SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin

0:01Welcome to the official Sastr podcast where you can hear some of the best Sastr speakers. This is where the cloud meets. Up today on the Saster Podcast. But the biggest real difference with a lot of AI leaders is there's just so much demand, right? Because what's happening in a lot of AI tools is everyone is in market simultaneously. The tools are either so disruptive, like a cursor or replet or lovable, or 11 labs will go from like almost nothing to 300 million this year. And so, of course, if you have insane demand, sometimes with virality, it is going to change the playbook because you're going to be servicing it, right?

0:42And I know, you know, at Bolt, which is one of the leaders in vibe coding, the head of sales there was one of our old sales team, like the old is new. And even there, and I know it's true at Lovable and Repla, just as three examples, they have so much inbound they can't service it. they have insane demand and servicing, but it's the same playbook. It's the same demos. It's the same everything.

1:07Case Haster, imagine having agents for every support tab, one that triages tickets, another that catches duplicates, one that spots churn risk. That'd be pretty amazing, right? Happy Fox just made it real with autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as two cents per successful action. All of it sits inside the the HappyFox Omnichannel AI First support stack. Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com slash Saster.

1:39Hey, everybody. Saster Annual will be back. May 2026, the world's largest SaaS and AI gathering for executives. Just as last May, we hosted 10 ,000 attendees with 68 VP level and above attendees, 36 % CEOs and founders, and 25 % were AI First professionals. It's the very best of S-tier attendees and decision makers that come to Saster Annual and AI Summit each and every year. But here's the reality, folks. The longer you wait, the higher ticket prices get. They're cheap now. They're cheap. So just get them. Early lock in your spot today. Use my code Jason100 for exclusive savings. Get your tickets at podcast.sasterannual.com or just use code Jason100 when you check out.

2:20See you there. Saster Annual and AI Summit 2026. It will rock.

2:27All right, everybody. Welcome back to London. Thanks for coming out. Appreciate everybody.

2:36If you've got, who's been to a Sassar event before? Anybody here? All right. Thank you. We have a tradition. We're usually at the end of these events. In case anybody wants to hear from me, we do an AMA until I pass out. But it's inverted this year because of the timing. We want everyone, I don't know if you've noticed on your teams, people have shorter attention spans these years these days have you noticed it like keeps getting shorter and shorter so tried to compress everything this year we this is just an ama we can talk about anything we'll we'll take questions in a moment just for fun we if on the general topic of like software occasion vibe coding let's see if you're curious i built a game for this event it's vaporcell.ai.

3:26You can play it now. The year is 2049. You're an account executive attending Saster AI London. The product doesn't exist, but the quota is real. You got to play this game. If you play it, it's just for fun because it's kind of a prop for vibe coding, but actually, if you play it and you win, you get an extra 50 % off coming to Saster annual in May. So it's 50 % off 50 % off. It's the cheapest tickets we've ever had. You just have to win. You just have to win this game. And it's actually, you could try it. The fact that I was able to build it in like an hour and a half on Repplet is pretty telling.

4:06It only goes so far. It only does so much. Other things wouldn't work. But it's kind of a reminder that if you want to rebuild something, revive with yourself and your team and it's been built before it it it does get easier so that's just for fun but but if you're bored you can do it here and you'll get an extra 50 off annual or if you went one person or maybe it's three three people to win it not that it's such a great prize but i think either one or three people get a one-on-one with me afterwards too so all you have to do is win the game trick this trick five prospects into buying from you with some jargon ai jargon and then it'll tell you want and there's a leaderboard so it's vaporcell.ai so that's the agenda for today i got i got nothing for now other than general ama but if anybody wants to kick it off with a general question therapy whatever you need let me know if anyone's got got something or i can make something up but anyone got a burning question wants to kick us off go ahead so the question is is inbound dead your traffic's down 50 % in the last 12 months.

5:16It's a good question. Let me step back for what it's worth. I really think this is a part of a woe is me narrative that I think began toward the end of 23 and has accelerated. Woe is you. Your SEO is harder. Woe is you. You don't have as many leads as you had during a lockdown, during a global pandemic. Poor you. And it leads to a narrative, and then I'll be more specific with the answer. It leads to a narrative, which I think is quite dangerous, which is that the go-to-market playbook is broken. It doesn't work anymore. You hear this. It's just not true. Now, here's how I think about it. The playbook that some folks are running from 2021, of course, does not work today or does not work as well.

