Why most B2B CRMs are about to die — Doug Camplejohn (ex-LinkedIn, ex-Salesforce) on AI-native CRM

What I am most excited about—and everyone listening knows—dude, gut check me here. The last question we ask is always what's the one thing founders need to hear now, or CEOs or revenue leaders need to hear now, to bridge the gap that they're drowning in. And I'll say it now and you got to listen to the end to hear it. It is the single best piece of advice that has ever been shared in 80-something episodes of this show. 100%. I totally agree.

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Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagined. Today's guest is Doug Camplejon, the founder and CEO of Coffee.ai, which is an AI-first CRM. Doug has a proven track record in building and scaling successful companies with startups that include MyPlay, MI5 Networks, and Fliptop, all of which achieved successful exits. With leadership experience at LinkedIn as the VP of Sales Solutions, Salesforce as the GM of SalesCloud, and Apple as a QuickTime product manager, Doug combines deep technical experience with strategic vision. He's passionate about creating transformative products and building great teams. This is an episode you don't want to miss.

Awesome. Doug, so one of the first questions I have for you is working at all these huge companies. What was the motivation, not necessarily just for Coffee, but to be like, "I'm going to go do a startup?" I saw you went from LinkedIn to Salesforce and then you did some investments. Was it the investing side that was like, "Oh, I should go try to just go build my own thing?" Like, what was that startup bug for you?

Yeah, it's actually funny. I'm really a startup guy. The exceptions are actually the big companies. So, you know, I started my career as an electrical engineer. I started at Apple. Everything in between until I got to LinkedIn—I don't know, 15, 20 years later—was startups.

Well, you got bought by LinkedIn, right?

So the last company got bought by LinkedIn. And frankly, like, we got there and we're like, "Oh my God, this is—you know, big companies obviously move slower. I'm gonna lose my mind here." And it was actually one of those things where I originally was just going to stay for like 12, 18 months, but I got to kind of rebuild the Sales Navigator team. We got to rebuild the product roadmap and I was having a lot of fun, right? I was really enjoying what we were doing and the culture there. LinkedIn is very strong product-culture-based on what Reed and others built at the beginning. And so I ended up staying longer than I thought I would.

And towards the end of that tenure, I was kind of getting bored. Bored is the wrong word. I would say my growth, my learning curve had started to flatten, right? I felt like I wasn't learning new stuff, which is always kind of my indicator of wanting to do something new. And Brett Taylor and Mark called and said, "Hey, you know, we think you'd be right to run SalesCloud." And I thought, "Well, that will increase the learning curve, right?" And so that's why I went to Salesforce.

And, you know, I think Salesforce is an amazing sales and marketing and business development, you know, corporate development company. But ultimately I wanted to get back to my roots as a startup guy. And so when I had the right idea, I left and started doing that in old tech.

And it sounds like you're taking a page out of Ben's book on going after the SMB mid-market as they did against Seibel. And he went out and got funding from old tech, but they're still able—we just got for one of our clients today a 9% price increase next year, which blows my mind that they could get away with that. But they know how hard that switch is.

Yeah, I mean, like, never rule out Marc Benioff, right? Like Salesforce is not going away. Listen, the thing that's amazing about Seibel that no one realizes is that it is a very fragmented market. And as you pointed out, Adam, like, once you're really locked in, it's hard to move. I mean, if you remember back in the '80s, there was a company called ACT that was doing desktop PC software. They're still around. They're still doing—you just don't ever hear about them.

Yeah, you just don't hear about them.

I mean, Seibel, which is now owned by Oracle, still a ton of customers for Seibel, right, out there. So this stuff never goes away. It just—every decade there seems to be a new player that emerges that gets some footing. So last decade it was HubSpot and really started to eat into Salesforce on the low end. And I think that when you have these disruptive technology curves like AI is providing now, you've got an opportunity for another disruption.

Yeah, 100%. So I want to go back—whether it be early days at LinkedIn, Salesforce, Coffee, or any startup you've been a part of—as you're building go-to-market strategy and motions. One of the things that we hear when we talk to founders is like there's this moment where it's like, "This is out of control and I got to do something or we're not going to survive." And we've heard everything from, "I got to fire the entire sales team because they all suck," to "Our tech stack that we just spent $200,000 on is awful and I got to rip it all out," and that sunk cost. The success momentum is garbage. We onboarded all of these customers but none of them are getting time to value, the 11x story, so to speak, where everyone cancels after a trial.

