{"id":354,"date":"2025-07-08T09:00:00","date_gmt":"2025-07-08T09:00:00","guid":{"rendered":"http:\/\/www.alaskansawmill.com\/?p=354"},"modified":"2025-07-10T13:16:01","modified_gmt":"2025-07-10T13:16:01","slug":"gtm-154-how-ai-is-reshaping-sales-tech-lessons-from-building-sales-cloud-sales-navigator-and-now-an-ai-native-startup","status":"publish","type":"post","link":"http:\/\/www.alaskansawmill.com\/index.php\/2025\/07\/08\/gtm-154-how-ai-is-reshaping-sales-tech-lessons-from-building-sales-cloud-sales-navigator-and-now-an-ai-native-startup\/","title":{"rendered":"GTM 154: How AI is Reshaping Sales Tech | Lessons from Building Sales Cloud, Sales Navigator and now an AI-Native Startup"},"content":{"rendered":"<figure class=\"wp-block-embed is-type-rich is-provider-spotify wp-block-embed-spotify\">\n<div class=\"wp-block-embed__wrapper\">\n<\/div>\n<\/figure>\n<p>The GTM Podcast is available on any major directory, including:<\/p>\n<ul>\n<li><a href=\"https:\/\/podcasts.apple.com\/in\/podcast\/the-gtm-podcast\/id1369291464\" target=\"_blank\" rel=\"noopener\">Apple Podcasts<\/a><\/li>\n<li><a href=\"https:\/\/open.spotify.com\/show\/2SA1dgQ2Yc5t4V5GcBLnD2?si=b9dcb3e53b2d4ad2&amp;nd=1\" target=\"_blank\" rel=\"noopener\">Spotify<\/a><\/li>\n<li><a href=\"https:\/\/youtube.com\/playlist?list=PLGXnz4Tyz3-SfJ5DPByHtUOQOFB3yJ6zZ&amp;si=Yj3qgzFty48-h9uI\" target=\"_blank\" rel=\"noopener\">YouTube<\/a><\/li>\n<\/ul>\n<hr \/>\n<p><a href=\"https:\/\/www.linkedin.com\/in\/camplejohn\/\" target=\"_blank\" rel=\"noopener\">Doug Camplejohn<\/a> is a serial entrepreneur and seasoned executive with extensive experience in B2B SaaS and go-to-market strategies. He has previously held leadership positions at major tech companies including LinkedIn, Salesforce, and Apple before founding Coffee, an AI-first CRM platform.<\/p>\n<h2><strong>Discussed in this Episode:<\/strong><\/h2>\n<ul>\n<li>\n<p>AI-powered CRM and sales automation<\/p>\n<\/li>\n<li>\n<p>Go-to-market stack optimization and simplification<\/p>\n<\/li>\n<li>\n<p>Building and scaling B2B SaaS companies<\/p>\n<\/li>\n<li>\n<p>Revenue operations (RevOps) and AI integration<\/p>\n<\/li>\n<li>\n<p>Serial entrepreneurship and company building<\/p>\n<\/li>\n<li>\n<p>Transitioning from big tech to startup founder<\/p>\n<\/li>\n<\/ul>\n<h2><strong>Highlights:<\/strong><\/h2>\n<p>04:35 From Fliptop to LinkedIn: how Doug navigated acquisition and scaled Sales Navigator.<\/p>\n<p>06:33 Why Sales Nav was a $250M business with a \u201ccrappy product\u201d \u2014 and how Doug turned it around.<\/p>\n<p>09:56 Doug\u2019s \u201cawesome test\u201d for hiring top talent (and the 90-day rule he swears by).<\/p>\n<p>13:26 The speed dating hack that landed Coffee\u2019s first sales leader.<\/p>\n<p>17:36 What Doug learned running Sales Cloud at Salesforce \u2014 and why he left.<\/p>\n<p>22:22 The biggest missed opportunity inside Sales Navigator (and what he\u2019d do differently).<\/p>\n<p>24:37 Why sales tech stacks are bloated \u2014 and how AI-native CRMs solve it.<\/p>\n<p>28:36 What makes a <em>true<\/em> AI-native product (and why Coffee is built different).<\/p>\n<p>31:36 The Rippling-inspired vision behind Coffee\u2019s GTM strategy.<\/p>\n<p>34:47 Three versions of Coffee \u2014 and why reps are swiping their own cards.<\/p>\n<p>39:44 AI agents vs. simple automations \u2014 what the future actually looks like.<\/p>\n<p>42:41 Why SDRs won\u2019t disappear \u2014 but their job <em>will<\/em> change.<\/p>\n<p>47:45 Data as the new moat: how to build durable product advantage in the AI era.<\/p>\n<p>50:08 Why Doug runs a podcast and thinks every startup should act like a media company.<\/p>\n<p>55:09 The new math of headcount: scaling to $100M+ with fewer hires.<\/p>\n<p>56:45 The \u201cTAM is dead\u201d take \u2014 and how Doug thinks about modern segmentation.<\/p>\n<hr \/>\n<p><strong>Guest Speaker Links (Doug Camplejohn):<\/strong><\/p>\n<ul>\n<li>LinkedIn:\u00a0 <a href=\"https:\/\/linkedin.com\/in\/camplejohn\" target=\"_blank\" rel=\"noopener\">https:\/\/linkedin.com\/in\/camplejohn<\/a><\/li>\n<li>Coffee: <a href=\"https:\/\/coffee.ai\" target=\"_blank\" rel=\"noopener\">https:\/\/coffee.ai<\/a><\/li>\n<li>Podcast: <a href=\"https:\/\/www.coffee.ai\/podcast\" target=\"_blank\" rel=\"noopener\">https:\/\/www.coffee.ai\/podcast<\/a><\/li>\n<\/ul>\n<p><strong>Host Speaker Links (Sophie Buonassisi):<\/strong><\/p>\n<ul>\n<li>LinkedIn:\u00a0<a href=\"https:\/\/www.linkedin.com\/in\/sophiebuonassisi\/\" target=\"_blank\" rel=\"noopener\">https:\/\/www.linkedin.com\/in\/sophiebuonassisi\/<\/a><\/li>\n<li>Newsletter:\u00a0<a href=\"https:\/\/substack.com\/@sophiebuonassisi\" target=\"_blank\" rel=\"noopener\">https:\/\/substack.com\/@sophiebuonassisi<\/a><\/li>\n<\/ul>\n<hr \/>\n<h3><strong>Thanks to our Sponsor: TriNet<\/strong><\/h3>\n<p>Every early-stage founder is told to focus on product and growth. But behind every product launch and revenue milestone is a team \u2013 and building that team is one of the hardest and important parts of the journey.<\/p>\n<p>\u201cBuild the team that builds the company.\u201d \u2013 that is part of your go-to-market strategy responsible for growth.\u00a0 Hiring the right people, keeping them supported, and creating the infrastructure to help them thrive is critical.\u00a0<\/p>\n<p>TriNet exists to make that easier. TriNet\u2019s full suite of HR solutions is designed to support companies at critical inflection points \u2013 from early traction to scale.\u00a0<\/p>\n<p>Learn more at: <a href=\"https:\/\/trinet.com\/gtmnow\" target=\"_blank\" rel=\"noopener\">https:\/\/trinet.com\/gtmnow<\/a><\/p>\n<hr \/>\n<p><strong>Where to find GTMnow (GTMfund\u2019s media brand):<\/strong><\/p>\n<ul>\n<li>Website:\u00a0<a href=\"https:\/\/gtmnow.com\/\" target=\"_blank\" rel=\"noopener\">https:\/\/gtmnow.com\/<\/a><\/li>\n<li>LinkedIn:\u00a0<a href=\"https:\/\/www.linkedin.com\/company\/gtmnow\/\" target=\"_blank\" rel=\"noopener\">https:\/\/www.linkedin.com\/company\/gtmnow\/<\/a><\/li>\n<li>Twitter\/X:\u00a0<a href=\"https:\/\/x.com\/GTMnow_\" target=\"_blank\" rel=\"noopener\">https:\/\/x.com\/GTMnow_<\/a><\/li>\n<li>YouTube:\u00a0<a href=\"https:\/\/www.youtube.com\/@GTM_now\" target=\"_blank\" rel=\"noopener\">\/@gtm_now<\/a><\/li>\n<li>The GTM Podcast (on all major directories):\u00a0<a href=\"https:\/\/gtmnow.com\/tag\/podcast\/\" target=\"_blank\" rel=\"noopener\">https:\/\/gtmnow.com\/tag\/podcast\/<\/a><\/li>\n<\/ul>\n<hr \/>\n<h2>GTM 154 Episode Transcript<\/h2>\n<p>02:09<\/p>\n<p>Now onto the episode. This episode explores how AI is reshaping the modern sales stock. Doug Campbelljohn, founder and CEO of Coffee, shares lessons from leading sales cloud at Salesforce and sales navigator at LinkedIn and why he believes the future belongs to AI. Native rep first platforms. You\u2019ll learn why most CRMs fail, what an efficient go-to-market stack should look like and how to hire top performers using Doug\u2019s awesome test. I love this part. He also shares a forward-looking take on AI agents, sales, tech consolidation and building high output teams with fewer resources. Doug is a multi-time founder and product leader. Before Coffee, he founded Fliptop, which was acquired by LinkedIn, and held executive roles at Salesforce and LinkedIn. Doug, thanks for coming on the podcast.\u00a0<\/p>\n<p>02:50 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Thanks for having me.\u00a0<\/p>\n<p>02:57 \u2013 Sophie Buonassisi (Host)<\/p>\n<p>You bet it wasn\u2019t actually too long ago that we were in person in New York team that next year it\u2019ll be our fifth annual event and we might have to pull an SNL and bring some velvet jackets into the play to indoctrinate some people into the five-timers club. And you\u2019ve attended every year, so if you attend next year you\u2019ll be a five-timer.\u00a0<\/p>\n<p>03:18 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>I need a five-timers jacket. It\u2019s awesome. You guys throw such amazing events and GTM Fund is one of the most pleasant surprises is both an LP and a portfolio company, just in terms of the value add. You guys do fantastic work.\u00a0<\/p>\n<p>03:33 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Thank you Incredible Well, thank you. Thank you for the kind words. We appreciate you. We appreciate everything that you do for the community and all areas that you\u2019re part of it. So we\u2019re fortunate to have you part of the community, but also very fortunate to be on the podcast with you today. We\u2019ve been wanting to have you on for so long and super grateful that we made it happen. So thank you for joining us.\u00a0<\/p>\n<p>03:53 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Thank you, excited to be here.\u00a0<\/p>\n<p>03:55 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>You bet, and there is so much Doug that I want to pick your brain on. You are a multi-time founder. As an operator, you\u2019ve led to the biggest sales platforms in the world LinkedIn. As an operator, you\u2019ve led to the biggest sales platforms in the world LinkedIn, sales Nav and Salesforce\u2019s Sales Cloud. You\u2019re an investor also a phenomenal human so let\u2019s start and jump right in. We\u2019d love to start at the part of your journey where you founded a company, flip Top. Its applications use data science to help companies close more sales and in 2015, it was acquired by LinkedIn, which is a dream outcome for many. Love to hear you know a little bit around that experience of going through that acquisition and joining LinkedIn and how that experience was for you.