SaaStr 800: 10 Ways AI Is Going to Change Sales. For Real with SaaStr CEO and Founder Jason Lemkin

23:18How did it go? It will know. It will remember. Or if you bought the product, everyone knows that you want to do the 30-day check-in, the 60-day, the 90-day check-in, but humans don't want to do it. They don't want to do it, guys. It's the truth. AI don't mind. AI is happy to do a 30-day check-in. And if you complain and you say, you know what, I'm disappointed that integration with Squarespace didn't really work that I was promised, the AI will say, I'm sorry, you're right, it doesn't work. Here's what we can do to solve it. It will be much better. It will – 80 % of QBRs and check-ins will be done by AI in the next 12 months.

23:49And it's already here. In our AI, it's already here. It doesn't – it's not quite all worked up on our back end, connected. But, man, it will be soon. It will be soon like a lot of these points. Okay, point nine, which I think, and then this goes into things that I think are going to come and happen. Bear in mind, we've been able to do a cheat a lot in SaaS, a cheat in B2B, which is that, look, we'd all love to have apps that are fully self-serve and all this. But if your app needs some onboarding, if it needs some hookups, if it needs some integrations, we plug the gap with people. We plug the gap with people.

24:26so many, almost anyone that sells the enterprise plugs a lot of gap with people, but our AI is going to push us here to do more self-serve because the AI is going to want to get you going on its own. What the AI can't do on its own is get four consultants to deploy your app as humans. AI, it's going to be a while before AI can replace forward deployed engineers and humans configuring your software. And so when the AI can close deals on its own, when it can do the follow-up on its own, when it can do sales on its own, you're going to want a true PLG self-deploying app. You're not going to want an app that requires humans.

25:05You're going to want an app that goes live that second because the support's going to happen, the questions are going to happen, the buy-in's going to happen, and then the AI is going to want to deploy your customer that then and there, not this month, not when the onboarding team has time. So it's going to push us to build better onboarding, more freemium, more self-serve products, even higher up in the stack, even for higher deal sizes, because this is the way AI is going to work. The AI is going to want to get that customer deployed instantly. So there'll just be more of it. And my last point here, and then I'll come up with some predictions, all this stuff outside of number four, which I forgot.

25:37Okay. So I guess it's really nine. All of these, I'm 100 % sure are going to happen over the next six to 18 months because it's already happening in our AI and it's already happening in e-commerce and post support. If you're skeptical of some of these things, and I know many of you You'll be like, there's no way this like Jason AI is going to join the sales call. It's not ready. It's almost there, guys. But don't judge everything that it is today. AI is constantly getting better. For example, our AI has only been live five weeks. Three weeks ago, it couldn't review a VC deck. It couldn't take a PDF and fully review it.

26:07Now it can. And that was just automatically. The rate of change is so fast in AI that don't judge it where it is today. Judge it where you can see it going. Now we've already had hundreds of founders reviewed their VC decks and board decks. If you're not sure if you can get funded, go to our AI, upload your VC deck and ask if it's good enough. It can ingest that deck right now. And here's an example on the right. And I said, we're almost ready for me and Brian Halligan, our AIs, to talk with each other. We try this now at the office. We bring up both our AIs and we have them talk to each other, but they can't quite hear each other.

26:38And me and Brian's digital guys, we talk over a little. It's close. It's close. We try to have these fun conversations where I ask digital Brian and digital Jason what they think of topics. Okay. But, and they're two, two old cotters out on the stoop. They can't quite hear each other. They need a little bit of help. What'd you say, sweetheart? What'd you say? They can't, they can't hear each other, but then here's the founder of the AI we use Delphi intelligence interruptions coming soon. They'll be able to hear each other and interrupt each other coming soon. It's all coming soon. So anything that you see out there that sort of it's working or it's close instead of being a naysayer and saying, it's not going to work invest, dig in.