Like, talk me through a moment where you were like you just looked in the mirror and you were like, "I gotta fix something," or where it came to a head. Yeah, I'll give you—there's lots of examples of that—but I'll give you kind of a large company example and a small company example.

So at LinkedIn, when I came there, Sales Navigator, the group I ran, was about $250 million in revenue. They're doing over a billion now. And, you know, the assumption was like, "Hey, listen, this is a $250 million revenue business. It's cranking. It's great." But when I really dug into the product, you know, we had no multi-year deals. We had no—what it really was was a few small features that were getting people over the line. But as soon as people were hacking the hell out of free and premium and trying to get those to work for them to avoid paying the premium Sales Navigator tax.

And so one thing was really starting to understand what was the magic moment when someone would convert, right? So we actually did—we had a team there called Bisops, which I got completely spoiled. You know, startups don't have things like this. But Bisops went in and said, "Okay, first of all, what is our biggest opportunity? Is it whitespace or is it actually doubling down on the customers that we have?" And it turned out that like we just were not anywhere near as highly penetrated into the companies that we already had engagements with. So there was a great opportunity. If we could come up with the right feature set to expand that, that was a huge opportunity for us.

And the other was, you know, we would churn out a lot of people in that first 30 days who had not engaged enough with the product. And so the team did all this machine learning analysis and figured out like, "Oh, there's an engaged seller metric." They came up with and said, "If you perform actions A, B, and C within the first two weeks, right, you are five times more likely to convert." And that was the magic moment. We're like, "Great, let's focus all of our product effort. Let's focus all of our customer success and engagement efforts around that." And that was a huge turning point for us in terms of just unlocking value.

So it wasn't that we had to kill something. We definitely had to rethink the product pretty radically to find value there. But it was something where we just didn't—like we were kind of on autopilot because LinkedIn is in this great position with the data set that they have to not have to be as sharp as you might have to be in a startup and be on top of that stuff.

And is that where the Social Selling Index started, like coming out? Where there's that whole social selling to try to figure out where people are actually utilizing the product?

Yeah, I'm kind of smiling because Social Selling Index predated me. So it was actually something that we looked at. That was another thing that we had data to go take a look at. And it turned out in a significant number of cases, a high Social Selling Index was inversely correlated with your close rate, right? Because you were spending too much time, like, "Hey, how are you doing? Let me comment on your posts," and things like that.

So once we actually had closed-one data coming in, once my team had built the CRM sync and we could pull in closed-one data, we kind of realized that. And so if you noticed in the years, like, Social Selling went from like on the homepage to kind of buried somewhere deep in menus. That's why.

Yeah, yeah, yeah.

So as you guys are building out Coffee and going against—

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Some of the bigger competitors—like, how do you drive market awareness for the organization? Because a lot of startup companies, and we're working with a couple right now, it's difficult for them because the concept of marketing and awareness isn't what they believe. Let's get a bunch of BDRs, let's do a bunch of calling. But then they're not getting the response rates, they're not getting the conversion rates. So how do you drive that awareness, especially when you're going up against these big competitors and you have a bunch of other ones like Pipedrive and Adio? Like, there's a lot of little people as well. So you kind of get stuck in that.

I mean, the approach we're taking—there's a great book by this guy Dave Gerhardt called Founder Brand that I highly recommend. He was the guy behind a lot of the success of Drift in the early days from a marketing standpoint. So a lot of what I'm doing is I have gotten very engaged on LinkedIn in the last few months and starting to build that audience. We just launched our own podcast, Revenue Renegades. We've got a strong list of folks there. So a lot of what we're trying to do is get in, well in advance of when the product rolls out, which will be over the next quarter or two, starting to build that momentum and that awareness. And I think that's the investment that we're going to do—more on these kind of brand building, marketing pieces. But I also think it's getting in front of a lot of those individual folks. So how do you get connected to all of the funds that are investing in early stage companies and incubating those companies? How do you become that natural part of the stack where they're like, "Oh, I got to go start a company. Let me get Google, Slack, Zoom, and coffee, right?" How does that become part of that process?

It sounds like a good stack. Coffee on top of all your sounds like a good snack to me.

Yeah, I mean, everyone needs coffee, right?

Exactly. I'm sure that played in the name.

Oh, there's—yeah, we're having a lot of fun with the names actually. I think that the addition sizes for pricing are probably going to be like tall, grande, venti, you know. So we're going to have a good time.

