The B2B Roundtable (hosted by Brian Carroll)

For years, B2B teams tried to make SDRs more efficient. More calls. More emails. More activity. Then AI arrived, and many teams tried to automate the same model. But what if the problem wasn’t needing a faster version of the old playbook? What if the real opportunity is to use AI to make people better at the things only humans can do? That’s the question behind my conversation with Craig Rosenberg. Craig has been gathering some of the best SDR and pipeline leaders in B2B through Scale Venture Partners’ Pipeline Council. What he’s seeing feels less like a completely new playbook and more like a return to fundamentals, with much better tools. AI can help us choose the right accounts, recognize signals, research buyers, practice conversations, and move faster. But the last mile still comes down to relevance, judgment, taste, trust, and human connection. About this episode Craig and I have known each other since the early days of B2B marketing and demand generation. I followed his Funnelholic blog back in 2008, and he reminded me during our conversation that my book, Lead Generation for the Complex Sale, was one of the first B2B GTM books he read. Several things Craig had recently been sharing from Scale’s Pipeline Council brought us back together. One of the big questions they’re working through is simple: What does a high-performing SDR motion look like now that AI can do so much of the work SDRs used to do? The answer isn’t fewer humans everywhere. In fact, Craig is seeing AI companies hiring SDRs and experienced enterprise sellers as they move beyond product-led growth and into harder-to-reach markets. Craig and I discuss: Why automating the old activity-based SDR model didn’t solve the pipeline problem How Glean uses AI to help SDRs get better at human conversations Why Craig believes the “last mile” of selling is still human What unmistakably human outreach looks like when buyers are surrounded by AI-generated messages Why AI companies are hiring SDRs and experienced enterprise sellers again How ICP and signals help teams focus on the accounts most likely to buy Why selling AI is becoming harder and business process may become the new software moat About Craig Rosenberg Craig Rosenberg is Chief Platform Officer at Scale Venture Partners, where he helps build and lead Scale’s go-to-market platform for software companies. Before joining Scale, Craig was Distinguished Vice President in Gartner’s sales practice. He joined Gartner through its acquisition of TOPO, the research and advisory firm he co-founded. Long before that, many B2B marketers and sales leaders knew Craig as the Funnelholic, where he built a following writing and speaking about demand generation, sales development, and B2B go-to-market strategy. He also co-hosts The Transaction podcast with Matt Amundson. Connect with Craig Craig Rosenberg on LinkedIn Scale Venture Partners The Transaction podcast Chapters 00:00 What Top SDR Leaders Are Figuring Out 04:41 How Glean Uses AI to Make SDRs Better on the Phone 09:09 The Last Mile Is Human 12:46 Why AI Companies Are Hiring SDRs Again 15:33 What Does “Unmistakably Human” Look Like? 22:06 Why Enterprise Prospecting Shouldn’t Always Scale 23:36 ICP, Signals and Choosing the Right Accounts 25:25 Why Selling AI Is Getting Harder A few things worth taking away The old SDR model treated people like “human robots.” Automating the same activity-heavy motion with AI didn’t solve the underlying problem of relevance. The better teams are using AI to prepare humans, not replace them. At Glean, AI supports account selection, research, signals, and practice while SDRs focus on getting better at live conversations. The last mile is still human. AI can provide information and suggestions, but judgment, taste, relevance, trust, and relationship building still require people. Being unmistakably human sometimes means admitting what you don’t know. AI can help you understand a buyer’s situation, but it shouldn’t create expertise or experience you don’t actually have. AI companies are hiring SDRs and experienced sellers as they move beyond product-led growth into enterprise markets. As Craig put it, “The minute you want to talk to people that aren’t coming to you, you need people.” ICP matters more when data is abundant. Craig shared an example where ICP opportunities converted at 37% compared with 17% outside the ICP. Signals then help determine when to reach out and what may matter. AI is also changing software competition. As products become easier to build and replace, Craig believes companies need to expand from TAM to “Total Available Problem” and become deeply embedded in customer workflows and business processes. A few lines that stuck with me “The reality is the most important thing now is trust building, humanity and relationship building.” “It’s that last mile, which is the human.” “The minute you want to talk to people that aren’t coming to you, you need people.” “Getting into AT&T doesn’t scale.” “There are accounts that are the absolute best fit for you right now. Why would we spend time on anything else?” “We’ve moved from TAM to TAP, which is Total Available Problem.” Listen and subscribe Subscribe to The B2B Roundtable wherever you listen to podcasts. Transcript Brian Carroll: Welcome to The B2B Roundtable. I’m Brian Carroll, and I’m excited to have our guest today, Craig Rosenberg. Craig is the Chief Platform Officer at Scale Venture Partners. What Craig’s doing is helping them build their go-to-market platform so that they can bring this expertise to help software companies drive growth. I’ve known Craig quite a while. We go way back in terms of what we were doing in the early days of B2B marketing and complex sales. I started following Craig’s blog, The Funnelholic, going all the way back to 2008. Craig first shared a Pipeline Council they’re doing with some of the top SDR leaders in enterprise and software sales. And then Craig did a post with Jason Vargas talking about the “taste layer” and bringing that to the SDR rep. What I’m excited about, Craig, for us to talk about is, you know, the more things change, the more they are the same. What’s coming up in the Pipeline Council that the rest of us aren’t talking about yet? Craig Rosenberg: Well, first I thought it would be important for the audience to know that, yes, you found me through The Funnelholic, but everyone found you through your book. Was it Lead Generation for the Complex Sale, I think was the name? Brian Carroll: Yeah, yeah, it was. Craig Rosenberg: And that was like the book. I mean, Brian, you were the OG out there with the book and talking about it. So I think that’s amazing to bring up. And even the fact that you brought me here because you saw these posts, for everyone who’s wondering if it’s important for you to share what you’re working on and thinking about on social, I mean, look, that’s how I met Brian in the first place. He had a book and was doing the speaking circuit. I had a blog. And then recently, he brought me back here after he read one of my posts on social. So there is a lesson in your intro in and of itself. Brian Carroll: That is true. And you also do a podcast, which is awesome. Craig Rosenberg: Thank you. Brian Carroll: So let’s go back to what’s coming up in the Pipeline Council that the rest of us aren’t talking about. Craig Rosenberg: I have two councils. I’ve got one where I brought together the folks that have figured it out. I’ll talk about that in a second. Then I’ve got my regular councils, which bring together people who are still trying to sort this out. Brian, from our conversation before, I’ll just go on the negative side. There was a moment where SDRs were basically human robots, right? They were basically conveyor belts of information. It was about how many emails could you get out, in some cases how many calls, and then the messaging was sort of one message. It was all about output. Or I think you said they were activity-based, right? They were machines. So we had that moment. We had to come out of that and sort of accept that the original iteration of AI here, and the way people thought AI would work, would be to somehow automate that motion, which was a highly generic, activity-based motion. We had this run of SDRs being these human robots and delivering activity. And frankly, let’s face it, they got meetings. Then everything changed and it got really hard. Then we said, “Well, we’re going to solve it by using AI to deliver what they were doing as robots,” and that didn’t work. Everything got really confusing. That’s why I put the Pipeline Council together at the Rosewood, so I could start learning more. I work with a woman named Christina McMillan, who I’ve worked with for years. She was at TOPO with me, but she was an SDR consultant for years. I said, “You know what? We don’t know anymore. We’ve got to go figure this out.” So we bring together the Pipeline Council, and it’s really interesting because we actually do know. The reality is the most important thing now is trust building, right? Humanity and relationship building. What we missed for, call it eight or ten years, was that, because we didn’t need it. Now, the truth is, from watching you, reading you, and listening to you for a long time, you would say, “Wait a minute. That’s what I was talking about back then.” But the truth is, I think we kind of lost sight of that. There were some really interesting things I learned from the Pipeline Council. I’ll give you an example. This guy Joey Lopez, he’s at Glean, and this guy amazed me. So I’m just going to give you this example of what he does. Most everything is AI and automated. Who they’re going to talk to, what types of companies, those things are served to them. Because, by the way, Brian, one of the things that was also happening during the SDR-as-robots phase was they were choosing their own accounts. They were going into ZoomInfo and just downloading names and sending emails. There was no thought process on who we should talk to. The AI will research the company, help them identify both educational information and signals. The AI actually sends emails for them. What he believes is: Can I focus on one thing? His choice is to focus on the phone, which is a highly converting channel for them. So they train and they practice this all the time. But ready for this? He’s a football, wrestling guy. Every day the SDRs come in and they huddle like a sports team. He’s like, “Look, you don’t just practice before the game. You get in the locker room and you go through the game plan.” But they actually practice. Let’s say that day they’re going to call CIOs. They all get trained on the CIO persona: what they care about, what their challenges are, day in the life. They get trained on the type of messaging that works under different scenarios. Then they go practice. Then they come back and huddle. Then they all spend the whole day calling CIOs, and that’s it. Then they optimize against it. It is just brilliant, right? Brian Carroll: It is brilliant. Craig Rosenberg: I’ve never heard anything like it. I told him, “Look, that is better than what me and Brian used to do.” In the practice, they’re using sales simulations where they can practice against the CIO persona, which is AI. Everyone asks me, and I’m like, look, I’m in a venture firm. We love AI. But it’s that last mile, which is the human, which is the thing that we’re learning. Brian Carroll: That’s right. Craig Rosenberg: He trains them on the human, and they go in and have these conversations. Then they listen to calls together, maybe like a halftime, and they optimize. That day, they just do really well with that type of person. I thought that blew my mind. It was incredible. The other things I saw were highly personalized direct mail. There are these groups where they’ll actually create custom gifts for someone based on what they care about. An example would be, if developers have a high predisposition for Legos, there are groups that do personalized Legos. Or they might know someone is way into archery, so they’d send them something around archery. It was these highly personalized gifts. And the conversion rates are the most important thing. We have to live by the numbers, even if it’s a great idea. Sometimes I have a great idea every week that doesn’t work. Brian Carroll: Sure. I mean, that’s part of life. Craig Rosenberg: Now that we’re our age, we can relate to this. But the conversion rates are really high. Everyone says, “Well, that’s a gimmick.” No, it’s not a gimmick. It’s personalized. If you send me a stress ball, that’s not going to work. Brian Carroll: Mm-hmm. Craig Rosenberg: But if you show me that you know me, then that’s going to be infinitely more effective. The other thing that was surprising to me was there was a guy in cybersecurity, which is one of the hardest markets to email, and he improved email reply rates to 6%. We haven’t seen 6% since 2021. What he did, again, was make the emails more relevant, more personalized. He tore everything down and rebuilt it in a way that was more highly relevant and highly personalized. So if I had to leave a theme, there are some really fun channels and tactics that I learned about, but at the end of the day, I think the key is that last mile. And I think that’s what leads you probably into the taste layer. Everyone wants to know what humans are going to do. Well, the humans are there to make sure that we’re building a relationship, that we’re being relevant, that this is something tasteful that we would send to someone. That’s what we saw. We went around the table, and that’s where we learned all those things. That Joey Lopez example, what do you think of that? That was incredible. Brian Carroll: I love that. Going back, Joey took it to another level. When I was running BDR teams, I created something I called “How to Talk to Me,” which was doing what Joey was doing. But with the role-play, we didn’t have AI to do role-play. It was our best educated guess on a persona. We did focus on just calling that persona because people would be reaching into multiple people within an organization. I just think getting that level of specialization matters. In sports, you need to get reps in, but they were practicing the reps before they talked to a live person. Then they were able to go deep, which I think is brilliant, because that’s how people get good: having that focus, having the understanding. It also helps younger, less experienced people who haven’t had the life experience, maybe calling an executive, to actually know how to talk to them. Craig Rosenberg: Yeah, for sure. By the