27:15The rate of change is insane. In five weeks, our AI does so much more than it did five weeks ago. Okay. So just don't judge completely as it is today. Squint or you're going to be left behind. Okay. Now a couple of quick thoughts, and then we can open up to questions. Things that I think are going to happen in sales. I'm not sure. The other ones, I'm sure. I know you're not sure. You're skeptics, but I'll bet you dollars to donuts all these last nine, 10 points. These are things I think are going to happen, but I'm not sure, but people may be missing this. Okay, the first one is I'm pretty sure when the AI closes deals on its own, you have to have more pricing transparency.

27:51And if you look at so many of the folks that have broken out early, and we can learn a lot from dev tools and support because those are the areas that are the biggest beneficiaries of B2B. Windsurf, Cursor, my God, lovable bolt. These are all businesses that have rocketed to hundreds of millions of dollars with dev tools in a couple months. But it has also utterly changed Zendesk and Gorgias and Intercom and TalkDesk and Genesis and all those folks too really early. One thing we can learn is that transparency is going to really help. If the AI is going to close a deal on its own, there's only so many pricing games it can play.

28:25It can play a few. It can tell you what list price is. But for example, on our AI right now, if you want to come to Sastra Annual, I would say 50 % of the folks that I've seen do that ask about Sastra, they ask for a discount. Okay. And the AI just gives it to you. The best discount we have today is JSON 20. If you want to use it and you're coming to Sestrator, go to our, go to buy tickets and type in code Jason20. You get 20 % off. Okay. And then they come on. Then they ask the AI, come on, there's got to be a better one out there. And the AI is honest. There were, but we're less than 30 days out.

28:54There isn't. They're used. Six months ago, there were better codes. They're like, come on, you've got to be hiding a code. And the AI is like, honest, I'm not hiding a code. It's Jason20. Now we could probably train the AI to hide that Jason20 code, make you ask a couple of times before you get it. but ultimately you're going to have to dial in a certain amount of transparency if you want the AI to close on its own, right? I'm sure there could be games. You could try to get 18 % off or 16 % off, but the endless games that sales teams like to play on hide the ball, it's just not going to work as well.

29:25You have to give the AI just a tight CPQ system has to really tightly lock down discounting when you get there and bigger and bigger deals. When you have contracting processes for configure price quote, you're going to have to do the same with your AI. You're going going to have to tightly lock down discounting rules and just live with them. And I think it's going to be great. I think it actually, the more friction you take out of a sales process, the more that closes, but I think it will accelerate some level of pricing transparency. AI it's got it. So the AI can do its job related to this. If the AI is going to close deals on its own, like you gotta be, you gotta have customers centric rollouts.

30:01If you want the, if you want someone to talk, discuss, sign, buy, and deploy on the run without a human, maybe a two-year deal is not the right choice. Maybe you're asking too much trust for a two-year deal. We may need more pilots. We may need more opt-outs. We may need more monthly deals. We may see things tilt more toward monthly deals with clear opt-outs rather than screw you and auto-renews. I'm going to ask every AI going forward, hey, is there an auto renew in this contract? Yes, there is. Can you take it out? No, I can't. I might slow it down. Maybe the AI adds the clause for you, but I think we're going to have to have more customer-centric terms so that the AI can close the deal on its own, just especially, right?

30:47Take friction out of it. And I think if nothing else, we may see an acceleration of monthly deals and an acceleration of easy opt-outs. I know sales folks hate opt-outs and they hate pilots, but put your customer hat on. If you're buying from some vendor you just discovered on a chat GBT search an hour ago, you really want to sign a three-year deal with no opt-out? Of course you don't. Of course you don't. So I think that to accelerate the AI closing deals on its own, we're going to want somewhat more transparent pricing and we're going to want more customer-centric terms. And I think it's fine.

31:23Honestly, if you force, if you make it really hard for a customer to leave, but they still leave, you know what? Maybe it makes it a little bit easier to hit the plan for the month, but it doesn't matter because when they leave, all that matters in B2B is your terminal state revenue, your ARR in two years, in three years, in four years. It doesn't really matter what your ARR is today. So masking churn doesn't really help. And I think AI will accentuate the fact that masking churn doesn't help. Okay. The third one, I have less ideas here. This is what I'm curious. But someone wrote something about our AI the other day on Twitter on Axe, and it was obvious, but it was profound to me.