5:59But here's what I say. The plays all work. Webinars, inbound, outbound, leftbound, rightbound, it all still works. and the interesting thing is if you look at a lot of the hottest ai companies like look at versell they just raised at 10 billion who's this ceo she was the chief business officer at stripe okay look at repli where we just did a whole sk with them there's zero to 250 million already this year vibe coding who's their cro zoom info okay if you go through all of the hot ai companies right now that are vaguely in b2b you will see a cast of characters from the is it the aughts is that what we say?

6:36No, no. From the tens, you will see B2B leaders that you all know from SASTR 2018 and 2017 running the AI companies. That wouldn't be possible if the plays don't work. Now, are they using different tools? Are they using more AI SDRs, things we can chat about? For sure, right? But the biggest real difference with a lot of AI leaders is there's just so much demand, right? Because what's happening in a lot of AI tools is everyone is in market simultaneously. The tools are either so disruptive, like a cursor or replet or lovable or 11 labs will go from like almost nothing to 300 million this year.

7:12We just, I mean, Amelia just literally spooled up 11 labs to do all the intros for all our speakers. Okay. We did it in like, she did it in 10 minutes. We used to have to pay an agency that would take weeks and complain about it and they'd be terrible. And they'd argue of the pronunciation of people's names. No, it's Limpkin. It's Jason Limpkin. We'd have to argue and they get angry. We literally did it today in the green room in like 20 minutes, right? That is so disruptive that this demand. And so of course, if you have insane demand, sometimes with virality is going to change the playbook because you're going to be servicing it.

7:46Right. And I know, you know, at Bolt, which is one of the leaders in vibe coding, the head of sales there was, was one of our old sales team, like the old is new. and even there and i i know it's true at lovable and repla just as three examples they have so much inbound they can't service it they have to look at the list each day and i mean i think brian who runs at a bolt is 69 i think he has three people on the sales team or something like four okay so how many leads can they follow up of thousands right so that is different but they're all classic b2b sales reps just instead of calling every lead and trying to convince them their fungible product is the exact same as another product, they have insane demand and servicing, but it's the same playbook.

8:31It's the same demos. It's the same everything. So I know that's not quite the question you're asking, but I do think it's important to understand that the playbooks may not work as well, but the plays are the same. And in many cases, it's the same players. So it's just a lot of folks in market looking for radically better solutions. And at the same time, CIOs and others are cutting budgets for old solutions. there is this it's not a paradox but it can feel like it if you i've written a lot about it on saster i just wrote it up with a bunch of gartner data this year gartner said overall enterprise software is going to grow the fastest it ever has at 15 a year at this scale right i mean it 400 billion it hasn't grown this fast ever but of that 15 almost half is taken up by price increases from existing investors everyone's raising prices and about half of the remaining half is new ai budget.

9:25So that means if you're not one of the ones that they're focused on for price increases or buying more, if you're not adding agent force or you're not an AI tool they want to add to, everyone else has to get cut. So the vendor count is getting stable or shrunk to make room for new offerings and price increases from the select vendors and the new AI guys. So it can feel like there's forces that are either punishing you in a way they didn't used to or their tailwinds. They're tailwinds. And the reality is if you talk to any vendor this year, that's a sponsor. The reason they're a sponsor is because they got tailwinds.

9:59The headwind ones aren't sponsoring anymore. It probably should be the opposite. The ones that have to headwinds should probably be here hustling for customers. And the ones that are tailwinds should be just back in the office, wondering what to do with the surplus of leads. But this is the, this is the odd, odd, odd thing about marketing. So that's the world we're in. and we can chat more about it folks have follow-up questions specifically on it is inbound dead so no inbound isn't dead the the art is like artisans that's here unqualified we know them pretty well we were just talking with the head of smb at salesforce asian force all of them have more demand than they can service all of them it's actually interesting they all have the same kind of issue is there's just not enough forward deployed engineers not enough solution are done enough folks to get the agents going they are all turning away customers because they have too much demand for an agent they can do everything for them so inbound isn't dead is seo dead if you're writing the classic playbook right i'll tell you our seo at saster here's an that looks we saster's a lot of things we do events we do a podcast we do multiple podcasts we got a podcast with harry we got two youtubes we got tweets but our blog if you've been with us for a while our blog is like our core it's like home base okay and our blog traffic was fairly flat for about four years going into this year our seo is down eight percent not not 50 but eight for real we can track it but our traffic's up 50 traffic is up 15 going up our viewership we will end this year at sastra.com twice as many readers as last year even though our seo is down now our seo is down eight percent and i think folks like g2 have said theirs is down like 30 or 40 percent or more so if that's your only play and you got no ideas and you haven't changed your product or your gtm since 2021 it's probably going to feel at least eight to 50 percent harder but for us like actually don't i mean most of our team is ai agents now so we don't really have anyone to tell me why our our viewership is up but i can tell you when i look at the content it's because people all want to read about ai gtm content okay they don't want to read about classic saster themes about cs teams and cros it turns out unless there's an ai thing they don't want to read it but because we have some of the best ai gtm agent content out there people are just devouring in.

