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Hey, if you're like me, you're feeling like AI has broken your marketing. How your team's working, the tools you're using, the results you're getting. And that's because it has, it's fundamentally changed. And on today's show, we're offering you a promise of how to fix that. And we've got a very, very special announcement you're going to want to tune in for and we're going to take you behind the scenes. I did a complete change of how we run HubSpot's marketing team. I'm going to give you nine founding principles for that change and I'm going to give you the new operating model that we are running to win at marketing in this post AI world. Get to today's show. Hey, Kieran, I wanted to share something with you. I'm completely changing everything about how we run the marketing team at HubSpot. You've been off in a new role. You've been building out all of our AI technology and how we do marketing and sales at HubSpot. So I think you haven't actually seen something I'm super excited about. I'm calling it the refounding of the HubSpot marketing team. And it's how we actually bring the HubSpot marketing team in what you and I call the Loop era. Because one of the big things that we're talking about is how we actually wrote a book called Loop marketing and it's how you do marketing in the AI era which is now available. For pre order, click that link.
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It's a system called Loop and that allows you to out learn out, market and outgrow your competitors, use AI to scale creative, get recommended in the AI
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engines and be remarkable at marketing in this post AI world. Please go pre order. It comes out in the fall is going to be the best marketing book of the year. We're biased. We wrote it but I wanted to re found our team at HubSpot to be the best loop marketers in the world. And so I wanted to walk through with you some of the ideas and plan for what we're doing. I want to get your feedback. How's that sound?
B
Love it. I think we have been talking for a long time about how the rules of marketing have changed, how you organize your team have changed and actually how you do work is changing.
A
I love that today's episode is really a cheat sheet in marketing strategy and organization. Right. So it doesn't matter if you're a leader or you're a marketer. We're giving you the inside secrets so that you can turbocharge your career. Right, Exactly.
B
Look, we were successful because we managed to ride the wave of inbound, managed to ride the wave of old plg. I jumped onto AI riding a little bit of the wave of AI. You want to make sure you can ride the wave, make your career, make your money in the next cycle. I think this is a great episode for you.
A
I want to go over with everybody the memo because we made some major changes how we run the team here at HubSpot. And I want to break it down. The first thing is that marketing has been changed by AI more than any other profession. And the reason for that is that marketing is the culmination of everything. It's the culmination of storytelling, which has been disrupted by. It's the culmination of research and insights been disrupted by AI. It's marketing. Is coding been super disrupted by AI. Marketing is all of the disciplines in work in one form and package to actually persuade someone. And so if you, like us, think marketing has been completely disrupted, then I want to bring you into the loop marketing era with all of us. When a buyer asks AI for a solution like yours, do you know if you're showing up or not? At HubSpot, we've got a great product that actually helps you get discovered in AI search. HubSpot AEO helps you show up in these moments with the right answers buyers are looking for before the first click, before the first fill. That's the moment HubSpot AEO is built for. Go check out HubSpot AEO. You can trial it for free and it's going to help you understand how you're showing up in AI Search and how you can show up even more. It's the new world, and Kieran and I have spent the last year testing, writing, thinking about how to bring people into this loop marketing era. And one of the reasons it's so important, Kieran, is because AI can feel like magic, right? Like, remember the first time you used AI, Wasn't it like the most magical experience in the whole world?
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It felt like you had superpowers. I still get that feeling when you've built, like, cloud code systems or you're using codecs or you're doing all of these different things. It still feels like you have superpowers, but I think it's like how you wield them. That's how you wield it.
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Well, I think that's the issue is just like magic, AI can vanish or you can spend all day and actually get nowhere.
B
Right.
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Like, AI could play a trick on you. Right. That you've doing all this stuff and actually not accomplishing anything. And that's where I think so many people and so many teams are right now, doing stuff with AI and not getting anywhere.
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People are. Yeah, I think that's 80% of queer people are. It's like the AI messy middle of AI where people believe they should use AI for all things, but it's not clear if anyone's really achieving anything.