32:00They're like, a great AI fills gaps. A great AI does things you didn't know it could do. For example, our AI alone, we have thousands of speaker submissions to Sasser Annual, to our events, for our podcast. We used to have a team of humans process them. They couldn't do it. But our AI does it now. Our AI reviews their presentation, reviews their ideas, reviews the speaker submissions. I had no idea our AI could do this. I get it now. We didn't even think about it, but Amelia threw in one for now. Everything goes through our AI. Okay, that's an example of a gap. I didn't know our AI could review VC decks really well.

32:36Trust me, put your VC deck in. It's honest in a way humans aren't. One thing I think all AI should do, ours isn't tailored to do it, but yours should be, is it should automatically follow up with a new capability. case study. Let's say you just closed OpenAI as a customer. Your AI should automatically push that case study to everyone in AI, in the space. Anyone that's in the funnel that would be interested in OpenAI as a case study, it should push to them. What I can tell you is our AI does 20 times more things than I thought it would do when it launched five weeks ago. I thought it would just answer questions about SaaS for content.

33:10I didn't know it could do ticket sales. I didn't know it could answer sponsor questions. I didn't know it could qualify sponsors. I didn't know it it could review speaker content. I didn't know it could review submissions. I didn't know it could review VC decks. So I don't know all the things that can do in sales and go to market, but if you hook it up properly, it's going to fill gaps, not just the gaps when your sales team is sleeping or doesn't want to work or is outgoing for a run or is working their side hustle, but it's going to fill all sorts of gaps for your prospects and customers that you didn't even know you needed filled.

33:39It's magical. It's magical for us already. Okay. And I think the last point, hold on, I might I have two more points. Yeah, the last two points. Then we can take questions remaining time. Here's what I think is going to happen. And it's possible I have this backwards, but I already see this. And maybe this is the most existential change that AI will have to sales. I think we're no longer going to tolerate the slow and vendor-centric sales processes that we've had since the dawn of SaaS. Right now, I go to a vendor and I click on a link. And between five minutes and three days later, an AE sends me their Calendly.

34:20Okay, and listen, I love Calendly. Tope's going to be there. He's going to come to Sastron. He's going to ask all your questions about Calendly and the day of AI. But this is not a customer-centric workflow to take days to get a Calendly link from an AE. Our AI never sleeps and is always kind, is always ready to take the meeting. And I think you're not going to be able to sell in 2026 the slightly laconic and I hate to say this because I'm going to make people mad, the somewhat lazy way we've sold the last 20 years, 10 years since I've been in SaaS. Once you have a great AI, this is the thing, you have to, going back, so many people thank our AI.

34:57They love our AI. Once you've had that, and so many people go back five, 10, 20 times already in the first five weeks. Once you've had that wonderful experience, you're not going to want to tolerate a mediocre A, a mediocre SDR that doesn't know the product. You're not going to tolerate it. And you're going to expect, you're going to expect the human experience and the overall sales experience to be as good as that AI. You're going to expect to be as good. and so whether that means we're going to have to step up our game step down our game or whatever we're not going to tolerate the way that selling has been the last decades and sass i know some folks are going to challenge me on this but pretty sure once you've taken once you've had that great hamburger once you've had that great taco once you've had the best steak ever it's really hard to go back to the crowd to eat at denny's it's just really hard and a lot of sales is like denny's today.

35:46It's a terrible, it's truly a terrible experience. And I'm just going to not tolerate it anymore. We tolerated it in 2021. We bought everything we needed because we were locked down. I don't think we're going to tolerate this once everyone has a great AI. We're not going to tolerate slow plotting, somewhat ignorant sales process. It's just not going to be tolerated. Okay. And here's my last interesting question. I don't know the answer to this one. Then we will open up to questions. Will human AEs and SDRs get better or worse in the age of AI? okay? I wrote a post a couple months ago talking about when AI was just started, but before we ran our own AI, talking about mech AEs, mech AEs that I thought what AI would really do is make every AE great.

