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the podcast that takes you inside the drama, decisions and choices that go with being the head of marketing. Hosted by five time CMO Mike Linton
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Mike Linton
advertisers and those who love them. The Chief Marketing Officer Confidential CMO Confidential is a program that takes you inside the drama, the decisions and the politics that go with being the head of marketing at any company in what is
Co-host/Interviewer
one of the most scrutinized jobs in the executive suite.
Mike Linton
I'm Mike Linton, the former Chief Marketing Officer of Best Buy, eBay, Farmers Insurance and Ancestry.com here today with my guest Shiv Singh. Today's topic where AI is taking marketing things that make you go Now. Shiv is the CEO of Savvy Matters, a co founder of AI Trailblazers, the former CMO of Lendingtree, and author of the book I think it's in its fourth edition titled Marketing with AI for Dummies. He's a provocative and prolific poster and he's delivered a number of recent posts which caught our eye, including who Remembers Wins? Where AI is taking Marketing and Creativity's coming Reckoning. So I invited him on the show to share his thoughts on all this stuff and the hyped world of AI. Welcome back Shiv.
Shiv Singh
Thank you. Thank you for having me, Mike. Great to be here.
Mike Linton
All right, let's start with a discussion of each post and then we'll put them all together in terms of what's a marketer supposed to do with all this stuff. First, I couldn't help but notice in your post where AI is taking marketing, which noun was in control of that verb? And it was AI was in control. It wasn't like marketing had any control. So I wanted to talk about the general theme. What prompted you to write it and what's the real takeaway here?
Shiv Singh
Yeah, no, great question. So first and foremost, and you'll see this as a narrative thread through this conversation, but we have no idea what's coming. And I was just in a conversation with a few CMOs and one of them mentioned and I felt accurately to a certain point, that it's just like the few weeks before COVID If you remember February 2020 or the first week of March, before the country and the world really shut down, we were starting to see the headlines. We were starting to get uneasy. We didn't know what exactly was coming, but we knew something was. It's similar to that, but with AI, with the one big caveat, which is the world will not open up again. We're sort of crossing a chasm and the world will never be the same. What do I mean by this? Fundamentally, at the most intrinsic level, what we're seeing with AI developments is it's getting exponentially smarter and more advanced than we can even imagine. The way we are maturing as organizations, as businesses, as marketing teams, that's happening at a far slower pace. What it means as a result is that we're going to have what I consider, and I draw this from some incredible academic research, a jagged frontier where AI is going to be so impressive, so powerful in some realms and in others, partly or largely because I hate to put it this way, but our human inadequacies or simplicity or prejudice and biases or anti AI realms, we're going to be moving a lot slower. So when I think about who's leading whom and what we're about to experience. Huge technological shift. Dario Amodi, the founder and CEO of Anthropic, likens it to imagine if you had a new country appear in the world that had an army of super intelligent transformers that was 100 times smarter and 100 times stronger than any other country, we're dealing with that coming our way. And in our wonderful, cute marketing departments, we already had enough pressures, we already had enough problems. We were already worried about our jobs. Our 10 years were already sinking, and now we have this thing coming at us. So it's a bizarre, crazy time.
Co-host/Interviewer
So one country with all those Transformers like Bumblebee in the.
Shiv Singh
There you go.
Co-host/Interviewer
You Know the favorite transformer, obviously, Bumblebee. When you, when you talk about, you know this, one of the things you say is the biggest variable and maybe the only real variable on this is leadership quality. You talk about that and then you talk about these leaders making fewer, harder bets. I want to talk about those two things and then I want to talk about invisible failure. So tell us about leadership strategic bets, and then we can vault into invisible failure.
Shiv Singh
Yeah, absolutely. So first, what's really important to note is that we're at a time where we're starting to see marketing functions change from being human only teams to human and AI agent teams. And it hasn't changed the org structure of the function, but that change is coming. What we're also finding at the same time with this change, where all of a sudden, as a leader, as a chief marketing officer, as an SVP of marketing, you're not just managing human beings, but you're having to manage an army of agents as well. In that case, it leads to a very interesting, provocative, thought provoking and important question is what does leadership look like? Just when we had figured out how to lead teams of human beings, we are finding that we have to bring the two species together, the humans and the AI agents, and get them to work well together. And it's a little bizarre because you have the AI agents that are much smarter in some respects. They're taking away job activities from the human beings. And then in other realms, they have to partner and work with the human beings and integrate into those traditional workflows.
