The B2B Roundtable

About This Episode Everybody talks about GTM alignment. Sales, marketing, and customer success all working together around the customer. But actually making that happen changes how teams work together, and that’s where most alignment efforts quietly stall. In this episode, Brian talks with Martha Mathers about where GTM alignment breaks down and what it really takes to fix it. Martha starts with pipeline first and top of funnel second, because pipeline is the one thing sales, marketing, and success can all agree on. From there, she walks through mapping the journey from the customer’s side, what happened when a new sales team at OPEXUS kept jumping straight to the demo, what thousands of sales conversations taught her, and why she listens first (and says as little as she can) when she steps into a new role. Here’s the thread running through the whole conversation: the problem you see when you walk in usually isn’t the whole problem. About Martha Mathers Martha Mathers is the CEO of TrueComp and a B2B marketing and go-to-market leader. Previously, she led marketing at Bloomberg Industry Group, BigTime Software, and OPEXUS. Her experience spans marketing, sales, customer growth, and leading cross-functional GTM teams. Update (October 2026): Congratulations to Martha on becoming CEO of TrueComp! During our conversation, I asked what marketing leaders need to do to become CEOs. Now she’s made that move herself. Pretty awesome to see, and her advice is worth revisiting. What We Cover Why Martha starts with pipeline before top of funnel Getting sales, marketing, and customer success working around the customer journey What changes when you think beyond the funnel and include expansion Enablement as the connective tissue across GTM What Martha learned from listening to thousands of sales conversations Using AI to learn from more data and conversations, not just create more content Why experience can get in the way when a leader walks in thinking they already know the answer How much consensus it really takes to make change in a large company Making change a step at a time instead of trying to do everything at once What marketers need to learn outside of marketing if they want to eventually lead the business A Few Things Worth Taking Away Pipeline gives sales, marketing, and success something they can agree on. Start there and work backward. Look at the journey from the customer’s side. That’s where the gaps between teams become easier to see. Listen to what customers and salespeople are actually saying. You may find that the story being told in the market isn’t the one marketing thinks it’s telling. Experience can create blind spots. Martha’s approach is to ask questions before assuming the answer that worked somewhere else will work here. Big companies take more consensus than you think. Knowing who needs to be involved is part of making the change. Change doesn’t have to happen all at once. Sometimes the better question is, “What is the change I can make this week?” A Few Lines That Stuck With Me “I’ve seen many leaders come in and assume by telling stories of everything they’ve done in the past, they will be able to fix the problem ahead of them.” “I listen first, ask a ton of questions, and share honestly as little as I can.” “Those are all different owners and different initiatives, but at the end of the day they all go back to the same account.” “We have a tendency to lead with the shiniest thing we can.” “I tend to value it, you know, more from an intelligence perspective than perhaps a content creation perspective.” “What is the change I can make this week?” Resources Mentioned Matt Heinz, whom Martha credits with the line “an MQL can’t buy you a beer” Gartner’s research on the B2B customer journey Chapters 00:00 Why GTM alignment breaks down 00:56 Where GTM alignment gets disconnected 02:33 Why pipeline should come before top of funnel 03:45 Aligning GTM around the customer journey 05:17 Expanding customer relationships after the sale 06:49 Why enablement is the connective tissue of GTM 10:30 What thousands of sales conversations can teach you 13:26 How AI can improve GTM alignment and enablement 15:53 The biggest mistake leaders make with GTM alignment 19:36 Stakeholder consensus and leading GTM change 23:34 How marketing leaders can prepare for the CEO role Transcript Brian Carroll (00:01) Welcome to the B2B Roundtable. I’m Brian Carroll, So everyone talks about GTM alignment. That’s from marketing, sales, customer success, all aligning around the customer. But actually making that happen changes how teams work together. And so the question I wanted to ask is: what really works? How do we actually make this happen in reality? And that’s why we have our guest today, Martha Mathers. Now, Martha has been the head of marketing at companies from Bloomberg Industry Group to Big Time Software to OPEXUS And I wanted to talk with her because she understands this. And something I saw