36:28And I still believe this. Going to our first point, I believe very soon every AE will come to every Zoom with their great AI, with the digital version of themselves. And that will make them only better because they will know everything about the product. They will help them. They won't judge them. They will know all the integrations, all the corner cases. They will know if you barely know your prospect, your AI will know a cold. And if you're actually not sure what your prospect does, your AI will know that two of its competitors already use your product. It will be magical to have this. And so the MEC-AE and the MEC-AE will automate follow-up and the MEC-AE will automate everything.

37:02And so I think it will make them great, but I'm also worried it may make them terrible because if I just wrote this article on SAST or this experience we had, where I'm seeing is a lot of AI SDR outreach is actually really good now. It's really good. And the follow-up is terrible. I gave an example here of, well, we have a podcast, but we really need it to be edited. Great. It needs to be pushed out. It's like a lot of work to produce our podcast. So I got this outbound from this, I guess it's SDR that wrote me the best email in the world. We can fully automate your podcast. We know all about the Sasser podcast.

37:37We know what you need. We know how to improve it. We'll take it all over for you. We'll do all the clips. We'll do the social promotion. We'll upload it to iTunes. We'll do the YouTube. We'll do everything for you. And here's our other clients where we do the exact same thing. I'm like, this is great. This is what we need. I'm in. I didn't even ask about price. I didn't care. I just said, I'm in if you could do this today. And then I turned out it was an AI that wrote it. The sales guy got back to me. What's your podcast called and how many do you do? What's it called? And how many do you do? If you guys know anything about podcasts, and I'm sure almost everybody does just go to iTunes or Spotify or YouTube, and just see how many we do.

38:11You literally, we've done 799 podcasts. We're coming 800. We'll be with Mark Benyap. It's going to be great. It's going to be all about AI and the world's best outreach. And then the AE asked me how many we do. It's an insult guys. It's an insult. So I made this little image up of this guy below. Sorry, talk to my AI on the Zoom. This might be where it goes. We might get better AEs, and I think we will for sure. I think the best AEs, we've got a great new folk that joined our tiny sales team at Sastr. He's already using our AI to answer all these questions, and he's already much smarter about Sastr than anyone that ever started before because of our AI.

38:46He's being a bit of a mech AE. But I got to be honest, I know a lot of folks are going to be like this guy at the bottom. Just like this podcast outreach, I'm not going to do the work at all. Talk to my AI. I'm just here to collect my commission. I think it's going to cut both ways. I think it's going to make some AEs much better. And I think I'm concerned it's going to make most of them worse. And it may be in the contact center where we look at them and like in support, a lot of folks are already laying off 30 to 40 % of their support team that isn't better than the AI. I think you may be at risk as an AE if you're not a MEC AE.

39:18You may get laid off in the next 24 months. Especially for transactional stuff, the AI, you may rely on the AI to do your job, but then we may not need you. I don't know. I think it's going to cut both ways. I'm not sure. I'm waiting to see. This one is an interesting one to see whether it makes salespeople better or worse. And for sure, the answer is both. But okay, those are my thoughts. And I think, Amelia, if we've got any questions, I'll try to stop the sharing. We can just chat about it to make folks have questions. A few people at the beginning, last night I answered. I know we did a whole separate workshop on Wednesday about this.

39:48So I pointed people to Delphi. Yeah. I refuse. I just want to give you a quick thoughts and we didn't train it on a lot of content. I'll tell you, so you, and I showed that screenshot, this presentation published and we did one before on it. It's on our YouTube slash Saster. It's a good question and I learned a lot from it. So listen, I love this app. You can try it. A lot of folks have, but you do have to ingest. And what it ingested for us is it, it has a combination of things. One, it has scraping. So it scraped every single 10 ,000 Sastra posts off sastra.com. So we put in the domain sastra.com.