way, one thing on the experience-versus-not thing. It’s a challenge because we do typically use less experienced SDRs in this process. But, on the other hand, it was interesting. We had a really successful leader. He’s not allowed me to talk about who he is ever. It’s a long story. He’s got a highly successful SDR team that’s scaling, let’s say, a hundred. Remember when everyone told us they were dead? Brian Carroll: Yeah. Craig Rosenberg: His issue with the experienced folks is that they couldn’t approach the buyer the way he wanted to, which was in a much more personalized way. If you think about it, if someone was highly successful during the SDR robot phase, are they really more experienced? I don’t know. Brian Carroll: Really, they aren’t. They’re experienced being repetitive and doing activity. But when it comes to actually connecting with people and being relevant, that’s something you need to train. It’s a skill. It’s something people need to develop, and it doesn’t just happen. Craig Rosenberg: Yeah, for sure. I was going through the numbers everyone was giving me. I’m like, “Who’s hiring?” Everyone raised their hand. It’s nuts because everyone told me SDRs were dead. Brian, I think we’ve seen this before, though. There was a moment where everyone tried to kill the SDRs. They keep trying to kill the enterprise sales reps, saying, “No, those old guys, they don’t know anything.” And now they’re getting hired at prices where, I mean, they’re unaffordable. But it’s the same thing. It’s your same theme. You need AI to help everything go faster for the human, but at the end of the day, that relationship is built with these people. We’re seeing that across the board. These AI companies came up through PLG. Some get to a billion without hiring go-to-market. But guess what? The minute you want to talk to people that aren’t coming to you, you need people. Brian Carroll: That’s right. You had shared something, I think this came from Adam Schoenfeld, about 39%, and maybe it’s higher, of AI companies hiring SDRs. Everyone thought these companies were building the technology that’s supposed to replace SDRs, supposed to replace salespeople, but they’re still hiring. So what do you make of this? Craig Rosenberg: First of all, you are right. It’s probably higher because that was six months ago when Adam did that. He looked at 150, I think a little more, top AI companies. Thirty-nine percent were hiring SDRs and SDR leaders. A year ago, I was talking to experienced SDR leaders who were crying because they weren’t going to hit their mortgage. Now they’re getting paid more than they ever did. Those top AI companies, frankly, look, I’m in venture, but you see their numbers. It’s extraordinary. They’re doing it by people catching fire from a brand perspective very early on, people coming to them, and typically a PLG motion. I’m all in favor of that. What we’re seeing now is that whole cohort is trying to get into enterprises, new markets, even mid-market that didn’t necessarily come to them. At a certain point, you have to do this. And they’re not just hiring SDRs. They’re hiring, like I said, experienced sales reps that were supposedly dinosaurs and out of the business. The second thing, though, is what we just talked about. I actually do believe there was a moment where SDR leaders were running the same playbook and they failed. Then they went to the next place and they failed. So in defense of the sort of fall of the SDR, the SDR leaders had not adjusted. Now they’ve adjusted, and now you’re seeing folks starting to share successful implementations. It was a return to humanity in many cases. But I will say AI is predominant in their systems and how they cue everything up. There’s the ability to provide information SDRs have never had before, the ability to give them both educational information and signals that tell them when to reach out to someone and how to be relevant. Those things are real. The fact is, what we need is that last mile to be people. That has been the breakthrough. Brian Carroll: You’ve said this a couple of times, bringing humanity back. What would you say “unmistakably human” looks like now, today? Craig Rosenberg: Man, that’s a really good question. Brian Carroll: I read probably a dozen things on LinkedIn where someone’s saying, “How not to sound like you wrote by AI.” And I’m like, why not try writing? Why not try actually writing yourself in your voice? Because there’s a backlash happening too, you know. Craig Rosenberg: Yeah. I know. You’re right. I think there have been two moments that turned people off to generic messaging. There were SDRs as robots just flaming the market with emails. Then there was, like we said, “Well, we could solve this with AI.” Even today, I got emails this morning that were clearly not written by a human. We’re surrounded by AI messaging all over the place. And so when we get a human, that’s something that’s really relatable. I’ll give you an example. You said try writing. I use AI every day. I originally tried to have AI write emails to folks, and then I said, “Okay, well, that doesn’t work.” Then someone said, “Well, it’s easier to be an editor.” And I used to say that. Then I tried editing it, and it was too hard. So I went the other way. I use AI, let’s say I’m prospecting, to tell me what kinds of things work. It can help me with the structure or the rubric of an email. What types of things work in the first sentence? Stuff we train on. It can look and say, “Hey, the best reps are doing this at the top.” That helps me a lot. I ask it for ideas in bullets. That’s my new thing. I get these great ideas, but then I write it. So I’m still faster, but more importantly, I’m better. AI does help me a lot, but I just couldn’t have it write it anymore. If it’s AI-patterned or templated, it just won’t work. I’ll give you an example of humanity. I was just talking to John Barrows, and he said, well, a young SDR gets this signal about a merger. He’s never seen a merger before, and he goes and writes about it. I’m like, “Dude, you can’t do that. I’m not going to answer.” So it’s like, you want to use AI? Well, tell me what happens in a merger. Tell me what things might be happening at this organization. Now I’m going to take it and write something more heartfelt. I might have even written, “You know what? I don’t know a ton about what happens in mergers. But I do know, just having experienced this, that this, that, and the other might be happening in your business. And that’s why I feel like we might have the ability to have a conversation about this use case.” Just being humble and approaching it that way might have worked. The other way is to do your own research and be okay with not being perfect. I thought that was a really good example from him because that would be an example where we’d use tech. We’d say, “It’ll identify if there’s a merger, then it’ll put together a message.” It’s like, yeah, but that person got 200 messages that all look the same. That shows zero understanding of that person and what they might be going through. So what’s your differentiator? How are you going to do it? I think when we talk about humanity, we have to be able to tell the buyer, “Look, it’s worth talking to me.” And that actually has to be done by you, the person. It’s one of the reasons I’m surprised people answer their phones, because I certainly don’t. But we’re seeing the data, and it does work. It works when you connect because ultimately that’s two humans connecting, having a conversation, and being able to talk it through, which says, “No, I’m not talking to a robot.” Brian Carroll: Yeah, and I think there is a lot to what you’re saying. My first job as an SDR, I was calling to set up appointments for sales training. My first day, I knew nothing about sales. I was frustrated in the week, and Julie, the manager, said, “Brian, just be people with people. Why not own the fact? You’re 22 years old. You don’t know anything about sales. And the irony is you’re setting up appointments for sales training.” The point being, the admission of who you are and what you don’t know can open up possibilities. I could talk about, “I’ve learned so much in the sales training already.” I think there’s this point that we still need to go back and learn what is unmistakably human and do more of that. I wanted to go back to when you did the meeting at the Rosewood. Was there anything that surprised you the most or was counterintuitive that you came away with? Craig Rosenberg: Counterintuitive? Well, I actually would say the most surprising thing was that I wasn’t surprised. I mean, that’s cheating, but I think everything ended in the same theme that we just discussed. I’m surprised people still answer their phones. They do. There’s tech to go do that. By the time we got to, let’s say there were 12 people in the room, when we got to number four, I was like, “I got it.” Then they kept going, and I’m like, “I still got it.” I’ll give you another one that was big. The SDR thing kind of blew up a year and a half ago. Now it’s back, and it’s like, what were the things that we forgot? Well, one, they want to get promoted. One of the people in the room was like, “One of my keys is that I have about 70% of my SDRs get promoted into sales.” I’m like, “Okay, that’s amazing.” And she’s like, “Now more talented people come. They stay longer because they know they’re going to move up.” I was like, my gosh, that’s an old theme that’s come back. Maybe the thing to say is that what’s old is new again. A lot of the fundamental things that we used to discuss with SDR team building, that I kind of forgot about, came back. Brian Carroll: AI has allowed us to scale activity. It hasn’t allowed us to scale relevancy unless you use it properly. Craig Rosenberg: Yeah. I actually do have a fun one for you. Brian Carroll: Okay. Craig Rosenberg: A fun one and one that we already knew, but is really important. The fun one did not come from the Pipeline Council. I like to just talk to people. These hot companies that are sort of breaking down doors, I just want to talk to whoever’s doing it. There’s a company in New York called Attention, and one of their highest-converting channels is the SDR taking a gift and walking in the doors of their target account. Brian Carroll: Wild. Craig Rosenberg: So I called him. He’s like, “Yeah, it’s the field SDR.” They also get a LinkedIn message saying, “Hey, the Attention guys just brought that.” It’s that motion because, guess what? We give donuts. It has our name on it. Or we could give whatever. But the fact that we made that personal effort, having the person who’s trying to reach out to someone show up at the admin’s desk and hand them that, that’s the ultimate in conversion. Now, you can’t scale that. But look, you and I, you’re the complex sale guy. I’m the enterprise guy. I keep telling people, guess what? Getting into AT&T doesn’t scale. You have to find your way in, then find your way across, and continue to do that. That was a surprising channel for me and really interesting. The other thing, though, that I did not mention before, that people are doing a lot better across the board, is ideal customer profile work. I knew this at TOPO, and people didn’t believe me because everything was about meetings. They didn’t care what. I kept saying, “Forget the term account-based marketing. Don’t worry about it. The most important thing is there are accounts that are the absolute best fit for you right now. Why would we spend time on anything else?” It was funny. When I’d go in and they’d say, “Can I look at the forecast?” I’d say, “Well, let’s run it against the ICP.” It was obvious. You’re getting a 37% conversion rate against the ICP and 17% against other accounts. That should tell you everything. What we see now, with data and the ability to do this, is that a lot of these successful teams are doing a way better job of choosing the accounts. The second part is, with signals and these things, you’re able to figure out when to reach out to them and what to say. Those two breakthroughs are huge. Brian Carroll: Yeah, and I think back, you brought up my book. By the way, it’s coming up on 20 years since that book came out. Craig Rosenberg: No way. I’m getting old, man. Brian Carroll: Yeah, I can’t believe it either. So 20 years ago, in 2006, there wasn’t an abundance of data. We now have an overabundance of data. It’s: What do we do with it? We can move from thinking ICP is how you build a list to, no, your ICP is how you know who’s relevant, and you focus on just those. You aren’t trying to build the biggest list possible. You’re trying to build the most relevant list. It makes perfect sense. Craig Rosenberg: Yeah, I know. Brian Carroll: What are you seeing right now, as you look across your portfolio, that a lot of us might miss? Craig Rosenberg: Well, I’d say to everyone, you’ve got to stop firing your CMO just because things are tough out there. The movement there has been extraordinary in terms of people getting shipped out. There is a point there, which is messaging matters. I think it’s really hard right now. It’s been a killer. CMOs who are pretty good are fighting with the organization, trying to find the best message and not getting there. Look, I work with startups, and it’s hard to run marketing at startups. It’s really hard. The good news is everyone wants to talk about AI. The bad news is everyone’s selling AI. AI is not the same as SaaS. Everyone says, “Well, yeah it is.” No, because SaaS you could load it and go. AI has to integrate with your data. That’s why you see this sort of forward-deployed engineer thing. To really understand it, you have to be able to get it in and get your data moving through the system. So it’s different. If you think about it, everyone’s pitching AI. Everyone knows they need to go to AI, but now everyone’s afraid of it. There’s also a whole naysayer element in the buying committee that makes it even harder. But more importantly, there are so many more products out there. You’re selling into your category, where there may be 35 other companies. Then you have horizontal AI companies like OpenAI and Anthropic coming at you from the other side. You’ve got other AI companies coming in and tangentially touching your message and your value proposition. That makes the ability to distinguish yourself really hard. Here’s the big thing. For AI companies, many of them come into the market as a wedge. They found a hole in the market and they filled that hole. In the SaaS era, if you found that wedge, you would be able to run with that wedge, go raise lots of money, and dominate by focusing on that