\u00a0<\/p>\n<p>04:35 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, you know, like any startups, you know you\u2019re either the hero or the goat at the end. So, like it\u2019s often a fine line between a great outcome and, just you know, a crater at the end. So, like it\u2019s often a fine line between a great outcome and, just you know, crater in the ground. We were in a space that was doing account and lead scoring and when we started, there was only a couple other companies. It was like before Einstein, salesforce\u2019s Einstein or Sixth Sense was just getting started. And then we woke up the next day and there\u2019s suddenly like eight companies that had all gotten like 30, 40 million in funding and were giving product away. And we\u2019re like, oh shit, so it was a crazy ride for that, which was we had pivoted from an earlier idea. And so we looked at the market space and we\u2019re like we could go raise another round. And we\u2019re looking at, like you know, four or five years of work and no one\u2019s really making the market happen right now. And LinkedIn came in and said, you know, we think you guys would be a perfect fit for the sales navigator team and we originally like thought it was, they wanted us all for our AI expertise. But it turns out that LinkedIn just didn\u2019t know much about connecting to CRMs and how CRMs worked, and so we were that team who built all the connectivity between Salesforce and Sales Navigator. And so, yeah, we got brought in and at first it was a kind of culture shock, coming from a small company to a bigger company.\u00a0<\/p>\n<p>06:00<\/p>\n<p>I probably I told a good friend of mine like I don\u2019t think I\u2019m going to make it here, I don\u2019t think I\u2019m going to last, and the don\u2019t think I\u2019m going to last, and he, his, he had. The best advice was do you care if you get fired? I was like no, I don\u2019t. He said, well then, just speak your mind and do it respectfully. But there was something about like not being afraid about being fired in a big company. That makes you very different than most other people in large companies. Um, and it was very liberating and I had a ton of fun. Linkedin\u2019s a great company and we had a we. I think it was a really successful outcome for everyone very cool and I\u2019d say most.\u00a0<\/p>\n<p>06:29 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Most people listening to this podcast are well familiar with linkedin sales.\u00a0<\/p>\n<p>06:33 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Now curious any kind of impactful stories from building there and building a product that many are extremely familiar with yeah, you know, like when I came into linked, you know and this is part of the be respectful, to be honest, like the business is already about a quarter billion dollar business, right, because LinkedIn is just such a machine with their data, and I thought the product was crap, right. And I told Jeff, the CEO, of that and I said, listen, like to be honest, I\u2019ve used it. And if I was starting a company tomorrow, I wouldn\u2019t pay for it, I\u2019d just pay for you know, I\u2019d use free or pay for premium. And he\u2019s like, but it\u2019s a quarter billion dollar business. And I was like, yeah, but it kind of sucks and like I mean just stuff that you wouldn\u2019t believe. It didn\u2019t have notes, didn\u2019t have product. We took them out of the free product and then we, you know, kept working on the roadmap and making it more and more interesting and useful. And it\u2019s interesting.\u00a0<\/p>\n<p>07:34<\/p>\n<p>Now, when we started the current company, I was looking, I was like, yeah, I kind of need to buy a copy of Sales Navigator. So it was a good testament that it\u2019s like, all right, we\u2019ve kind of built something that was kind of useful. But yeah, and it\u2019s over a billion dollar business right now. It\u2019s just, it\u2019s a machine. So LinkedIn was a great, a great experience of kind of learning how to going from starting and, you know, owning the whole show as a startup, to kind of operating inside of a bigger environment. But LinkedIn was really good and still very good at acquiring companies and putting the CEOs in charge of a product line and so they keep, you know, renewing the blood inside of the ecosystem and keeping things fresh.\u00a0<\/p>\n<p>08:20 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Incredible. Well, we have you, Doug, to thank for lists and sales now, among many other features that are beloved of the most creative out-of-the-box thinkers.\u00a0<\/p>\n<p>08:47 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>You know Lindsay Edwards, Tom Lee, just the list goes on. Just fantastic folks and some that have gone on to start their own companies now. So I was really fortunate and that\u2019s why I ended up staying as long as I did and was just because I really enjoyed the people I was working with.\u00a0<\/p>\n<p>08:59 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>And how did you think about building Because that\u2019s a common challenge for many around recognizing patterns of success, operational excellence, seeing not only, maybe, a track record, but the potential for somebody. How do you think about hiring, maybe at that time, but also now at your current company? That we\u2019ll chat more about as we go.\u00a0<\/p>\n<p>09:18 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah. So there\u2019s like I\u2019ve developed a few philosophies about like hiring, retention and firing, and I have a kind of we can talk about all three, but I\u2019ll start with the hiring piece. Hiring is it\u2019s easy to say, my God, this person is amazing, it\u2019s you know, or somebody just whiffs the interviews and they\u2019re terrible. The hard part is that people tend to be nice. When you\u2019re going around the table and doing things like, hey, thumbs up or thumbs down, or like scale of one to five, you know, would you go hire this person? People tend to round up. People are like oh, they seem very nice, you know, like I think they\u2019d fit in well with the culture.\u00a0<\/p>\n<p>09:56<\/p>\n<p>We have what we call the awesome test, and the awesome test is basically, if you can\u2019t say, fuck, that person was awesome, we got to get them on the team, keep looking, and it\u2019s a really high bar.\u00a0<\/p>\n<p>10:09<\/p>\n<p>And we\u2019ve passed on some amazing people in the process and made some mistakes. But I\u2019d rather make mistakes of not hiring somebody than hiring somebody who\u2019s like oh, you know, I think they\u2019ll be good enough. And even with that you don\u2019t get it right most of the time. So we also, whenever we bring somebody on, we also put a meeting on the calendar 90 days out, and we say, listen, like we\u2019re going to really focus on making you successful in this first 90 days, but 90 days in, you and I are going to go have a meeting and we\u2019re going to see if it\u2019s working for both of us, are going to go have a meeting and we\u2019re going to see if it\u2019s working for both of us.\u00a0<\/p>\n<p>10:46<\/p>\n<p>And because I realized everybody who didn\u2019t I hired, who wasn\u2019t the right fit, I knew within the first 90 days and usually even sooner. So I use that as a forcing function to be you know we\u2019re going to hire for the awesome test and I actually keep a running list when I meet with somebody. Like if I\u2019m like, oh my God, that sales rep was amazing it\u2019s a sales navigator list, but I have a running list of awesome people that when I need to go recruit, I just go back to the awesome list and be like you know, maybe they\u2019re unattainable but like I always know what I\u2019m striving for.\u00a0<\/p>\n<p>11:16 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>I\u2019d say that\u2019s a common theme that we hear about some of the best leaders is that they have some kind of continuous list around. You\u2019re always recruiting, you are always tracking who the best people are.\u00a0<\/p>\n<p>11:26 \u2013<strong> Doug Camplejohn (Guest)<\/strong><\/p>\n<p>awesome people are right, yeah absolutely yeah, and I think that that it\u2019s also no one bets a thousand. So I think that that kind of backup plan of like, hey, if it\u2019s not, if it\u2019s not, if we got it wrong somehow and it\u2019s just not totally knocking it out of the park in the first 90 days, then then make the tough decision because the the uh, because it\u2019s the classic saying of A players, high A players, b players, higher C players, the minute you start to let that bar slip, the whole kind of quality slips and then you\u2019ve got people who are really productive and high quality people who are like why should I work so hard, why should I kill myself if you\u2019re allowing that to happen?\u00a0<\/p>\n<p>12:03 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Yeah, only as high quality as that kind of lowest bar or pillar on the team, and you have that transparent conversation around 90 days, which I think is fantastic. I love that candor and just overall expectation for a candidate. How often does it work out? You know, like you said, nobody ever bats 100. What does that actually look like?\u00a0<\/p>\n<p>12:22 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>I\u2019d say we\u2019re like two thirds, three-quarters, kind of there. It\u2019s funny. I\u2019ll tell you another story about like a hiring process. You probably know Yako Venekuj, who\u2019s like winning by design, legendary. We had the good fortune of working with Yako right as he was getting winning by design off the bat with Flipped Up the Last Company and my VP of sales, tom. We were starting to ramp our sales team and we were working with Betts Recruiting, carolyn Recruiting and Carolyn Betts and she\u2019s fantastic.