#203: Strategy | Why Cookie Cutter Marketing Doesn’t Work with Gurdeep Dhillon, CMO at ContentStack

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Listening to B2B Marketing with me, Dave Gerhardt. Hey, welcome to this episode of B2B Marketing with me Dave Gerhardt. Today's episode is a master class in modern enterprise marketing featuring Gurdeep Dhillon. He is CMO at Content Stack. Guardeep has built an impressive career leading marketing at some of the biggest names in enterprise software from SAP to Adobe, Marketo to zora. Now at ContentStack, he's challenging conventional B2B marketing wisdom and rethinking how enterprise companies should approach demand generation and brand building. In this conversation, we dive deep into why marketing is ultimately a game of memory and reputation, not just lead generation. We explore how Gurdeep is transforming marketing at ContentStack with a bold account based approach. Why he believes today's B2B CMOs need to take more risks risks to make an impact and why? There's nothing more important in B2B than brand. Whether you're leading marketing at a growing company or just interested in where B2B marketing is headed, you're going to get a ton of value from this conversation. Let's dive in with Gurdeep. All right, I'm excited to do this one. We're recording this towards the end of the year. It'll probably be out early next year. But best part of my week is talking to great CMOs about B2B marketing, and I have a great one here. Gurdeep Dhillon is the CMO at ContentStack. He's built a career in marketing at a bunch of companies you've probably heard of that we'll get into. But Gurdeep, good to good to see you. Good to have you on. Thanks for coming on my podcast here.

Thanks, Dave. Good to see you again.

So we'll get into Content Stack, we'll get into the life of a cmo. But just kind of let's replay your career story a little bit just to give people some context as to where you're coming from.

Yeah, I'll give you the flyover. Started my career at SAP, spent a lot of time there. It's crazy when I think about it, 13 years, but I did a lot of different things so it felt new and fresh. Ultimately ended up leading marketing for their CX business, which was the marketing cloud, Sales cloud, Service Cloud and Commerce Cloud. Had an opportunity to go to Marketo, which I was a huge fan of Marketo mostly because of their content because I was never allowed to use the product at SAP and but I felt like I was part of the marketing nation because I read all their definitive guides and all the content. Anyway, had a chance to go over there with Steve Lucas and ran Demand Gen, which was awesome. But it only lasted a year because then Adobe bought us. So I went over to Adobe, was there for another two years running marketing for the Marketo and Magento businesses within the DX business at Adobe. Then I left Martech, went to Zora and was kind of on the finance side of the house. So looking at subscription billing, revenue automation, kind of the next phase of the subscription economy, which was super cool but definitely a departure from marketing to marketers. Coming to Content Stack nine months ago has felt awesome because I love being the icp. I love being back in the world of marketing the marketers. There's some, there's extra pressure that comes with that, but I absolutely love it and it's been awesome so far.

So you mentioned you were following Marketo, like, as a early day. And for me, it was HubSpot, obviously. Like, there's, there's kind of two. Right. But a similar story where, like, I was at a company, we didn't buy HubSpot, but as a marketer who's coming up junior in my career, I tell this story all the time. It's like my boss was like, yeah, I need you to make a marketing plan for X, Y and Z thing we're doing. I'm like, a what? You know, and so I, I Google marketing plans. I find HubSpot, they had awesome content. I go to their blog or use their template, I make a great marketing plan. And she's like, wow, you're super smart. And I'm like, HubSpot rocks. Right? And then, you know, a decade later, I end up buying HubSpot. Marketo had a similar influence on people.

Yeah.

Do you think those two examples, like, is that possible today? Or did we come up in an era where, like, there wasn't as much content? You know, now I hear, you know, there's so many companies and content, pieces of content and podcasts and videos and articles and whatever. Like, is it possible to be the HubSpot or Marketo from, like, an educational brand standpoint today, do you think?

I love that story. It's funny, you know, ChatGPT didn't exist then, right? So we were like, shoot, what do we do? Where do we learn? And we, we would go to the, to the vendors, right? We would search for the things we cared about, and it was the vendor's job to be present with content that answered our questions. I would say 100%. It's possible. It's a lot harder, though, because the cost to create content that's kind of mediocre is now zero, which isn't great for anything other than if it even still matters. SEO optimization, right?

Yeah, that's a good point. Like, back then, if you were the only guide to building a marketing, you know, a B2B marketing budget, like, you would get all the attention on that article, right?

You'd show up right now. It's like, man, there's going to be. It's a sea of noise. So I would say it's possible. I would also say it's an imperative because the only way to rise above the noise in this new world with AI making everything worse from a noise perspective is authentic, relevant content that really does create, I think, what you and I, like, you with HubSpot, me with Marketo, what we developed was a trusted kind of advisory relationship where we felt like they were making us better marketers. So then obviously, when it came time to making either technology decisions or deciding where we wanted to work, of course we thought about them first. So for me, yeah, I think it's not only possible, but it's an imperative. It's just a lot harder now. So. Yeah.

Which is a good challenge. If you're the right type of. If you're the right type of mindset, it's a good challenge, right?