wedge. Now you can’t, because it’s too easy to make software and it’s too inexpensive. We like to joke that four kids in Brooklyn will create your product in a month and be coming at you. If you sit on that wedge now, you’re actually asking to get flanked. That’s an incredible challenge. A company today has to go in via its wedge, and then the things that used to happen eight years after a company existed, you have to do now. We have an investor here who said we’ve moved from TAM, looking at the biggest market, to TAP, which is Total Available Problem. We have to expand the problem set as fast as we can. Brian Carroll: Wow. Craig Rosenberg: The other thing is moating. Moats are really hard because, like I said, it’s the same problem. Building software is easier than before. Then you’ve got the threat of the frontier labs. Anthropic can take you out in a night and not even know you existed. Your moat now is integrating yourself into business processes and workflows as fast as you can, because that makes you harder to pull out. It’s funny because everyone’s talking about CRM and whether there are new CRMs. Except the reason SAP and Salesforce don’t die is because they become the business process. Tearing them out means you’re tearing down your entire business process. Everyone thinks it’s the data. Data moves now. You can move data in less than a day. It’s actually the business process. There’s a lot to learn there for these companies. The faster you can become integrated into their business process and become the business process, the stickier you are and the bigger your moat can be. But if you don’t do that, then you’re easily replaceable. I talked to a RevOps leader I’ve respected and known for years. He said, “We look at our tech stack every month, and we’ll tear stuff out every three months.” I’m going, “Is that good?” He’s like, “Yeah, because guess what? I can always look at what’s better.” Ripping and replacing is actually not that hard unless they’re dug into my business. Those are things I think people may not know about that are really important to take in and think about. How you sell, how you message, what you do in the sales process, and what you do in the post-sales process are different. There are big challenges today. There are different approaches to how you think about things. If I had to give you anything that I’ve learned, that’s more of what I’ve learned from the investors looking at the market that I’ve found fascinating. Brian Carroll: Well, Craig, I just want to say thanks for the conversation today. It’s been so great catching up with you and hearing your perspective. The more I listen to you, the more I’m remembering how aligned we are in so many ways. So I just want to say thanks for joining us and being on the show today. Craig Rosenberg: Yeah, thanks for having me. It’s great to see you and talk to you again. I’m going to have to flip through your book again. That was one of the first B2B go-to-market books I ever read. So it’s really cool to catch up.

A company reaches a key moment. The strategy changes, the target buyer shifts, and leadership decides to focus on the enterprise market. But the go-to-market system underneath the business may still be built for an earlier stage of growth. Corey Livingston shares why rebuilding your GTM should start with understanding and clarity, how marketing can build trust with sales before results appear, and what leaders should measure before the pipeline is visible. About this episode Financial reports show how a business is doing, but they don’t show if the go-to-market engine is ready to support the company’s next phase of growth. That is the tension at the center of this conversation with Corey Livingston, Vice President of Marketing at DartPoints. Corey has spent more than two decades leading B2B marketing through growth and change. She has worked inside companies moving upmarket, entering new segments, and trying to build several GTM motions at once. Her starting point is not another campaign. It is understanding the growth hypothesis, determining whether each motion is in the build, activate, or scale phase, and getting the organization aligned around what it can realistically produce next. We talk about why moving into enterprise requires more than changing the target account list, how marketing earns credibility with sales, why alignment must extend below the CRO, and what leaders often get wrong during the first 90 days of a GTM rebuild. About Corey Livingston Corey Livingston is the Vice President of Marketing at DartPoints. She has more than two decades of B2B marketing experience, including leadership roles at Level 3 Communications and OneNeck Solutions, as well as fractional CMO work across multiple companies. Her work focuses on GTM strategy, sales and marketing alignment, enterprise growth, and helping companies build the operating systems required for their next stage of growth. Connect with Corey Follow Corey Livingston on LinkedIn Chapters 00:00 Why healthy dashboards can hide a broken GTM system 00:49 What dashboards miss in a GTM rebuild 02:36 Why moving upmarket changes the entire motion 05:35 How to diagnose the gap between strategy and execution 09:02 How marketing earns sales’ trust before results 17:58 How to decide which GTM motion comes first 21:00 What to measure before pipeline shows up 26:23 What leaders get wrong in the first 90 days A few things worth taking away GTM is a lifecycle, not a switch. Leaders need to know whether a motion is being built, activated, or scaled before deciding what to measure. Moving upmarket is not just a strategy shift. Enterprise buyers require more credibility, stronger proof, deeper content, and tighter coordination with sales. Sales trust comes from clarity, follow-through, and quick wins, especially while the longer-term GTM system is still being built. Alignment with the CRO is not enough. Marketing also needs to earn the trust of frontline sales leaders and the people doing the work every day. You cannot scale every motion at once. Investment decisions should connect to the company’s growth hypothesis, resources, timing, and near-term revenue needs. Pipeline is a lagging indicator. Operational readiness, engagement from the right accounts, and qualified meetings can show whether the motion is beginning to work. For an early enterprise motion, one of the most useful questions is: are we meeting with the right person at the right account, and are they moving to a next step? A few lines that stuck with me “I look at GTM as more of a lifecycle, not a switch.” “A corporate strategy and vision is not a go-to-market strategy.” “Sales trust comes from creating clarity. It comes from follow-through and quick wins.” “You can’t scale everything at once.” “You can’t get to pipeline without engagement.” “Are we getting a meeting with the right person at the right account?” “Most leaders try to fix things too fast in the first 90 days.” Listen and subscribe Subscribe to The B2B Roundtable wherever you listen to podcasts. Transcript Brian Carroll: Welcome to The B2B Roundtable. I’m Brian Carroll, and we’re going to talk about something people don’t often talk about. A company hits an inflection point. The strategy shifts, the buyer changes, and the dashboard shows green. But the system underneath was built for a different version of the business. The gap doesn’t show up in a report. It shows up when things start to stall, and nobody can explain why. My guest today is Corey Livingston. She has spent more than two decades in B2B marketing, leading at companies including Level 3 Communications and OneNeck Solutions. She has also done fractional CMO work across multiple companies. Today, she is serving as the Vice President of Marketing at DartPoints. I invited Corey because she has been through these inflection points in several different seats. Corey, welcome. Corey Livingston: Thank you, Brian. It’s great to be here. Thanks for having me on. Brian Carroll: We’ll dive right in. When you step into a GTM rebuild, perhaps at a mid-market company, what are the things you usually see first that dashboards don’t show you? Corey Livingston: When you step into a company that is evolving its strategy, in my experience, in almost all cases, that evolving strategy involves moving more upmarket. You look at the numbers. You look at the financial reports. You talk to all the right people. It tells you what is happening in the business, how it is performing, and its underlying health indicators. But it doesn’t tell you whether the go-to-market engine is mature enough to support the next stage of growth, the next inflection point, or the new segment you want to penetrate. You have to start by diagnosing where you are. Where is the business in the go-to-market lifecycle? Are you in the build phase, the activate phase, or the scale phase? I look at GTM as more of a lifecycle, not a switch. You don’t just declare that you’re moving upmarket or moving into a PLG motion, or whatever it might be, and then it happens. You have to understand where you are. If you don’t know where you are in the lifecycle, you’ll end up measuring the wrong things, investing in the wrong places, and expecting outcomes the operating system isn’t ready to produce yet. Brian Carroll: That makes a lot of sense. Could you give an example, without naming the company, of where that stood out to you and what you did? Corey Livingston: As I mentioned, I’ve worked across many different companies that were operating in either SMB or mid-market. That was their customer profile, and many of them wanted to move into enterprise. The deals are larger. The revenue is stickier. There is more opportunity to differentiate. I used to have a boss who would say, “Where there’s mystery, there’s margin.” There is also more opportunity to be consultative. Brian Carroll: Mm-hmm. Corey Livingston: But going into enterprise or moving upmarket, whether it is the lower end of emerging enterprise or the Fortune 500, is not just a strategy shift. It is a motion shift. The go-to-market operating system for enterprise is fundamentally different from SMB or mid-market. I’ve worked in environments where companies were pursuing all three segments: SMB, mid-market, and enterprise. In SMB, buyers move fast. There are fewer people involved in making the decision. The stakes are lower, and the go-to-market engine can rely on lighter content, simpler messaging, and more transactional motions. You also tend to get much more inbound from SMB than you would from enterprise. Enterprise is the opposite. The cost of entry and the burden of proof are much higher, not just in what you need to spend, but also in the credibility you need to get the door open. Enterprise buyers operate in much more complex environments. In my case, I’ve always worked in the IT and technology sector, where IT environments are highly complex. The stakes are much higher for the people influencing or making the decision if something goes wrong. There is much more risk involved. They want credibility and familiarity. It is the old saying, “Nobody ever got fired for hiring IBM.” There is still a version of that in our modern marketing world, especially when you move upmarket. That means your GTM system has to evolve. What worked for SMB and mid-market is not necessarily going to work. It may provide some foundational elements, but the system still has to change. You need deeper content. You need much clearer use cases. You need reference customers who have worked in these enterprises before. You need strong stories, proof points, more orchestrated outbound, and much tighter alignment with sales. You’re going to be working hand in glove with sales. You also need a sequencing model that matches how enterprise organizations actually buy, which is a more complicated buying journey. Brian Carroll: How do you tell when a strategy has changed, or needs to change, but the GTM system hasn’t caught up yet? Corey Livingston: In my current role and my previous role, I had a significant part in helping shape the GTM strategy. The first thing I do is understand the growth hypothesis. When I walk into a business, the first question I ask is: What is the hypothesis for how we are going to grow? What channels are we using right now? Are those the right channels? I interview the executives, the C-level team, and everyone on the go-to-market team. The go-to-market team is not just marketing. It includes product, sales, and, in my industry, solution architecture. It is about doing the research, conducting interviews, and asking the right questions. Where do people think the go-to-market system is today? How well is it working? Where is it not working? I’m looking for areas of agreement and areas of difference. I want to make sure those differences are not so significant that they could undermine the strategy we need to build for the next phase of growth. I start by asking what we have today and whether that operating system can get us to the next phase of growth. I can’t necessarily determine that on my own. When you’re building GTM, one of my strengths is bringing everybody together, getting everybody on the same page, and listening deeply. Those are considered soft skills, and I don’t think they get enough attention. But that is the first place I start. I don’t walk in and immediately start executing a GTM plan. In many environments I’ve entered, there isn’t really a GTM strategy. There is a corporate strategy. But a corporate strategy and vision are not a go-to-market strategy. A corporate strategy does not explain how you are going to activate in the market and begin producing results. You also can’t scale everything at once. I have to prioritize the areas where we have leverage and anchor everything to the growth hypothesis. What are the sales quotas? What are the revenue projections? What motions already exist, and where are they in the lifecycle? If the growth hypothesis says growth will come from retention and expansion, I would start there, unless there is foundational work required that would delay our ability to activate and reach our sales or revenue numbers in a way that conflicts with the plans presented to the board. Then I look at the next motion. It could be channel, inbound, or events. Which motion is most mature? Which one can we activate fastest? Which one aligns with the near-term revenue picture? That is where I start. Brian Carroll: Those are some great pointers for people thinking about moving upmarket or entering the enterprise. You mentioned sales quotas and getting alignment with sales because this is a significant shift for the organization. Corey