
How to Win podcast with Peep Laja · 2025-05-19 · 21 min
Key moments - from our scoring
Substance score
51 / 100
Five dimensions, 20 points each
The episode dives into a fundamental shift in B2B software buying behavior, supported by Winter's research of 300 CMOs, CTOs, and CFOs from companies earning $50M to $1B+. Rather than starting on Google, 72% of B2B buyers now begin in private communities - Slack groups, WhatsApp channels, and platforms like Pavilion and PMA. Dave Gerhardt and Kathleen Booth discuss why community has become 'the new Google': it delivers trustworthy information faster than parsing through potentially AI-generated search results. The hosts explore the evolution of dark social since Chris Walker popularized the term, connecting it to timeless principles from Seth Godin's 'Permission Marketing' and word-of-mouth strategy. Critically, they address how startups actually penetrate these communities without violating unspoken anti-pitch norms. Success requires consistency - daily participation answering questions, making introductions, and adding value - not paid sponsorships or attempts to game the system. Carabiner Group's case study of Cliff Simon's participation in Pavilion generated 1.7% of their pipeline, later leading to acquisition by SBI. The real investment is building a loved brand and differentiated narrative, then letting community members organically mention you.
72% begin in private communities like Slack channels, WhatsApp groups, and platforms like Pavilion before moving to public sources. They ask peers what solutions they use, and two or three names typically emerge as top recommendations before buyers validate on Google.
Community delivers trustworthy, high-fidelity information faster than Google, which often returns low-quality or AI-generated content written by people without real experience. Buyers prefer asking trusted peers directly rather than parsing multiple search results.
Become an active, consistent member by reading posts, commenting, answering questions, and making introductions - never promoting your product. Dave Gerhardt recommends spending 10 minutes daily contributing value. The Carabiner Group case study shows this approach generated 1.7% of pipeline through Pavilion participation.
Rather than expensive sponsorships, invest in creating something communities will talk about organically - original research, surveys, reports, or compelling marketing campaigns. Alternatively, pay influencers or team members who can authentically participate and advocate for your product without direct pitching.
Use self-reported attribution by asking 'How did you hear about us?' on lead forms and during sales conversations, combined with qualitative observation of direct messages and conversations you participate in within communities. This gives a sufficient understanding of ROI without perfect attribution.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode has a few concrete data points (the 72%/9% split, Carabiner Group pipeline attribution) and the 'sneezers as influencers' framing, but the bulk of advice reduces to 'be helpful in communities,' 'be consistent,' and 'build a brand' - platitudes that fill most of the runtime without adding new mechanisms or tactics a sophisticated B2B marketer hasn't already encountered.
would you rather go on Google and search and parse through three pages of results that may or may not be AI generated? Might have been written by a 20 year old content marketing manager who googled to get the answer?
the meta thing is like, huh, More people are starting to know we exist. More people, more of the right people are talking about us
The episode openly acknowledges it is retreading a 2019 topic and explicitly leans on Seth Godin's permission marketing and 'sneezers' concept from the early 90s; the framing of 'community is the new Google' and 'brand as the last moat' have circulated widely in B2B marketing for years, and nothing here reframes or challenges those orthodoxies from first principles.
I feel that dark social was a hot topic in 2019, yet here we are
He initially talked about this concept of this was like, OG influencer marketing. He called them sneezers
Dave Gerhardt built community-led growth at Drift as CMO before founding Exit 5, and Kathleen Booth runs Pavilion, one of the largest B2B professional communities - both are legitimate scale practitioners directly relevant to the topic, not career podcasters or abstract thought-leaders.
this is what we did at uh, Drift, this is what I did at another company before that
we went into our Slack analytics and after he joined we figured out he was the single most active person in Pavilion Slack
The episode grounds several claims in real numbers - Winter's 300-person study (72%/9%), Carabiner Group's 70% pipeline from Pavilion and subsequent SBI acquisition, and one sponsor attributing 21 ICP opportunities to Exit 5 - though the primary data source is the host's own research product, and most tactical advice remains vague.