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And this is one of the key points if you want to turbocharge your career. You're watching this episode. You want to win. You want to be one of the best marketers out there. One of the first things you have to understand is that AI without outcomes is not marketing, it's art. AI just for the sake of AI is art and entertainment. It is not marketing. And I think all the great teams now are going to be obsessed with outcomes. Not that they weren't before, but even more so and about how they drive better outcomes with AI and in a world with AI, because you can do so much, Kieran, and it feels like magic. You need a lot more focus, you need a lot more constraints, or everybody's just going everywhere. AI without systems is like chaos. Right. And so that's what we actually kind of rolled out at HubSpot on the marketing team is how do we refound this team in the spirit of loop marketing? And in the book, Kieran, we make some important arguments that in loop marketing, it's all about how quickly can you learn, how fast can you move, and how obsessed can you be about outcomes. And I don't think the marketing of the last 10 to 20 years has been that way. Right. I think the marketing of the last 10 to 20 years has been like, how can I optimize this campaign? How can I game this system? How can I automate this thing? And it's very different, I believe. Do you agree with that?
B
So AI has increased the competition for everything. And so what great marketing is. Is also changing because you cannot get away with, like, good enough. And I think a lot of marketers used to just be able to optimize for algorithms, which is, you know, the kind of intersection between technology and marketing. It's like, hey, I can optimize some things and tweak things, and I can move my things up because of algorithms. What I'm seeing is we are getting back to basics a little bit. Like, AI is causing us to get back to basics, where you actually have to really understand your customer, you have to understand how to drive engagement. You have to do cool, you have to be able to do cool and you have to be focused on real outcomes. And AI is a tool that allows you to do that. But it is only as good as your deep, deep domain expertise. And I think AI rewards marketeers who have over the years practice real marketing and now have deep domain expertise that they can deploy through AI. AI is not really the best marketeer. It just isn't like all of these AI tools that are being launched. If you allow me to go on a slight tangent, all of these autonomous AI marketing agents from startups are pretty terrible. Like they're all, they research a bunch of stuff, they spit it into an LLM, they have some logic and they spit out some bland. A couple of the paid tools are pretty good. We've had super scale on from Patrick, that's pretty good. But most of the autonomous, quote unquote non paid marketing tools that create content and all these things suck. And why? Because AI is not a replacement for real market and domain expertise. And I think you're arguing that there's core principles you need to apply across your team and how they use AI. Be more prescriptive. Don't just say use AI for the sake of AI and like you just look at the usage go up. Well, we're AI native. This is awesome. There has to be some real principles and outcomes.
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Every marketing leader I talk to is like obsessed with what percent of their team is using AI. That's such a bull thing to look at, right?
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Yeah. There's no measurement of like what percent
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of my team is using gmail. Right?
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Like, who cares? You could be using AI and doing the most dumbest with it.
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Correct? Correct. So you know which most people are, right? So like let's say you're out there and you're like, okay, cool, I want to do something differently, I want to work differently. Well, before we even give you the full playbook, because we are going to go through the loop playbook in detail in many episodes. But you need to understand the principles behind the playbook. And when I put all this together for the team, I had nine principles, Karen, that I thought were super important. I want to go through them quickly for everybody and I think if you adopt how you work by most or all of these, you, you'll be wildly successful. It will transform your life. I'm biased. I have been doing these and it has transformed my life. The first one is we're AI by default. You know Humans and AI together can build remarkable ways to achieve results neither alone could do. I think that's really important. It's not humans or AI and it's not like, oh, I'm going to outsource AI to everything. It's like, how can humans and AI work the best together possible? And that the unique strengths of both is actually how you get new outcomes. That's the first one. Next is like strategy first. Just don't go and do magic AI, that has no impact. Right. Like, we don't want to do that. The third thing here is progress is greater than perfection. Learning is the ultimate compounding investment in this new loop era in this post AI world. I know you believe deeply in this one, Karen, like, break down for everybody why using loops to learn is so important.