It is definitely a good challenge. You need the right team, you need the right mindset, you need to invest in content formats like this, like we're doing today, where people are going to be excited about almost subscribing to the content. Right. You got to create content so good people would pay for it.

Right.

And you know, we call it audience marketing, but it's really just focused on who you're ultimately wanting to sell to but not worrying about selling. It's classic content marketing, but it's just evolved and it's now more important than ever because of Gen AI.

I like that. I like to write stuff down while we do this, but audience marketing is good. I often talk about what. What we do as brand marketing, but I think that brand marketing gets confused in people's heads as like, is that billboards? Is it out of home? And then it. But it's also different than content marketing to me. So I really do like audience marketing instead of content marketing or brand marketing.

Yeah, it might. It might all be under the same umbrella of like, brand. But, you know, it's content. It's knowing your audience, it's knowing what they care about, it's mapping the content to their needs. I think it all is in pursuit, though, of what I like to call brand relevancy, which is. Is your brand relevant in the minds of the right people at the right accounts, especially in B2B. And if it's not, then you got a problem.

So I want to. I wanna use like what you're doing at Content Stack to like, get into the tactics and team and everything. Question for you that came to my mind is you're a CMO now, but you came up very much in like the demand gen was your functional area. Right?

Absolutely. Yeah. I think I spoke at one of the Drift conferences when I was at Marketo.

That's right.

And it was all about demand gen. Yeah.

Yeah, that's right. Okay.

Yeah.

So there's probably not a section of marketing that has been more disrupted or changed over the last 10 or 15 years than demand gen. You could make the case for any. But you know, demand gen used to be like, let's do content syndication with like some kind of shitty, you know, outbound syndicating platform. But nobody was doing it and it was new and so like we could actually get leads. Or the way to generate leads would be to like write an ebook and gate it and like, oh my God, we're generating qualified leads for the team.

Can we actually talk about how, please, content syndication, like, is it okay now to say that it really was just like a black market for names?

Like, yes.

Is it okay to talk about that now? Like, what the.

Yeah, I, I equated to like depends on what type of site you're reading. But like, for me it was like, people are really going to hate this because they already classify me as like tech bro in marketing. But like I used to like read barstool sports all the time, right? And you scroll down to the bottom of those barstool sports posts and you're like, this guy thought he had a pimple on his neck. You won't believe what happened when they popped it, you know, and it's like this like insane image. And I'm like, those companies, like, that's where they put your content. Like, but what was. You know, maybe it was with like Tech Target or some, you know, like vertical specific. You know, you're selling to CIOs. But right at a time where that didn't. Nobody else was doing that then. Like, sure, you, you know, a practice could be content syndication. But yeah, there's a lot of people in teams that are just stuck in that old way. I'm curious, like content stack aside, if you and me. Well, I guess that's what we're doing because you're on my podcast. If we're just riffing on like the what is demand gen today? What is the role? Because there's like, there's that world which has changed. But then also I see everything get. And I worked with a really great two really great demand gen leaders at my last two companies. They were the most stressed out person on the team because they were like, dude, the content team and the social team and video, they just get to go do stuff. Everyone feels like everything is on my shoulders. Like if traffic is down, it's on me. If meetings are down, it's on me. If pipeline is down, it's on me. If we need upsell cross sell expansion. So is that demand gen? Like what is your. How does Gurdeep Think about, yeah, demand gen today. What does that mean?

It's funny they say hindsight is 20 20, Dave, but in my mind it always has been and always will be about brand and reputation. Now from a pure how do you think about and articulate your demand gen strategy? It has definitely evolved. If you think about even like my Marketo story, it was all about lead generation. Lead generation was like the greatest thing ever. It was all in pursuit of an MQL and automation was going to drive this incredible engine that would deliver the right leads from the right accounts. You hand them to an SDR BDR and they're going to be pipeline and you're going to be in great shape. Okay, fine. That unlocked a lot of scale in terms of channels and communications. You could deliver scoring, you could do super cool. That's kind of evolved now into account based, intent based shifting from a lead funnel to an account funnel. But I think we're missing the point. If we're honest with ourselves and we look back at when we were all running those lead gen programs, the percentage of leads and a lead is a person, right? So the percentage of leads that actually ended up buying technology, minuscule. That was true at every company that I, I've worked at. Ultimately, yes, people buy software, but it's the account, it's the buying center that you have to build. It's a longer term engagement. And the reason they buy is because of your reputation and because that they are, they trust your brand. And even, even he's going to get mad at me for outing him. But John Miller, who founded Marketo, has admitted that lead gen wasn't the thing, it was brand all along, brand and reputation. And so for me, that has never changed. Our job as marketers is to make sure that our icp, our target account universe, knows who we are, believes we are awesome and engages with us with great content. And that produces demand. And then you got to break demand down into different categories. We could probably talk about that too.

Wherever you are right now, listening to this, if you're on a run, if you're in your car, can you just hit pause and go rewind 30 seconds? Because what my friend here just described is that is marketing. That is marketing. We get into silly arguments on LinkedIn about this term and that term and it's like, do people know that you exist? Do people believe that you can solve their problems? Are you a reputable company in the space? If so, yes. Then when they are ready to buy something, they're going to raise their hand like that's.