Co-host/Interviewer
So how do I know? Like this leadership thing, how do I even know if I'm a good leader in this space? Like what? Because I hear you. Like, it's hard enough just to lead a team of humans and now I have to go, what, recruit a bunch of people off of our agentic people, off of a Multbot? Like, what do I, what am I, how do I even know I'm doing a good job here? Because there's no roadmap.
Shiv Singh
Yeah, so. So I'd say that there are two or three factors to consider. The first is some of the fundamentals don't change. You know, you're looking at the quality and the quantity of output from your team and how does it, you know, drive business? Measurable results. Those fundamentals fortunately don't change. And when I say your team, your team of human and AI agents, the second piece though is you need to assess whether do you have the right tools in your leadership quiver or the right arrows for what it takes to lead a team of human beings. And that you probably do, otherwise you wouldn't have gotten to the point in your career that you have. But then AI agents who are super strong in certain capabilities, have very low EQ often, but are super smart and make much quicker, automated, multi step and autonomous decisions. So in that case, it's more about orchestrating and having a bit of humility because they're smarter than you on the human side. It's guiding them to work together, but also with the confidence that you've been to that movie before. So different skills for the AI agents and for the human beings. And there's actually some really interesting research out that shows what does it take to lead a human team only. An AI team only. And then how do you bring them together that, that we can draw from. But it is early days fundamentally.
Co-host/Interviewer
And as part of this being leader, one of the things you're, you believe is that means you make fewer, harder strategic bets than you used to. What do you mean by that?
Shiv Singh
Yeah, so this is where it's, it's, it is a very difficult time to be a chief marketing officer and it's arguably only gotten more difficult in the last two years. So I sit on the board of a Fortune 300 public company, you know, 15 billion in revenue, 30,000 employees, and I, and I do some private boards as well. And what's increasingly happening in the boardroom is conversations around we want to drive up productivity, we want to drive up efficiency. We're reading a lot about AI. Everyone's talking about AI. We need to invest behind AI, which means that we need to find the money somewhere for those investments and we need to make our traditional business functions operate more efficiently. And when that conversation takes place, the first function that they look at to save money and to put pressure on to say you should be able to do more with AI and do it more efficiently is marketing. Unfortunately.
Co-host/Interviewer
Yeah. Richard Sanderson just was on the show saying of the Fortune 100, the pressure on them to show real results on AI this year is enormous. And real results mean you're going to do a lot more with a lot less.
Shiv Singh
Absolutely. And he previewed the results of that survey at a last AI Trailblazer Summit. So I'm pretty close to it. But with that in mind, practically what it leads to is a few things. Firstly, the CMO has to immediately flip from being a peacetime leader to a wartime leader, whether they are at war or not. That's the first step. The second step is they don't have the room in their budget to do as much experimentation and testing as they once did. When I was growing up in the marketing world, I could tell my CMO I'm going to put 10, 15% aside for testing and some bets will work out well, some won't. When I'm being asked to save 20, 30, 40% of my overall budget, I don't have a percent to put towards testing. What that means is, and what the CEO is looking for much more aggressively is place bets that win. There's no room to fail. Which means the CMOs are being forced to make fewer, harder, more strategic bets where their careers are much more on the line and the era from experimentation is ending.
Co-host/Interviewer
You have to say when we say win, that's almost always through the lens of financial winning versus any other winning right now because used to be able to say, look, I'm going to run a pilot and this thing could take two years, but it's going to work. I'm thinking all the loyalty programs, for example, I rolled out, that takes too
Mike Linton
long maybe for some of this.
Shiv Singh
Without a doubt, we all bound by the quarterly earnings cycle which the CFO controls and he's looking or she's looking for predictability, repeatability, all of those factors. There is unfortunately less and less time and that's what makes it so hard. You know, the sands are shifting beneath the feet of the CMOs in terms of the technology changes. The pressures from on top around cutting budgets and using AI are changing much greater. And it leaves a CMO with two choices. Make big bets based on their gut or use old rule books that where they have a higher degree of predictability. Yeah, but the only problem with the latter is they only last. Yeah, until they last.