B
Yeah. And I would say that the first two really resonate with me, which is people ask me, you know, what is the job of a marketer in a world where AI is a core part of how you do marketing? I think what you're describing is judgment and taste and understanding what is the right things to do and deploy AI for? I think the era that we're in today, the rewards go to the people who learn the fastest. So there is an existing playbook of how you do marketing, and that playbook has been written about in every blog post. It has been written about in every social post. There is ebooks on it. There is like collateral everywhere on this. All of that is in the LLM. LLM is giving you the best version of marketing to do, which means everyone is doing the best version of marketing to do. One thing that we have learned from creating a marketing methodology, I think in inbound, and I wonder if you agree, is that was transformational at some point in time. That was transformational because a small group of people were doing it and it was so differentiated from what everyone else was doing. At some point, it becomes the only thing that people do and the results start to average out for everyone because everyone is doing the same sort of thing. Now. It's still impactful, but it's not the most impactful thing. And I think you need to start to be counter to what the best practice is. And, and you can only do that through learning iteration. Now, we have done a lot of that learning iteration, we put it into a book. But I think that's why your speed of learning, speed of iteration, speed of experiment, it rewards the people who are outside of the edges of best practice.
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You gotta be differentiated, you gotta be early. And if you're Watching this show, you are early and you have the opportunity to start building and also interpreting these principles in your own ways. Right. And I wanna share a few more with you. 10x customer value drives 10x business results. If you obsess about customer value, you win. The cool thing is AI makes it not just easier, but brings in new ways to drive value with customers. Create remarkable experiences, remarkable ads, remarkable content. With AI that was just not possible. Super deep personalization, all of these things create really remarkable value. We talked a little bit earlier about outcomes, but outcomes over activities. Like if I was probably going to put one thing on a T shirt, that would be the thing I would put on a T shirt. We also just talked about number six, which is learning velocity compounds. You know, we talked all about like progress over perfection and that the sister principle to that is learning velocity compounds. The more you learn, the further ahead you get of everybody else. If you can be differentiated and then you can work on that differentiated marketing strategy consistently, you will get not just a little ahead of everybody else. You, you will get 10 times further ahead of your competition and everybody in your market. Right. That's the point that we're trying to make.
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There's always kind of been best practice narrative around doing marketing for a company is like don't be controversial now because of the way the online works. Controversy sells.
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Right.
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Like there's these things that you used to do that do not scale anymore, do not work anymore because they are the known thing to do.
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Kieran. When I was failing at marketing many times in my life our friend Brian Halligan would send me an email and it was the most soul crushing email. I think you probably got this email too and it would just say the definition of remarkable is to be remarked upon. And that was him just telling you you're not, it like you're just do, you're just, you're just churning out some stuff. You're not doing anything that is different and interesting and valuable. Right.
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Not getting talked about.
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Yeah, you're not getting talked about. You're irrelevant. You're the world's apathetic to you. Yeah, that's the whole thing. Okay. As we're kind of closing things out, we had a couple last principles that I think are super important. Outcome inflexible, goal flexible. I think one of the things we've learned is that humans get very tied to the goals they have even though that sometimes those goals suboptimize the outcomes that they're trying to achieve. And so everybody needs to have the context of like what is the result we're trying to get? And yes, I might have a sub goal that gets to that outcome, but if that sub goal doesn't make sense, I should raise my hand and we should figure out a different goal. Right. And I think if once you're on a bigger team, more than a few people, this becomes a real problem that we all have to solve.
B
Can you give an example of a outcome versus goals?
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So like let's say for example, you run social media at your company and the goal of your small team is to generate leads for your sales team. But you're like, ah, social media is not that great at lead gen. So my goal is going to be how many impressions I can generate. Well, if those are low quality impressions, you suboptimize the goal, the team goal, which is like to generate interest and demand for your sales team because you're not even talking to your target audience. Right. And so you're off there doing a goal that actually doesn't achieve the outcome.