What it's all about.

I remember getting beat up with my first time marketing role. I had done marketing for a year before we brought in a real sales leader. And in the interview process and he had, he was like, you know, 20 years older than me. And so he's like, here's this arrogant little, you know, social media marketer, I'm going to kick his ass. And I'm like, wait a second, am I interviewing you or are you interviewing me? And he, he gets up, we get on the whiteboard and we break down all of the like, you know, lead flow of the business. And he's like, dude, I gotta tell you something. You don't. What? You don't have leads, you have contacts. Like lots of people on your email list is not people that are going to raise their hand to buy our product. And I'm here, you know, touting around like, look at how many content downloads we got this month. He's like, none of that stuff matters. Yeah, it is all about being, you know. Now the challenge though is in B2B. Like I always struggle. Like you go to a company's website and it's like the only option is to contact sales or request a demo. And like, that's bad marketing. Because if that's the only path that we have to get in touch, like, of course I'm never gonna do that. And by the way, the only time I request a demo, I'm sure you as cmo, like, if you're shopping software, you're only gonna hit demo, like request a demo. If you're like at the 5 or 10 yard line, you're like, okay, we know we need, we need a cms. We need a marketing automation platform. Like, I think it's between, you know, this company, this company, this company, I'm gonna reach out to all of them and then we're gonna go buy. That's how people buy. It's not like, oh, 100%. Yeah, I was in content stacks, like, you know, nurture seque. I decided that I'm going to go spend, you know, 100 grand on a CMS today, right?

How dare you say that my nurture, my nurture drip isn't producing.

Sorry, sir, I've never, I've, I've never actually looked at your nurture. So I can't, I can't, I can't say it.

But I just, we don't have one, right?

Because you know, it doesn't work. But I just like, I like when we can simplify things and just think about things at a higher level. Like you need to have a brand and you need to have a reputation. If you can do those things and then plug in the tactics, then yes, you can have an effective nurture. Yes, you can run ads, yes, you can do abm, you can do whatever you want. But it starts with like the company strategy of like, how do we build a brand? And I go back to. Do you know about Eugene Schwartz and like the breakthrough. Maybe it was cl. Yeah, Eugene Schwartz and Breakthrough Advertising.

No, no, I haven't seen that one.

He basically came up with this like he was the first one. This is probably, you know, 50 years ago, was talking about like stages of awareness for selling a product. And it's like people have to be like, problem aware, solution, awareness, vendor award. Well, that's how I'd like summarize the day. And it's like, I need to know.

That I have this problem.

I need to know that there are companies that exist that can solve this problem. And I need to know that you are one of the vendors. I just love going back to stuff like that. From a principal standpoint, that's brilliant.

It's so simple too, but it's so relevant. And actually in this climate, especially because we've been kind of in a demand neutral to demand negative environment and you know, let's say best case scenario, 10% of your target account universe is going to be in market to, to actually do something like that's your playing field. To actually generate demand in the short term. And it's not even generating demand. I, I just say demand capture the, the scenario you described where, you know, I've already made a decision. I just need, I need. I probably wouldn't even be me. I'd probably send my team to go click on, talk to sales or get a demo from three different vendors and then have them do the research and make a proposal. I want to be in all those deals. So I got to make sure that, you know, I'm playing the game from a partner marketing perspective that I'm. That I do have that path to raising your hand on my website. You know that we are showing up in the analyst reports, we're doing good at paid search. Like all that stuff's got to be there. But that's not generating new Demand. It's the 90% that are out market that I really care about playing kind of a longer game with. But I don't control their timing. I can help influence it. That's the challenge right now, is that the need is clear. Like for us. I don't. Everybody has a different definition of like, what is pipeline Here at Content Stack it's identified need and timeline, meaning they're going to do something within a year. And if those two things are true, then we consider it to be pipeline. And right now the need is absolutely clear. Like everybody's ready to modernize their digital experience platform.

Actually. Yeah. Will you sprinkle in? Will you tell people like what Content Stack is? So as we talk through this stuff.

They can absolutely talk about that. Yeah. So Content Stack is, we're about to celebrate our seven year birthday, but started out as the first headless CMS in the market and has evolved into a composable DXP we call it, which is a digital experience platform competing with what is a headless?

For a non technical. For a LinkedIn thought leader like myself. What does headless CMS mean?

So headless CMS is a departure from the traditional coupled CMS where the front end and the content management system are tightly linked. When you decouple that, it's called headless and it allows you to basically publish content in an omnichannel way across whether it's your website, mobile app, scoreboard, kiosk, anything you want out of a single cms. And so content management's been around for a long time. There's kind of two cohorts of vendors in this space. There's the legacy, we call them the monoliths, that's the Adobe site cores of the world. And then there's the new crop of headless CMS players. So we started out as just a headless cms, kind of replacing some of the legacy systems. And then now we've evolved into what we call a digital experience platform, which includes things like personalization, gen AI powered content creation, but on brand, which I think is really important with retrieval augmentation these days, it's getting really good and then hosting as well. So basically powering digital experiences. And so that's the space we play in. There's a significant shift in the market of wanting to modernize, to be able to deliver dynamic personalized experiences. So the need is there, but they're like, yeah, I don't know if it's a this year project or a next year project or a second half project. And so I feel like my team, what they're, what's keeping them up at night is what kind of content, what kind of experiences do we need to create to help these companies and the people at these companies create that sense of urgency to act sooner and then there's a whole other group, the 10% that they've already decided I got to make sure we're in all those deals. So that's how we kind of bifurcate it in terms of our thinking.