Co-host/Interviewer
Until they last. You need the west coast offense to fight Bumblebee.
Shiv Singh
That's it. You need something else.
Podcast Host
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Co-host/Interviewer
Tell me about invisible failure in this Context. What does it mean?
Shiv Singh
Yeah. So this comes from Ethan Mollick, this incredible University of Pennsylvania academic and researcher, and the study he. He did with a few others, which is all about the idea that when it comes to AI, it's. It's a jagged frontier, it's incredibly powerful in some realms, and it's just so stupid and so dumb in some other realms. As time goes by, it's dumb in few and fewer places. But they're invisible failure points. Because right now, for the advocates or the enthusiasts or the folks who are leaning in or leaning forward in your marketing function, they're going to use AI and get incredible benefits out of it, and they're going to try and push it through the teams, through the functions. At the same time. The detractors, and there are many of them, and they're detractors for a good reason, will always be able to point to the five or six things where their AI is not working effectively. And they will use those five or six things that they discover those. Those failure points that will first be invisible failure points, what will then hopefully be at least transparent to say, we should avoid using this thing.
Co-host/Interviewer
Not as good as you say.
Shiv Singh
Yeah. Now. Now a little bit of that tension and dynamic is totally fine. But where it gets wrong is if you think back to our earlier conversation, the CMO at the same time is getting pressure from the board, getting pressure from the CEO, having to cut his or her budget and make big bets. So when you bring all of these pieces together, the invisible failure points, the budget pressures, the pressures coming from the board, the desire, the need to make bets that actually win, it creates a tsunami of drama.
Co-host/Interviewer
That's. That's really a good point. We did a show with the CEO of Typeface, who basically said, if you are going to highlight a failure, you're a blocker. If you don't have another test to put up, if all you're doing is running around. Because I said, how do you know if you're a blocker or just a good business person?
Mike Linton
And he said, if you're a good
Co-host/Interviewer
business person, you're looking for more test
Mike Linton
things versus just highlighting the failure. If your whole job is just highlighting failure, you'll look in the mirror because you're a blocker.
Shiv Singh
Yeah, but you know the funny thing, Mike, is that that's very much true, with the caveat that CMOs are expected to do tests with a much higher success rate than they've had in the past because there's less money to play with.
Co-host/Interviewer
Yeah. Hey, I want to flip over to all the activity going on in creative, we got nano banana, iPad crush. We're still in the first inning of AI's creative impact. Tell us what you see.
Shiv Singh
So firstly, I see a lot of noise and a lot of bias and a lot of prejudice. And I want to say this in as clear terms as I can, which is we have to cut the crap and get away from that. And the bias and the prejudice comes from language of we human beings, we're so, so special. We have imaginations, we can create, we have emotion, we have foresight, we, we have art, we have the humanities, we have eq. And assuming that AI cannot fake any of that. So the first thing I want to say and just put it out there is in many cases across those dimensions as well. The AI is performing And Nano Banana 2 is just one more iteration of this, one more development moving in that direction. It's performing nearly as well. It's faking. It doesn't take the way we think, but in its own way it's able to fake the way we think creatively in a way that is mind blowing and hugely frightening. That's the first piece. The second piece is we have to stop being stubborn. We like go back to these old tropes about, you know, creativity is the ultimate business differentiator. Yes, I do believe creativity matters a lot. But one is not the ultimate differentiator. And in many cases decent versus mind blowing creativity is good enough to move a brand forward. And we have to, and I know this might sound blasphemous, but we have to accept those realities because that good enough creative, when it's done by AI, is so much more personalized and so much more quickly optimized that it makes up for that delta between our brilliance, our human brilliance and what an AI might be creating. So that's, that's a second point. And then the last thing I would say is we have to draw inspiration from outside our field. And where I've been most inspired is actually from James Cameron, the director, you know, the famous director avatar Avatar. You know, firstly he saw the power of technology with CGI so that a decade ago and he's not concerned about what's real and what's fake. He's like, I'm just going to do phenomenal storytelling and these enable me to do it. More recently in the last year, he joined to the board of Stability AI, which is one of the image and video generation tools. And the reason why he did that was he wanted to make a statement to the film industry to say there's changes here. It's as good as the technology, if not a hundred times better than when I was creating the Titanic and Avatar and that what would take us two years to create? And he's quoted and I have a recording of this saying, what would take me two years to create, I can now do in six weeks. We marketers have to embrace that reality. We cannot deny it. And if James Cameron, who's in the film industry is able to do it, so can we. And think about creativity.