B
Right.
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So you're going in two different directions. So you need to actually work and say, hey, this goal doesn't make sense anymore. We need to come up with a better goal that that I can make sure there's a dotted line to the objective that my team is actually trying to hit.
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Right? Yeah. The thing you actually want to happen.
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Exactly. Okay. And the last two I'll put kind of put together. It's like in marketing, understand the rules of the game. And the more you make the rules of the game, the easier it is to win. And understand that any game you're going to play, you want to play at a fast pace to win the game. Don't be afraid to lose the game. And AI right now I see most marketers, Karen, afraid to play the game and playing not to lose. The AI marketing game versus actually playing to win.
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Take risks.
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And Kieran, one of the biggest radical things we've done, there are three big things. We changed how we hired and we're hiring for AI builders versus traditional marketers.
B
Huge. We should just pause in that like you actually have changed the job profile.
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Job profile, the job, wreck the job process. You now need to build with AI as part of the interview process, which is completely different than you would have done. Every role, every role. And before it would have been like put a doc or a PowerPoint together. That is now obviously elite. So that's one major change. The other major change is we're working with you and your team to embed AI engineers in with the marketing team to rebuild workflows in new ways that would have never been possible before. AI, right. Like that's incredible.
B
Yeah, it's really for AI, it's understanding the depth of the workflow again, the nuance of how someone does their work and making sure that can scale to everyone. And so I know the thing you and I talk about is that you learn from the best and you can scale those workflows to the best. And that's what we are collaborating on.
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You want to make your best teammates the work they do available to everybody. And that's what we're trying to do and get the knowledge and wisdom of a whole team and systematize it. And then I want to close out with I think the biggest thing we're doing. Kieran, we are rolling out an entire new operating model which is I think pretty cool. We're moving much closer to how a product and engineering team works than a traditional marketing team. We are now moving to a six week sprint model. And for that six weeks there are two types of sprints. They're like team level sprints where if you're a member of a team, you have your goal and you have your tests and activities that you are working on towards that outcome in a very time box. Six weeks period of time. And all of this is transparent. Everybody's gonna be able to see the sprints, access the progress with AI and it's going to also lead to a whole new level of transparency to then we're going to have kind of like team wide sprints. We call the mission sprints of like, hey, there's a big rock. We as a team need to move forward. We're going to cross functionally coordinate across marketing to move that. We're going to have a sprint leader and coordinate on a very tight weekly basis with standups with really important mechanics. Like why don't you talk a little bit about the sprint mechanics because I think you've pioneered a lot of these and I stole a lot of them from you.
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Again, I think if you listen to this podcast, everything we say we believe in because it eventually does come to fruition. And so we talked about some time back last year, we said, hey, we think marketing is going to move much more to be like an engineer. That discipline. That does not mean we did think marketing is not going to be creative. It's just going to look more like you would see a product and engineering team. And so what you've set up is these six week sprints. And what I love about it is Every sprint has an outcome. And what you're basically mapping out is, I actually believe in the future my marketers are going to be able to do a lot of different things. They're going to be, like, much more, like, generous than niche people. So I should just have a sprint where I have a collection of folks that can get together with a core outcome I want to achieve over the next six to 12 weeks and then maybe one sprint or two cycles and I can have a group that just go after that outcome. Right. You don't have to go, oh, this? Does this team on it? Does that team own it? Does this team own it? No. Like, who are the best people? I have this thing that I need to go after in one or two sprint cycles. I'll put those collection of folks into that sprint with a clear outcome working model and they can go after it. Right. And that, I think that is a very different way of working. I think marketing is fundamentally broken because it still has such a tree structure with all these teams with, like, deep domain expertise. And it's hard to make everyone work together because they're all so different in what they do. And you're kind of breaking that model.