Livingston: Yes. Brian Carroll: How do you build trust with sales before you have results to point to? Corey Livingston: That is always much more art than science. In my experience, sales trust comes from creating clarity. It comes from follow-through and quick wins. It is hard to earn sales trust, but it is very easy to lose. I don’t necessarily come in with a 90-day plan for sales. I would probably do that for my CEO, but not necessarily for the sales organization. They need clarity. They need enablement. They need early wins. My strategy is always to build trust by helping them move faster, not by asking them to wait for the perfect GTM system to materialize before I deliver anything. Early in my career, and I think this is true for many of us when we’re starting out, we think we know it all. We’re going to do the things we know need to be done, and sales can wait because they are not part of the strategy. Now, when I walk into a new role, I’m working with the executive team and the GTM team to understand where we are, where we need to go, which motions will get us there, what we already have, what we need to build, and what we need to activate. At the same time, I’m thinking about how we can get into market faster while we are building the operating structure we need. I think sales appreciates that. It starts with talking to them and listening. What do you think you need to be successful? It is basic, but it also requires honesty. Here is where I am. Here is how long I think it will take based on the budget and resources I have. During those first 90 days, I will probably work twice as many hours just to put something in front of them so they can begin seeing traction earlier. They appreciate that you are doing what you can to enable them and that you are not making perfect the enemy of good while you build the longer-term plan. Brian Carroll: Could you share a lesson or a story about something you wish you had done differently, so someone else might avoid the same mistake? Corey Livingston: If you’ve been in B2B marketing long enough, you probably have plenty of scratches and bruises from trying to align with sales. The bigger the company, the harder it is. I’ve worked at $10 billion companies, $200 million companies, $50 million companies, and $10 million companies. The smaller the company, the easier it is to align. That is one reason I now like working in a certain size of company, where you can have more impact and where sales and marketing need each other, particularly during an active growth phase. In larger, more complex companies, I’ve found it much harder to align. The business is more mature at $10 billion, so I’ll add that as context. The other thing I’ve learned is that sales leaders at the top of the organization are not the only people who matter. The mid-level sales leaders, the people the teams report to, typically the GMs and sales vice presidents, are often the people individual sales reps listen to first. Brian Carroll: Mm-hmm. Corey Livingston: I’ve had experiences where I had total alignment with the SVP of Sales or the CRO, but I was out of alignment with the next layer down. In some cases, I’ve also worked in environments where sales simply did not want to align with marketing. That is a broader issue in our industry. Marketing is sometimes not trusted or is seen as lacking industry knowledge. Marketers may be viewed as too focused on pretty colors and pictures and not focused enough on understanding the day-to-day work of the sales team. In those environments, it is nearly impossible to be successful. Sometimes, you simply have to move on. Brian Carroll: Mm-hmm. Corey Livingston: In other environments, it is about continually building trust with the mid-level sales manager. It is not just about focusing on the highest level of leadership. It is about working with the people in the trenches every day. What are your objectives? What are you trying to achieve? You also need to let them know you understand how sales works and ask questions that are not coming only from a marketing lens. I have never carried a quota, unless you count marketing and selling fractional services, but I know enough because I have embedded myself in those organizations. When I ask questions from the sales team’s perspective, such as, “Who is your highest-performing rep? Who is your lowest-performing rep? Where do you need the most help?” it helps me align much more effectively. Then, again, it comes down to following through. Brian Carroll: The big takeaway I’m hearing is that you cannot just align at the executive level. You have to move one, two, or three levels down to the frontline managers. Corey Livingston: Yes. Brian Carroll: Those are the people who see the day-to-day experience of the reps. Corey Livingston: Yes. Not everyone is able to do this, and that is another reason I now align more with midsized companies. I talk to reps one-on-one. What are they struggling with? Where do they think they need help? Even in my current role, if one of my salespeople contacts me and needs help, I will drop what I’m doing to help them. It is about understanding their world and understanding how they get paid. As long as the request is aligned with the direction we have all agreed to pursue, those little touches matter. Maybe you were willing to work an extra hour to help someone pull a list. I don’t care about my title. I will do whatever it takes. We’re all in this together. That is what people on the sales team and the product team need to feel. They need to feel that you are just as invested in their success as you are in your own. Not everyone operates that way, but when someone sees that you are willing to jump in, even if it is just helping write an email or pull a list, it matters. No matter your level in the organization, those small things go a long way toward building trust and creating alignment. I will never stop doing them. Brian Carroll: What I’m hearing is that you’re doing things that help reps have more effective selling time and add value to their day. At the same time, you’re working on the strategic initiatives that will contribute over the long term while still meeting short-term needs. Corey Livingston: Yes. It is similar to Maslow’s hierarchy of needs. People need oxygen. They need water. I’m definitely securing my own oxygen mask, but I also have one to give the sales reps. Even if I had something due and helping a salesperson was going to put me behind on a deliverable to the executive team, I would have no problem saying, “I need an extra hour or two, or an extra day. I need to help this salesperson. They have a deal on the line, or they need to increase their prospecting activity.” I don’t think anyone would argue with that. No one ever has. Marketers have to come down from the ivory tower and understand that, in B2B in particular, most organizations are going to be sales-led. You have to accept that reality and not fight the system. I’ve seen many B2B marketers try to fight it. They say marketing should be this or marketing should do that. But at the end of the day, sales is the tip of the spear. As long as we are aligned with the go-to-market strategy, marketing has to be the foot soldiers. We provide air cover, but we also need to be on the ground doing reconnaissance and whatever else sales needs to be successful. That should happen not just at the organizational or academic level, but also one-on-one. That is the attitude I encourage and look for when hiring people for my team. Brian Carroll: How do you manage when several different motions are competing for attention? How do you decide what comes first and what has to wait? Corey Livingston: Once you have the motions built, I’ll go back to something I said earlier: you can’t scale everything at once. You have to return to the growth hypothesis and understand where you are in the lifecycle. If you are in the build phase, it may take twice as much time, or even three times as much time, to reach the activation and scale phases. This is not just a decision I make on my own. It is a decision made as part of the GTM team. I may be facilitating or leading the conversation, but we all have to agree on where to place our bets in the short term versus the long term while we are building. We also have to align the investment with those motions. For example, when you don’t have an established brand in the enterprise, it will take time for buyers to understand who you are and for you to build credibility. In that case, you might prioritize channel partners. Large channel partners already have relationships. They serve as technology advisors to CIOs, CTOs, and other leaders in enterprise organizations. The best short-term path may be to invest in building your partner ecosystem. Make sure partners are aware of you and your capabilities. Attend their events. They are often the people who will recommend you. It is rare for a CIO to come directly to a vendor’s website. They may conduct some research, but they are unlikely to fill out a form. That is not how their buying process typically works. They also have many people prospecting them at any given time. So you have to ask whether channel is the fastest path to revenue and what the tradeoffs are. You may have to pay an agent commission in addition to the sales commission, so you have to balance that. Could inbound be the priority? Inbound is not usually a strong enterprise motion, but you may need to keep investing in it to generate smaller deals while you build toward larger ones. It really comes down to triangulating where growth will come from. It could be retention and expansion. If that is the expected path to revenue, you need to assess everything around where you are in the lifecycle, what investment is required, what the timeline looks like, and how much budget is available. It is like solving a Rubik’s Cube. Once you decide, you have to get everybody on the same page and make sure the executive team is aligned. That is what will be communicated to the board. They need to see consistency in the thinking and commitment to the plan. Brian Carroll: As you measure the plan and its outcomes, I think many marketers treat pipeline as the main scoreboard. But pipeline is really a lagging signal. It shows what has already happened. Corey Livingston: Yes. Brian Carroll: What do you trust as a leading indicator besides pipeline? Corey Livingston: I trust engagement signals. Whenever we are launching a motion, we are looking for good signals. We want to understand what is working before we double down on the investment. I would not say I am risk-averse, but I am cautious. During almost all of the 20 years I’ve worked in B2B marketing, budgets and resources have been constrained. That is simply the nature of the work. When we are first investing in programs, I look at different indicators depending on the phase. If we are in the build phase, the indicators are more about operational readiness. What did we deliver? If we are moving into a specific vertical, do we have case studies and references? Do we have thought leadership content? Do we have a dedicated web page? Do we have relevant experience? Those indicators are more about completing the work we need within a specific period of time. If we are in the activation phase, we now have enough assets and a minimum viable approach to launch into a specific segment. You cannot get to pipeline without engagement. If no one is engaging with you, looking at anything, responding on LinkedIn, responding to email, picking up the phone, or visiting your website, that is a sign that you may need to reassess the strategy. You are not going to get to pipeline without engagement. With account-based marketing, which is one of our motions, we look for movement among high-fit accounts. We look at website intent. Are those accounts visiting the website? What are they doing? What does their search pattern tell us? Does it indicate active research? We also look at partner-sourced engagement. Are we getting meetings when we attend partner events? Are partners contacting us about opportunities? What is the quality of our inbound interest? Are people engaging with our content? It is a great time to be a B2B marketer because you can measure almost everything and have so much visibility. The challenge is separating noise from a meaningful signal. Those are the things I look at, and they can be difficult to communicate when you are not yet in the scale phase. When the motions have not been in market for long, you are trying to communicate progress before the final outcomes appear. Most organizations, especially the C-suite, are highly outcome-oriented. They want to know: How many opportunities are there? What is the value? What stage are they in? What is the commit? What is the best case? When will this close? When you bring them engagement metrics, the reaction may be, “Okay, but what does that mean?” You have to continually explain why those indicators matter. Even when you are looking at lagging indicators like pipeline, you still need to work backward. What are we doing? Are we focusing on the right accounts? Are we prospecting? Where are the leads coming from? All of those things matter before you get to pipeline. Brian Carroll: From your experience, are there any key indicators that tell you the company is moving in the right direction and making progress? Corey Livingston: One of the things we look for is whether we are getting meetings. Meetings are a major indicator. To me, that could represent a potentially qualified lead. Is it a qualified meeting? Was there an outcome that led to a possible next step? That is one of the most important indicators I look at. There are other signals, such as opens, click-throughs, and whether the right accounts are visiting the website. Do they meet our ICP? But meetings are one of the biggest indicators. As you move into enterprise, I think you have to throw BANT out the window: budget, authority, need, and timeframe. That is especially true when you are just beginning to enter enterprise accounts. When the motion is early, the question I work on with sales is: Are we getting a meeting with the right person at the right account? That is what we look at most. Are we moving to the next step, and why or why not? That tells us whether it was truly the right person or whether there may have been a product-fit issue. It could have been a strong, qualified lead. It could have been the right person at the right account and matched our ICP, but perhaps something was missing in what we could offer, and the opportunity could not move to the next step. That is still an