Co-host/Interviewer
Well, and this is. Look what the marketplace. Eventually the marketplace rules. It's not the people putting stuff in the marketplace. And the marketplace has accepted so much evolution. I mean, we did a whole show on, you know, Tony the Tiger and artificial characters, which, you know, there's been artificial characters for a long time.
Shiv Singh
Yeah.
Co-host/Interviewer
You can make a case that a lot of this is just an evolution
Mike Linton
of, of creative in, in another way.
Co-host/Interviewer
So I, I think that is, is really interesting. Can I tie this back to the
Mike Linton
first point, which is, you know, about leadership? So I've.
Co-host/Interviewer
We've seen a bunch of consumers rail against AI, A bunch of industry folks
Mike Linton
rail against AI creative.
Co-host/Interviewer
We've talked about governance.
Mike Linton
What should you be doing in this space when you're playing with all this stuff?
Shiv Singh
Yeah, I sort of feel I've been to this movie before and it makes my eyes roll. I think back to, you know, 2009, 2010, when I was at PepsiCo and we were starting to say that, you know, digital marketing is a real deal. A lot more of your dollar should move to digital. And we started to put hashtags in our super bowl ads. And a whole bunch of creatives and a whole bunch of marketers were like, you guys don't know what you're doing. You don't know this art. You don't know what it means to move hearts and minds. And, you know, history showed they were completely wrong. We're going to be in the same place all over again. And I'd say if. Because a few things are happening simultaneously. Firstly, our tastes and preferences and as consumers are fast changing. We don't have necessarily visceral negative reactions to AI the way the creative community or the marketing community may at times. And a good example of that is you see this in those Coca Cola ads and they ran a second generation of them this last winter. They do incredibly well in system one testing and makes everyone tied to the advertising industry furious. It's a funny, bizarre dichotomy. Regular human beings don't mind AI as much as we in our industry do, that's one piece to it. The second piece is this change is coming whether we like it or not and it is going to get normalized. It's. And the economics of it are so much better than the six month, nine month marketing campaign. And I work with a lot of brands who are very proud of the fact that they only take nine months to go from concept to add on air. And I'm like, folks, we're in the new world order and you need to get on board or you're going to have a stalled career.
Co-host/Interviewer
Well, we've done, we've done a bunch of shows on this where it's like marketers should not think they're special. And that always, if thinking you're a special function, like imbued with this special creative and other judgment that no one else has, that is a such a dangerous place for a marketer to think
Mike Linton
they are because they will resist all
Co-host/Interviewer
this stuff and then get trampled.
Shiv Singh
Yeah. You know, and that's where the challenge is. We spend, I would humbly suggest too much time talking to ourselves and in our own industry.
Co-host/Interviewer
You and I talked about that in why Kitty can't, where there's 10, 24 awards given out again to marketing, which
Typeface Sponsor Representative
is by market, which is a lot
Co-host/Interviewer
of award, way more than the Olympics gives out, I think. So, yeah, it's like, it's a lot of awards.
Shiv Singh
I think we're waiting for marketers to have the Nobel Prize of marketing to come next. But in all seriousness, you know, I think it was in last summer, last fall, I was hosting this conference and I interviewed this friend of mine who's a chief product officer from Visa on stage because I'm a former Visa executive. You know, we were having a good conversation and I asked him, you know, what has changed in your world with AI? And he was like, two things. Firstly, they've rolled out an entire framework and an ecosystem for how AI agents talk to each other and commerce transactions take place, which is great. But the second thing he said is, internally what's changed dramatically is that between our business analysts and our technologists, historically the most important handoff artifact used to be the functional specification. And he said that has now changed to being a built demo of what needs to get built by the technology team. So the business analysts are, are vibe coding. They're actually creating the application that they then hand over to the technologist to build more completely in marketing we have to adopt that mindset. And, and now I think with what I'm going to say, Mike, you're going to, you might get a few folks saying, never let the sky on your show ever again.
Co-host/Interviewer
We have that for a lot of our guests.