Winter surveyed 300 B2B SaaS, CMOs, CTOs, CFOs, relevant VPs, from 50 million to 1 billion plus companies
at 1.70% of their pipeline came from Pavilion and they've since been acquired by sbi
Peep asks genuinely practical questions (what do you actually spend money on, how do you think about ROI) and shares a concrete personal tactic (asking customers to post on LinkedIn), but there is no pushback, no pressure on unchallenged claims, and the conversation stays firmly in agreement throughout, limiting the depth that friction could have produced.
If I wanted to spend more on community marketing this coming year, what do you actually spend money on? Like what do you buy actually?
how to think about the ROI or the business case here
Computed from the transcript - who did the talking, and the words that came up most.
In this episode, Peep Laja is joined by Kathleen Booth and Dave Gerhardt to unpack the real buying behavior behind B2B SaaS in 2025. They break down the power of dark social, peer communities, and brand storytelling in an era where Google is no longer the first stop. Learn how to win trust, get talked about, and drive growth - without a single paid ad. Chapters: [00:00:00] Buyers No Longer Start on Google [00:01:00] Dark Social Isn’t New [00:02:00] Community Beats Search [00:03:00] Trust Comes From Peers [00:04:00] Why “Dark Social” Caught On [00:05:30] How Real Word-of-Mouth Works [00:06:30] Winning Starts With Being Mentioned [00:07:15] LinkedIn’s Real Role in Buying [00:08:30] You Can’t Game the System [00:09:30] Influencing the Influencers [00:10:30] Brand and Peer Trust Collide [00:11:30] Build a Narrative, Not Just Features [00:12:30] What to Spend on Community [00:14:00] Create Shareworthy Artifacts [00:15:00] Showing Up Consistently Matters [00:16:30] Case Study: Carabiner Group [00:17:30] Making the ROI Case [00:19:00] Track What Actually Matters [00:20:00] Key Takeaways: How to Win
Transcribed and scored by The B2B Podcast Index.
Speaker A: Actually, you don't have to spend a dollar. Imagine this. Become an active member of the community.
Speaker B: Welcome to how to Win with me. Pepe Plough. A deep dive into stunning winners in B2B SaaS to determine how much is strategy, how much is luck, and how do you win? How do B2B SaaS marketing leaders start their vendor search in 2025? I don't even check Google first anymore. That's what 72% of B2B software buyers shared in winter 2025 by a research study. Folks are starting their vendor research somewhere else entirely. Winter surveyed 300 B2B SaaS, CMOs, CTOs, CFOs, relevant VPs, from 50 million to 1 billion plus companies about how they discover new software. And here's where they start their search. Dark Social 72% begin their journey in private communities before moving to public sources. Marketing leaders overwhelmingly turn to peer networks on private Slack channels, WhatsApp groups and professional communities first. I feel that dark social was a hot topic in 2019, yet here we are. The new study shows that people, that's how people buy and that's the first step. What do you think is different in 2025? How has dark Social evolved?
Speaker C: I'll be honest, I always have had kind of a, a hate, hate relationship with the term dark social. I feel like it's always been there, right? It's not like something new was created in 2019. What's happening is as old as time. Buying is about trust and that's never changed. And how people come to their feeling of trust has evolved and will always continue evolving. And I think especially in the next few years, we're going to see it evolve even more with AI. To me, what's happening now is I think very much a result of what happened in Covid, which is, you know, we had this period of time that was very unusual in the world where everybody was sort of forced to figure out new ways of, of getting information and of, of also forming human connection. And so community really took off during that time. Like community's been around forever, but it took off because there was this need and there was, it was an outlet. There's no like completely dialing back that change. I've been saying for a few years, like community is the new Google and it's because it's just easier, right? Like everybody still wants information. They can and what's the easiest and quickest and best way to get it. And the answer to that right now is through communities. Because I think I said this in response to your post. Like would you rather go on Google and search and parse through three pages of results that may or may not be AI generated? Might have been written by a 20 year old content marketing manager who googled to get the answer? Or would you like to go into a community and ask a marketing leader or five that you really admire what's working for them? I know exactly what I would do in that situation and that's what I see all the time. We just want good information quickly. We want to know we can trust it, uh, and we want it to be easy. And right now community is delivering that better than anything else.