her talk about recently in a panel discussion on YouTube is that for her, they started by focusing on the pipeline first and top of the funnel second. So, Martha, welcome. Martha Mathers (00:53) Thank you so much, Brian. I’m really excited to be here. Brian Carroll (00:56) I wanted to ask you when you think about companies that you’ve worked with, where do you see GTM alignment getting the most disconnected? Martha Mathers (01:05) Yes, a great question. And I think it can happen in a couple different places. To your your first point, I think in terms of beginning with pipeline, I always think about where are those places where sales and marketing come together could be success as well, thinking about all of those combinations. But what is the thing that everybody cares about? As a our friend Matt Heinz once said a long time ago, an MQL can’t buy you a beer. I believe that is that remains true. And now there are all kinds of debates about MQLs. But from a pipeline perspective, that is something that marketing can typically see their way easily to sales needs and must have in order to hit their number. And often with expansion motions, you have success thinking about quite a bit as well. And so I always start there. Can I see where pipeline is coming from? Can I see how marketing is contributing to it? and just depending on where I’ve been in the stage of the company, OPEXUS was one without a go-to-market function. And so we started by building pipeline and thinking about how each capability would begin to execute against it. I’ve been in other organizations that are bigger and at greater scale, but they don’t have that shared understanding. So just establishing that layer first of where does pipeline come from and where should it come from, and how can marketing contribute is is something I try and do as early as possible when moving into a new. Brian Carroll (02:33) Well, it as you were talking about thinking pipeline first and top of the funnel second, was there something that changed for you that made you look at it that way? Martha Mathers (02:41) Yeah, I I think there’s, you know, the debates that you can often have as a marketing leader with a head of sales around the quality of an MQL. And it at the end of the day, it’s finding that common currency and that that lingua franca in terms of I may be very excited about what’s happening on LinkedIn. And that matters a ton. Don’t don’t get me wrong there. That helps a ton in terms of brand awareness and reach and just how someone thinks about your company. and As does every dollar and investment that brings a a new kind of contact or buying group in the door. but that was something that sales didn’t necessarily care about unless they’d maybe been on the ground at an event and had a good quality conversation. So by starting with pipeline and showing where a marketing investment actually turned into a quantity of dollars that maybe then turned into a quantity of dollars booked was something that we could hold hands around and agree on. And then once I had that data layer, I can back my way into how to invest at different points in the funnel to get the pipeline that we need to grow the business. Brian Carroll (03:45) what’s it take to get sales, marketing, and the post sales teams all working around the buyer journey? Martha Mathers (03:54) Yeah, one thing that we did at OPEXUS was we really had a lot of missing capabilities when I started, as well as a couple of other executives. And for us, it was starting with a customer and starting with the customer journey. That’s something that you’ve you’ve heard, we’ve both heard Gartner talk about quite a bit over the years. Brian Carroll (04:14) Yes. Martha Mathers (04:14) and I had the I had the opportunity to do a good bit of research around too. It’s not mapping your sales and marketing and success activities. It’s really considering that journey that the customer is is navigating throughout. And so I think if you can start there and think about what brings a new buyer to us, what engages them in a conversation, what makes them consider our solution, and then how do we get started and onboard someone? Those are all different owners and different initiatives, but at the end of the day they all go back to the same account. And so I I always look at start with that buyer, map those key touch points, understand if you have the data to get underneath what’s happening at each and every one of those stages. And then those places where you can build that strong cross-functional coordination and handoff, I think become much more apparent, both in sharing information across teams, but also pinpointing the areas. for example, just a kind of quarterly business review where there could be sales marketing. and success implications. Brian Carro