How do you create urgency?

It's, that's the million dollar question a lot of different ways. Obviously, digging deeper into the pain points and the need and showing what good looks like. We're actually getting creative with like offers and incentives. So we, for the first time I was like, hey, have we ever like actually published an incentive for customers to do this faster? And they were like, no. And I was like, well, why don't we try it? So we introduced this thing called Retire the Legacy. And it's basically saying if you're an Adobe or Sitecore Oracle customer for CMS, we'll cut your contract in half, come to ContentStack. And it's actually going really well because people are already thinking about it and that's kind of a catalyst for moving quicker. So I would say, you know, there's content you can do, but I think offers incentives.

Yes. We were just talking about this. This came up in Exit 5 recently. Like, yeah, because we were like, let's do a, let's do a fun, like little Black Friday promo for Exit 5. And then it started a discussion in our community, like, why don't B2B, like technology companies or B2B services or whatever you sell? Why, why is it like a lore that like you can't discount when in every other industry discounts and promotions drive purchasing? Especially in, in a case where like you have a product that like, people know, they know they want to buy it. Like, oh man, I've been, I've been waiting. I was told my son I was going to get him a Nintendo Switch, you know, whatever. And I just saw a deal for it and I'm like, okay, you know, why don't I, instead of waiting for his birthday, like, why don't I get it now and I'll give it to him at Christmas. Boom. Now we won. Yeah, that's, that's an amazing campaign by the way. People are going to take notes on this. So I love it because it's not just a straight up discount. It is tied to like, if you're using X, Y and Z, we can switch. It's very authentic and like on brand as opposed to just doing a 20% discount.

100%. Yeah.

What's your perspective on that though? Like, I feel like offers in real life, marketing offers drive purchases, but in B2B, we're always like, we don't do offers here.

Yeah. And it gets complicated. Right. Especially in B2B SaaS because you've got the actual software license, but then there's implementation. So it gets a little dicey. I think what we're, we started with just the initial offer and now we're talking to some of our partners about what we can do for customers after they buy and in the migration phase. So it does get a little more complicated than just, you know, switching from an iPhone to Samsung. But I, I think psychologically a hundred percent, we should be leaning into these more B2C like tactics because at the end of the day, if we're going to do audience marketing, what does that mean? It means we're marketing to people. Yes, it's all account based. We want to make sure those people work for the right companies. But we're marketing to people, so why wouldn't we lean into more of the psychology behind a value exchange, which is what B2C is really all about. So I'm all in on it. I think I'd like to be bolder. But we're testing it out to see and then I want to use our own product like personalization to target specific segments and cohorts and even one to one of like very specific tailored offers, which I think is kind of the Next Frontier for B2B.

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I like what you said. I would like to be bolder. That says something to me about your personality as a cmo. Can we elaborate on that?

I mean, take risks, man. Like, but why?

What happens? Like, why should you be doing that in.

Because I don't want to do cookie cutter marketing. It's A, it doesn't work, B, how are you going to fight? I mean, look at Content Stack, right? Like we are. It's David versus Goliath, right? Adobe, I used to work there. It's huge. They're almost too big to fail. There's no world where I'm going to put a dent in this market by playing it safe. It's just not going to happen. So being bold is a prerequisite for us achieving our goals as a company. And that mindset, what it does is it unlocks some risk taking. It unlocks us trying things we've never tried before and being okay. If it's, it doesn't work, it's fine. But let's at least try. I hate templates. I hate, like, oh, what's our marketing plan template for the Quarter like that stuff is. It just drives me crazy because yeah, you gotta have some structure and you gotta have alignment with sales, but at the end of the day it's about the ideation and innovation. So yeah, I just feel like that the CMO, today's B2B CMO, has to be bold to make a difference.

Well, I think I asked you about it. Cause man, I resonate. So this, this is hitting for me like, makes me want to be like, I'm going to get out of exit five. I'm going to back in the field. Yeah, I'm going to give me back in. No, because I think it's easy. And I'm saying this because I know like lots of people listen to this and we play this game where it's like, it is so easy to get like. And I still go through, I get obsessed with like best practices and I'm like, oh, what, what are they doing for this targeting and what does nurture look like and how are they retargeting this and doing a battle and this campaign? But to me, the real difference makers in marketing and I've been able to talk to like folks like you and others through this podcast and my career. It's the ones who think that way. It's the like, hold on, wait a second. Do people know we exist? What are the crazy things we can do? It doesn't have to be stunts, but like how can we be bold? Because I think people forget that marketing is a game of attention.