12:15Okay. And if we could sell that content, I mean, Amelia and I would buy islands. Okay. If we could sell because the demand for that content is so high. So my point to everything is you got to find that this is like my other talk tomorrow. You got to find the tailwinds and lean into it. There is AI budget. There is AI budget for new vendors at the CIO level. And if you're an existing, if you have existing customers and you have something that truly changes the game for efficiency, it truly changes. You can replace lots of humans for your agent. Your customers are going to want to meet with you and they're going to want to buy it, right?

12:48Salesforce is at 42 billion growing like 9%. And I know they're a public company, but I'm pretty convinced if they could deploy agent force overnight for every customer, they could grow twice as fast, right? So find that tailwind. That's your job right now for your teams. Figure out what it's not building a copilot or putting AI in your homepage. It doesn't create budget and it doesn't change. It doesn't change how your customers do business, right? What can you do with AI to make your product 10 times better? And it's probably replacing humans for many of you, even though people think that's a tough topic.

13:22That's the reality. It's replacing humans in some fashion. That's why customer success took off. I mean, support took off so quickly because if you train a support AI pretty well, a lot of folks really have replaced 20 to 50 % of their support team. Even Mark Benioff, I think, redeployed 3 ,000 or 5 ,000 folks in support even there at Salesforce. we all know tons of folks that have done it. Sierra just said they went from one to a hundred million in a year. Brett Taylor, ex, you know, ex CTO of Facebook, co-CEO of Salesforce, just going out to people and saying, you can replace a lot of your support teams with AI.

13:55So you've got to find your version of that, your, your tailwind to grow. But if you're running the exact same playbook as 2022, nothing's changed. Yeah. That inbound's going to be harder. SEO is down and vendor consolidate. The odd thing, and I will take another question. It's just such an odd thing when overall B2B software budgets are at a record size and accelerating, plus 15 % at hundreds of billions of revenue, according to Gartner. And folks that have product market fit with AI B2B are growing like crazy. But at the same time, it's not free. People think that CIOs have infinite budget. They don't.

14:35There's a little bit of elasticity. But at the end of the day, companies only have so much revenue and they only have so much profits and they can only apportion so much of that to software and IT. And so it's not all free. And when they're giving this money to these hot AI companies, they're cutting it from everybody else. They are cutting it from everybody else. And if they're not arguing with you on renewals, and a lot of folks have felt it, it's worse. They're calling up vendors and saying, we're just cutting back this year. were just, and if you guys haven't ever been at it, in my brief tenure as a VP at Adobe, it was pre-AI, but I lived it as a VP at Adobe.

15:10And you'd go around the room and you'd say, there were human layoffs and there were app layoffs. Okay. And everyone at the boom of cloud wanted more apps and they'd say, fine, but everyone go, every single VP around the room, give me one or two to cut. You'd have to cut one or two. And it's still happening. It's just done more from the top down at the CIO level. So if you're on the bubble, if you're an attachment to a CRM that you don't quite need, right? This is where, you know, so many folks, you know, outreach and sales off struggled and Gong took a lot of this market because Gong built everything.

15:43And, but one of the things Gong did is they stole budget from sales off and outreach and other folks, right? They stole it. And it's already happened for this calendar year, but CIOs and others have gone around the room and said, give me an app, give up an app or give me two. If you want to add one next year, you want to add a couple of apps, I'll find your budget. You got to give up two. You got to give up to you have a hundred like marketing tools. You need a hundred, maybe 96 is, is enough. And, and, and I, I find even in my own investing portfolio, I just got an investor update yesterday of a pretty successful company.

16:19That's partly through its AI transition. They're at mid eight figures in revenue. They had a million and a half of trim last month, a million and a half of trim last month from happy customers that, you know, no CSAT issue. issues no other issues they literally said just we're cut they're cutting apps next year we're an attachment we're an attachment to cera and we got cut and the ceo who i love to death failed they failed as a team because they didn't get above the cut line they now they didn't lose all their customers but they lost two that's a 1.5 million last month not because it didn't work it wasn't great and not because they didn't have ai in it but because this two cios just went around the room and that was the one that got cut.