\u00a0<\/p>\n<p>12:57<\/p>\n<p>But we were not like, we\u2019re just not. It wasn\u2019t happening fast enough and we said, listen, we\u2019ve got three open roles. We want to fill them with the best people. Why don\u2019t we do a speed dating day? You bring us your best candidates right and we will clear our calendar. I\u2019ll clear my calendar for the day. Tom and Jaco will be in the office, clear their calendar and we promise anybody who meets our bar we will make an offer to at the end of that day. So they were like all right, let\u2019s go. We\u2019re going to get a whole bunch of you know nice little bonus checks if this works out.\u00a0<\/p>\n<p>13:26<\/p>\n<p>And the way we did it, I saw Jaco for dinner last night and he said they\u2019re still doing this. Now is candidates, would come in and remember, these are sales candidates, so this process won\u2019t work for everybody. These are sales candidates. So we brought everybody in and we said here\u2019s how the interview is going to work. We have a half an hour, we\u2019re going to take 10 minutes and we\u2019re going to interview you, and then Tom and Yako would say we\u2019re going to debrief to each other as if you were not in the room.\u00a0<\/p>\n<p>13:54<\/p>\n<p>So they would let\u2019s say, let\u2019s say it was Yako and I and you were interviewing Sophie. So it would be like we would come ask you a bunch of questions and then I would turn to Yako and be like so what\u2019d you think? And he might go. Yeah, I think I didn\u2019t believe her last year\u2019s number. I thought she was bullshitting us on that. And I said, yeah, like I didn\u2019t think her argument for this was that like we would be that transparent and critical. And then we would say, sorry, you\u2019re not a fit to everyone, because in our opinion, the sales interview started at that point. So if somebody couldn\u2019t go and convince us that and it was remarkable, it was like two-thirds of the people were like okay, well, thanks for having me in, you know, and would just leave and I\u2019m like you\u2019re in sales Come on.\u00a0<\/p>\n<p>14:44<\/p>\n<p>But you know, if you know Olivier, who\u2019s a GTM fund member and working with SIG Coffee, we hired him on the spot. He was one of the hires that we did that day because he said, respectfully, I disagree, and let me tell you why. And within five minutes he had basically convinced Jaco and Tom that he should go meet with me. I spent five minutes with him and I said, yep, he\u2019s the guy, and he became our head of sales Amazing Well first of all, olivier with him and I said, yep, he\u2019s the guy, and he became our head of sales.\u00a0<\/p>\n<p>15:06 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Well, first of all, olivier is incredible, but second of all, that\u2019s a really interesting process.\u00a0<\/p>\n<p>15:11 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>It\u2019s an interesting hack for hiring and I will use it again in the future in terms of salespeople, and I think that just in general, I think that you don\u2019t need to. I\u2019m a big believer in the recruiting process, that speed matters and your gut matters. So I think that what we try to do with folks is we\u2019ll do for any other position, we\u2019ll do a phone screen, we\u2019ll try to do all of the interviews in one day, we\u2019ll give at the end of each day. We\u2019re basically you\u2019re not getting. Before you wake up the next morning, you know whether we\u2019re moving forward. And then we try to do just a final presentation or some kind of exercise if it\u2019s engineering or coding exercise and then we basically make the offer contingent on references.\u00a0<\/p>\n<p>15:55 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Extremely quick. There\u2019s something I heard that always stuck with me and I think about it now in terms of what we\u2019re recruiting is really how you run, the process is how you run everything. And in terms of what we\u2019re recruiting is really how you run the process is how you run everything. And so, as a candidate, how you run that process like you said, if somebody\u2019s holding a rebuttal against what you\u2019ve shared is indicative of how they work.\u00a0<\/p>\n<p>16:14 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Their speed around responding is indicative of their operational excellence and it\u2019s a frustrating thing in big companies, like I saw this at LinkedIn and Salesforce, where it would be like oh yeah, you know we can\u2019t get everybody together, so this interview is going to drag out over weeks, right, like you know, when people\u2019s availability and you know, you just lose all the momentum and your best advantage. You know if you\u2019ve got really great talent, they\u2019ve got lots of choices and so your key is to our goal was always everybody should leave the interview process going. Damn, I want to work for that company, whether we offer them a job or not.\u00a0<\/p>\n<p>16:49 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Absolutely love it, Doug. And if we think back to more of your timeline, after over four years at LinkedIn, you went on to serve as executive vice president and GM at Salesforce\u2019s Sales Cloud. What are some impactful stories or moments from your time there building?\u00a0<\/p>\n<p>17:08 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>It was kind of wild. I mean, like I, as I said, I didn\u2019t think I would last long at LinkedIn and ended up being there four years. I, you know, had another year to kind of hang out and invest if I wanted to at LinkedIn, but I was kind of you know, I try to always optimize for learning and my learning curve felt like it was flattening at LinkedIn. But I was kind of, you know, I try to always optimize for learning and my learning curve felt like it was flattening at LinkedIn, like we were, you know, built a great team, we\u2019ve got a great roadmap, you know. But it was kind of rinse, lather, repeat. So mine was.\u00a0<\/p>\n<p>17:36<\/p>\n<p>And I got a call from, you know, Bill Patterson, brett Taylor at Salesforce and said, hey, you know, would you ever consider? And I was like, oh, san Francisco, similar kind of value system, a space I know a thing or two about, I think, like all of you, I felt like, yeah, there\u2019s probably one or two things we could improve about Sales Cloud and so felt like there was an opportunity to go do great things there. And so I joined Salesforce in beginning of February 2021. And, as you know, six weeks later, the entire world was on Zoom, like we\u2019re all remote. So that was an interesting process and I think Salesforce I you know I love the company working there, but I think it\u2019s a very different environment. They\u2019re a sales and marketing and corporate development machine. I learned so much working with Mark, working with John Samorjai and the corporate development team Just the way they think about that whole process. They\u2019re incredible.\u00a0<\/p>\n<p>18:39<\/p>\n<p>But I am a builder, I\u2019m a product guy, and Salesforce does a lot of their product stuff through acquisition and so over time they built up a lot of these pieces and it was this kind of Frankenstack and really hard to kind of, you know, do rapid change and do a lot of innovation in the core product and so I think the combination of that and I just had this idea that I couldn\u2019t let go of and that\u2019s what I ended up leaving and starting Airspeed with. The following year I\u2019ve worked with Steve Blank, who\u2019s an incredible, you know, kind of the founder of the lean startup movement and an incredible marketing mind and learned a lot from him years ago. But you know, I do think like Mark is probably one of the best, if not the best, marketing executives out there and he is just amazing at thinking about staying on bleeding edge. First, because if you think about Salesforce, they\u2019re always looking at its agents, its mobile, its social, it\u2019s like everything. They are right there and thinking about that stuff.\u00a0<\/p>\n<p>19:43<\/p>\n<p>And just the way that he thinks about acquisitions and sales LinkedIn, you know, did obviously some acquisitions. But I think much more conservative Mark really swung for the fences on that stuff. So if he said, for example, I want to build a billion dollar marketing cloud, it was almost like who\u2019s the leader, who do we need to acquire? And then finally tell me the price, whereas a lot of other companies are like who can we afford or what\u2019s in the realm of that? And just they think at a different level. So the level of kind of investment that they did and the M&amp;A they did was just next level.\u00a0<\/p>\n<p>20:19 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>That is the resounding feedback that we get from all fronts around Mark. I mean that you read on the internet, but also you heard directly. Uh, craig Swenstred, who\u2019s the founder of, qualified On and he worked directly under Mark2, exact same thing.\u00a0<\/p>\n<p>20:35 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, and he does it all in text. You know he\u2019s, he\u2019s, he\u2019s working in Hawaii crazy hours and you know you want to reach him. It\u2019s just like you call him on his mobile or you, you, you text him, right, so he runs a how many kajillion billion, you know dollar company just off of his phone.