Yeah, it totally is. And that's now more than ever, it's more important. Right? Because attention is, it can be a.

Gimmick because that, that can like gotta be authentic. Devalue your brand. Right. If you're the lunatic. You ever seen a. I don't know if they have these where you are, but like, you ever seen these little like, you know, franchise like tax shops like Turbo Tax or whatever and like around, you know, April, they hire some people to just like be in the streets, like dressed up as a Statue of Liberty, like flipping signs and doing nonsense. Like you can do that. It might not attract the right people to your brand. Right. But I think it goes back to what you said at the beginning. It's like thinking about the brand and reputation and like, how do we get people to know we exist? Because I think marketers, we often obsess over like, but, but how are they going to know about this feature and how are they going to know how we're different than. The number one goal is to like get someone to go to content stack website, get someone to hear about content stack, go to the website and say, hey, I heard about you through this thing. This is interesting. Tell me more. That is the position you want to be in. Like that's marketing's job is to bring your sales team those tell me more opportunities. And you either tell them more through marketing or sales.

I can't remember who. I saw a post on LinkedIn the other day, see if I can find it, but it was brilliant. Basically the punchline was that marketing is a memory game.

Yes.

That we are playing a game of memory and whoever plays that game the best, especially in a crowded space. If you're in a crowded space with lots of competition, you're playing a memory game. And if you suck at that, you're done. You're not going to grow, at least from a new loco perspective. And your competitors are probably doing a good job of playing the memory game with your existing customers, which means now your churn and net retention is at risk. So it's like a double whammy. I'll try to find it, I'll send it to you. But like the guy nailed it with the fact that it's a memory game because I totally agree. That's what we're trying to achieve. Yeah.

And the way that, the way that you're going to like get that recall in the memory game is not by sending out a, you know, 17 email sequence.

That's an annoyance game. Yeah. Maybe memory for the wrong reasons, but no, it's that. That's not what it is. That's not the game. You're right.

And so I think, like, I love when marketing is about this stuff, like let's, let's come up with bold ideas, let's come out, let's come up with creative ways get people to pay attention to us. So I'm, I'm really, I'm resonating with this. Yeah.

I think platforms like this are important, Dave, because I mean, you work with a lot of companies. The hardest part, and I think it's easier for someone like me who works at a company that sells Martech, because we wouldn't exist if not for marketing.

Oh, that's what all my listeners tell me. They're like, yeah, this. All you do is market to marketers. You have easy job.

But like where I'm going is convincing your leadership team, convincing your peers in the C suite, convincing finance that lead gen isn't the play, that content syndication isn't the play, that it's, it's brand Building it's reputation, it's investing in these other areas that are maybe not going to drive immediate return but are laying the groundwork for the future. Selling that vision is just as important as building the plan to execute because you got to get the buy in from your team because then you're going to map your KPIs and outcomes to that. So that piece, I mean I experienced it in my previous role, marketing to finance. Like nobody in the company except the marketing team, maybe some sales understood marketing and so it was really hard to change minds. I'm sure you probably see it across all different sectors of B2B. So I do feel fortunate in that way. But I can empathize with others where it's hard to sell this.

Yeah, but I still think the same stuff. Like as much as I joke about it, it's like the same things like whether you're. If your buyer is in cybersecurity or finance or HR or manufacturing, guess what? They still want, they still want to be smarter, they still want to be entertained, they still want to be educated, they still want to like, yeah, get creative content like those, you know, maybe we're good at it because we know marketing, we know the space. I think the path would be different if I didn't know like I don't know developers well, but I kind of know how I would go about researching developers to find out like what we should create content around for them.

Yeah, absolutely.

How do you sell that though to the team? Because I feel like it's great to have the vision, but is it a goals thing? Because if the. Yeah, it's great, man. Gurdeep, you got all these cool ideas but like, you know, pipeline is like behind this month.

Yeah, I mean that is the game. Right. So I mean I got a board meeting tomorrow that I'm building slides for and, and it's definitely something that I've got a nail in terms of storytelling of how things are going. When I interviewed with contentstack I said show me a company that has a pipeline problem and I'll show you a company that has an awareness challenge. And when I got here I realized absolutely that was an issue. Like the accounts that should care about us and should know about us didn't and we had to change that. On the flip side, we were making some minor mistakes in terms of the demand capture side, which we fixed. Ultimately what I've reoriented the business around is an account based funnel. And our job as marketing is to move our target accounts through a journey from being Unaware to aware to engaged to in conversation with us to then in pipeline and ultimately being a customer.

Wait, just for context, what is the. You don't have to tell me the exact ACV range of like the customers. Right. I think that's helpful for people when they think about, okay, he's gonna, he's doing ABM and this. What is the average deal size for a customer of yours?