important signal. Brian Carroll: For someone in the trenches right now, what do you think most leaders get wrong during the first 90 days of a GTM rebuild? Corey Livingston: I would say most leaders try to fix things too quickly during the first 90 days. The first 90 days are really about diagnosis. It may not take the full 90 days. It may take 30. But leaders often either take too long or jump in and try to fix things too fast. The diagnostic piece is critical. Listen. Interview every executive. Understand the situation from their point of view. Many people struggle to answer a question I ask: What does marketing success look like at the end of 90 days or at the end of six months? That is a very difficult question for many people to answer. I don’t think that is a bad thing. It means you have an opportunity to shape how you should be evaluated and to educate the organization. In many companies, when I do receive an answer, it is usually: How many leads did you produce? But we all know marketing is much more than leads. You are not going to generate leads if you do not have brand awareness and credibility. I’m glad brand awareness and credibility are coming back into focus because they are incredibly important. My advice is to spend time listening, interview the right people, and understand how they think about growth. Try to surface any conflicting information that could undermine your approach. If you find conflicting views, bring the people together in a forum rather than addressing it only one-on-one. You can say, “Here are some things I heard that I’m struggling with. Can we have a conversation about what this means and how we can get on the same page? If we don’t, here will be the impact.” I think that demonstrates thoughtfulness. Once you do that, you can also tell the leadership team, “The sooner we align on this, the faster we can move.” There may also be low-risk activities you can begin while conducting the diagnosis. For example, in a recent company, we started doing LinkedIn outbound and testing our messaging. We looked at who was responding. It was low-risk and did not require a large amount of messaging. Those activities can contribute to what you are learning while you conduct the broader diagnostic work. Once you have that picture, it becomes much easier for marketing executives to perform effectively. They have spent time understanding everyone’s point of view, focusing on the areas of alignment, surfacing the areas where alignment is missing, and developing a solution. That is when you are seen as a more strategic player at the table, but also as someone who can execute. Brian Carroll: The overarching theme I’m sitting with is clarity and helping the collective team gain clarity together. Corey Livingston: Most seasoned marketing or GTM leaders know that, but it is becoming a lost art. I can’t tell you how many times I’ve stepped into environments where people were not talking to one another. They were talking around one another. It is a skill, and a valuable one, to be the facilitator and the person who brings everyone together. Brian Carroll: Corey, thank you. I appreciate you joining us today. For our listeners, here is a question I would like you to take back to your own team: Are you measuring what you built, or are you measuring whether it can get you where you are going? Corey Livingston is the Vice President of Marketing at DartPoints. You can find her on LinkedIn. Thanks again for listening, and thank you, Corey, for joining us today. Corey Livingston: Thank you, Brian. This version is ready to paste into the WordPress code editor beneath the show notes.

Most GTM teams have gotten very good at tracking what buyers do. They can see form fills, intent signals, CRM activity, demo requests, and pipeline movement. But those systems often miss the people, pressure, risk, trust, and hidden stakeholders shaping the actual decision. In this conversation, Scott shares what he learned from studying more than 10,000 buyers across 15 industries, including why so many people who influence a deal never appear in the CRM, why B2B buying is more emotional than we admit, and how personality, culture, and hidden stakeholders shape complex deals. The big question behind this episode is simple: Even if our lead systems worked perfectly, would they really explain what drives a buying decision? About this episode In complex B2B sales, the visible buyer journey is often only part of the story. The CRM may show one set of contacts. The real buying group may include several others. The business case may look rational. The actual decision may be shaped by fear, trust, confidence, internal pressure, and personal risk. Scott Gillum calls this The Hidden Buyer Journey. His research shows that many of the people who influence deals are never entered into the database, and many of the signals that matter most are not captured by traditional lead and pipeline systems. Scott and Brian discuss: Why human-to-human selling still matters as AI and rep-free buying grow How one sales team nearly missed the real executive concern in a deal Why 85% of buyers in a buying group may not be visible in the database Why complex B2B buying is emotional, even when the process looks rational How personality and culture influence buying decisions Why empathy is not a soft skill in complex sales How sellers can use AI to become better with people, not just louder at scale About Scott Gillum Scott Gillum is the founder and CEO of Carbon Design, a marketing services firm focused on understanding buyer behavior and improving B2B growth. He is the author of The Hidden Buyer Journey: How Personality, Culture, and Hidden Stakeholders Decide Your Deals. Scott’s work focuses on the hidden forces that shape B2B buying decisions, including personality, buying-group dynamics, organizational culture, and the stakeholders who influence deals but often never appear in CRM or marketing automation systems. Scott Gillum on LinkedIn Chapters 00:00 Introduction: Scott Gillum and The Hidden Buyer Journey 01:06 The human-to-human selling relationship 02:15 When the CRM tells the wrong story 04:10 The 85% of buyers missing from the database 06:14 The emotional gap in complex sales 08:03 Buyer confidence versus vendor confidence 11:28 The two-thirds rule and personality-based selling 15:16 Why empathy is not a soft skill 18:18 How sellers should adapt under pressure 20:44 Using AI to move closer to the customer 23:42 Closing thoughts A few things worth taking away 1. The CRM may not show the real buying group Scott shared an example of a deal where the sales team thought the need was real-time project profitability. But late in the deal, the CEO’s behavior showed a very different concern: cash flow. The visible activity told one story. The person with the most influence over the decision was telling another. 2. Hidden stakeholders are not a small problem Scott said his team found that 85% of buyers in a buying group were not in the database. In one example, a company gave its team 100 contacts for an opportunity. After reading the email threads, they found nine people in the actual buying group, and only two of those nine were in the system. That changes how we think about attribution, lead management, sales process, and account strategy. 3. Complex B2B buying is emotional because the risk is real Scott put it plainly: buying the wrong iPhone may be frustrating, but nobody gets fired for it. Making the wrong million-dollar SaaS decision is different. That risk creates pressure. And that pressure shapes how people make decisions. 4. Buyers need confidence in themselves, not just confidence in the vendor One of the most important ideas in the conversation is that sellers often believe their job is to make the buyer confident in the vendor. But in a complex sale, the buyer also needs confidence in their own decision. They need to believe they can defend the choice internally, manage the risk, and survive the consequences if things do not go perfectly. 5. Personality and culture shape how people buy Scott explains what he calls the two-thirds rule: certain personality patterns tend to concentrate in industries, roles, accounts, and buying groups. That does not mean every person is the same. But it does mean sellers and marketers can get smarter about how different buyers process information, evaluate risk, and build trust. 6. Empathy is not soft. It changes outcomes. Scott shared an example from email analysis where a seller who showed empathy and understood the buyer’s situation had a much better path through the deal than sellers who tried to drive the process harder. In complex sales, empathy is not about being nice. It is about understanding the pressure the buyer is under and adapting accordingly. 7. AI should make sellers better with people, not just louder at scale Scott’s warning is direct: we chose scale because we were not good at conversion. AI can make that problem worse if it simply produces more outreach. But it can also help sellers understand buyers, buying groups, and corporate culture more deeply. A few lines that stuck with me “We have a tendency to make purchase decisions emotionally, and we rationalize them later.” “You buy the wrong iPhone version, you’re not going to fire yourself. You make a bad decision on a million-dollar SaaS implementation.” “Turns out they’re not putting the people in.” “Titles and roles don’t make decisions. People do.” “We chose scale because we weren’t good at conversion.” “We train on tools. We don’t train on buyers.” Resources mentioned The Hidden Buyer Journey: How Personality, Culture, and Hidden Stakeholders Decide Your Deals Scott Gillum on LinkedIn Carbon Design Listen and subscribe If these conversations are useful to you, subscribe to The B2B Roundtable: What Dashboards Miss. A short review also helps other B2B leaders find the show. Thanks for listening. Transcript Brian Carroll: Welcome to The B2B Roundtable: What Dashboards Miss. I’m Brian Carroll, and here’s the question behind today’s conversation. Even if our lead systems worked perfectly, would they really explain what drives a buying decision? My guest today is Scott Gillum. He’s the founder and CEO of Carbon Design and the author of The Hidden Buyer Journey. Scott spent seven years studying more than 10,000 buyers across 15 industries. And here’s what he found: we’ve gotten very good at tracking what buyers do, but we still don’t understand enough about the person making the decision. Because the real buyer journey often happens somewhere our dashboards can’t see. Scott, welcome to The B2B Roundtable. Scott Gillum: Thank you, Brian. It’s good to be on. It’s good to talk to you again. It’s been a few years, so I’m excited for our conversation. Brian Carroll: You’ve described four selling relationships in the book, and you said the human-to-human one is disappearing. What are we losing right now? Scott Gillum: I think it’s a value equation. In the book, we talked about the number-one driver of purchase decisions being trust and reliability. So if the tools advance to be more trusted than the human, and you already see some of that in the research where buyers want a rep-free experience. They’re well through the buying process before they talk to a rep, if machines can do a better job of giving information and conveying that to be credible, and the audiences trust those sources, they’re going to do it. This is an opportunity. The book is really about how we elevate this human-to-human selling experience so we can preserve the most important thing, which is the human connection, when it comes to making a purchase decision in B2B. We have to take a hard look at how we’re training our reps, the information we’re enabling them with, and whether we really understand the buyers at the other end of the deal. Brian Carroll: I wanted to talk about a deal where the CRM told one story, but the people inside the decision were telling another. Scott Gillum: It’s in the enterprise space. It’s a SaaS company. The sales team was hearing one thing from the buyers they were having conversations with, and they thought the need was around real-time project profitability. Their system is an ERP system. It was focused on project work. Fortunately, they had put all the buyers they were dealing with into their database, which isn’t common. Two weeks before the final presentation against the incumbent competitor, the CEO began showing signs of activity. His intent signals were throwing off cash flow. He searched for cash flow 35 times over the last two weeks. So we brought that information to the account team before the final presentation. They had already crafted the presentation around project profitability. I’m like, “Why are you on project profitability? He’s on cash flow. What is going on here?” This was a fast-growing company. They were burning through a lot of cash. We had to make the connection between the real-time profitability view and cash flow, and how their system was able to do that. A lot of times, buyers aren’t telling you what the real need is because they don’t really understand it. They’re just told to go look for things. Then, when you get down to the key decision maker, he has a very specific thing he’s looking for: how can you get greater visibility into cash flow? That was picked up through intent signals because they had put that contact in the database. When he hit a form, we could track his activity and bring that information back over. The unfortunate thing is, when we looked at this, 85% of those buyers in a buying group aren’t in any database. Brian Carroll: Tell us more about this 85%. Scott Gillum: It was one of the biggest discoveries. For 20 years, I’ve been working with clients on marketing attribution. Why can’t we connect these assets we’re developing to deals? It was always this big mystery. Maybe the salesperson just didn’t put the information in the system, so we can’t track it back. Turns out they’re not putting the people in. We discovered this by reading emails between the reps and the buyers. We did it over five organizations, ten deals, end to end. This was a lot of data, a lot of emails going back and forth. What we discovered was that 77% of the buyers in the buying group enter late stage. They enter during trial, demo, and final presentation. The sales rep’s behavior is to get everything set up for the trial, get the paperwork, get the MSA, get the tech team ready. They don’t take time to enter those buyers. They keep their primary contact in the database because they need that person to open the opportunity, but all these other people are showing up and