I like it. I think a lot of people don't realize how much or how simple naming could be. So I started my career in pharma and medical device, and the hundreds of millions of dollars that's spent naming drugs—a lot of people don't realize is, like, you would never know unless you spent time there. But something as simple as coffee, like how you can play off of that—you know, most people drink coffee. We could go on and on and on. It was not cheap. We paid $100,000 for the domain for coffee.ai.

I bet you did.

Worth every penny.

Yeah, I love it. I do. I love it. We, you know, when you talk about those aha moments, I want to tie this back to the go-to-market gap, which is the stabilization to foundation to repeatability to scalability. And most, if not all, founders we talk to have this "build it and they will come" mindset. We're going to start a company and we're immediately going to have repeatability, right? The customers are going to come rolling in the door and I'm going to hire four sales reps and they're going to all do everything the same way and it's going to be amazing. I've yet to see that happen, barring a few companies. I think, you know, publicly, Clay certainly seems to be the closest, but I'm sure they had more than their fair share of struggles as well. Clay, by the way, has been around for a long time. They wanted to move. Most people don't realize this, right? For many years, and then suddenly it feels like that's another one of those 10-year overnight successes, right?

Yeah.

But when you look back, like where do you think—in your experience, you've led a lot of teams in a lot of companies—where's the real gap? Is it stabilization to foundation, foundation to repeatability, or repeatability to scalability, and why?

That's a great question. I do think that there is, to your point—I think the whole lean startup movement actually, in some ways, was. I used to work for Steve Blank, you know, who's kind of the spiritual godfather of that movement that Eric Ries took on. But I do think that there's a general premise that if it's not working very quickly, you give it up and you pivot to something else. And I do think that, you know, listen, products are much easier to build right now than they've ever been. It is still really hard to go find that true product-market fit. Not just like people are using my stuff, but people are actually opening up their wallets and paying for it and enjoying it and renewing, right? So I love—I was talking to Adam Robinson the other day from RB2B, and he—I love the fact that he's like at four million ARR for RB2B and said we don't have product-market fit, right? And almost every founder that you're referring to would say, you know, we've got over a million in ARR, we've got product-market fit, right? So I do think there's that level of—to me, the Jeffrey Moore style "crossing the chasm" gap is about how do you go from "I've built product, I've got some people who are engaged in using it" to "I've really found an audience and I'm delivering a complete solution for that audience, and that audience is now—I can rinse and repeat that motion." And I think that is where a lot of startups fall off before they ever see the scaling part of it.

It's so funny. I was just talking to a rep today, and we were talking about challenges with closing, getting deals across the pipeline. We talked a lot about their ICP, their buying persona, the value proposition. But I brought up crossing the chasm, so it's funny that you brought that up because I think that is a really big challenge that people like—books from, I think, 2001. It's like an old book, but you look at it and reread it, and it's really some of the same challenges that we've been struggling with. They just kind of have gone away.

Yeah, I mean, listen, if you were going to design the ultimate go-to-market system, you would basically say here are the customers that are ready to buy your product right now, right?

Yep.

Then the next layer of the onion would be here are the set of folks who are looking to buy something in your category right now. The next layer would be here are the set of folks who should be looking at stuff in your area, and how do you go do that? And you mentioned ICP. I think it's remarkable to me the companies who don't even have an agreement on what their ICP is between their sales and marketing department. So you've got no kind of alignment across all these go-to-market functions.

Yeah, it's funny. I was just building a board deck with another client, and I had the CMO and the VP of sales. We were kind of just going through the deck and getting everything together, and the marketing guy did something really interesting. He goes, "Let's stop calling it sales and marketing. Let's just go commercial, and let's blend everything into the commercial strategy and enable that with the investors to have that commercial strategy conversation versus like sales versus marketing, or here's top of funnel versus midfunnel, bottom of funnel." So here's our commercial strategy, and we built the deck around the commercial strategy.

Yeah, which I think will start tearing some of these down. I totally agree with the ideal customer profile. So based on that, and you've been in this space for a while, how often should people be pressure testing their ICP, buying persona, value propositions in today's market? People buy from people. That's why companies who invest in meaningful connections win. The best part: gifting doesn't have to be expensive to drive results. Just thoughtful. Sendoso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I led sales for a Sendoso competitor, and I could tell you no one does gifting better than Sendoso. If you're looking for a proven way to win and retain more customers, visit sendoso.com.