Speaker B: Kathleen speaks about the new reality. Your average piece of content on Google is either low quality or likely not written by someone who actually lives the truth. Asking the inexperienced peer is a shortcut. It's high fidelity information. Like one CMO in our study said, my WhatsApp group of CMOs is my first stop. Google is still important. Half the people Google tools in a category when looking for vendors, but it is no longer the automatic first stop. Only 9% start there. Google is mostly used by buyers to validate what they heard from peers. So Dave, what do you think is dark social a ah, fringe term that people hate or have private communities, WhatsApp groups and so on actually become a primary marketing channel.
Speaker A: So I got a couple things. Number one, it's always been a thing. Call up our buddy Chris Walker. It's because he started provocatively and proactively calling it dark Social and named it. And just like anything in marketing, go go read Seth Godin's book permission marketing from 1999, right? Go go go read marketing books from the 80s. It is all the same things. We argue about them online but you can lump them all into the same exact things. It's timeless, those principles. A book, word of mouth marketing that was written probably in the early 90s, right? It is all the same. We just gave it a term. And Chris is super smart and I'm a big fan of his and he has a strong voice online. He started talking about it a lot and gave it the term dark social. For me, I've been doing dark social marketing since even before any of them because this is what we did at uh, Drift, this is what I did at another company before that. It's essentially building word of mouth online in channels that are harder to track. So on top of that, like I think a couple other things happened. Number one, social media exploded. Which means like it used to be social media and marketing and I think now Social media has become the marketing channel. It's not a channel that you give to the intern. Things change with privacy and tracking and pixels. And so like almost a lot of those things are now harder to track directly. Then you add the rise of communities like Pavilion and others, right? And the challenge is in those communities, you can't promote your stuff. You have to do it in an authentic and organic way where you're talking about the product, products and things that you actually use. And so the best way to do that is to be authentic, is not drop a link. And by the way, there's not gonna be a link there, but two days later, someone's gonna go to that website. It's gonna show up as direct search, right? And so we just like to name things, we like to obsess with tracking everything perfectly. But this has actually been the only way of marketing that I've ever known. And it's why I love like you, Pep and Winter. It's like I remember you talking to me about Winter. You're like, yeah, right now, ah, we just need more people to know we exist. And I'm like, amen. Like that marketing can be that simple. We like to just name things and argue about things because we people are
Speaker B: increasingly more reliant on trusted peers networks as a, as a filter. But how does a, uh, startup, you know, if you're not Salesforce or HubSpot, how do you get inside those recommendations so people on Pavilion would actually recommend you?
Speaker C: Well, first I just want to say I totally agree with everything that Dave just said because like the behavior I see is just what he described, which is like step one, you go and you ask a question, what's the best solution for X? Or what are you all using for? Yes, bunch of people. Name a couple of vendors and it seems like two or three emerge as the ones that everyone's plus wanting. And then you go and you don't organic search. You direct you. It's direct branded search, right? To those companies websites to be like, all right, do they really do what everyone says they do and do they meet my needs? And so to get an at bat, like you have to be one of the names that's mentioned. And I think Dave said something really important which is like, go to market through community is not going in and just selling like that never works. If you ever want to see it really like extremely inaction, go try and do that in Reddit and see how you're like torn to shreds. But I think like that's an extreme Example, but most communities are like that. There's an unspoken rule that you're not going to be there pitching yourself. And so it's about being helpful, which is kind of like, weirdly, the same principle HubSpot was talking about 10 years ago. Like, stop selling and start educating. It's just manifesting differently. And again, I think it goes back to what we all want as human beings. We don't want to be pitched. We want somebody who's going to add value. And in community, that's like, help first. Be somebody that, like, makes introductions, answers questions, teaches people something, solves their problems, and earn trust. But here's the thing. It's like, both beautiful and also challenging because most marketers, what they suck at is consistency and playing a long game. Most people are looking for quick fixes, which is why a lot of them will always default to, like, the classic approaches of lead magnets and paid ads and things like that. And not to say that those channels don't work, but this is a different play and you have to be willing to, like, really be consistent about it. It's the same thing with, like, LinkedIn personal branding, which I know you both know a lot about.