A
Totally breaking that. Mara, we want people to be super contributors, super generalists who can do much more and own much more of the process. And I think that if you're building a career marketing, that's the way this is going. Also, in a world of AI with, anything's possible and you can have the world's shortest attention span. I think focus and constraints have never been more important. And this sprint model allows everybody to have really helpful focus and constraints. And what I love about it is I tell everybody there's two outcomes to a sprint. Either you achieved your outcome or you learned a lot.
B
Right.
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Like, that's it. There's no failure. You either learned a lot or you achieved your outcome. And both of those things matter a ton. And oftentimes you accomplish both of those things, you achieve your outcome and you learn, which is really, really powerful.
B
Yeah, we should do a whole episode in a couple of months. Like, you've basically bought up the existing marketing team structure and moved it much more to, like a fluid sprint model that's very outcome focused and you probably will get a lot of learnings that would be really valuable.
A
We'll do a future deep dive. Any questions you have about the sprint model in the short term, drop them in the comments and. And I'll read those comments and answer them. But, Kieran, in September, we got the loop book coming out, Loop Out, Learn Out, Market, Outgrow. It's available on Amazon, wherever you get your books, Barnes and Noble, Target, whatever. Please pre order it. We worked really hard on it. We think it's incredible what we went through today with the how to Operate and Work and build a Marketing Team in the Modern Era is all founded and all predicated on the book and wouldn't have been possible without the book. And we're going to be doing lots of more episodes on marketing and so we'll see you very soon on marketing. It's the Grain Let me tell you about a show I love hosted by my friend Ross Simmons. Each episode hosts an in depth analysis of some of the greatest creations and creators of all time with deep dive conversations on the creative process that went into building companies, brands, stories and more. If you like learning about history, learning about the creative process, you'll love this podcast. This podcast is perfect for anyone who wants to learn how to systematize their creativity but still be organized. Ross just did a fantastic episode about Reddit and AI distribution in the playbook that everyone is missing. Listen, wherever you get your podcasts, this data is wrong every freaking time. Have you heard of HubSpot? HubSpot is a CRM platform where everything is fully integrated.
B
Whoa.
A
I can see the client's whole history.
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Calls, support tickets, emails, and here's a test from 3 days ago I totally missed HubSpot grow better.
Episode Date: June 24, 2026
Hosts: Kipp Bodnar (HubSpot CMO), Kieran Flanagan (HubSpot SVP of Marketing)
Podcast: Marketing Against The Grain
This episode centers on how the world’s best marketers are adapting their strategies in the era of AI, specifically as the landscape shifts further for Q3 2026. Kipp Bodnar reveals the foundational changes he has made to HubSpot’s own marketing organization in response to AI’s disruptive impact, announcing the team’s “refounding” in what they term the “Loop era.” Through candid discussion with Kieran Flanagan, they share the nine principles underpinning this new operating model, dissect how AI commands a rethink of marketing basics, and unveil tactical changes driving differentiation for leading marketers.
[00:00–04:37]
AI has “broken” traditional approaches to marketing, dramatically affecting tools, workflows, and outcomes.
Marketing is uniquely disrupted because it amalgamates storytelling, coding, research, and persuasion—each now transformed by AI.
Quote:
“Marketing has been changed by AI more than any other profession ... all of the disciplines in work in one form and package to actually persuade someone.”
— Kipp Bodnar [02:26]
It’s not about how much you use AI, but whether you achieve meaningful outcomes with it.
“AI without outcomes is not marketing, it’s art. AI just for the sake of AI is art and entertainment. It is not marketing.”
— Kipp Bodnar [04:47]
[01:12–06:10]
The “Loop” system, also featured in their upcoming book, “Loop Marketing,” is about out-learning, out-marketing, and outgrowing competitors with AI.
Winning in this era depends on rapid learning, speed, obsession with outcomes, and counterintuitive actions.
“It’s all about how quickly can you learn, how fast can you move, and how obsessed can you be about outcomes.”