Yeah, so I think this year it's going to end up around 160k, but anywhere from 100 to 400k depending on we're enterprise solutions. So it's perfect. It's bigger companies. So we have about 10,000 global accounts that we would consider to be ICP. And I need to show month over month, quarter over quarter, how those accounts are progressing in their journey with us. And when I got here, I wasn't happy with the percentage that were in kind of this unaware category. And so my story is the marketing that we're doing, everything that we can track is showing that the accounts are moving down that funnel in their journey with us. And we have more engaged accounts than ever. Are they in pipeline? Maybe not all of them. A higher percentage than before, though. Am I pretty confident that as the urgency rises and as they're ready to make a technology decision, are they going to be in our pipeline? 100%. And so those are kind of the leading indicators that I'm like, look, we're doing all the right things, we're hitting the right accounts, there's high levels of engagement, and we're converting the right number into our pipeline. That is a very different conversation than, oh, we generated a hundred MQLs and our conversion rate was this. And like, that's. I don't want to be playing that game. I want to play a holistic game. I don't want to fight over attribution. I want to just. Our job as a company is to engage all accounts. So I came in and I said, marketing owns the pipeline, full stop. Now, obviously, partners are involved, sales is involved, marketing's involved.

BDR doesn't mean you had to obviously create the definition for pipeline with the sales team. Like you're not saying here, and here's what pipeline is, we're going to own this. But let's agree, we worked on it together, 100%.

We worked on it together, we agreed on the definition, we agreed on the process, and we agreed that marketing is going to touch pretty much every deal. And so if that's the case, because, you know, you know, the classic fight between, like, what's partner sourced and what's marketing sourced? For example, like if you go look.

At all the touch points. I have no familiar.

Never experienced that.

Yeah, absolutely not.

There's touch points on every source, on every deal. And that's just the nature of. So I don't want to fight that battle. I want to say to my board tomorrow when I get in front of them that of the 10,000 accounts we care about X percentage are here. This is how it compares to the previous period. So far that's going really well. And I'm educating not just them, but also my peers on the C suite of this transition and they're really bought in. So it's good.

That's a great answer. And it's. I need to replay this back for people to. So basically like if you had this vision for how you're going to do things, but the operating system for the company is based on the old way, which is website traffic, form submissions, lead gen and then you're telling them about like, hey, we gotta do this like brand stuff. Like that's where that doesn't match because like, well Gurdeep, you said you're gonna generate, you know, 1200 leads this month and we don't have any. You're like, well no, no, no. This is why it's so important that like you have clear goals and then the strategy and then the tactics. Like Gurdeep standing up in front of the company saying here's our philosophy on marketing. Like I think so often we get right into the tactics. It's like, here's how we're going to do marketing at content, Content stack. We sell $100,000 deals. We think the universe of those, we think there's 10,000 companies in that universe. We're going to do a full account based motion. We want to take them through this stage, this stage, this stage. We're going to measure marketing like this. Cool. Everyone agreed? Everyone on board. Okay, now I'm going to show you the results quarterly, annually, whatever. Right. That. Do you feel like that's where this kind of all goes haywire? When the company strategy does not match the. And the marketing strategy are misaligned?

Yes, I think that is where it goes haywire. But also right now we're talking about engaging our stakeholders, engaging our investors and engaging the board. There are still metrics that matter and analytics that matter to make the marketing team better. And in that world you do want to go down to like the channel level. You want to, you want to understand the efficacy of your, of your Marketing, but that's not a story for hey, how's the business going? How are we mapping to the corporate objectives? So I think what you said is exactly spot on. If you can create that connection of the marketing strategy to the corporate strategy and the basically the ICP product market fit, then then you're good. But you still gotta do the other half which is, is your marketing team enabled through the right insights to get better every day. So you gotta play both sides of it. Otherwise if you only do the other, the first part, it's great from an optics perspective, but I worry that you're not actually getting better as a team.

All right, so give me a, give me a quick overview of the marketing team that you have like set up to, to go and do this. How many people are on the team? Not that it matters anymore because you could just have one marketer and AI agents. That's what they're telling me. But how many people on the team? What are the rough roles and buckets people?

Yeah. So we're growing the team significantly. I'm hoping to be around 70 people next year including a significant investment actually for the first time in India with building out a team in Bangalore. But basically I've got four functions underneath the CMO office which is product solution and brand marketing. So this is core product marketing which includes competitive intelligence, analyst relations and pricing and packaging. Also our creative team sits in there. And then solution marketing. I've got a team called integrated marketing which is a new team that combines content, campaigns, customer marketing and then a new team that I haven't figured out the name yet but it's combining social media, PR and influencer marketing. So if you have any ideas on that. I don't know what to call it.

But like, okay, now you're, you're speaking my language.

It's a great combo. Right. And the person who was going to run that team was, was running social. But they're so good and they have this great mind for it.

Sure.

Have them do. Do all of it. So kind of all earned media.

Nice.

Plus social media.

Well I think that's the new way of doing. That's like new PR to me anyway. It's like I think so too. It used to be like PR and comms kind of sat over here with brand. But like I think social is part of pr. The new PR is like can you build a strong brand on social online, especially if you're selling to marketers.

Yes, exactly that. And she's really good at that. So I'm excited about that team, the.

Thing you said that stood out to me the most is you're making it up.

Yeah.