16:58It was great to have, but not mission critical. And it got cut to make room for another AI app. In fact, one that's also speaking at this event. All right. Anybody else got another question?

17:12Hi, I'm Patrick. Quite a specific one. In a podcast the other day, you said something along the lines that AI SDRs didn't work, but then Sonnet 4 and now it works. Can you elaborate a little bit on that? It's a rich question. two different threads one we really none of these products these sdr products i think worked before claude 4.1 sonnet or claude 4 this year right repli didn't work lovable didn't work base 44 didn't work nothing i mean they were out there they weren't very good until the magical moment when claude 4 came out and everything was kind of magical gamma didn't gamma was around since 20 We read about Gamma, and we love Gamma for AI presentations.

17:56One to 80 million it will do this year. But it was founded in 2020. So it was five years to one million, and then one to 80 this year. It's not a coincidence that all of these apps took off January, February, March of this year. That's when the LMs got better, okay? So in a way, it doesn't matter. But if you bought a lot of overhyped go-to-market SDR tools before February, March, or April of this year... they just didn't work well. Right. And, and I mean, literally we were a million, I it's on our saster.a slash agents website. We were at this company qualified that does AI inbound and outbound.

18:34We use it on a website and we were with the CEO that they've been around for like five years. He was the ex CMO of Salesforce. Okay. They've been doing this for trying to use AI to qualify inbound leads since like 2019 or something. Okay. Repeat founder, great guy. I'm like, I don't have any of your numbers, but this really took off around February, march this year right it's like yeah like that's what your product actually worked he's like yeah that's when it finally actually worked after five years right same with gamma replic was founded almost 10 years ago right and blew up it'll go it was 10 years to a million and then one to 250 million so so you kind of almost after if you had it's let it's less an issue for this room than maybe the maybe the the less techie of the world but if you had a bad experience with almost any AI, LM, GTM, other product before March of this year, write it off.

19:23It was a different time. It was different LMs, different world. Okay. That's a base point. The second point, which is not the same question, but it's related. Plenty of folks, whether they tried to deploy an AI sales agent before or after Q1 of this year, so many folks just told someone on their team to do it or hired an agency that didn't know what they're doing. Okay. Literally Amelia and I were on a call with global technology leader. We all know and love. We've all heard that's pretty AI forward. Okay. Pretty impressive company and said, we're, we're, we're thinking about buying our first AI SDR.

20:02We're just going to buy it and hand it to our SDRs and have them figure it out. Have them figure it out. It's not going to work. You got to train it. You got to train it for a month. You got to train it every day. You've got to iterate an onboarding. So that's another failure mode that I've already heard like 10 times since I've been here today. folks like well if i can i just buy one of these tools and turn it on and walk away you can't we've said this in every workshop wednesday the million i've done with every other speaker it still doesn't work so one failure mode was like pre the fours pre pre you know clod four and gpt four pre the four is the stuff digit the lms weren't good enough and the other one was we bought it and and just turned it on and we didn't magically get millions of revenue don't work that way right and the real way if i just summarize it and we'll talk a lot about it at this event here's the other mistake folks make if you want amelia makes this a lot of times on our on our live webinars or work ai workshop Wednesday and Wednesday here's the captain obvious thing for any ai sdr bdr even aes as we do more of them csms first you gotta have it work in the real world with humans then you tell the ai what worked that you there's no magical prompt okay the prompt is here's the script that i use with a customer that i closed then you iterate that prompt and then you hook it up to data like Salesforce or HubSpot or other sources of data or Snowflake.

21:21And then you have to ingest the data to keep working with that prompt to make it better. It's not that complicated. Okay. So many folks are like, oh, well, Saster's AI SDR works because you have inbound leads. I'm like, well, everyone has some inbound leads or it's just, you know, you've got the only, as long as you closed any customers, you can train the AI to be almost as good as you and work 24 seven. It's that simple. but folks think that like i'm gonna buy i have no inbound leads at all i have no inbound i've never done outbound so i have no inbound leads i've never done outbound but i'm gonna buy a tool and turn it on i'm gonna make millions like how the f would that work just this is to the sales rep that got a commission at that vendor but you know it doesn't work and you can laugh but i would say 80 of the conversations amelia do you agree that we have are a version of that i bought a tool i bought a tool and i have no leads i bought a tool and i have a lot of leads but i didn't connect it to my leads it didn't magically work and like so you just figure out what works in the real world and then train the ai to just do it again and again and again with more and more and more data and then read every email it sends read every response it ingests and some of them will be dumb and some of them will be wrong and all these tools have some bit of training and you say hey That was wrong.