\u00a0<\/p>\n<p>20:52 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Yeah, Pretty amazing Simplicity. What\u2019s one painful perhaps lesson that you learned from scaling Sales Cloud or Sales Nav that shapes how you\u2019re building now.\u00a0<\/p>\n<p>21:06 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>I think you know I\u2019ll take a look at Sales Nav. I think we probably, probably the middle of my journey there, got a little defocused. We were like we acquired some companies. We were doing kind of like DocSend, like document tracking things. We were trying to do some pipeline stuff. It was almost like starting to bleed into being a CRM a little bit and I think that and I see that a little bit in the user interface today the team\u2019s done some amazing stuff, but I think there\u2019s also bloat that\u2019s happened in the product and I see that a little bit in the user interface today. The team\u2019s done some amazing stuff, but I think there\u2019s also bloat that\u2019s happened in the product and I\u2019m partially responsible for that.\u00a0<\/p>\n<p>21:38<\/p>\n<p>But I think that you know, just like LinkedIn never wanted to call themselves a resume site in the beginning. You know, if you really understood that was like the core value offering was like seeing somebody\u2019s resume Right, and then obviously it grew into the feed and lots of other value props seeing somebody\u2019s resume right and then obviously it grew into the feed and lots of other value props. If you really think about the core value prop of Sales Navigator, it\u2019s prospecting, it\u2019s building lists right and because LinkedIn has great data for that. So everything I think the things that we should have continued to focus on was more of how do we make search better, how do we make list building better, how do we do updates, how do we do notifications around that stuff. And then I think that there\u2019s still one of the missing, and I\u2019ve posted on LinkedIn about this.\u00a0<\/p>\n<p>22:22<\/p>\n<p>One of the missing pieces that has not been realized to its fullest extent yet, I think, is the whole warm introduction path, the whole. How do you leverage your network? Because I think when you\u2019re in a sales organization, you\u2019ve got your book of business, you\u2019ve got, like, let\u2019s say, you\u2019ve got your named accounts. You should be able to just have those connected into Sales Navigator and say who are all the folks that are connected, like automatically queue up the introduction messages you know, like just make it as simple as possible on the connectors to go make that happen and then also just really see, like what are true connections and strength of those connections. I think there\u2019s just a lot of activity to be mined and there\u2019s companies like Centralize and others that are tackling it from the outside, since you know it\u2019s a gap in what LinkedIn\u2019s done right now. But I think that was an opportunity that I missed and is still kind of missed in Sales Navigator today.\u00a0<\/p>\n<p>23:13 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>I think that is the hardest part too is understanding the true connections, Because nowadays everybody is extremely connected over LinkedIn. It\u2019s an incredible platform for that connectivity, but it is hard to infer the context of those connections sometimes.\u00a0<\/p>\n<p>23:28 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>And I think it\u2019s hard in product management in general. I think it\u2019s hard not to just keep building features Like one of the things I have such great admiration for Google for doing In product management in general. I think it\u2019s hard not to just keep building features Like one of the things I have such great admiration for Google for doing. I mean, they\u2019re what? 25 years old now and it\u2019s still. I mean they finally added a link, you know, for company or ads, like you know, but it\u2019s still the search bar.\u00a0<\/p>\n<p>23:49<\/p>\n<p>And if you remember when they came out, it was the era of portals. It was all about, like you know, your news homepage and all your information. And to have that level of discipline to say like it\u2019s so important that we have a simple interface and it\u2019s really fast, and to not and say that\u2019s always the number one feature. And I think very, very few companies and product managers kind of have that level of discipline to keep doing that in their products. And that\u2019s why you end up with a lot of these big, bloated products after 20, 25 years that are really hard to use.\u00a0<\/p>\n<p>24:21 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>And sometimes the products bloat. We\u2019re also seeing sales tech stacks off of the bloat now too. You know the average rep\u2019s juggling over 10 tools. Why do you think that the modern sales tech stack feels more bloated than ever right now?\u00a0<\/p>\n<p>24:37 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Well, I think it\u2019s. You know, I think it was just, you know, part of Salesforce\u2019s brilliance was the whole AppExchange program and all the APIs early on, and they realized, like we can\u2019t do it all ourselves, so we\u2019re going to open this up and let a lot of other pieces plug in. I think the failing of Salesforce is that they didn\u2019t continue to innovate, you know, and catch up to that stuff themselves. Right, because there\u2019s, you know, there\u2019s a lot of companies. Frankly, that should just be core functionality of Salesforce. I mean, if you, I mean, and these are great companies, but you look at a company like Scratchpad, for example. They, they\u2019re was just like. It is such a pain to put data into Salesforce. We\u2019re going to create a browser interface so you can do inline editing. Clary\u2019s initial value proposition was hey, listen, it\u2019s impossible to see what my forecast is or my pipeline looked like a week ago versus today. Let me just give you a visual snapshot of that. Like, these are all features that Salesforce should have built right, and as a result, you\u2019ve got all these other products that have kind of gone on and it was kind of like.\u00a0<\/p>\n<p>25:44<\/p>\n<p>I think products go through this cycle of like you know best of breed and you have a bunch of these things and then the cycle changes and then you start having consolidation in this whole suite, right? So if you walk way back to the early days of productivity software, microsoft upended things with Microsoft Office by consolidating word processing and spreadsheets and presentations. Same thing with Google when they did their suite, and I think then you start looking at oh, now I\u2019ve got Notion, and now I\u2019ve got Airtable and I\u2019ve got, you know, otter or different call recorder, granola, whatever you want to use, and I think that will you know. Those things all go through cycles and I think we\u2019re due for a cycle in sales tech and I think that what I see happening is I\u2019ll call it the big consolidation, right? Companies realize they\u2019re spending way too much money on different tools that each do one thing kind of well and they\u2019d much rather have a suite that is easier to use, makes the reps more productive, is a lot more cost effective and does 80% of the things that they need.\u00a0<\/p>\n<p>26:49 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Do you foresee greater M&amp;A around that large consolidation period or, more so, the building out of different necessary features from more of the big tech companies?\u00a0<\/p>\n<p>27:01 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Well, I think it\u2019s hard for some of the big tech companies. I mean, you have to remember, salesforce is 25 years old now, hubspot, I think, just turned 19, 18 or 19. Like that\u2019s an old tech stack. It\u2019s really hard to do that and, trust me, when I was inside Salesforce we tried to. I mean, there were teams that were trying to build basically starter SMB CRMs and Salesforce has a ton of great engineers, ton of great user interface designers right, there\u2019s no lack of talent for going to build that stuff from scratch.\u00a0<\/p>\n<p>27:38<\/p>\n<p>But the problem is when you have to go put it on the stack and make it backwards compatible with the upgrade path. It just means like you could have this great starter experience and then you suddenly upgrade it to professional or enterprise edition and everything you know degraded. So it\u2019s really they\u2019re in a tough position on the low end. Frankly, I think companies like you know who are in second or third place you know, or third or fourth place, even, like you know, dynamics or other folks. I frankly think the only way they\u2019ll ever leapfrog or have a chance of leapfrogging Salesforce is to basically hit the reset button and start with something where they can have an entirely new experience and also migrate their older users over.\u00a0<\/p>\n<p>28:14 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>How much of this do you think is related to building AI natives? Like I\u2019ve heard, you refer to the pre-ChatGPT times and some other podcast episodes that you host, actually as BC, which I love, and I guess that makes the time after ChatGPT AC, if you will. So how are you thinking about around consolidation?