Shiv Singh
Okay, good, that makes me feel better.
Co-host/Interviewer
Knock yourself out.
Shiv Singh
Okay. But we have to be ready for the reinvention, transformation, or the burial of the brief, because the brief is this. We've all grown up with a brief. I mean, I, I, I ran a six month project, I won't tell you in which company where we were finalizing the right brief template. I mean, is that that special, that important in that time? But the brief is invariably a static document and we're moving into a moment where institutional knowledge, insights, all of those pieces are living and breathing. And just as you know, product teams have moved away from functional specifications to vibe coding actual applications to show their technologists what it should look like. We have to move away from briefs to creating live experiences. Like the next time someone pitches me on an idea using, I don't know, a sketch or a storyboard, I'm like, why didn't you just take two or three hours and create a entire ad to tell me, show me what you wanted to go and shoot? So our entire language has to change.
Co-host/Interviewer
Well, this is agile for marketing.
Shiv Singh
Just.
Co-host/Interviewer
And on, on steroids.
Shiv Singh
Totally. And we have the tools now for it.
Co-host/Interviewer
Yes, on steroids. Hey.
Shiv Singh
Hey.
Co-host/Interviewer
So, all right, let's go to the third post. Who remembers wins? Yes, and give us the Cliff notes on that. And, and then, and then we'll, we'll talk a little. We'll, we'll delve into it a little bit.
Shiv Singh
Yeah, absolutely. So, so I, I live in the Bay Area, in Silicon Valley, in the heart of Silicon Valley, and through the startup ecosystem and the venture capital ecosystem and even the tech giants, there's a new technological concept that's captured the minds and imaginations of a lot of those leaders. And I think it has incredible implications for the marketing world. And that is this idea of the context layer or the context graph. They come at it from the perspective of that if you want AI agents to work effectively in an organization, the AI agents can't just know what decisions were made, but they need to know the sausage making, how the decisions were made, the ups and downs of the choices of the team meetings, of the debates, of the legal team involvement, of when something was tested and failed. The traces or the decision traces are as important as the final output. They say that's the only way you can train the AI agents to work as effectively or more effectively as a human being in a autonomous or semi autonomous fashion doing multi step decisioning over time. So context layers, context graphs are huge for them I believe, and this is what I wrote about, is that it has, and I'm going to be writing a lot about this in the next six months is it has huge implications for marketing. Because if you think about it, let's just say, you know, in a wonderful CPG brand, the marketing team is planning their fall campaign. You know, it's February, March, good time to work on it and everyone, you know, does a lot of brainstorming. Maybe they even use an AI pilot to help them create a brief that brings together the insights they bring in the agencies. They do a cute agency day where all the cross functional teams of the agencies there are discussing the brand opportunity, the campaign brief and they land on an idea and they all are fired up and maybe it's going to use a growth oriented campaign using TikTok and some influencers. They spend the next two, three months building it out, developing the media plan and they launch it into the wild. And then it fails. And it fails because two years ago that same brand had the same idea but it was sort of stopped because there were some legal issues and therefore only launched in a half assed way. But fast forward two years, the reason why they did not know about that was because that decision or the, the, the, the history of that earlier campaign was lost in a slack exchange. They had definitely changed agencies by then. There was some team turnover. The CMO unfortunately was so distracted over the last two years that he can't think, or she can't think back to that earlier, earlier campaign and didn't make that connection and therefore the history repeats itself and they're making the same mistake.
Co-host/Interviewer
And this happens a lot. Then you get a lot of pressure too where if someone doesn't bring that up they're like, well, it's a different world now so we don't need to pay attention to that. Or you know, that was the old regime. We're new, you know.
Shiv Singh
Yeah, we're different. So, so. But Mike, now imagine this alternative scenario where every decision, every team meeting, every legal review, every draft media plan, every creative brainstorm is captured in a context layer. So that when you're next having that AI pilot create a brief, it's not starting from scratch, it's incorporating all the learnings of that previous campaign and not just the results but all the decision making steps. They would be so much more powerful. That's the idea of having a context graph and A context layer.
Co-host/Interviewer
And we now have the technology marketers have a context graph now really that isn't either in their head or in their collective leadership group.