influencing deals. Clients would give us all their contacts for an opportunity. Let’s say they gave us 100 contacts. Then we read all the emails and found nine people in the buying group. When we cross-referenced that, only two of the 100 were actually in the buying group. Brian Carroll: What’s getting in the way of people doing this? Scott Gillum: It wasn’t until we started reading the actual emails between the sales reps and the buying groups that we could see this. It’s about having access to see where the hidden buyers are. Now we can fix that. We have a lot of different ways to fix that, and they’re sitting there. Brian Carroll: You called this an emotional gap. What does this gap look like inside of a purchase? With complex sales, buyers still require technical evaluation, procurement, financial approval, and a business case. That all seems rational. Tell me more about this emotional gap. Scott Gillum: We have a tendency to make purchase decisions emotionally and rationalize them later. That’s been true in B2C for a long period of time, and I was involved in research about ten years ago that showed that’s the case in B2B buying as well. The reason is the risk equation. You buy the wrong iPhone version, you’re going to be upset with yourself, but you’re not going to fire yourself. You make a bad decision on a million-dollar SaaS implementation, and there’s high risk involved. We forget that risk. We also forget this is a person in a role, with a persona in that role, sitting inside a buying group, inside a corporate culture, inside an industry. All those things add pressure to the decision maker. We know this is true because we sit inside organizations and see how we operate every day when trying to make decisions. But we never consider that equation when selling something. It all exists. It influences people. People make decisions very selfishly, too. Depending on your personality type, you have different motivations for your behaviors. In the past, we didn’t have the tools to pick up those signals. Now we do. Brian Carroll: We think our job is to help the buyer have confidence in us, when what we really need to do is help them have confidence in themselves. Scott Gillum: Yes. It’s the pressure. It’s the risk involved. How do we help an individual or a team of individuals? Typically, what we found is that three or four people drive deals through organizations. How do you give that small group confidence and trust? How do you convey trust? When we looked at purchase drivers, buyers identified things like product, reliability, and product utilization. But all of those factors are realized after the decision. So something else is being conveyed before the decision. That something else is: I feel confident in this provider. I feel like I can trust them. I feel like this person is credible. I feel like this company is credible. I like their reputation. That’s what drives purchase decisions. It’s not just the feature functionality of the product, because that’s realized after the decision. Most buyers don’t trust your ROI. They don’t trust your case studies. It’s very rare that any vendor can repeat the same results in that company. There is something else going on. We know that to be true, and I want people to be conscious of it. Brian Carroll: Why do you think we have that gap around understanding the emotional side of complex sales? Scott Gillum: It’s difficult to manage. How do you teach a rep to manage someone’s emotional decision-making? It’s hard. That’s one reason I try to make this easy to understand through personality types. At the industry level, there’s the two-thirds rule. People flock together in industries and roles. They have similarities. How you choose a degree in university is often driven by your personality type. That degree takes you into a role where you find similar personalities. That role puts you in a company or industry where certain personalities flock together. One example is the airline industry. Half the people working in the airline industry are in operations. This is an industry where planes can’t drop out of the sky. It has to be data-driven, analytical, and detail-oriented. There is a personality type that matches that: the Conscientious personality type in DISC. As a result, you find that 65% of people in those roles skew toward Conscientious. Depending on the company and how much efficiency matters to the business model, you will find more Conscientious types. There’s a certain logic to it. That’s often the feedback I get when people read the book: it’s perfectly logical. Why aren’t we doing anything about this? At the industry level, company level, and group level, I’m trying to make it easier to incorporate this into everyday activities. Brian Carroll: You just talked about the two-thirds rule. What does that change in practice, and how did you come up with it? Scott Gillum: That took seven years to figure out across the fifteen industries. When we started doing this, we started at the persona level. A client came to us and said product marketing had handed the go-to-market team 17 personas. How do we action that? It was impossible. What it really was, was 17 different selling scenarios. We said, let’s look at your audience and profile them. We took an AI personality profiling tool that was built for recruiting and used it to understand the personality types of buyers. We started seeing similarities at the role level. The first thing we looked at was data scientists. Two personality types made up 90% of that role. If you know that, you can customize language for those buyers. Most of the research showed that one personality type will be at least 50% of the audience. That’s true at the role level, account level, and industry level. So you can aim personalized content at half of your audience, and I mean deep personalization. You can take the insights around DISC and train AI content generators to write in the language of those buyers. We have built custom GPTs to do this. You can take one email and make it truly personalized by putting it in the language of those buyers. In the book, I give an example where I take an old IBM Selectric ad, adapt it for today, and then change it by personality type. You can see how the language changes based on buyer preferences. We now have the ability to do highly customized outreach. Brian Carroll: What difference can it make? Why should people invest in this? What have you found when you’ve run campaigns or outreach using this? Scott Gillum: It impacts every level: response level, engagement level, conversations. There are examples in the book of companies that used this to set up weekly conversations and to build personas in ways that helped with client retention. Role-based personas give you the professional view of a person in a role: title, responsibilities, and the typical things. But if you add the personal side, you get something more useful. One example is CISOs, chief information security officers, in cybersecurity. These people are highly technical, but we forget they’re also highly emotional. The amount of risk they manage is enormous. I don’t know how they sleep at night. We told a company selling cybersecurity solutions that they were not addressing the raw emotions of this buyer and the pressure they face every day inside the organization. If you combine the business language with the personal language, you have an opportunity to separate yourself from the crowd. You can change your language and messaging to be more empathetic, build credibility, and build trust because you understand their situation. It makes a huge difference. Brian Carroll: Some people think empathy is not something we need to focus on. They see it as a soft skill that doesn’t necessarily have a place in business. What do you say to that? Scott Gillum: I say BS. When we were reading emails, we were watching seller behavior. I saw two dominant personalities, two Northeast dominant sellers, selling to a Midwest Conscientious buyer, and it was not going well. I also watched a female seller from the South selling into a West Coast company. Her tone and empathy stood out. One of the buyers she was dealing with had been out for surgery, and she opened by talking about the recovery and hoping she was doing well. This is a small sample size, but there was much greater success and a shorter sales cycle with the person who showed empathy and understood the buyer’s situation inside the organization. The other sellers were just driving the deal. They were nonstop driving. You could see the buyer on the other end starting to tune out. The communication started to gap. They weren’t responding. Watching that play out in real life, you could see that this buyer didn’t really want to engage with that kind of seller. Brian Carroll: From the perspective of a leader listening right now, what should they have their team do differently on their next five accounts? Scott Gillum: First, go get an AI personality profiling tool. They’re not expensive. They’re effective for BDRs and SDRs, the people who initially have contact with customers. They’re also helpful when closing the deal. Start by assessing yourself. That’s the most important thing. Then assess the people you’re going to talk to. Some tools show your attributes versus the attributes of the people you’re talking with, so you can adjust your style. One of the chapters is called “The Sales Chameleon.” We give an example of Ben, someone we found in the research. He is something different in each company, but he knows where his value is. Understanding your value and being able to adapt to the buyer, the situation, and the organization makes a world of difference. That’s the future of a salesperson: someone who understands how to convey value, but do it in different ways. Brian Carroll: How do we get people to start acting this way? People are nodding and saying, “This sounds great, but I need to make my number.” What do you suggest they do? Scott Gillum: There are no other technologies that are going to fix us from a scale-volume perspective. They’re beyond the top of the yield curve. They’re declining. You’re starting to see consolidation in the tools. This is no longer about throwing a wide net and seeing what you can drag back. This is about how I do better with what I have. This is about conversion now. Every deal is precious. Your buyers do a lot of research on a solution. How much research are you doing on your buyer? Opportunities are going to be smaller, precious, and fewer. How do I convert them at a higher rate? You do that by understanding the person on the other side of the deal as a person, not as a title or role. Titles and roles don’t make decisions. People do. You have to understand that person, their situation, their role, and their organization. You have tools to do that, but you also have to put in the time and do your homework. Either you use the tools to enable you to become a better seller, or you use the tool to replace you. That’s where the investment is going. There is far more investment going into sales technology than sales training. Brian Carroll: Right now, AI gives us the ability to scale outreach. But unless we really understand our buyer, all we’re doing is hurting ourselves. Scott Gillum: We chose scale because we weren’t good at conversion. We train on tools. We don’t train on buyers. Those days are over. Most of your market is not in-market. If you are lucky enough to capture someone who is in-market, you better do a really good job with them. You better get to a close. It’s time to invest in people learning how to be better with people. Brian Carroll: What can we do right now so that we’re using AI in a way that moves us toward the customer? You’ve already talked about using tools that help us analyze personality. How else? Scott Gillum: This is what I call a hack. It’s so simple, and we should be doing it. You can understand corporate culture and decision-making without ever talking to anyone. Before you even approach them, you can understand how they make decisions and how fast they make decisions by understanding the corporate culture. Take the senior management team. Culture rolls down from the top. Profile that senior management team, and you will learn their priorities and how they make decisions. One company we profiled was a construction company, a top 50 Fortune 500 company. Twenty-one out of 22 executives we profiled on their website had the same personality type. They had different backgrounds and experiences, but the same personality. You knew immediately this was a dominant organization. It was a driven organization. Once you understand that, you can align your messaging. Dominant personalities want to see use cases and case studies that are as similar as possible to their organization. They want to see the outcome. They want to see return on effort. That is how you approach them with your messaging and value proposition. It is sitting right there. All we need to do is harvest it. Brian Carroll: What are the nuances? Scott Gillum: Education is fascinating. You can go into LinkedIn, go into the company section, look at people, and then look at the education of the people who work in those companies. You can see the top degrees. If a company has a certain personality, say Conscientious, you’re going to find engineering degrees and science backgrounds. It makes sense. If you’re dealing with a company that has a lot of scientists, like R&D, you’re going to have a distinct personality type. What we learned is that the more advanced degrees you have, the more likely you are who you are as a person. If you’re happy in your role and your job, there’s a reason for it. Your background and personality have led you down that path. If you’re fortunate enough to match that, you’re probably happy. If you’re not happy in your current position or job, there’s probably a mismatch between who you are as a person and either the organization or the role you’re in. Brian Carroll: Scott, this has been a fascinating conversation. I’ve learned so much talking with you, and I know our listeners have as well. This has been Scott Gillum, founder and CEO of Carbon Design and author of The Hidden Buyer Journey. Our systems can tell us what the buyer did, but they don’t often explain what the buyer feared, what they trusted, or what they needed from the people selling to them. Scott, people can find you on LinkedIn. We’ll put the link to your book, The Hidden Buyer Journey, in the show notes. Thanks so much for sharing your insights with us. I really appreciate you being here today. Scott Gillum: Thank you, Brian. I really appreciate it.