Speaker B: LinkedIn's role in software buying process is not what you think. Sure, they turn to it, but they're not looking at ads. What they are doing is checking personal connections who work at vendor companies, searching for organic posts from actual users mentioning the brand, hoping for a case study or a review of some kind of organic content that people consume over time on LinkedIn is informing people's consideration sets. As one CMO put it, I'm already starting with some base knowledge of the product space based on my LinkedIn content.
Speaker A: Can we build on a piece of that, by the way? Because this is the trap that marketers fall into. And I've been in. This is like, let's say all of a sudden you start to notice that you're getting inbound from Reddit in that example, right? The natural reaction as marketers and as your CFO and whoever inside the company is gonna be like, oh, we're getting a bunch of inbound from Reddit. We gotta go do more on Reddit. And you're like, well, we didn't, we didn't do anything. Someone just, you know, wrote. Someone happened to mention us in that post. And so then it becomes this whole thing, like, let's do more on Reddit. But then when you actually try to do more, it's like, this is the hardest. This is a cool topic because this Topic of dark social word of mouth. It is like the furthest thing from direct response. And so you can't just like, the takeaway is not like, oh, let's go post in more communities. Because we're noticing that communities are driving referrals for us. It's like, actually, no, if you zoom all the way out, the. The meta thing is like, huh, More people are starting to know we exist. More people, more of the right people are talking about us. And I don't know if it was in permission marketing. I think it was in Seth Godin. He initially talked about this concept of this was like, OG influencer marketing. He called them sneezers. And it was like, you want to find the sneezers in your industry? Because, like, you know, if I'm hanging out with you two and, and one of us sneezes, you infect me with the germs and the message spreads. Right? And that's ultimately what this is. And so it's more like, okay, how do we influence more of that? And so it's hard because we want to treat marketing like this coin machine. Like, we just got a bunch of things from Reddit, let's go back there with more money. And it just doesn't work like that.
Speaker B: Here's something we do at Winter with some success. Every time a customer says something good about us in a conversation with someone in our team, in their replies to our newsletters or our live chat, we ask them, um, hey, could you please post about this on LinkedIn? Not everyone will, but a lot of people do. And that's the most powerful form of advertising. Getting sneezed about more often also depends, uh, on peer connections. Like, more people need to know you and like you. So how do you, how do you facilitate peer connections today without being pushy?
Speaker C: It is, I think, peer connections, but it's also honestly brand. And Dave, I saw you post about this recently and I was like, nodding my head in the background. I think you said, like, brand is the last moat. And I really, I believe that, like, with AI getting harder to know what to trust, like, what's really human, what is real, and it is only going to get harder. I see people post all the time about companies that they haven't been customers of and maybe they don't even know anybody, but they, like, there's a brand lore or legend that has happened and people, like, love the brand and they trust it. And so I think there's two ways to come at it. One is this community play of forming peer connections. The other is investing in a loved brand that forms an emotional connection in the mind of your broader audience. And I think when those two collide, that's when like the magic really happens. Because one person will be like, well, I'm a customer of in this case Drift. And then like five more people will be like, I love Drift. They're awesome. And they might not have even ever used Drift. But the result is like, you get this momentum that's pretty magical. And I think like that's something I've seen with like Drift is an example of it. Gong. Udi Letter Gore built that at Gong where people would just be like, gong's amazing. And half of them had never been customers. So I think it's those two things, brand and peer connection, that are really important together. But I'd love to hear your perspective. Dave.