Meaning? Meaning yeah, yeah. Meaning that. I think so. So often we're married to, like, team structure because of how some other CMO at some other company, like, oh, this company has product marketing and partner marketing and demand gen and web team. It's like, what are the jobs to be done inside of your marketing Org? And let's get on a whiteboard and just like, draw them up. And like, you know, David, who I worked with at Drift, who was a CEO, was awesome at this. He'd be like, let's just get in the room and whiteboard out. Like, what are the things we need to do as a marketing team? And then like, every team needs a leader because you can't just have a ton of ICs and so like, oh, interesting. We could bucket, like, we could put social PR and, you know, influencers together and we can call that team Blank.

Yes. And almost let them figure out what it should be called. Right. Like, it's not. I don't need to. I don't need to name it. I feel I have conviction about them being together under one leader because I think the work. I love that you said the work that needs to be done is super aligned. So I'm excited about that team. I have a digital ops function which is not marketing ops, it's marketing ops plus. So it's our, it's our web team, including web dev, it's our MOPS or MOPS function and analytics. And it's what I call prospecting operations. So managing helping. The BDRs and the AES use all the tools available to us to do prospecting at scale. And so they're kind of like a center of excellence, but I called it digital operations. And they, they're part of a broader team of teams within the company that we call go to market ops, which is cool. They all work together. Sales ops, customer success partner. And then the last team is. It's called global marketing. So this is the team that's responsible for aligning at the regional level with the field for both marketing and bdr. So they're organized by region. It also includes partner marketing and our corporate events team. So essentially every event we do as a company is run out of that team, whether it's small, medium, large, T, shirt size, whether it's first or third party, or whether it's a partner event. We think of events as a system and the system is designed to accomplish certain outcomes and having it all under one umbrella really makes sense there. So anyway, those are my four teams and we have resources all over the world. We're a remote, remote first company.

Each one of those teams. Do you have four direct reports? Each one of us?

Four direct reports, Yep. And that's a. It's a recent reorganization that we've done. But I'm excited because I've got four. I've got the right structure with the right leadership and then I also have a shared chief of staff with our CEO. So it's fun.

Perfect.

Yeah.

And then the chief of staff can just tell the CEO like all the nonsense that's happening in marketing. So you. There's no.

I actually lost a bet. I lost a bet with the chief of staff. He's a huge Buffalo Bills fan and I'm a Niner fan and we got creamed the other day and now that.

Person has grown up being a Buffalo Bills fan. So it's a short term pain, but you know.

Well, yeah, I throw in a wide right every once in a while when I'm not happy with them. But hopefully folks listening get that reference. But anyway, I lost about after wear Buffalo Bills jersey at our company kickoff in February. So that'll be fun. That's brutal.

Yeah. All right. And then you mentioned like, you know, we kind of riff briefly glossed over like, you know, team. You made a comment about like marketing, planning, whatever. Obviously you do do marketing planning. Can you give me just like a couple minute overview of like how you run marketing just from like a rhythms and routine. Like do you do monthly planning, quarterly planning. There's quarterly campaigns. People want some type of. The more people that I'm talking to, it's like the creative stuff is great, but you need like a marketing operating system to run a high performing team. So I'm curious how your, what your view is.

Yeah, our cadence is I like to have agility to, you know, react in the moment, but also be super aligned for six months out. And so one of the things that we do that I really love is we do a biannual kind of campaign theme alignment meeting. And that meeting is between marketing, sales, product and partner. We look six months ahead and everybody comes to the table with ideas on what are the themes that we should be taking to market. And there's inputs to that. So there's product roadmap, there's, you know, major events, there's some of our, you know, our M and a roadmap. Like there's lots of stuff in there that are contributing factors, but everybody comes to the table, we leave that meeting with alignment on the short list of themes that some may end up being marketing campaigns, some might not. But the themes that we're going to prioritize six months ahead of time and what that unlocks is a cross functional alignment, but B, it gives the team the Runway. To plan effectively for the big rocks we need to move then within that we leave space for agility. So for example, retire the legacy that we talked about earlier that came to life in a week and a half from like a strategic meeting about creating urgency to a campaign live. So I need both. So we do that six month lead time planning. We produce quarterly plans so everybody knows what we're doing and when. Obviously we have an annual plan, but that's more a macro with pipe targets and all those things. And then we have agility to make changes within the quarter. We don't do anything more granular than quarterly.

Oh, how good is that?

At least from a documented plan perspective?

Sure. What about, do you feel like the annual sometimes? I mean you've been at big companies, so I'm sure like SAP, you're like creating the like three, three year plan. But do you feel like, is it hard, do you find it hard to do like annual planning? Because so much changes you need to make rough estimates and adjust. Just things change so quickly and you don't want to be married to something.