About this episode Here’s something most B2B marketers know but do not always say out loud. We have gotten very good at measuring things. Attribution. Pipeline metrics. Sourced revenue. Influenced revenue. Cost per lead. And yet, a lot of B2B brands are still forgettable. Not because the marketers are bad. Because the system keeps pulling them toward what can be tracked, reported, and defended in the next pipeline review or board meeting. That is the tension at the center of this conversation with Lindsay Cournoyer, Fractional CMO and Brand Marketing Consultant at LC Consulting, and former CMO at Blue J. Lindsay has led marketing at companies including Axonify, Coconut Software, and Blue J. At Blue J, an AI-powered tax research company, she helped 5x revenue and raise $122 million in Series D funding. But that is not the main reason I wanted to talk with her. I wanted to talk with Lindsay because while that growth was happening, she made a brand bet that many B2B marketers would struggle to defend on a dashboard. She invested in out-of-home advertising. Billboards. Elevator ads. Radio. Physical media in a B2B SaaS company. That is not the usual B2B playbook. But Lindsay believed the company needed something that the usual performance channels were not delivering: awareness, trust, and memory in buyers’ minds before they were ready to enter a sales process. Her line from LinkedIn captures the problem clearly: “B2B brands are so obsessed with being measurable that they forget to be memorable.” That is where this conversation starts. We talk about why performance marketing can capture demand but cannot create all of it, how Lindsay made the case for out-of-home inside a B2B SaaS company, what she measured before and after the campaign, and why brand work can feel risky when marketing already has to justify itself more than other functions. If you have ever felt pressure to optimize for a metric instead of an outcome, this episode is for you. About Lindsay Cournoyer Lindsay Cournoyer is a Fractional CMO and Brand Marketing Consultant at LC Consulting. She has led marketing at B2B companies including Axonify, Coconut Software, and Blue J, where she most recently served as CMO. At Blue J, she helped the company grow revenue 5x and raise $122 million in Series D funding. Lindsay works with B2B SaaS founders and leadership teams on brand strategy, messaging, and go-to-market. Connect with Lindsay Connect with Lindsay Cournoyer on LinkedIn Chapters 00:00 Introduction: B2B Brands Are Too Measurable to Be Memorable 01:53 Why Brand Has to Create Demand Before Performance Captures It 03:29 The CEO Saw the Brand Problem 04:24 The Marketing Tax and Why Brand Needs CEO Support 07:35 Making the Case for Brand Inside the Business 10:11 How Lindsay Measured Awareness and Consideration 13:50 Staying Steady When the Bet Feels Risky 16:55 What to Do When Your Company Doesn’t Value Brand 22:26 How to Make the Case for Brand Investment A few things worth taking away Performance marketing has a role, but it mostly captures existing demand. Brand helps create the demand performance later captures. B2B buyers need to remember you before they are ready to buy. If you are not already planted in their mind, you may never make the shortlist. Out-of-home can be targeted in B2B when you know where your buyers work, commute, gather, and pay attention. The marketing tax is real. Many marketing leaders spend too much time justifying their function rather than doing the work that creates long-term value. A CEO who understands brand changes the entire marketing environment. Without that support, big brand bets are much harder to make. Brand can be measured, but not always through the same dashboard logic as demand generation. Lindsay used pre- and post-campaign surveys to measure awareness, perceptions, consideration, and likelihood of purchase. A brand campaign can move more than awareness. In Lindsay’s case, they saw an increase in awareness and purchase consideration. Sometimes the best thing a marketer can do is accept the reality of where they are, protect their sense of worth, and look for a better environment where marketing is understood. If a CEO does not understand brand, use examples from their own life. Show them how brands earn memory before the buying moment. Sometimes you have to earn the right to make a brand investment by first showing how marketing contributes to pipeline and revenue. A few lines that stuck with me “B2B brands are so obsessed with being measurable that they forget to be memorable.” — Lindsay Cournoyer “Marketing’s true job is to carve out that place in your buyers’ brains.” — Lindsay Cournoyer “We have to build brand awareness and trust and credibility before you really step on the gas of performance marketing.” — Lindsay Cournoyer “There are companies out there who actually get it. They are very hard to find, but they are out there.” — Lindsay Cournoyer “Sales have to be there. And then you may get the shot.” — Lindsay Cournoyer Resources mentioned The B2B Roundtable episode with Jon Miller on what comes after the MQL Growth Isn’t a Headcount Problem. It’s a Precision Problem, with DeAnna Ransom Listen and subscribe Subscribe to The B2B Roundtable wherever you listen to podcasts. Transcript Brian Carroll: Here’s something most B2B marketers know but don’t say out loud. We’ve gotten very good at measuring things: attribution, pipeline metrics, sourced revenue, influenced revenue, cost per lead. And yet, a lot of B2B brands are forgettable. And it’s not because the B2B marketers are bad. It’s because the system keeps pulling them from what they know is the right thing to do, and they’re forced to do things that are tracked, measured, and can be reported at the next board meeting. It’s harder to attribute when you focus on brand. It’s harder to justify in a pipeline review, so it often gets pushed aside. Welcome to The B2B Roundtable. I’m Brian Carroll. And in this podcast, we talk about the things that dashboards miss. My guest today is Lindsay Cournoyer. She’s been a marketing leader at companies including Axonify, Coconut Software, and most recently served as the CMO at Blue J, which is an AI-powered tax research company where she helped 5x revenue and raise $122 million in Series D funding. That’s impressive, but that’s not the main reason I wanted to talk to her. I wanted to talk to Lindsay because while this growth was happening, she made a significant investment in out-of-home advertising. And this included billboards, physical media in a B2B SaaS company. It was the kind of bet that’s hard to defend with a dashboard. And she did it anyway. So today we’re going to talk about why. And if you’ve ever felt pressure to optimize for a metric instead of an outcome, this conversation is for you. And Lindsay has a line that names the problem really well. She wrote this in a recent LinkedIn post: B2B brands are so obsessed with being measurable that they forget to be memorable. And that’s where we’re starting today. So Lindsay, what were you seeing that made that feel true? Lindsay Cournoyer: Yeah, it’s a great question. And I will say the obsession is real among executives and board members. I think back to what Jon Miller talks about all the time, that people want marketing to be a gumball machine and act like a gumball machine. You put a dollar in and you get three out. And it’s supposed to be this really predictable thing that you can just game the system and get to the revenue that you want. But that’s just simply untrue. Performance marketing has its place. Its role is to capture the demand that’s been created for your brand. But if you just lean into performance marketing and focus on that, you’re missing the whole front part. Really, what I believe is marketing’s true job is to carve out that place in your buyers’ brains and be the solution that comes to mind first when a buyer thinks of your category. And if you don’t focus on building your brand and trust and reputation before you get into performance marketing, you’re really missing the whole point of what I think marketing is here to do. Brian Carroll: You made this significant out-of-home investment, which is unusual in B2B. That’s not something people typically do. And it was a big bet. What was the problem you were trying to solve that the usual marketing metrics and channels weren’t solving? Lindsay Cournoyer: Yeah, it’s another great story. Really, the reason I took the role is because the problem to solve was named by the CEO in my interview process. And it was, not enough people know about us and the awesomeness that is our software. It’s like, we have this great product, but the CEO knew that if everyone in the market didn’t know about it, the company was not going to get where they wanted to go. So he inherently understood the need for brand. I was winning already out of the gate. And like I said, that’s really why I took the job in the first place, because of that understanding of the need to build brand awareness and trust and credibility before you really step on the gas of performance marketing. Brian Carroll: It sounds like your CEO was enlightened thinking about this idea of brand, because that is not the experience that a lot of B2B marketers have. Lindsay Cournoyer: Yes. I think we undergo a lot of scrutiny in marketing that other departments just don’t feel. We’re continuously having to justify ourselves and our decisions and our plans and our budget and our headcount. And there’s just this kind of skepticism around marketing that exists. It’s pretty pervasive. It’s not in every company, but I’d say it might be in most. It’s really tough to operate in that kind of environment and carry that kind of tax. I have experienced it, and it really does just tire you out and take you away from the really important work that you should be doing when you have to be doing PR for your team all the time. This was a brand new product. It didn’t exist. It was AI for tax research, essentially a ChatGPT-like experience where you go in and ask your tax question and up pops the answer with all the verifiable sources. It didn’t exist before. And it was a much cleaner and more enjoyable way to do tax research than what accountants have dealt with in the past, with hours of painstaking research and judgment calls and asking the partner. It just didn’t exist. So the CEO really knew this is brand new to the market. We need to go introduce it to the market. I am grateful for that, but I realize it’s not the case in every company. So I do think, unfortunately, we do have to do some explaining about brand and why awareness matters and why building trust and credibility with buyers matters. Really, I think CEOs should be curious about brand. If they’re not, that’s a mistake. They should take it upon themselves to go and talk to their marketing leader and really start to do their own research and understand why awareness building and credibility and trust is so important. That shouldn’t always be on us. So I would encourage any CEOs out there listening who don’t know a lot about brand or marketing and kind of see it as this black box, to really make an effort to understand the craft and the strategy behind it. I think in certain cases, there are just CEOs or executive teams or boards out there who aren’t going to do that. And if you find yourself in one of those companies or situations, unfortunately, sometimes you just can’t get through and win, and you will just carry the tax ongoing. Brian Carroll: That’s the double burden. You have your job to do, and then there’s the need to justify the very existence of the function or your team, and you’re constantly doing PR. Lindsay Cournoyer: Yes. Yes. Yes. Brian Carroll: How did you get there? How did you make that case? Lindsay Cournoyer: I really did something that we all do a lot of. I had to essentially act kind of like a professor on brand. I created a really detailed brand strategy deck that I presented at an executive offsite planning meeting. And I explained that we have to carve out a place in people’s minds as the category leader and a new solution that they can trust, and that we are already leading the category and are really the horse that they want to bet on. So I went through quite an extensive educational exercise with the team, and the response was really positive. These are people who really didn’t know that much about marketing, and they leaned in and they were super excited. At the end of that presentation, I went through all of the things you need to do to build brand and credibility and trust and get that place in people’s brains. And the culmination of that work was an out-of-home campaign and a big multi-channel brand campaign that was tremendously successful. So I had the support of the internal team, which was amazing. But I will tell you that there were skeptics. One of our board members was not happy with my campaign idea and expressed their displeasure. And, of