\u00a0<\/p>\n<p>28:36 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, I think it\u2019s just a very different. You know, frankly, if you were building software before the internet, you made certain design decisions. If you were building software before mobile, you made different design decisions. And we\u2019re in that same huge inflection point and, frankly, it\u2019s the biggest one in my entire lifetime of AI. Same huge inflection point and, frankly, it\u2019s the biggest one in my entire lifetime of AI. And I think if you were building stuff before, you then are trying to glue pieces on the side and glue AI on the side.\u00a0<\/p>\n<p>29:03<\/p>\n<p>We have a saying at coffee you can\u2019t have good AI with bad data and, as we know, most of the data inside of CRM is not great, and so I mean I\u2019ll give you a simple example, great. And so I mean I\u2019ll give you a simple example like in Salesforce, unless you\u2019ve attached something like Snowflake on the side, or now they have their data cloud, but it\u2019s a separate product again, it\u2019s not built in. When you update a field like stage, you\u2019ve lost the old data. So you have no history to know like this, this much time in this stage, or this was you know? Here are all the actions that happened. You\u2019re kind of overriding and losing data and if you really want to have a predictive system and I think what an ai native system is, a system that is constantly learning from the data inputs it has and knowing like, oh well, if this rep, you know, forecast this way, this rep forecast this way, it\u2019s constantly kind of figuring this stuff out. You can\u2019t do that unless you have all the data and you don\u2019t throw it away. And that\u2019s a great example of you know. Frankly, even Adio is a fantastic, you know, kind of next generation. I would call it CRM, but it was also built BC before ChatGPT, so they don\u2019t have that architecture where you know you\u2019re constantly holding on to data.\u00a0<\/p>\n<p>30:17<\/p>\n<p>And I think things that are AI native are we\u2019re a belief. Some folks believe it can all be unstructured data. We believe it has to be both structured and unstructured data. But we are we lean in very hard to make sure that the data that we\u2019re pulling from your calendar and email is super high quality. We\u2019re enriching it. We\u2019re pulling in your conversation data. We\u2019re going to be pulling in your product usage data, your customer service data, your marketing data. That all has to sit in the proper format because then when you can feed that to AI, then you get these amazing insights. But you have to have that history and it\u2019s very. The only way for the kind of the legacy players to go do that without completely ripping out the engines on the plane in flight is by continuing to bolt things onto the side. So Salesforce will sell you everything, but it\u2019s going to be multiple pieces that you have to stitch together.\u00a0<\/p>\n<p>31:10 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>That makes sense and you spent years helping reps understand buyers and now, with Coffee, your company, you\u2019re helping teams understand each other and data. What inspired the shift?\u00a0<\/p>\n<p>31:36 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>another startup and, uh, kind of three things came together at once. One was we built out our own go to market stack. I went wow, this is still kind of a shit show. It\u2019s too expensive, it\u2019s way too complicated. This is crazy that we have to spend this much money and buy this many tools, as you said, to stitch together all this stuff just for a early stage company. Uh, two was, as we just talked about, like everything we were, every tool we were using was built BC before ChatGPT, and I just think the design decisions were just different. And the third was, frankly, watching Rippling you know the powerhouse company in the HR space build this what they call a compound startup, and so Rippling\u2019s.\u00a0<\/p>\n<p>32:11<\/p>\n<p>For those who are not familiar, rippling didn\u2019t just go in and say we\u2019re going to build a better payroll system. They said you know, the employee record is the axis around which all of these HR apps and even other kind of IT and finance apps rotate. Employee record and payroll is a great wedge for that. We\u2019re not going to be able to build everything at once, but let\u2019s build the front end and the back end with the end. State in mind that ultimately we could offer up many, if not all of these apps ourselves over a long period of time, and in the short to medium term we\u2019ll just integrate in with a ton of different other apps, and so that was kind of the final unlock for me, which is a lot of sales tech ends up being we\u2019re going to solve this one problem.\u00a0<\/p>\n<p>32:58<\/p>\n<p>And you know, some companies some of the ones we mentioned and others get to a hundred million dollar plus just kind of solving that one problem. But then invariably they kind of look up and they go, okay, what\u2019s next? And then they try to acquire or build their way into it, and that\u2019s challenging. And so I think what we did at Coffee that I think is very different than other companies is say, okay, what does that end state look like? And we just realized there was no way to really solve the go-to-market problem unless you were solving the CRM problem. So that\u2019s where we started.\u00a0<\/p>\n<p>33:31 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Very cool and, for anyone unfamiliar with Coffee, give us maybe a two-sentence overview.\u00a0<\/p>\n<p>33:36 \u2013 <strong>Doug Camplejohn (Guest<\/strong>)<\/p>\n<p>Yeah, so Coffee, we call it the AI-first CRM that works for you, and that\u2019s because most CRMs today feel like you\u2019re working for it instead of the other way around. And we\u2019re actually launching three versions of Coffee, and so there\u2019ll be a. We call it single shot, so it\u2019s a one user version of the product. So every rep I know has their own shadow CRM. They have some combination of Notion or Evernote or Granola and Fathom and Google Sheets or Excel Doc, and that\u2019s how they\u2019re really keeping track of their pipeline, and then they\u2019ll selectively copy and paste things into the CRM for their manager\u2019s benefit. Right, that\u2019s just broken, that\u2019s fundamentally broken. So we want like what I saw in Sales Navigator is that reps would be like this makes me more productive, so if my company won\u2019t buy it, I\u2019ll just swipe my own credit card and I\u2019ll buy it myself. And we want that to be the same case with coffee. So you\u2019re like, hey, listen, if you\u2019re using Salesforce and you\u2019re like, okay, this is just, this is painful to go use, but so I\u2019m keeping my shadow CRM, you can still swipe your credit card and buy a one seat license of coffee and make yourself more productive.\u00a0<\/p>\n<p>34:47<\/p>\n<p>The second audience is you are a small startup. You\u2019re graduating from spreadsheets or maybe you tried a CRM that\u2019s not really working for you. Yet we can be that CRM. The big difference is that it is so automated that you connect your Google account, you connect Zoom and all of a sudden it\u2019s populated. You\u2019re just going about your daily work and the CRM is keeping up to date for you.\u00a0<\/p>\n<p>35:09<\/p>\n<p>And because we\u2019ve built these high-end scale systems, we don\u2019t think we\u2019re going to hit the ceiling the way other systems like HubSpot or Adio or Zoho or, you know, pipedrive and others have in the past. And then the third version of it is we\u2019re building a companion. We\u2019ve basically done real-time integrations with Salesforce and HubSpot, real-time integrations with Salesforce and HubSpot. So if you are that company that\u2019s spending hundreds or thousands of dollars per rep on a dozen different tools and you\u2019re like I really want to consolidate some of these, we can consolidate some of that stack for you and still allow you to keep Salesforce or HubSpot as your system of record. That was more than two sentences, but that\u2019s coffee.\u00a0<\/p>\n<p>35:48 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>It was pure value, so we\u2019ll take it. But that was. It sounds like you\u2019ve really baked in all the different learnings throughout your entire career and experience and seeing firsthand where the pain points are into the new product, which is really, really exciting.\u00a0<\/p>\n<p>36:01 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, it\u2019s really been fun. The last year has been a blast, and I think that, in some ways, the best products are when you\u2019re building it for yourself, or when you\u2019re building it for yourself and you know, I mean no day like Salesforce is a great company, hubspot is a fantastic company and they\u2019re great products, but I, for me, personally, I was never putting data into them because it was all manual and I\u2019m just that\u2019s not how my brain is wired. With coffee, which we were on one of those CRM systems before, and we switched at the beginning of this year to dog food, our own product I just I have meetings, I send emails, I like you know, I take some notes and it\u2019s just automatically there. And then, like, my calendar for today is like here\u2019s your AI generated meeting briefs for all your meetings today and at the end of the day, I can just click the follow-up button on every meeting and here\u2019s an AI-generated email that\u2019s drafted from the call transcript I just had and I get these notifications that are hey, listen, it seems like for that last conversation, you might want to update these fields in your deal, so do you want me to do that for you?