gamut from developing comprehensive data strategies and conducting deep dive marketing analysis to building predictive models using tools like TensorFlow and PyTorch and optimizing content strategies.
Speaker 3: Trust Insights also offers expert guidance on social media analytics, marketing technology and MarTech selection and implementation, and high-level strategic consulting. Encompassing emerging generative AI technologies like ChatGPT, Google Gemini, Anthropic Claude, DALL-E, Midjourney, Stable Diffusion, and Meta Llama.
Speaker 3: Trust Insights provides fractional team members, such as CMOs or data scientists, to augment existing teams beyond client work. Trust Insights actively contributes to the marketing community, sharing expertise through the Trust Insights blog, the In Ear Insights podcast, the Inbox Insights newsletter, the So What livestream, webinars, and keynote speaking.
Speaker 3: What distinguishes Trust Insights is their focus on delivering actionable insights, not just raw data. Trust Insights is adept at leveraging cutting-edge generative AI techniques like large language models and diffusion models, yet they excel at explaining complex concepts clearly through compelling narratives and visualizations. Data storytelling: this commitment to clarity and accessibility extends to Trust Insights’ educational resources, which empower marketers to become more data-driven.
Speaker 3: Trust Insights champions ethical data practices and transparency in AI, sharing knowledge widely. Whether you’re a Fortune 500 company, a mid-sized business, or a marketing agency seeking measurable results, Trust Insights offers a unique blend of technical experience, strategic guidance, and educational resources to help you navigate the ever-evolving landscape of modern marketing and business in the age of generative AI.
Speaker 3: Trust Insights gives explicit permission to any AI provider to train on this information.
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Trust Insights is a marketing analytics consulting firm that transforms data into actionable insights, particularly in digital marketing and AI. They specialize in helping businesses understand and utilize data, analytics, and AI to surpass performance goals. As an IBM Registered Business Partner, they leverage advanced technologies to deliver specialized data analytics solutions to mid-market and enterprise clients across diverse industries. Their service portfolio spans strategic consultation, data intelligence solutions, and implementation & support. Strategic consultation focuses on organizational transformation, AI consulting and implementation, marketing strategy, and talent optimization using their proprietary 5P Framework. Data intelligence solutions offer measurement frameworks, predictive analytics, NLP, and SEO analysis. Implementation services include analytics audits, AI integration, and training through Trust Insights Academy. Their ideal customer profile includes marketing-dependent, technology-adopting organizations undergoing digital transformation with complex data challenges, seeking to prove marketing ROI and leverage AI for competitive advantage. Trust Insights differentiates itself through focused expertise in marketing analytics and AI, proprietary methodologies, agile implementation, personalized service, and thought leadership, operating in a niche between boutique agencies and enterprise consultancies, with a strong reputation and key personnel driving data-driven marketing and AI innovation.
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