Shiv Singh
Yeah, well I, I would humbly suggest it's very often not even in their head or in their collective leadership group because there's so much turnover and change. I'd say practically none. Because the technology is new, but you can build it today, in 2026. You can build it, but you have to look at your martech stack and ad tech stack very differently. You have to understand the AI extremely well and, and choose products and solutions and then build them into the way you do work so that you're building a context graph that stands the test of time and helps you for not weeks ahead or months ahead, but years ahead as well.
Co-host/Interviewer
And that is a lot of thinking that people are going to, should take away from this because that's one of the reasons I think a lot of teams that stick with their agencies and the teams stay together, they essentially have a context graph if they are functioning really well.
Shiv Singh
Yeah, but it's, but we, we do know us human beings are not perfect. And even with the agencies you have turnover, you have exactly files lost in directories. I mean the agencies are developing their, you know, AI solutions like WPP open because they want to keep that information for them. But it needs to be within the marketing function of a brand and but when built right, it becomes, it's the brains of your business and it becomes everlasting both to feed human decisions and agentic AI decisions.
Co-host/Interviewer
Well, also it's just way faster a context graph.
Mike Linton
It's way faster thinking.
Co-host/Interviewer
And what you said is losing is not fatal.
Shiv Singh
Forgetting is very true, very true.
Co-host/Interviewer
Which I think is really a good
Mike Linton
thing because if you forget that means
Co-host/Interviewer
you're going to lose for the same reason.
Mike Linton
Not a new reason.
Shiv Singh
Yeah, yeah, you'd much rather lose for a new reason. So I do believe context graphs are going to come into the mainstream in the next 24 months. It is more of an architecture decision versus a campaign decision, but is yet another example of where us marketers have to rethink the definition of our roles. It isn't just about how great our last super bowl campaign was or our employee feedback scores or the fact that we were able to optimize our performance marketing engine. We have to play both the short game and the long game and build for an AI centric world.
Co-host/Interviewer
And part of this shiv is some of this is long term thinking. In a short term world you have to have the courage to put the long term thinking out there, along with all the short term pressure dealing with. Right.
Shiv Singh
Without a doubt. But in this specific instance, this is an opportunity for the marketer or the CMO to go to the CEO and the CTO and say, this is what I need. This is what's needed to drive the business for years to come. Are you going to help me build it? And this is why it matters. Because it's only when you have that can you have an agentic AI workforce sitting next to your humans.
Co-host/Interviewer
Yeah. Or else.
Shiv Singh
Yes.
Co-host/Interviewer
Wait, well, so we're getting to that. I kind of jumped my own question train of thought here. Um, we, we've talked about all three of these posts. Put it together now. Put the post together. Tell our audience what they should be doing.
Shiv Singh
So first and foremost, I would say there's no time to lose. You know, you want to be up to your ears in AI. You want to have those wild dreams and those nightmares about it. If you aren't having either, it means you're not up to your ears in it. Secondly, you want to make sure that you're not coming to the table with certain biases and prejudices. So saying, for example, only human beings can drive creativity is, I'd say, a dated bias. Or saying that we just want to treat AI as a little tool that will nudge the process along. It's like a better Microsoft PowerPoint is the absolute wrong way to think about it. Third, you want to think in terms of revisiting your martech and ad tech stack completely because you want to allow for the creation of a context graph that sits within your company. That's your own ip. Fourth, you want to retrain your employees and your leadership team to know what it means to work with AI agents side by side. You want to be able to spin them up for specific tasks and activities. You want to rebuild your workflows to have AI agents scurrying around within them as well. And then finally, and in some respects, most importantly, don't make the mistake that many of us, or at least I did as I was building my career, which is, I assumed I was further along than my consumers. They're doing more with AI. They're embracing AI. They're using it as, and as a friend of mine said earlier today, Shannon, they're using it as the operating system of their lives. And if we aren't personally as marketers or professionally in our functions, we're already two steps behind.
Co-host/Interviewer
All right, so giddy up, as they say. Hey, you know I would be remiss if I didn't ask about the arguing between Anthropic and the DOD and what this means to not just marketers, but everybody and how to think about governance and privacy and all that other stuff going on right now. Give us what's going on through your head.