I think it's almost a continuous thing, to be honest, right? I think here's the reality of all the go-to-market stack today. Back to that kind of onion analogy or the layers analogy—it's like we are all taking these approximate stabs with different disconnected systems as to who is our ideal customer, you know, when are they ready to engage? What's the right message we should go deliver to them? You know, are they properly onboarded? Are they engaged with the product? There's all—you know, it's really kind of a mess. One of the things we say at Coffee is you can't have good AI with bad data.

Can we like put that on a billboard somewhere?

Yeah, exactly. Exactly. And I think that, listen, you know, as you know, most of the data in today's CRM is crap, right? You know, in fact, the last company we had—

Flip Top, we were doing kind of account and lead scoring—you know, Einstein before Einstein. And the thing that was really fascinating is when we looked at all these across hundreds of clients, the only data you could trust in the CRM is when the rep was going to get paid.

And so the thing we said was, if a rep—what fields does a rep need to go get their commission check? Okay, the deal. We have to say the deal closed. Here's a proper dollar amount. Here's at least one contact that's associated with it. You know, you probably had some things that you could rely on, and the data quality fell off a cliff after that because you were relying on them to do it manually.

So I think this whole notion of how are folks engaging with my company, and the more that we can automate the ingestion of that data and the synthesis of that data—some of it structured and some of it unstructured—how do you fuse those things? I think the better off you're going to be able to get a real TLDR as to what's happening with an account and have a unified front across your go-to-market teams.

I can go super deep on data because I don't think—and we talk about this a lot—garbage data in equals garbage data out 27 ways from Sunday. And no one wants to spend the time, I don't even want to say the money, the effort to make sure that their data is clean.

Dale, I forget—we were just talking about this with someone the other day, or I was reading something about—oh, it was Kyle Nordon who's the CRO of Outreach. You know, Kyle, we're all part of GTM Fund. Kyle's one of the best revenue leaders I know. And he was posting something the other day about the incredible success that his BDR team has seen by not just changing how they reach out and what they're saying, but the quality of the data so that they're not spending time reaching out to numbers that are—oh, sorry—numbers that are disconnected, sorry, emails that bounced.

And I think that not enough people realize that you could have all the BDRs, the best AEs in the world, the best CEO. Hell, you could have the best product. If your data sucks, you have no chance because you don't know what you're doing.

So I'm going to put you on the spot for a minute. When it comes to data—specifically people data, numbers data—like, where are you getting good data? Is there a single source like Zoom Info or Apollo, or whoever? Or are you a big fan of a Clay and massive waterfall enrichments with your preferred providers that we do not need to mention if we don't want to because they're not paying to be here? But I'm curious your thoughts.

Yeah, we've kind of taken a waterfall approach. So we don't think there is a single approach for any person or company data. And frankly, you know, we have enrichment built into Coffee. So you don't have to go out and immediately go buy a third-party data source. That's very cool.

But one of the things about it is that by no means is that all of the niche pieces. I mean, we kind of feel like the broad-brush stuff should be covered by our enrichment. So you can get, you know, industry, revenue range, LinkedIn profiles, titles, things like that when we have matches for that. And the rest of it should just be AI searching for stuff in the background.

So if I have a very specific thing—I sell a remote work solution, right?—no data provider is going to have that out of the box. But I should just be able to have a smart field that says, "Go take a look at the career pages of all of the companies in my Coffee instance and go take a look if they use the word 'remote' in their job postings, right?" So then you can kind of fill in those missing pieces there.

But yeah, we haven't found a single magical source that does it all. We did a huge data exercise when we got started in the summer of last year where we probably looked at 40 or 50 different vendors and got all their data tables and did a bunch of bake-offs and we ultimately selected multiple of them to kind of waterfall for our in-house thing. And I think that will be an ongoing process.

But I'll give you an example of how bad the data stuff is in CRM. So we have a free app. We're going to have a whole bunch of these little free apps as part of our demand gen program called CRM Grader that we rolled out. And the idea was, go connect your CRM and we will give you a score as to what's the quality of the data in your CRM across your deals, across your contacts, and across your companies.

And one of the customers that signed up early on—I was looking at this thing—and we have a tool inside of Coffee we call Revenue GPT, which is like a ChatGPT-style interface. Ask questions. So I was like, "Hey, what's the average?" You know, we were working with this customer and he said, "What's our average sales cycle?" And he gave me a negative number. And I was like, "Oh, something must be broken in our software. So we better take a look at this."