\u00a0<\/p>\n<p>37:08<\/p>\n<p>And so we were kind of like nudging you along in that process as well. And then finally, like I should just be able to, the same way, I ask a question of ChatGPT. I should just be able to ask that of my CRM. Like you know, I shouldn\u2019t have to go spend a bunch of time building reports for weeks and weeks. So that\u2019s kind of how we think about it and a lot of ways I\u2019m just building this for myself Explains why you are one of the busiest yet most responsive people.\u00a0<\/p>\n<p>37:33 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>And how is it different now building AC, if you will so, after ChatGPT, compared to previously, before? What are you doing differently?\u00a0<\/p>\n<p>37:41 \u2013<strong> Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, I think what\u2019s really interesting and I was chatting with Richard White, the CEO of Fathom, at this as well, because I don\u2019t think it\u2019s talked about that much is building with AI is still a little bit like, you know, building a bespoke suit, right, it\u2019s not like you can just say here\u2019s a bunch of data, let me go throw it at this. You know open AI or a cloud or you know Google model, and I\u2019m going to get great results. There\u2019s a lot of tuning and tweaking and being like okay, let me do prompt engineering on this, let me figure out how to format the data properly and give you. So there\u2019s a lot. It\u2019s almost like this iterative process. That\u2019s very different than traditional software design I\u2019ve done in the past, where it\u2019s like, okay, here\u2019s the user interface screen and let\u2019s go connect it to the database. So there\u2019s this in-between step that there\u2019s a lot of kind of nuance and creativity in, which just means it\u2019s really exciting.\u00a0<\/p>\n<p>38:34<\/p>\n<p>And you know, what we\u2019re trying to build is we have an assumption that the models are the worst they\u2019ll ever be today and so it just gets better. So start with really making sure the data is in the right format, and we might have to do a lot more work on prompt engineering right now. That might not be the case in the future, but we want to basically give people the ability to have these kind of insights just automatically served up for them. I mean, if you want a great prompt, we do this thing in the product that just automatically looks at your website and comes up with a description of what your business is. So when you\u2019re creating a briefing, it should say oh, I know what GTM fund is Right and I know what my product is, so I can kind of map those two and like let me think about what that conversation is. So it\u2019s just a lot of super smart stuff you can do when you are bringing the right data to bear. But it is by no means just plug into the OpenAI API and you\u2019re done, yeah.\u00a0<\/p>\n<p>39:35 \u2013<strong> Sophie Buonassisi (Host)<\/strong><\/p>\n<p>And inevitably agents is a huge conversation right now. How are you thinking about or incorporating agents right now in the product or in your go-to-market?\u00a0<\/p>\n<p>39:44 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, and I think, like I\u2019ve talked to a bunch of folks like Joe Mura, who\u2019s the CEO of Crew AI, super smart guy, other folks who have been building agent-like technology, and I think that there\u2019s a lot of stuff that\u2019s really people are calling agents. That is really just workflow, like if you say, if this happens, do this, that\u2019s not really an agent. An agent is like you give them some autonomy, so an agent is actually you\u2019ve gone in and said so you can almost think about them as employees, right, and I do think that, like the AISDR is a good example of that, although there\u2019s some bad versions of that. But I think it\u2019s ultimately about saying, just like you would in training an employee how do I educate you about my customers, my ideal customer, my buyer persona, my products, my competitors, all of those things, and how do you let it go through a process of automating some of those stuff? And so I think we\u2019ll have SDR agents that get better. I think we\u2019ll have CSM agents that are getting better. We\u2019ll have RevOps agents that get better, that are just on these continuous tasks, like we had this group at LinkedIn called BizOps, and to me it\u2019s like agents are.\u00a0<\/p>\n<p>40:53<\/p>\n<p>Ultimately, the ideal state of agents is if you could replicate even a fraction of what that team did, it would be phenomenal because they would constantly be forward seeking things like okay, what is the moment in which somebody is a committed Sales Navigator user? So they would do all this analysis and they look at all the data and they\u2019d be like you know what, when somebody does three searches on Sales Navigator or saves their first list, they\u2019re 2.4 times more likely to you know, stay on and not churn. That should just be an agent Just be constantly looking at the data and saying, hey, I found a pattern Like here\u2019s something to go do. Or we would ask questions like what\u2019s a bigger market opportunity for us? Going after new logo customers or going deeper into existing accounts. Again, that should just be like an agent that\u2019s constantly looking at the data that\u2019s out there and saying like, hey, I\u2019ve got this insight for you and serving it up. And so that\u2019s where I\u2019m very excited about the possibility of agents. But I think we\u2019re just scratching the surface right now.\u00a0<\/p>\n<p>41:49 \u2013<strong> Sophie Buonassisi (Host)<\/strong><\/p>\n<p>The speed at which startups can build with that kind of data at their disposal would just be incredible.\u00a0<\/p>\n<p>41:55 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, no, it\u2019s amazing, and things like the MCP interface on top of Claude that lets you kind of wire up different apps and kind of put those things together is becoming incredibly interesting. So, yeah, I think it\u2019s like the sands are shifting very quickly. There\u2019s never been a time in my entire career and I\u2019ve got a few gray hairs that it has been this exciting or changed this quickly.\u00a0<\/p>\n<p>42:24 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Absolutely. And the inevitable kind of spicy question that everyone\u2019s talking about, Doug, is what do you think of the SDR role in the next, you know, three to five years with AI? Any thoughts on that being so close to the role itself, even AEs?\u00a0<\/p>\n<p>42:41 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, I mean listen, I think like I hope all the boring shit gets automated right. So, like, what we\u2019re trying to do with coffee is like I shouldn\u2019t have to go log meeting notes and I shouldn\u2019t have to go, you know, get reprimand\u2019s an example of just like what AI and good automation can do. I think that the AI SDRs have are probably more promise than reality today, because a lot of them came out and effectively just became spam cannons. So if you\u2019ve got a bad process, you know you don\u2019t know who your ICP is, you don\u2019t have good messaging, you\u2019re not targeting that. Seeking an automation on that is just gonna, you know, do worse at scale, right, but I do think that a lot of things are getting automated very quickly.\u00a0<\/p>\n<p>43:32<\/p>\n<p>Like you know, we had Amanda from One Mind was on the Revenant Renegades podcast and they are handling a bunch of inbound stuff in an amazing way where I mean, let\u2019s be honest, most people don\u2019t want to talk to a salesperson. They\u2019re doing most of their research than they can up front and if they can just interact with somebody, that today you can kind of tell is fake and probably not too distant future it will look just like this conversation I won\u2019t be able to tell distant future. It will look just like this conversation. I won\u2019t be able to tell, but I\u2019m talking to somebody who has the knowledge of all the systems engineers in my organization, all of the. You know all the best practices, so you\u2019re never going to have to be in a meeting and be like I don\u2019t know the answer to that.\u00a0<\/p>\n<p>44:14<\/p>\n<p>Let me get back to you, right? So I think a lot of that initial qualification, a lot of the initial discovery call stuff, and there\u2019s actually companies now that are thinking about we want to have a buyer agent that will go if I say I want to go buy I don\u2019t know call recording software, let\u2019s just say and there\u2019s 22 of them, right, here\u2019s my requirements Go, set up meetings with these 22 companies, go listen, go have sales meetings with all of them, get all of this stuff and normalize it into a table for me that is specific to my needs, and so it\u2019s going to be AI buyers talking to AI sellers at the top of the funnel and just automating a lot of that process, and I think that\u2019s a good thing. So I think there will be job loss that\u2019s going to happen in this, but I also think it\u2019s an opportunity for people to upskill and uplevel into higher value roles.\u00a0<\/p>\n<p>45:07 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Absolutely, and I\u2019m sure there will inevitably be a lot of roles that we don\u2019t even foresee that emerge to from this rapid change.