— Kipp Bodnar [05:14]
AI rewards those with deep domain expertise and the ability to use AI as a multiplier, rather than a replacement.
“AI is a tool ... but it is only as good as your deep, deep domain expertise.”
— Kieran Flanagan [06:33]
[08:05–15:23]
AI by Default:
Humans + AI collaboratively achieve results neither could alone.
“It’s not humans or AI ... it’s how can humans and AI work the best together possible?” — Kipp Bodnar [08:18]
Strategy First:
Don’t pursue AI for its own sake—tie it to strategic impact.
Progress > Perfection (Learning Compounds):
Emphasize iteration and rapid learning over perfect execution.
“Learning is the ultimate compounding investment in this new loop era.”
— Kipp Bodnar [08:41]
10x Customer Value:
Obsess about delivering exponentially greater value to customers; AI opens new doors for remarkable, personalized experiences.
“If you obsess about customer value, you win. ... AI makes it not just easier, but brings in new ways to drive value with customers.”
— Kipp Bodnar [11:05]
Outcomes Over Activities:
Activity metrics are meaningless without corresponding outcomes. T-shirt-worthy: “Outcomes over activities.”
Learning Velocity Compounds:
The faster you learn, the bigger your gap over others.
Outcome Inflexible, Goal Flexible:
Stay fixed on results, adapt goals as needed to get there.
“Humans get very tied to the goals they have even though ... those goals suboptimize the outcomes.”
— Kipp Bodnar [13:12]
Understand (or Make) the Rules:
Know the rules of the marketing game, but don’t hesitate to make your own for an unfair competitive edge.
Play at Pace, Play to Win:
Move fast, take risks, and avoid playing “not to lose.”
“AI right now, I see most marketers afraid to play the game and playing not to lose the AI marketing game vs. actually playing to win.”
— Kipp Bodnar [15:15]
[15:23–19:59]
Hiring for “AI Builders,” Not Traditional Marketers:
Every new marketing hire must now demonstrate AI building skills during the interview process.
“You now need to build with AI as part of the interview process, which is completely different than you would have done.”
— Kipp Bodnar [15:40]
Embedding AI Engineers With Marketing Teams:
AI pros now work shoulder-to-shoulder with marketers, rebuilding workflows and scaling best practices.
Adopting a Sprint-Based Operating Model:
Marketing now mirrors product and engineering teams, with six-week “sprints” clearly tied to outcomes.
“There’s two outcomes to a sprint: Either you achieved your outcome or you learned a lot.”
— Kipp Bodnar [19:31]
Super-Generalists Over Deep Silos:
Marketers are expected to be “super contributors”—flexible, multi-skilled, outcome-focused.
“We want people to be super contributors, super generalists who can do much more and own much more of the process.”
— Kipp Bodnar [19:00]
On AI Usage Metrics:
“Every marketing leader I talk to is obsessed with what percent of their team is using AI. That’s such a bull thing to look at, right?”
— Kipp Bodnar [07:52]
On the Need for Differentiation:
“You gotta be differentiated, you gotta be early.”
— Kipp Bodnar [11:05]
On Organizational Focus:
“Focus and constraints have never been more important. And this sprint model allows everybody to have really helpful focus and constraints.”
— Kipp Bodnar [19:00]
On Remarkability:
“The definition of remarkable is to be remarked upon ... you’re not doing anything that is different and interesting and valuable.”
— Kipp Bodnar [12:41]
This episode gives a front-row seat to how the top 1% of marketers are fundamentally rebuilding their strategy, team structure, and mindset for the post-AI world. With unfiltered advice, real organizational changes, and a focus on transformative learning and differentiation, Kipp and Kieran make a compelling case for marketers to become “Loop” thinkers: blending AI, speed, and relentless focus on value to outpace the competition.
For a deep dive into their methods, pre-order their upcoming book “Loop Marketing,” which underpins all these concepts and will be released in Fall 2026.