course, our CEO was a little like, “Are we doing the right thing?” And I just stayed steadfast. Yes, we are doing the right thing. Their argument was that this was too broad, it’s not targeted. But actually, out of home can be very targeted. For example, where are the offices of the firms you want located? They’re in specific cities or specific areas or specific neighborhoods. Go buy out of home and put a billboard right out front of their office or in the elevator that they ride up and down every day. It’s really about getting their attention through an untraditional channel, but I think it’s a myth that it can’t be a targeted play. Brian Carroll: It’s really interesting. I was just thinking about when we had Jon Miller on our podcast earlier. We talked about the problem of the MQL, that it’s the last 5% of people who actually express interest. But what about the 95% who don’t, who aren’t yet in consideration, who don’t quite even know the problem? And as you talked about, you’re introducing something new, a new category, something that didn’t exist. After it launched, how did you know it was working? What did you measure? What changed? And what did you have to admit you couldn’t measure? And so you needed to build that trust with the internal team to say, “Yeah, we’re still doing it because it’s the right thing.” Lindsay Cournoyer: Yeah. Well, there actually is a very clear way to measure awareness. And it’s not cheap. You have to put some money behind it. But what we did is we developed a survey, which we took to market through a third-party partner. And it basically asked people, have you heard about us? What do you think about us? Who do you see as the category leader? Are you going to consider buying software like ours in the next year? Which product are you leaning toward? So we asked a lot of what I think were smart questions just to understand current awareness and perception levels in the key markets that we wanted to win. What came back was really interesting. Our awareness was actually quite high. We had done a really good job spreading the message and the product through events and partnerships. So we were starting from a strong place already, which I think was surprising to some of us. But we came out strong, and we did a three-month campaign in four key markets where we used out of home and radio, which is another underutilized channel. Accountants love radio. They listen to sports talk, and we did SiriusXM. It was a great channel to reach them. Then we let the campaign go. And afterwards we went back and surveyed again. The goal that we were going for was a four-point lift in awareness, which is statistically significant. We could say, okay, this campaign worked. And we got much more than that out of the campaign in the results that came back. And then, interestingly, this was amazing. Not only did the awareness lift in a big way, but consideration also moved. So people who had seen three to four versions of the creative reported a much higher likelihood of buying us. That was all I needed. We worked so hard on this. And to be honest, I was scared shitless running this campaign. It was a big bet. I was freaking out. My agency had to calm me down several times because I’m like, this has to work. This is really important. And they assured me, “Lindsay, it’s going to work. It’s going to work.” And it did. The outcome was so amazing that, since I have left to work for myself again, they’re going to keep going with the brand investment because it’s something that worked and it needs to be sustained. Brian Carroll: I think a lot of marketers are dealing with similar feelings. They’re overwhelmed. There’s anxiety because they constantly have to justify their job. There’s constant input given from peers. You wouldn’t tell the CFO, “Hey, have you thought of this ratio versus that ratio?” Lindsay Cournoyer: Exactly. Yes. Brian Carroll: What are some of the things you’ve needed to do to help yourself stay steady when every day people are wondering, why do we have marketing? Lindsay Cournoyer: You know what? I honestly felt like this campaign was big enough and high profile enough that my job was on the line. If it didn’t go well, there’s a high likelihood that I may be exited because it was a lot of money and a big swing and a big bet. Like I said before, I was terrified. But I know this kind of investment is so important, and I believe in brand marketing through and through. So I really had this internal dialogue in my head of, “You know what, Lindsay? This is the right thing to do. Don’t go down the death spiral. Just keep positive that it’s going to work.” And the creative was really strong, super resonant. Somehow I stayed positive and I believed in the campaign. And to be honest, if I lost my job over it, I would have been fine with that. Brian Carroll: And so I’m just wondering if you were talking to someone else who is a CMO right now, as a peer or someone who wants to ascend to that role, what advice would you give them to be able to stay steady as they’re making these big bets and doing things that don’t show up in the dashboard right away, like you just did? Lindsay Cournoyer: My advice is if you find yourself in a situation where you have a CEO who understands the value of brand, they’re going to let you take a swing like this. And they’re going to support you as they should. If you’re in a company where the CEO doesn’t get brand or why it’s important, you’re likely never going to get the go-ahead to do something like this ever. So I would say, when you’re interviewing for a role, and if you believe in brand and want to take a big shot like this, you really have to do your due diligence and go deep on the CEO you’re working for and the board and how they perceive marketing and whether or not their portfolio companies are doing stuff like this. Because if you see that they’re not and all they care about is performance marketing, I think that’s a really clear telling sign. Brian Carroll: I think there’s a lot of people who are listening who are like, that sounds great, but I’m where I’m at right now. And maybe because there is this anxiety in the field of marketing, especially technology marketing right now with the rise of AI, with the questions about how buying is changing right now, and how we no longer can put forms up and do content marketing the way that we used to. So I’m just wondering, for that person listening right now who wants to influence their team and they’re stuck in this tactical role of seeing marketing as the demand gen function only, what advice or suggestions would you give? Because maybe some people are where they are and they’re saying, “How do I influence or even try to make a difference in my organization?” Lindsay Cournoyer: The first thing we have to acknowledge is just sometimes you can’t make a difference. And it’s up to you. The truth is a lot of us just need jobs and income to support our families. I had this conversation on LinkedIn. Lisa Adams posted this exact comment on the post about the tax. Sometimes we don’t have a choice. We have to work in these companies that don’t get it. I think you can either just accept it and do your job and earn your paycheck, but you can’t let it suck your soul. You have to be able to say, this is the situation, and detach yourself from it to continue to work in the company. But if you can detach and just do the best job and collect your paycheck, it sucks, but a lot of people do operate that way because we have to. We don’t have a choice. At the same time, I would start looking at the brands who are doing out of home and who are doing brand activations. Start to network with their marketing team people. Follow them on LinkedIn and engage with their content. You can work your way into a better situation eventually. Brian Carroll: I think for some people, just that encouragement you gave could give us license to say, accept the reality where you are, but also open your eyes and don’t let that determine what your worth is. Don’t let that steal or take you down that downward spiral. Because I think a lot of people are in situations where they don’t feel that marketing is valued. And therefore then they are like, “Well, then I’m not valued.” And what you’re saying is, no, there is a way out. Lindsay Cournoyer: There is a way out. There are companies out there who actually get it. They are very hard to find. I’m working with a client right now where the CMO actually started in marketing. His first business was marketing services for a particular industry. And he gets it. He’s taking these big brand swings. He just gave away a Tesla at a conference to draw people into the booth. It was amazing. He’s leaning in and he’s super interested and he wants to input on strategy and jam on brand and marketing. He’s like a unicorn. And they’re hard to find, but they are out there. And when you find one, marketing becomes fun again. I am having more fun working with him than I’ve had in quite some time. He just gets it. So they do exist. Brian Carroll: I like that phrase, fun. How can we get marketing back to fun? And what drew us to it? A lot of people, I don’t know about you, but I didn’t go to school aspiring to move into B2B marketing. It was something I fell into, and then I just loved it because I love the complexity. I love the learning. I loved that there’s a variety of things. Yes, you can get specialized, super specialized, but at the same time you have to have a bigger, more strategic view of things. What are your thoughts on this? Lindsay Cournoyer: I also didn’t know I wanted to be in B2B marketing, but I love it for all the same reasons that you do. And it’s interesting. Again, in the post that I just wrote about this tax that marketers face, Chris Walker actually commented on it and said, this exists in tech, PE, VC-backed companies. And if you go work in a different industry, it’s a totally different game. So that really got me thinking. We all want to be in tech and we all want to be in SaaS. It pays well and it’s fast-paced. It can be fun. It can be brutal. But what about thinking about other industries? I was just contacted by a potential client whose business is in rocket science. And I was just like, my God, this is fascinating. How cool would it be to work on something like that? Totally different. So maybe another part of it is going to work in a different industry. Brian Carroll: I wanted to ask to close, if a CMO or VP of marketing, a marketing leader, has an hour with their CEO this week to make the case for brand investment, what should they say? What advice would you give them? Lindsay Cournoyer: I always like to bring it back to an example that they themselves will see themselves in. Think about buying a new car. You want an electric vehicle. You’re going to look at Tesla, Polestar, I don’t know, all the other brands that now make electric vehicles. But when you think of electric vehicles, you think of Tesla first. They own the category. There you go. There’s the example of how they’ve done well because they are planted in people’s brains. If you’re buying an EV, you’re buying a Tesla. Now there are more options, and we won’t get into the Tesla thing, but bring it back to an example and a scenario that they themselves have been in. I think I’ve seen then the light bulb go on. Brian Carroll: And if they’re proposing an idea or a bet, any thoughts you have on perhaps the smallest version of a bet if someone wants to move in this direction, but they haven’t won the credibility or trust yet to make that big bet? Lindsay Cournoyer: I hate to say it, but sometimes you have to show results from performance marketing. Be able to tie your activity to pipeline generation and revenue. And I feel like once you can clearly make the tie of how marketing is impacting on the revenue front, that really sometimes opens up the territory of brand. Brian Carroll: Really good. I think for people, we still need the big picture of what’s the impact we’re making on revenue, pipeline contribution, and using that as the basis to make the investment for things that aren’t going to show up in the dashboard. What you’re saying is you’ve got to start with the dashboard, right? Lindsay Cournoyer: Yes. Sales have to be there. And then you may get the shot. And that’s what happened with me. I feel very grateful that I got to do a campaign like that. Brian Carroll: Well, Lindsay, this is exactly the conversation I hoped it would be. And for our listeners, if you have more questions or follow-up for Lindsay, Lindsay is doing work right now as a fractional CMO and brand consultant with LC Consulting. She works with B2B SaaS founders and leadership teams on brand strategy, messaging, and go-to-market. If this episode was useful, please subscribe to The B2B Roundtable wherever you listen to podcasts. Thanks again, Lindsay, for this great conversation. Lindsay Cournoyer: Thanks so much, Brian. It was awesome to chat with you.