And so my VP of engineering goes off and looks and goes, "No, actually it's the correct answer. What the reps are doing is they're not putting anything in the CRM until they have to get their commission check." And so actually, they're putting the create date after the actual close date when they're putting information in. And the average deal is like minus 17 days or something like that.

So that's an example of CRM gone really wrong.

I love that. Now, I was just looking at your site before you jumped on, and I was going to ask one of my questions. I'm going to ask, "What's better: the Website Grader from HubSpot or the CRM Grader from Coffee?" But I think they're very different. They're meant for different products.

I mean, HubSpot has been our inspiration for that. So we were like, yeah.

And I love it because you need a funnel, right? You need people. I'll be super interested how many people actually will connect their CRM into something that they're not completely—I think it would be okay if we had, like, if we were collaborating with Coffee, we knew the customer would be like, "Yes, go integrate, go connect Coffee and grade your CRM because it actually would help us."

Because we go in every place and we're like, "Okay, first thing: let's rebuild the CRM." We just did a hundred-million-dollar company on Sugar and we just did a whole conversion to HubSpot. So it was kind of a pain, but that was not fun.

By the way, I'll be super—and we did it in 45 days. Like, it was a lift.

Yeah, it was a lift.

So a few things to your point. First of all, you're right. We—the friction of CRM Grader is much higher than Website Grader, where you just say, "Hey, listen, put in your email and name and we'll send you a report on your website." We will have free products coming out over the next quarter that are kind of more like Website Grader where you're just literally putting in some information and getting a report sent to you and don't need to connect your CRM.

But the connect—I've always been kind of surprised about how many people are willing to go connect their CRM, especially small and medium businesses. Obviously, when you get to enterprise, they're like, "Here's my committee. Here's my security review," all of that piece. But I've always been amazed that somebody with admin access is like, "Oh, yeah. I'll just do that," the way they connect their Google account. "I'll give you all my data."

Yeah.

And so it's also—I've always been surprised in both at Fliptop and through even with Sales Navigator when we did the Salesforce integration—the number of Sales Navigator customers that would just go connect to Salesforce without having to go through some kind of big security review first was surprising to me.

Yeah, it's—I mean, we work with companies where you'd be amazed. I mean, Dale, you know what I'm talking about. Like, we've gone to companies that have, call it, a sales team of 20 and 18 of the 20 have super admin access. Like, it blows my mind. Like, to be clear, we're a company of three and we don't even all have super admin access. Like, that's how locked down. Like, one person, maybe two, should have super admin access, not 20 of your reps who create workflows.

Yeah. What's my login? "Forgot password" at Revenue123password.

Yeah. No, but it also speaks to one of the biggest strengths, as you know, of companies like Salesforce: that API system, that kind of AppExchange ecosystem. And so the ability of people to kind of get that information out of that system, you know, makes it easy.

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Also makes it easy for folks like us—folks like you—to migrate folks into different platforms. So Doug, when we talk about AI, and we talked to a lot of people about AI, and we were talking to someone, Dell I think yesterday when we were on a podcast, and it was about what's the future of AI, right, for sales. Yeah. And there's a lot of, oh, you know, it's not just data enrichment. You know, you have to look at more than that. Like it has to be how do you allow people to focus on revenue-producing activities and all that fun stuff. But I think that's table stakes. When I think—and I admittedly I've not looked at your website in depth because I wanted to have the conversation—but when I look at, when I think of like the AI-powered CRM, what I'm thinking is I don't have to drag my deal from one stage to another based on what's going on, and it's going to put the deal in the proper stage and I don't need to fill out that I have a decision maker because based on the conversations and the emails and all the data you're ingesting, Coffee knows that there's a decision maker associated with the deal. I'm probably thinking about this at a too high of a level, but is that where the vision is? Is that the CRM works for me as the rep instead of me having to work the CRM?

So the last part of it is actually our tagline. If you went on our website, which is "The AI for SER. It works for you." And I did not go to the website, so I could be your marketing part.

No, I'm not. You could be our marketing.