22:37You know, SASTR AI London is not December 4th, okay? Or whatever mistake it makes. And you do it every day for about a month. And then the mistakes start to go away and they become recurring and it gets trained on better more and more. It's not that complicated, but you've got to sell it. Just like anything, going back to doing the SASTR, if you can't sell it yourself, the AI can't sell it for you. It's that simple. You can't sell yourself the AI can. So thanks for a big answer, but thanks for the question. So for Legion, for SASTR. Yeah. What do you think, what kind of skills should we uplift in 2026?

23:11And what's the like the golden nugget channel or the main channel? Which one do you think that it's? Well, I'll give you two answers. First of all, for for for marketers in general, for B2B marketers. I talked to I talked to a great marketer when I came in at an AI focused company saying she's pretty confident about her job. Things are going well, but she, she was nervous. The world's changing so much. She was worried for her job. And I said, you should be, everyone should be worried for their job. Every CRO or CMO should be worried for their job. On the one hand, it's the same people in the same place, but there's so much change and you got to get ahead of it, right?

23:52If you don't get ahead of it and build skills, it's going to be hard. So the advice I gave there, and then I'll, I'll give a second piece of advice. the number one basic advice is become proficient at like a couple tools here or otherwise a couple leaders okay right now today if you are world-class at agent force or clay or qualified or artisan or any of the tools here really doesn't matter which one pick two or three leaders that that that have decent revenue that people have heard of and it and and you go through the deployment yourself you do the training we talked about you onboard you get it working in your company and you can point to the metrics, just like Amelia is going to do tomorrow.

24:32Here's how we had 7.2 % open rate, and here's how long it took. And here's how, if you have those skills, you will be infinitely hireable for the next 18 months because only like 2 % of marketers have those skills. So become the expert in deploying agents. And it doesn't need to mean, you know, every agent or even needs to be technical, but you need to pick a few leaders and deploy them yourself. Not, not tell someone on your team to do it, which is what we see. Do it yourself, do it watch it iterate it train it iterate every day spend a week non-stop deploying it and then work on it every single day for a month you will learn so much and you will become infinitely deployable that's sort of at the agent level you know i think on on and just sort of generic demand playbook i don't i i'm still learning i don't have all the magic ideas but i think if you think like like buying geo vendors and just figuring out how to automate LinkedIn posts is going to save your job.

25:30It's not, I think you just, just like always, we got to be careful of LinkedIn bullshit and charlatans because even if it's like a little bit better, it's not going to, it's not going to save you. If the CIO is canceling your app that they like, it's not going to save you. I don't know all the answers, but you need to, it's, it's, it's harder and harder to sell fungible products that don't show massive instant ROI. And I think back a lot, the first podcast that Mark Benioff did with us earlier in the year, I asked him what he thought of Palantir, obviously one of the biggest successes in AIB2B.

26:08He said, he went on to say this a lot. Other times he's like, I'm jealous of how much they charge. Pretty funny. They charge more than he does. But I really love the thing he said next. He said, I'm jealous in a way. I wish, I love what they're doing for forward deployed engineers. And what Mark said was, I wish everyone at Salesforce could go live even before they pay. They could go live before they even pay. Think about this. And this is a marketing and sales weapon. The way we used to buy B2B software for years was, I need a CRM. I need a marketing automation. Your friends would use it. You saw your last company.

26:46you'd talk to a sales rep that could answer six questions, you'd buy it. And if you're lucky by the end of the year, you might deploy it. I mean, in the old days, if you've been around for a while, you might have customers that were new for year two that never even deployed in year one. Okay. That don't fly today. It flies a little bit, but it don't fly much. Okay. What Mark's point was, he said, I know I can't deliver this today. It's not feasible, but the technology is there. I wish every single customer would be live on an agent force or whatever, a gentic sales before they gave me a dollar.

27:17Think about that. This is my best advice. Get as close to that today as you can for your customer. When you look at the ones that explode, the cursors, the gammas, go back and use them again. Think about how much value you get in the free program. Think about how much value you get in the first month. What can you do with AI to provide that much value to customers before they even pay you? If you provide insane value with an agent before they pay you, they're going to be kind of happy to pay you rather than the sucker bet that we all made for for the better part of two decades a sucker bet i think it works like someone gave me a demo the demo kind of works i can't use it myself but i i you know i need that and then half the time it's a horror story so my that's my best idea is make your provide insane value before you get a check and then the percent of your leads that's going to convert it's going to skyrocket It's whatever it is, it's going to skyrocket.