You don't want to be. And the reality is 90% of the time you're going to look back and be like, wow, we did 40% of what we thought we were going to do. I mean, it happens on a day. You probably get this too. You wake up, you think your schedule is going to be one thing and then it's completely different. If you extrapolate that over a whole year for a marketing org, I think it's totally true. So what I prefer to focus on the big rocks, which are essentially like immovable objects. You know, you're going to have. We're going to have our big content con event in June and that's a forcing factor for product releases and major campaign launches and rebrand and blah blah, blah. But not trying to over plan super granularly. It pays dividends because then the team can evolve and solidify the plan over time. So my guidance to the team is always focus on the big rocks. Get alignment there. Let's do the theme alignment. And if we don't go too much more granular than that in terms of six months out, I feel good because then we're not going to waste cycles on things that we know the pace of change is so fast it's not worth it. Now finance would say, well, that's fine, but I need to see your budget plan for the whole year. So I've got to, as a leader, make some bets on how I expect to spend our money quarter over quarter over quarter, how I expect to divvy up that money across people, tech and programs, and then negotiate if there's any agility within that. So I've got to play both games. But for the team, I try to keep as much agility as possible, if that makes sense.

Okay, we made it very far in this podcast, and I haven't asked you about the hottest topic in marketing, which is AI.

Al.

He was a very popular point guard in the early 2000s called Allen Iverson Is Devastating Practice.

We're talking about practice.

Did we talk about practice? Devastating crossover Shout out to the six people who listen to this podcast that know Allen Iverson. What's your I'm trying to ask the right question without leading the witness here. What's your overall perspective on where marketing is going with AI?

I'm really excited. I think it has the potential to bring out the best in marketing and marketers, and I sincerely mean that. I think that it's been a little bit spray and pray so far, but it's starting to kind of. There's, there's use cases that are starting to crystallize. But then I get more excited about the future vision where it's like even us at Content Stack, like, what's the future we're building for? We're building for a future where, you know, you come up with a, with a campaign idea and you're able to basically go from prompt to live with that campaign, including all the assets you need and everything on brand. Because your brand lives digitally in this like vault that the LLMs or the Gen AI tools can access. You've freed up your time to go live for things. Like a digital campaign is 95% faster than it is in today's world. And so the agility that unlocks and the creativity that unlocks is super exciting. Because as marketers we like to spend our time on the higher value, more impactful content and experiences. To your point earlier in the call, like, is it still possible to create Those relationships like HubSpot and Marketo did with you and I? It is. I think AI will help us if we focus the AI on automation of the things that maybe don't tap into the more creative side of what humans have to offer. So that part I'm really, really jazzed about. I think there's even some nerdy stuff that's just so cool, like the innovation that's happening around identifying your icp, enriching account data, enabling. Like, I mentioned prospecting at scale companies like Klay Keyplay. Like, there's just such cool stuff going on that's leveraging AI. I'm pumped about it. And I think we're moving from this, like, spray and pray phase to now, like, pragmatic practical use cases. And my team, it's an imperative actually to be AI first wherever we can.

Yeah, dude. I think people, I think the V1 was like, everybody got into the content side of things and everybody sees AI as just like a way to write kind of crappy content. But you know what's possible now? Like, it's crazy playing with tools like Claude, for an example. I can go into Claude and I can say, like, hey, can you help me generate, generate a landing page for this event that I'm doing? And it generates the code for me and then I can go and I can plug in that code and edit that myself. Like, I think you came up through Demand gen. I'm sure you're similar where, like, I see myself as like a full stack marketer. I'm not just a word guy. I like to do the stuff. I'm like, it's not just the copy stuff. It's like, you're not gonna have to wait for an animator, you know, on your video team to take three weeks to animate a video. You can. You're not gonna have to wait for like three, you know, two weeks to get a design thing done. We still need humans. But I think the time to shipping work is going to shrink and you're going to be able to just move much faster without having to wait for other people to, like, help you get things over to the finish line.

Totally. Yeah. It's good. You know, there's a. There's a dark side. We won't talk about that. I think it'll sort itself out. But, yeah, I'm pumped. I think it's. I think it's fun. Super fun.

There is a dark side. There's a dark side to everything, right? Money is. Money is good. Money is bad. AI is good. AI is bad. There's lots of good things. You know, you see people on Instagram now, they say, smoothies are good for you. And then I see a guy that's like, no, no, no, no, no. If you blend Your stuff up in the smoothie, it's actually really bad for you. So there's.

You can never great.

You can never win. All right. Guardip is great to see you, man. This is a great interview. We're doing an event in San Francisco in May, and I think you just found your way under the short list of my invite to come hang out and maybe, maybe speak at that event. We'll see. We'll see how the next couple months go. But you're out there, so I gotta. It'd be great to do it. I think you have a great perspective, and I know this will be a great episode. And hey, you're. You're hiring, so I hope you get. Actually, we just had a CMO on a couple weeks ago, Sylvia from Kanji, and she messaged me today and she's like, I didn't realize you had such an audience. She's like, the amount of people that know me now from this podcast and are, like, applying to our roles. And so let's give Gurdeep the bump, too. All right? If you believe in his philosophy, go find him on LinkedIn and send him a message. And seems like you, you could join a very thoughtful marketing team over there. So thanks for rocking with me on this episode. See you later. Appreciate you doing it.

Thanks, Dave.

Hey, thanks for listening to this podcast. If you like this episode. You know what? I'm not even going to ask you to subscribe and leave a review, because I don't really care about that. I have something better for you.

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