About This Episode Most GTM teams are using AI to make existing work faster. But faster isn’t the same as different. And the teams that are actually pulling ahead aren’t automating the past — they’re reimagining the work itself. In this episode, Brian talks with Liza Adams about what separates teams that are getting faster with AI from teams that are actually changing how they work. Liza shares the story of Megan, a senior marketing leader who used AI agents to orchestrate across marketing, sales, and CS until her work outgrew her title entirely. That story illustrates the bigger idea behind the conversation: what happens when you reimagine the work first, then redesign the roles and the org around it. About Liza Adams Liza Adams is the founder of GrowthPath Partners, where she helps B2B GTM teams move beyond AI productivity into AI-driven transformation. She spent 25 years leading GTM teams at companies including Smartsheet and Juniper Networks, and has worked with AI and machine learning long before ChatGPT. She is passionate about elevating the strategic value of marketing and helping leaders use AI to become business leaders, not just functional leaders. What We Cover The AI adoption plateau and the three patterns that cause teams to stall Why your belief about what AI can do is the cap of what your team will ever build Using AI as a sparring partner vs. a validation tool, and the research behind why it matters The difference between what’s hard for humans and what’s just historically hard How AI doesn’t care about your org chart, your silos, or your titles What CEOs are starting to want from CMOs and why most marketing leaders aren’t set up for it Why reimagining the org chart starts with reimagining the work, not the other way around A Few Things Worth Taking Away AI for productivity should be the floor of our expectations, not the ceiling. If we only make old work go faster, we can project how it automates the human out. But if we use AI to do something different, we’re innovating, and when the business grows, humans are essential. People aren’t stupid. They just need to see what’s possible. Talking about AI capabilities is different from showing someone a workflow that pulses the market 24/7 and surfaces which customers are about to churn. Humans that use AI as a sparring partner outperform pure human teams and pure AI teams. But humans that use AI to validate their beliefs actually perform at a lower level than an all-AI team. In the RACI model, AI will never have the A. It will never be accountable. It will never lose the job for you, pay the fines for you, or go to jail for you. Don’t start with “what does the org of the future look like?” Start by reimagining the work. When you reimagine the work, the roles become clear. When the roles are clear, the org chart follows. A Few Lines That Stuck With Me “The cap of what our teams will ever build, do, and use AI for is limited by what they believe it can do.” “AI transformation can’t happen when we’re in a hamster wheel.” “AI will never lose the job for you, it will never pay the fines for you, and it will also never go to jail for you.” “It’s like hiring a bunch of actors before you even know what the script is.” “AI is making the mechanics a lot easier. I think our biggest challenge now is us.” Resources Mentioned AI Is Cannibalizing Human Intelligence. Here’s How to Stop It. by Vivienne Ming (Wall Street Journal) What Harvard Learned From 776 Professionals Using AI (Harvard/P&G research on AI and cross-functional collaboration) Chapters 00:00 Why Getting Faster With AI Isn’t Enough 03:20 Why Teams Hit the AI Adoption Plateau 07:43 AI as a Teammate, Not Just a Tool 10:10 Using AI as a Sparring Partner 12:35 What Work Is Only “Historically Hard”? 18:12 AI Can Do the Work. Humans Own the Outcome. 19:32 From Org Charts to Work Charts 26:19 What CEOs Need From CMOs Now 34:33 Reimagine the Work Before the Org Chart Transcript Brian Carroll (00:00): Well, I see this a lot in sales and marketing teams. People are using AI, some are using it really well. They built workflows, they built custom GPTs, they’re getting faster and better. But there’s a big difference between getting faster with AI and actually changing how your organization works. Welcome to the B2B roundtable. I’m Brian Carroll. And my guest today, Liza Adams. She’s the founder of GrowthPath Partners. And she spent 25 years leading GTM teams at companies like Smartsheet, Juniper Networks, and she’s worked with AI and machine learning long before ChatGPT. And now she helps teams figure out how AI can actually change the way they work. Something Liza recently said that stuck with me is you can’t reimagine the future by automating the past. Liza, welcome to the B2B roundtable. Liza Adams (00:50): Hi Brian. I’ve been looking forward to this all week long and it feels like every time you and I get together we’re always laughing. So I’m still kinda laughing over here. So always a pleasure. Brian Carroll (01:02): I’m so glad to have you on today. And it’s funny, I’ve had multiple people tell me, Brian, you should talk with Liza Adams. And it was fun to be able to