No, we're still kind of, you know, in early stage in stealth, so there's not a lot of product information yet on the website, as I'm sure Dale saw. But the general idea is, you know, it should be doing most of the work for you. Now, our particular view on the example that you gave of the opportunity pipeline is it—we may not be ready to automatically create and move opportunities for you, just because I think you're going to say, "Oh, that was a misinterpretation, or you moved that too soon." But I think what we can do is say, "Hey, based on what I heard from your last email exchange or the transcript of the last call, et cetera, you know, this seems like we should go create an opportunity." And there's one—but you kind of get a one-button confirm for that to go move something or make it happen.

But the other thing is there is no one-size-fits-all for AI. So, you know, everybody thinks now AI equals ChatGPT equals LLMs, but you know, there's machine learning, there's all kinds of different variants of it. So, you know, we're going when we say AI-first, we truly mean from the beginning. Like for us, you know, we never throw away data in Coffee. So we have a data lakehouse in the back end. So simple things like, "Hey, what does my pipeline look like compared to a week ago?" Right, we can go do for you, or what were the last five states of this field? Right, let me go see what that was, let me roll back to this previous version, right. So I think that's a big part of how do you have AI? Because again, over time, you know, AI is great for things like, let me give you a meeting brief for this meeting. Let me go summarize that call that just happened. Let me suggest some action items. Let me draft a follow-up email for you. Let me give you a TLDR so anybody can go take a look at an account or a person and see kind of what's the current status of our company, our company's interaction with that person or that company.

So it's all great for that stuff. But ultimately it should be about, "Hey, you know, I noticed that we're this far into the quarter and you know, you're a little behind on your pipeline coverage." Or, you know, things are—how do you start to get more proactive? And the only way to do that is to make sure you've got history that you're capturing.

I love it. I would try it. When I think of all the companies that we work with that have bad data hygiene and poor CRM—and CRM that have to be ripped out—and like reps who don't want to work them, and managers who are never going to do anything about it because the rep's the top rep, and at the end of the day, if the deal closes, well, I can't forecast the deal, but the deal closes. Yeah. I'm excited to see it, to try it, and to learn more. Thank you.

Let me ask one last question before we go into some rapid fire. So go-to-market's changing, right? You know, it changes arguably every day. We talked about how often you need to update things such as ICP or buyer persona. But with that, be a Nostradamus for a minute. Where's go-to-market going? What's the future of go-to-market in the next three to six months? Broadly speaking, much broader than CRM.

I like to think about it from the buyer's perspective going backwards, right? Because I think so much of what we've done is seller push forward. So I think about myself as a B2B buyer or just a consumer in general. You know, I want to be able to have as much information that I can go get myself, right, and not have to talk to a person, right. So, you know, things like—uh, I saw you had Yako's book on your back shelf there, Adam.

So, you know, yeah, behind the chair. Revenue Architecture. So, um, I've known Yako for a long time, and you know, Amanda Kao from OneHead actually was collaborating with him recently on effectively having a virtual Yako, if you can imagine something. How, either exciting or scary that might be. There's a lot of Red Bull involved in that.

Um, depends if he has shoes on.

Yeah. Yeah. No shoes. He's in his van. He's drinking a lot of Red Bull.

But, you know, imagine effectively having an AE or an SE rather on your website that you can just query and talk to forever and get any information you want about the product. It's not like some secret hidden pricing page, or, you know, you have to go do a trial before and talk to certain reps. So I think giving buyers a lot more of the power is a big trend towards that.

I think the other piece is we've all gotten really good. Our internal pattern recognition systems have gotten good at filtering out spam calls, spam messages, all that stuff. The idea of the AI SDR, which is like Sales Loft and Outreach on autopilot, I think is a fail, right? I don't think it's the right approach. I think like what Mark Kosaglo is doing in Operator, and I think other people who are saying we have such precise data that you can effectively craft something where it's like, "This is an email that would not make sense to anybody but me," right? It's that targeted to my business, and it's about helping. The same way that I think that HubSpot kind of pioneered this inbound marketing—"Let's create content that helps"—I think at a macro level they've done that. I think it's now down to a one-to-one marketing level of one. So it's really about like, how do you help the buyer in their journey? And how do you not try to force-feed a lot of stuff through a funnel?

I love it. That's great. That's great. I think it's spot on. Let's end with some rapid fire. I wanted to take that out since Adam was talking so much. I had to jump in a little bit. It's so rare that I get to talk when I'm on a call with you. Let's be real. Like, let's be honest with one another here. What's the hardest leadership lesson that you've learned, and how did you resolve it?