Shiv Singh
Yeah, I mean, this is a really challenging moment and I think it is extremely important for marketers because it has brand implications, it has ethical, it raises ethical questions and very. And those two questions often fall in the hands of the Chief Marketing officer. So. So firstly, just to bring everyone up to speed, Anthropic was in negotiations with the Department of War to finalize a deal, a $200 million deal. So that Claude, that's the large language model from Anthropic, would be deployed across the Department of War in a lot of very important mission critical, critical use cases. They hit a roadblock in their negotiations because the Department of War wanted to have a clean level of access, whereas Anthropic was very worried about the large language model being used to do surveillance on American citizens and for autonomous warfare without humans in the loop. Now, depending on who you talk to, you'll get a different view on who is right and who is wrong in this. But what's a little frightening is the net result of it is they couldn't agree to terms and the Department of War decided that Anthropic would not be permissible. It would be taken off the supplier list for the US Federal government and it would be given a classification. It's Policy 3542, I believe, which supply policy, which meant that it would be treated as if it were a Chinese software company trying to steal trade secrets from us here in the States. What that means is it's not clear whether Anthropic can work with any company that does business with the federal government. Now this is a moving target. It's going to evolve over the next few days. And Anthropic is now suing the federal government. The federal government is saying if you don't let us use it the way we want to use it, we don't want to have anything.
Co-host/Interviewer
And ChatGPT has waded into this thing. They're both poking at each other in the super bowl and I think you called that a little food fight, which lots going on. So how does it end?
Shiv Singh
Yeah. So in the short term, if this stays the way it is, what's frightening, and as a proud US citizen, what's frightening about this is our federal government because they're in this argument with a large language model provider, arguably, as of today, the best. They're not going to have the best technology at their fingertips. I don't like that when our federal government doesn't have the best technology at its fingertips. Secondly, what it also means, and this every company is going to deal with this is firstly, across businesses and their marketing functions, it's going to be a question of can you and. Or can you not use Claude? And Claude is not only the best tool for writing software, but it's also the best large language model for writing in general as well. So it's used a lot by marketing functions. So that's a problem. And then finally, where it's worrying also is that we. It's really an example of the more serious, difficult ethical questions that are going to hit us as we seek to use these large language.
Co-host/Interviewer
And this is just beginning. When you carry. This is the, you know, the easiest ethical question you're going to see because you're going to. It's going to get more and more and more.
Shiv Singh
Yeah. So that's all the horrible news. The one silver lining, and I'm like working to create a silver lining out of this, thank you.
Co-host/Interviewer
Because I don't want to have to go to the dentist to get an uplift after this,
Shiv Singh
is that we are on the cusp of facing harder, more serious ethical questions for our brands, which elevate the role and the importance of, of the chief Marketing officer if she or him chooses to take on that responsibility of brand ethics. And I think we should. It elevates our role. It sort of allows us to pull our chair back up at the big boys or big girls table. And we need to start thinking about all of these questions ourselves.
Co-host/Interviewer
All right, speaking of the future, what predictions do you have on what big things will happen before the end of 2026?
Shiv Singh
So I have a couple of predictions. Well, I just launched my 2026 ones, but let's see how they do over the course of the year. But a few things. One is work identity is going to continue to shift, which means especially in the middle layers of a marketing function where you have managers who are just gaining confidence, they're running a small team, they feel they're experts in their little sub function. All of a sudden they're going to feel inadequate and worried and insecure because these AI tools are going to be able to do half their job.
Co-host/Interviewer
They already feel that way. Let's be clear. When I was in that space, yeah, I felt so.
Shiv Singh
Yeah, so. So it's it's going to create a lot more anxiety and stress and worry. And when you have those emotions, you don't have a high performing team. So that's one. And that's going to be a leadership challenge for the marketing leaders to manage through. The second one is we are going to see much more AI driven creativity, regardless of all the noise around it. And some of it will just be damn good. And it's just going to be that in the future. The third is the pressures from the board and the CEOs will only increase over time. But the best or the strongest or the bravest of marketers will realize that they need to rip off the band aid and rebuild their function. And I work with a lot of marketers. The best ones are recognizing they have to rebuild their function from scratch versus treat AI as another lipstick to put on your pig. Yeah.
Co-host/Interviewer
As Tom Goodman said in his show on this, if you design the department around AI, you get a different department. It's like when you design the manufacturing plant around electricity instead of around the machines that were there during steam.