say, Well, guess what? We’re talking this week. Brian Carroll (01:16): So the question I wanted to ask you first is what’s really separating teams that are changing how they work from teams that are just getting faster? Liza Adams (01:25): Yeah, you know, the biggest aha moment for me is really mindset, right? Like I’ve always said that the cap of what our teams will ever build, do, and use AI for is limited by what they believe it can do. So if we primarily think that this is gonna be just a chatbot or a fancy search engine. Guess what? That’s all we’re ever going to use it for, right? And I do have a lot of empathy because if that’s what we believe, and our companies are expecting us to build fully agentic workflows that cross functions, guess what? There’s a big grand canyon between those two beliefs, right? And that’s just one. You know, there’s also this mindset around AI used for productivity, making existing work go faster. And I actually believe that that should just be the floor of our expectation of AI. Because if we simply make old work go faster, you can almost project how it can automate the human out. But if we actually use AI to push our thinking so that the outputs are better, so better, not just faster, but better. And then better yet, if we actually use AI to do something different, meaning reimagine the work. We now are innovating, do things that weren’t possible before. With innovation, you know, we have a better shot at growing the business. And when the business grows, humans are essential. Right? And I actually can’t see a business continuing to grow without needing more humans. But if we simply improve productivity, then we can see how humans are not as essential to the business. Brian Carroll (03:14): Something I’ve noticed with companies is when they do start using it, and every company has to varying degrees, there’s this AI adoption plateau. And I wanted to talk to you about it because I hadn’t really heard that until our conversation. So what does that look like inside a real company? Liza Adams (03:34): Yeah, a few things come to mind and again, Brian, you and I have talked about this before the show, right? That I don’t have best practices because I do believe best practices are still being written and they’re evolving and they’re moving so quickly and oftentimes the shelf life is relatively short. But what I do have is pattern recognition, having worked with and continuing to work with a lot of go to market teams. So I’ll share with you my thinking on what I’m seeing. Time and time again, and some of these patterns, you know, tell me what generally might work and what generally is going down the wrong way, right? And I think again, the mindset, right? Like what you believe AI can do is the cap of what you will ever build. So if we don’t shift that mindset, there’s a plateau there at some point, right? The other thing is, being able to see what’s possible. So people, I know this so well now, people aren’t stupid. They just need to see what’s possible. I mean we can talk to them till they’re blue in the face, that you can build agentic workflows across functions. And then these agents can use tools, it can use our browsers, it can you know, navigate our systems and our laptops and put files in the folders. But those are features of AI, those are capabilities of AI. We actually have to show them what’s possible, right? So you know show them how it can pulse the market consistently and give us insights 24 by seven and be able to tell us what is still aligning with positioning and what isn’t. Like show them what that looks like, right? Show them how we can use signal from various sources, and those various sources might have lots and lots of data. AI can collect all that, synthesize it, give us insights and anomalies, and determine which customers are about ready to churn, or which customers are giving us enough signal that they’re probably a good candidate for an expansion. So think about those workflows, not just the capabilities. Until they see what’s possible, there’s gonna be a plateau, right? So the whole notion of inspiring people, what’s possible, sharing you know, these use cases, sharing these workflows, everybody doing it, because the ideas are brand new, right? No one’s ever navigated this before. So we need like absolutely the rising tide lifts all boats in many instances. The other place where I’m seeing a plateau is where we do workshops and we do trainings and things like that. So we inspire people, they get going, but then we go back to our day jobs. And what happens is I’ve always said, you know, AI transformation can’t happen when we’re in a hamster wheel. So we actually need to give people the space, the time, the safe space and time to learn, right? Because this isn’t a one and done, do

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 w

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

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 g