Speaker A: How do you be liked? How do you get people to talk about you online? And I think that comes from not having this laundry list of features and it becomes having a strong like it comes all the way back to probably what the purpose of you starting the show in the beginning. Pep. And so many great interviews you've had on. It's like the 8020 in this game is like is your narrative and your company story and your strategy and how do you differentiate and how are you going to win? And then if you do that and you resonate with your buyers, like the conversations are going to take care of themselves. If you strike a story around a pain point in a clearly defined niche or audience and those people are online, they're going to talk about products on forums, right? You could go to any. Go to pick any hot pick any hobby, CrossFit, running, knitting. Go find those communities online and people are talking about new products and innovative ideas and strategies or wherever your goal is to. Your goal is how do you be that for who you sell to and B2B. And that comes down to having a strong story. All those brands you mentioned, HubSpot, inbound marketing, they created a movement around that that was bigger than the brand. Drift, conversational marketing. It's not the fringe brands who get those mentions in those communities. It's the. It's the communities that start sucking up mind share by having a strong point of view in the if I wanted
Speaker B: to spend more on community marketing this coming year, what do you actually spend money on? Like what do you buy actually?
Speaker A: You don't have to spend a dollar. I would say I would have somebody on your team. Imagine this. Become an active member of the community. And that means reading the Posts, liking the posts, commenting, adding value, never pitching your product. It's like the same thing how you'd build an audience on social. So go in there and treat like, buy a Pavilion membership. And if that's what you want to, if that's your investment, then be like, I'm going to comment every single day. I'm going to spend 10 minutes every single day in Pavilion and I'm going to treat it like my inbox. I'm going to spend 10 minutes every single day and exit five, I'm going to treat it like my inbox. Pep, I remember you from back in the day on, um, inbound.org and growth hackers. I remember being in those communities early and we were like posting articles in there, but we were doing it in a way where it was like, you know, I would be in there contributing all the time and then maybe one out of every 20 posts. I would say, by the way, we wrote this thing, that'd be number one. It's like, like it's not about spending. Number two would be. My real play would be to create something that members of these communities are going to talk about. And so I would invest that money in something interesting from a marketing campaign. It would be like original research, something entertaining, something informational, a report, some, A survey, some data. We did something crazy at a conference. Like, those are the things that are then going to trickle down into those communities and that's how people are going to talk about them. And um, um, it's a little bit counterintuitive because you can't just say, well, we got all the budget in the world. Can I just, can I just pay? And I can just like, you know, be, you know, get, get mentions in these communities. It doesn't work like that. This is like the craziest part. You have to make a product that people love and a product that people enjoy using and you have to build a great experience. A good example of this is, uh, like, everybody's talking about Clay right now because Clay. Clay is everywhere. So another play is like they basically pay a bunch of people to like, post about using their product. That's a community strategy that gets people talking about it on LinkedIn, doesn't necessarily necessarily get people posting on, on LinkedIn or Exit 5. But I think influencers is becoming another part of this where if you can't post directly, you can pay people who can post directly and you can basically pay for their word of mouth. That is another possibility.
Speaker C: I totally agree when I talk about this, because I do get this question a lot. I mean there's obviously ways to pay to get access to communities. You know, there's sponsoring, there's, there's all you sponsor events, you can sponsor other things. And I think we're probably very similar to Exit 5. I mean I'm an Exit 5 member, a great community and I think from like a, an ethos standp, we probably approach it similarly. And I always tell people like sure, cut a check, sponsor things. But like if you do that without organically participating as members, it is throwing good money after bad. And we actually have a great case study on our site of a company, Carabiner Group that I think is like the example of how to do it, which is first they joined and there's this guy Cliff Simon who was their head of sales and he literally, I think we, we went into our Slack analytics and after he joined we figured out he was the single most active person in Pavilion Slack. And it was all like value add. It was all making intros, helping people, answering questions. He just was like everywhere. I don't even know how he did it, but he made this commitment to like throw himself into it and he looked at it as part of the job and that's, that's I think a piece of it. Which is if you're an employer, if you're a go to market executive, like uh, this is something I think needs to be a part of your team's job descriptions. Like you, you gotta hire people who are willing to lean in. What wound up happening is that people just got to know like and trust Cliff. Right. And so what happened is eventually people would be like, well what's a great rev ops agency? And of course everyone was like, well you should talk to Cliff at Carabiner Group. And in our case study it was something like at 1.70% of their pipeline came from Pavilion and they've since been acquired by sbi. So it's a huge success story. But again there was no easy check the box solution there it was Cliff going in and then Seamus, the founder who went to every event we threw for three years and just sat at the table and participated that led them to that. So no easy path. But if you're willing to commit and participate, I think not only can you get business, but like oh, by the way, all of these people learned, became better operators and grew their careers because of what they gained personally from the community too. So if you approach it like that, I think there's a lot of value. But you cannot half asset.