Shiv Singh
Totally. Yeah. And then the last one I would say is, and I'm doing a lot of research into this and working with a lot of teams on. But the very nature of how we define expertise, how we define who is a marketer, who's the marketer that's exceeding expectations. What is their job description? What is their role? What do we reward them for? All of that is starting to change. And where that change needs to begin actually is with the Chief Marketing Officer's own job Description. I encourage CMOs to go back to the job description that they were hired with, rewrite it for an AI first world and realign that with their CEOs, and then go back into the function to lead. So I think that's going to be a big shift as well.
Co-host/Interviewer
All right, well, we'll have you back towards the end of the year to talk about all this stuff if you would like to come or you'd like to join us again. Which brings us to our traditional last question. Funniest story you can tell on the air and or practical advice we have not yet discussed. You can take both or one, but you must take at least one of those two.
Shiv Singh
Well, I'll take both of them. So just last week, and it's a bit of a cliche maybe, but I couldn't believe it. I've built my career in marketing. I've written three books. Last one on marketing with AI and just last week my mom calls me up and she says, shiv, I was at a dinner and I just couldn't explain what you do. What do you do? I don't know how to answer that question. And she's like, aren't AI taking all the jobs? And if so, what are you actually doing then? So it got worse and worse and I don't know how to resolve that.
Co-host/Interviewer
This is where you got to say, I'm becoming Bumblebee.
Shiv Singh
I'm transforming.
Co-host/Interviewer
There you go.
Shiv Singh
Yeah. All about Bumblebee. And then the advice or the practical tip is, you know, Claude Cowork came out just less than a month ago. Oh my gosh. Everybody has to spend at least an hour a day in Claude Cowork. So what it is like Claude Code, which is Claude code is an amazing AI programming tool. It lets you program incredibly well. Claude Cowork is the same thing, but for non programmers. Very simple exercise that I did. I had like 200 odd research papers on different facets of AI and business. I pointed Claude Cowork at that fold on my hard drive and said, read all of these, create summaries and then categorize them into seven different folders and move the files and put them in those folders and then stack, rank them in terms of importance and highly cited as to which ones I should read first. And they did that in a matter of two minutes. And that's a tiny use case. You extrapolate that to what a marketing function can do with Claude Cowork, if, of course, arguably, if the Department of War lets us use them and it's mind blowing what you can do and Claude Coworker is available and anyone can use it.
Co-host/Interviewer
All right, so as we said earlier, giddy up everybody. Thank you for joining us, Jev. And thanks to everyone for listening to CMO Confidential. If you're enjoying the show, please like share and subscribe. New shows drop every Tuesday and all of our more than 160 episodes are available on Spotify, Apple and YouTube, which include it's a Bird, It's a Plane. Holy shit, It's AI Parts one and two. Is your next best customer an AI bot? Synthetic influencers. Should brands do it themselves? And of course, Shiv's first show. Why can can't. Hey all you marketers stay safe out there. This is Mike Linton signing off for CMO Confidential.
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Host: Mike Linton (Former CMO at Best Buy, eBay, Farmers Insurance, Ancestry.com; CRO at Ancestry.com)
Guest: Shiv Singh (CEO, Savvy Matters; Co-founder, AI Trailblazers; Former CMO, LendingTree; Author, Marketing with AI for Dummies)
Date: April 14, 2026
Episode Focus: How AI is fundamentally transforming marketing, CMO leadership, creative work, risk-taking, organizational structures, and the ethical/operational challenges marketers are facing in 2026.
This episode dives deep into AI’s accelerating impact on marketing, exploring what leaders should expect, how organizations must respond, and why the old rules—and mindsets—of CMOs are under existential pressure. Mike Linton and Shiv Singh unpack Shiv’s recent posts which sparked industry debate, covering:
The episode is thought-provoking, candid, and sometimes a bit foreboding about the speed and depth of AI’s transformation. Both Linton and Singh bring humor and honesty—poking fun at marketing’s insularity, awards obsession, and biases, but urging courageous, open-minded action fast.
Shiv’s Parting Advice:
“Giddy up, as they say.” (37:55, 48:17)
Perfect for:
CMOs, marketing leaders, agency execs, and anyone who wants a clear-eyed, actionable synthesis of where AI is taking the marketing industry—and how not to get steamrolled, replaced, or left behind.