\u00a0<\/p>\n<p>45:15 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Always, always. I mean people have the same conversation in the agricultural to industrial revolution and the industrial revolution to the information age, right. So you know we\u2019re just going through another big change and, as you said, I think that I\u2019m an optimist at heart. That\u2019s part of the entrepreneur. You know mindset and I think that if you zoom back the aperture, you know, I think it\u2019s up and to the right, right in terms of where this is all heading. I think when sometimes you get very narrow, you can be in these wild. You know ups and downs and it can look, you know, bleak or you can be overly enthusiastic or overly pessimistic, but I think that this is all net positive.\u00a0<\/p>\n<p>45:53 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>And you mentioned earlier that you\u2019re a product guy. What are your thoughts around AI and product now, as product becomes even easier, if you will, to build? Still very much, so challenges and tribulations, but at the same time, what does that mean for your moat as a company, any company?\u00a0<\/p>\n<p>46:13 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, it\u2019s a great question. I mean, like we had a team. You know we\u2019re a remote team, but we had an in-person session recently, because we get together every few months, and my CFO was like vibe coding an internal app, right, and in like two hours she had built an app for, like, onboarding new users and setting, adding people to the white list, and I\u2019m like this is insane, but I think it\u2019s it\u2019s like 80 of the way there. I think it\u2019s great for prototyping today, right, and this is changing fast, but I think it\u2019s a lot of um. I still think there\u2019s value in creating package software and in complete experiences where you\u2019re building the interfaces, you\u2019re bringing all the pieces together.\u00a0<\/p>\n<p>46:53<\/p>\n<p>Despite what Klarna said, you know, a while ago, they\u2019re like, oh, we\u2019re doing away with Salesforce, we\u2019re just going to build ERP and Salesforce automation ourselves and we saved these millions and millions of dollars. And, of course, then a few months later, they were like okay, we had to go buy Salesforce, right, because this stuff is harder than it looks. I do think there\u2019s a lot of people who will build custom stuff and there\u2019s always been people. I mean, if you go back, you know, decades, Goldman Sachs was building a bunch of their apps in-house because they wanted all this proprietary advantage. And again it goes through these cycles where they\u2019re like we\u2019re going to build it all ourselves, we\u2019re going to buy package software, we\u2019re going to build pieces, and I think it\u2019s going to be the same thing with AI. So this notion that, like, no one will buy package software, everybody\u2019s going to vibe code everything themselves, I don\u2019t buy, I think, but I do think that there\u2019ll be a lot more creativity.\u00a0<\/p>\n<p>47:45<\/p>\n<p>And as far as moats, I do think data is a very interesting moat, and so I was talking to Sam Jacobs from Pavilion earlier today. They\u2019ve got 10,000 members in that network. They\u2019ve got a phenomenal set of data that\u2019s been built over the last 9 or 10 years that you can start to encapsulate some of that expertise. In our case, I think when you\u2019re having all of these conversations, with your call recorder stored in one place, combined with your emails, combined with your you know notes, combined with your website and product interactions, all of that data coming together is just hard to replicate, and I think that becomes an interesting moat when somebody is like this knowledge is not easy to replicate when I go to a new system. Knowledge is not easy to replicate when I go to a new system and that\u2019s why I said like these patterns over time become really important. Because if it\u2019s just like I can go suck data, suck a snapshot of data out of one system and put it into another system, that means there\u2019s not a lot of moat there.\u00a0<\/p>\n<p>48:41 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>But when you\u2019ve got knowledge that\u2019s built up about your organization over time, that\u2019s an interesting moat Interesting, I entirely agree, and actually we\u2019re trying to build the same thing here in GTM Fund, where we\u2019re taking all of our proprietary information data and we\u2019ve built an AI tool and that just helps us better diligence, better serve value to all of our portfolio companies whenever needs surface and so forth. So just taking that unique recipe rather than each individual ingredient, and kind of encapsulating that recipe as the moat right now or one of the moats.\u00a0<\/p>\n<p>49:10 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Yeah, and I think what you guys are doing is fantastic. I think, like the most important thing I would say to anybody right now is just get your hands dirty, just try this stuff right. Try tools, like you know, like some stuff\u2019s going to a bunch of stuff\u2019s not going to work, but, like you know, play around with a bunch of different prompts, read a bunch of stuff, try some vibe coding. Just get really familiar with the tools, because that\u2019s ultimately the organizations and the individuals that are not embracing this stuff are going to be the ones that are left behind.\u00a0<\/p>\n<p>49:37 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>That\u2019s great advice. And, doug, you have a phenomenal podcast actually it\u2019s called Revenue Renegades and you\u2019ve got really great guests on. I love the episode with max. I really like the episode with alexa grable and been listening to a bunch of other ones too. I\u2019m curious around your go-to-market strategy because you are fairly early and perhaps you can speak to the stage that you are with coffee. You know why you investing in brand, in podcasting, and how does that play into your overall go to market?\u00a0<\/p>\n<p>50:08 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>I\u2019m a big believer in kind of rising tide lifts all boats. So I, our kind of go to market strategy is about how can we be of of service right to the audience that we\u2019re trying to serve. So you know the degree that we can, you know, you know, do posts on LinkedIn or the blog, the degree we can do podcasts and we want to have a bunch of events. You know, frankly, they\u2019re not nothing to do with selling the product, but if you\u2019re basically providing value to the audience, I think that\u2019s it just becomes an incredibly efficient flywheel. Right. We have an advisor, chris Lockhead, who wrote the book Play Bigger, which if your listeners haven\u2019t read it\u2019s like the Bible on category creation and startups, and he\u2019s like you should. Every startup CEO should think about themselves as a media company now, and you should think about how you\u2019re thinking about YouTube and LinkedIn and whatever channels make sense for you, and so I think about it that way.\u00a0<\/p>\n<p>51:11<\/p>\n<p>There\u2019s another company, a gentleman who worked with me at LinkedIn, who started this company, leland.\u00a0<\/p>\n<p>51:17<\/p>\n<p>If you haven\u2019t checked that out, oh, that company, yeah.\u00a0<\/p>\n<p>51:20<\/p>\n<p>So Leland is a phenomenal company that started off doing kind of like we\u2019re going to go pair you with a coach to go get your MBA and now it\u2019s gone into, you know, getting into all kinds of different education programs, advancing your career, getting these like certifications, you know, staying for LSAT and those kind of things, and their content strategy is phenomenal.\u00a0<\/p>\n<p>51:42<\/p>\n<p>Like you look at the events page on there and it\u2019s all about like here\u2019s a Q&amp;A with somebody who is a Harvard admissions director or here is like the best way to go advance your career in RevOps or like whatever it is, and it\u2019s all, of course, ties back into their services and offerings, into their services and offerings. But you could have a ton of value out of just attending those services and never buy anything from Leland, and I just think there\u2019s goodwill that comes from that and I also learned in the process. The thing I really enjoy about Revenue Renegades is I invite people on the show that I want to learn from, and every single time there\u2019s some takeaway from me personally, where it\u2019s helping me build my business, learn from, and every single time there\u2019s some takeaway for me personally, where it\u2019s helping me build my business as well, and so I hope, in doing so, that I\u2019m allowing the listeners to to learn something for their own enterprises.\u00a0<\/p>\n<p>52:35 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Kim very much, so vouch for. It\u2019s definitely a podcast that is tactical and you can learn from. So I think you\u2019re doing a fantastic job. Thank you, Thank you and I love that preeming. A fantastic job, Thank you, Thank you and I love that preeming. I always think about it as any company that sells anything is a service company. So if you focus on the service, you\u2019re in service to your customers. Like you said, it really is goodwill. And if you just purely focus on servicing your customers to the best of your ability whether that comes through media, through events, however it is that is what will drive that revenue flywheel and just constantly being in service.