Speaker B: My last question would be how to think about the ROI or the business case here. So I can sit all day long and comment on Pavilion stuff or pma, uh, which is a community of product marketers, which is my primary buyer at Winter. And I inquired about you know, like some things I can do with them and it's like crazy expensive, you know, like, oh, I want to speak at a conference, $40,000 and so on and so forth. And in the end I'm like, oh my God, annual commitment is like 200k. I could do a lot of things with 200k. Do you think like investing in this kind of like community paid engagement things is a better ROI than, I don't know, running ads or putting any, you know, marketing dollars anywhere else?
Speaker A: There's kind of this slippery slope of like you remember when Forbes and Inc. Used to be like a big deal from a marketing perspective. If you got your CEO to get a guest column in Inc. And then over time everyone realized like it's just all crap and it's all paid and anyone can do it and the quality goes down. And so it's like if you run an event and all the speakers have to pay 40 grand to speak, then like the universe of people who you're going to be able to get to speak. So that kind of has diminished. Does it work the same for me though? The way that I would think about is we see it all the time or uh, we hear companies that we work with is people will tell you, they will tell you if you, if you invest in product marketing alliance pep, they will tell you that when they buy Winter, whether it is self reported attribution or somewhere in the notes or in talking to a salesperson or whatever, they will tell you that they, they heard about you through that thing and they're going to want to do more with you. And so I think it's never going to be some perfect number in a pie chart to show you the ROI on it, but I think you can get a pretty good feeling. And we talk to sponsors now and you know, we're working with one company that does event management and they're like, yeah, we can attribute 21 ICP opportunities to exit five because people tell us that they, they heard about us through Exit 5 and it's just self reported and that is perfectly good enough to measure the success of it. And so a little bit of like, let's not over, let's not over complicate how to measure that stuff. Uh, at the same time, yeah, you
Speaker C: gotta ask how they heard about you. And it's if you just rely on what your attribution systems tell you, you're gonna spend money in the wrong places. The qualitative information is really where it's at. It goes back to what we started with. If you're participating meaningfully as an individual, you're also just gonna know where it came from because you're gonna see the conversations happening. You probably were a part of them. But when it shows up in your lead form or you know, more often than not, you're like they're coming directly to you through a DM in the community. It's not that hard to figure out when you're doing it that way. But if you also layer qualitative attribution on top of that in the form of a uh, how did you hear about us that you know? I think that gets you as far as you really need to get to get a sense for what the ROI
Speaker B: is Key Takeaways on how to win in dark social 1. Own the conversation inside peer communities 72% of B2B buyers start their search in private groups before anywhere else. Treat Pavilion exit via WhatsApp groups like your daily inbox show up consistently, answer questions, make introductions and never pitch when someone asks which tool should I use for X? Your brand becomes one of the first three names mentioned because people know, like and trust you. 2. Build a brand worth talking about, not just features worth buying. The strongest moat isn't your tech, it's your narrative. Create a movement bigger than your product. A sharp, differentiated story plus memorable brand creates emotional connections that turn both customers and onlookers into sneezers who spread your idea. As Kathleen noted, half the people who recommend tools have never been customers, but they still promote you. 3. Fuel and track word of mouth on purpose. Create share worthy artifacts like original research, nifty features and explicitly ask happy customers to post about them. Forget perfect attribution, focus on self reported discovery with a simple how do you hear about us? Field the qualitative data beats your attribution system every time. When multiple buyers say Reddit, that's your signal to get more of your customers to post about you on there. And that's how you win. Thanks for listening. Tell your friends.
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