I think "hire slow, fire fast" is probably one of the key things. Everything starts with people, right? So we do this thing for my last couple of companies where when you join, I give the culture presentation and I say, "My job is not to create a family, right. My job is to put together like the most winning sports team I can, and to that end, we're going to put a meeting on the calendar 90 days out." I always feel weird saying this, but like in 90 days, we're both going to know whether this is working or not. And I think by having that forcing function, it's going to be unless it's a hell yes, it's a goodbye, right?

Yep. I could not agree more. Could not agree more. What if you lose everything tomorrow? What's the very first move you're going to make?

Define lose everything.

Coffee is gone. Everything that you've put into Coffee is gone. You can't go back to LinkedIn. You can't go back to Salesforce. The bank accounts or the exits are dry. You have a little bit of money, but like you arguably have to start over. What are you going to do? Where are you going to start?

That never has scared me. I mean, I think that they will find in the next 50 years that there's a gene for optimism and a gene for perseverance.

And I think they're the two most aligned indicators for success in entrepreneurship. So, you know, I feel very fortunate. I've got a great partner, my girlfriend. I've got my kids are all doing well. I've often, my dad died when I was pretty young, and the two things that kind of shaped a lot of my worldview is he was. I remember visiting him and he was kind of going, "There's so much more I want to do," and I thought about that. He's in his 60s, and I realized like I could be 150 and I'd still be like on my deathbed going, "There's so much more I want to do." So I've always had that kind of sense that there's more stuff in the world than I'll ever be able to experience. But the other thing is, if I get hit by a bus tomorrow, what regrets would I have or what issues would I have? And you know, there's a short period after my divorce where it was really, really tough with the kids. But other than that, I'm in a place where anything you could throw at me, I've got my core community. I've got my belief in myself, and I'd go figure something else out.

That's awesome, dude. An optimism gene. Yeah, I like that. We're going to find it for sure.

I like that. I love it. What's one piece of advice you were once given that you completely disagree with now? Something you were given in the past and now you're like, that was bullshit.

I think I'll just go back and reiterate on the lean startup movement. I think that people give up too soon, right? I think that one of the reasons, frankly, for Microsoft's success is they're not particularly brilliant at products, but by like the third time they usually put out a decent version, right? So with Windows, it was Windows 95, right, after a bunch of fiascos before that. And I think that belief that if your core assumptions are correct, right, then you should keep going. I think that too many startups are like, "Yeah, we did that for 6 months and we didn't have a million in ARR, so we're going to pivot to something else," or "This got really hard and I just don't have the perseverance to push through it." That's the cause of a lot of unnecessary failure. So the whole lean startup belief that you've got to go measure everything and if you're not hitting your metrics, go move to something else is wrong.

I like it. I agree. All right, Doug. So most of our audience is revenue leaders, founders, CEOs. Many of them listen to the show because they're drowning in whatever their particular go-to-market gap is. What's your single most powerful piece of go-to-market advice from experience you would give to someone who's drowning right now?

Drink coffee.

I think that it all starts with your buyer's journey again. So many people are focused on their internal processes, internal systems, how are we pushing stuff out to customers? I'm a product person first and foremost. I'm a builder. I always, for myself and product managers, always said go use the product yourself. Go be a secret shopper kind of your product. A must. I think for most companies, if they actually were a secret shopper to their own selling process, they would discover a lot of waste, a lot of friction, a lot of noise, a lot of things that are putting customers off. So I think for me the first thing is, how do you make that as simple as possible? I think there was an old, it might have been a Hemingway thing, where he was writing a letter to someone who said, "I'm sorry it's so long, but I didn't have time to write you a shorter one." And it's kind of that same analogy. I think many companies build up these very complicated processes and need to spend time going back and simplifying it, starting with the buyer and working backwards.

That might be, and this is a great place to close, that might be the single best piece of advice we have ever got on this show. Because if you don't, and I don't—Dale will tell you I'm not great at giving out praise—if you're not putting yourself and everyone talks about secret shopping and this stuff, but like every CRO, how often do we talk about your sales process doesn't align with your buyer's process? Your 17 different sales stages in your CRM are not how your buyer buys. If you're not going through that process and saying, "Would I buy from me?" and if the answer is not hell yes, you need to change your damn process. That is the takeaway from this show. Doug Campleon, thank you so much for checking us out. Go check out Coffee.ai. I am excited to try it when it's available for release. We're glad that you spent some time with us, man.

Thanks, guys. Really fun.

Thanks, Doug. Thanks, man. Appreciate you.