\u00a0<\/p>\n<p>53:11 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Well, and I think GTM Fund is such a great example of this. I mean, I think that that I mean you\u2019re selling money right. There\u2019s lots of people who are selling money right, and obviously Andreessen Horowitz, really, you know, a while back, really led this idea of the value added VC that a lot of other VCs copied, which was like we\u2019re going to give you PR professionals, we\u2019re going to give you recruiting professionals, all that stuff, and that\u2019s fantastic. I think that, um, the Slack community, uh, for anybody who\u2019s not in GTM fund, you should go invest in GTM fund, you should go invest in GTM fund. Um and uh, but it is, it is, it is one of the most amazing resources in terms of, you know, people posting like, hey, here\u2019s a great candidate, or I\u2019m looking for a candidate, or I\u2019ve got to, um, uh, I\u2019m thinking about a comp plan.\u00a0<\/p>\n<p>53:57<\/p>\n<p>How do you think about it? I mean, like, I don\u2019t know what the number is. It\u2019s like 300 plus LPs you guys have and it\u2019s, yeah, it just it\u2019s an amazing resource that I would pay just for that access to that resource. So for me, as an investor and a portfolio company, it\u2019s, it\u2019s been such a bonus and it\u2019s that exact example. Like you\u2019re using content with the. You know when you bought sales hacker and made that into GTM. Now you\u2019re doing the same strategy and doing it so well there in terms of that whole community and I just think that that ends up building a lot of goodwill in the audience and just pays back in spades. So I think that\u2019s the way to do it right now. I don\u2019t think the way to go build a startup is or an early stage enterprise of any sort is by throwing a bunch of money at ads or doing the kind of the old school methods. It\u2019s about adding value and doing it through content.\u00a0<\/p>\n<p>54:50 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Adding value, always in service. We\u2019re fairly aligned in our thinking there. Doug, and you shared some incredible hiring strategies tactics earlier in our conversation today. Are you hiring for any roles at Coffee? I think listeners would be pretty excited to build with you as a leader, so if there are any roles, we\u2019d love to plug them in.\u00a0<\/p>\n<p>55:09 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>You know, we\u2019re at June 24th and June 25th we go live on the website and so we\u2019re starting to ramp up our go-to-market efforts, and so we definitely want to talk to some folks in that area and always like, if you\u2019re awesome, I want to talk to you, even if it\u2019s not a role that we have right now. I\u2019m always recruiting, I\u2019m always looking for amazing engineers, amazing, you know, marketers, salespeople, et cetera. But I think that the other thing that\u2019s really changed with AI is, I think, the notion of saying I have to have a company that has hundreds or thousands of employees to get to $100 million. Those days are no longer here. Right, I think?\u00a0<\/p>\n<p>55:48<\/p>\n<p>You know, I think there\u2019s a lot of entrepreneurs right now and Max talked about this in the podcast who will maybe just raise, you know, two or three rounds and be done, and maybe never have to hire more than 100 people to get to a billion dollars, you know, market cap or run rate. So I think that the bar continues to be very high and I think that\u2019s the kind of people we want to bring in, but we\u2019re deliberately going very slow in our hiring.\u00a0<\/p>\n<p>56:16 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>So the goal for anyone listening is to make Doug\u2019s awesome list in sales now. Yeah me also.\u00a0<\/p>\n<p>56:22 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>And if you\u2019re an SE like we\u2019ve had conversations with sales reps, ses, like you know all kinds of folks and and I will have my VP of engineering, dan, be like that person was awesome let\u2019s add them to the list and so we keep the list going.\u00a0<\/p>\n<p>56:34 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>I love it, I love it. And last question here, Doug what is one widely held belief that revenue leaders have that you think is bullshit or no longer serious?\u00a0<\/p>\n<p>56:45 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>You know, I think the whole idea of kind of the classic TAM, right, it\u2019s like, oh, it\u2019s like people are like, oh, my ideal customer profile are companies between this number of employees who you know are in this industry, and that kind of stuff is way too broad, right, I think we\u2019re getting to this era of really niching down, and so I think that we\u2019ve got to look for a lot more signal on that, because I think that the kind of conversations where it\u2019s just, I mean, you get these as well, you get them in your inbox or your LinkedIn inbox.\u00a0<\/p>\n<p>57:26<\/p>\n<p>Hey, Doug, as a fellow Carnegie Mellon alumni, right, who also loves sailing, I, you know that\u2019s. It\u2019s ridiculous, right. So you know, obviously there\u2019s other companies that are really and POCUS is driving the signal stuff with other companies. But that level of I think VPs and revenue leaders just need to abandon this idea with other companies. But that level of I think VPs and revenue leaders just need to abandon this idea that there is this big TAM, that\u2019s this. It\u2019s a bunch of very small, you know, connected micro ideal customer profiles and buyer personas.\u00a0<\/p>\n<p>57:59 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>I love it. I love it. And Doug, where can people find you?\u00a0<\/p>\n<p>58:03 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>On LinkedIn is the best place, so just come, follow me. I\u2019m pretty open. Dcoffeeai is my email if anybody wants to email me directly, but I\u2019m on LinkedIn every day and trying to interact with folks who are following us and come to our website and so we\u2019ve got a waitlist for coffee and so you can sign up for that. We\u2019re going to be letting in new sets of folks every month before we do our GA.\u00a0<\/p>\n<p>58:28 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>Doug, are you a pretty big coffee drinker? I got to ask about the name.\u00a0<\/p>\n<p>58:32 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>I am a pretty big coffee drinker. I\u2019m like you know. I\u2019m trying to keep it to three cups a day.\u00a0<\/p>\n<p>58:36 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>I love it. I love it. I actually gave up. I randomly decided to give up caffeine on the weekend, like this weekend, so I made a cup of tea actually for our conversation beforehand, because I was inspired. Coffee flavored. That\u2019s good, cool.\u00a0<\/p>\n<p>58:49 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>Well, if those of you who don\u2019t know, coffee is for closers. That was the genesis of the name and we\u2019ve just had a ton of fun with it. So we\u2019ve got the coffee shop merchandise place, We\u2019ve got all kinds of different spoofs on coffee.\u00a0<\/p>\n<p>59:03 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>The branding is on point, so LinkedIn email and we\u2019ll drop also the podcast into the show notes for anyone listening. Doug, this has been extremely insightful. Thank you for coming on. Thank you for your time. We appreciate you always, in all capacities.\u00a0<\/p>\n<p>59:17 \u2013 <strong>Doug Camplejohn (Guest)<\/strong><\/p>\n<p>It\u2019s great talking to you, Sophie. Thank you.\u00a0<\/p>\n<p>59:19 \u2013 <strong>Sophie Buonassisi (Host)<\/strong><\/p>\n<p>To the listeners. Thank you for hanging with us and we will see you next week.\u00a0<\/p>\n<p>The post <a href=\"https:\/\/gtmnow.com\/gtm-154-how-ai-is-reshaping-sales-tech-doug-camplejohn\/\">GTM 154: How AI is Reshaping Sales Tech | Lessons from Building Sales Cloud, Sales Navigator and now an AI-Native Startup<\/a> appeared first on <a href=\"https:\/\/gtmnow.com\">GTMnow<\/a>.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>The GTM Podcast is available on any major directory, including: Apple Podcasts Spotify YouTube Doug Camplejohn is a serial entrepreneur and seasoned executive with extensive <a href=\"http:\/\/www.alaskansawmill.com\/index.php\/2025\/07\/08\/gtm-154-how-ai-is-reshaping-sales-tech-lessons-from-building-sales-cloud-sales-navigator-and-now-an-ai-native-startup\/\" class=\"read-more-link\">[Read More&#8230;]<\/a><\/p>\n","protected":false},"author":1,"featured_media":329,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[18],"tags":[],"class_list":["post-354","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-business"],"_links":{"self":[{"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/posts\/354","targetHints":{"allow":["GET"]}}],"collection":[{"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/comments?post=354"}],"version-history":[{"count":1,"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/posts\/354\/revisions"}],"predecessor-version":[{"id":355,"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/posts\/354\/revisions\/355"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/media\/329"}],"wp:attachment":[{"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/media?parent=354"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/categories?post=354"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/www.alaskansawmill.com\/index.php\/wp-json\/wp\/v2\/tags?post=354"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}