40:23We put in sastraannual.com. Now it didn't pick necessarily, the scraping doesn't pick up documents. So for example, our first sponsors, for our sponsors, we have a prospectus. At first, it couldn't answer good sales questions. Like it didn't answer them. But then we just uploaded the PDF of the prospectus and it instantly got 98 % of it. Okay. So we had to upload some PDFs. So if you have sales collateral, you should upload it. Sometimes it got confused with old versions of the prospectus and new ones, right? For example, I thought Sastra annual was in September this year in the beginning. It moved to May, but then there's just training.

40:55So I just wrote in Sastra annual is May this year. Now it doesn't get it wrong. Okay. It's similarly, it made up like Sastra Europa we've done for years. It's typically been in June. It can't be June this year because Sastra annual is in May. So it started to make up that it was in June because there was nothing. Then I told that it's going to be in December and now it's perfect. So we had to do a few of those things. So we had to upload some documents, some things where it's confusing because it wasn't on the web. We added this. So probably we add one or two things a day to the database. And then it actually, it connects with our YouTube automatically.

41:29So every single video, we have thousands of YouTubes from everyone. Eric Wan, Stuart Butterfield, everybody. And we'll have 200 sessions from SAS January this year go up. It ingests them. All the YouTubes transcribes them and ingests them all. You actually, it's not as hard as it sounds. you can actually just get transcripts out of the YouTube API. It turns out it's pretty simple. But every single thing that's been said at every Saster angle since 2015 and every digital event we've done, CEOs of Notion and Webflow, it's all there. And all you have to do is just, we just had to hook it up to youtube.com slash Saster.

42:00Okay. And my YouTube. And then it actually is connected to my Twitter and LinkedIn. And so every single thing I've ever done on LinkedIn and I have thousands and thousands of LinkedIn posts and Twitter posts, it's all adjusted. So all our social media, our YouTube posts, our blog, all our content, and some PDFs that are basically sales collateral we put in. And we watched it. So that's pretty good. And then you see where the corner cases are and you upload more material. But it's a couple of hours of work to do that. But if you want to be great, you need an AI ops person. Amelia and I each do a little bit of it.

42:37So each day we spend 10 or 15 minutes upgrading it, fixing little things that like the hallucinations are rare. The only, the hallucinations are like, we didn't have SAS Europa 2025. So it made it up. That was hallucination. Mostly it's just corner things that gets wrong and we just correct it. And, but that's how it works. And it's, and, and I, it is what I learned from Gorgias in the support space is when they first rolled out their AI, they thought it could all be automated, right? But what I learned is small businesses don't know how to do this. So actually it is work. It takes them a week or two in many cases to get their customers.

43:12They have to train them. Okay, where's your pricing list? Because Gorgeous, they integrate with Shopify. So anything that's Shopify, they can ingest into their AI. But there's often other sources of data and other things. So they do have to teach them a little bit how to train it. But it's easier than you'd think if you do it. Just got to do it. And the other thing I learned, if you asked, you can try Brian Halligan's too. It's on the Delphi website. His is fun. He's the chairman of HubSpot. Brian, I think Brian's a better CEO than I ever was, a better executive. I think our AI is better. He thinks his is very good and his is very good, but I tested a lot.

43:47I talked to Brian's AI a lot. It's pretty good. But we have 12 ,000 pieces of content, 17 million words. I've written more and we have more executives that have come to Saster than he's written and trained his AI. So my AI is better. There's definitely a point of diminishing returns is what I've learned, but mine is better. So the learning is the more you can train up to a point, the better. That's one reason it's very good. So it's just something to think about. I think this training can be, ours is muchly automated, but you're always going to want to add a human on top of it to get it to that nth degree.

44:22So that's my rambling answer. That's a good answer. There was a combined two questions that you wanted because you already answered about the hallucinations. there was a similar question on if we added any guardrails so that it doesn't like mispromise any pricing it's a good question we haven't do you think that generally guardrails are super important in ais um look maybe i don't actually know that listen what's really interesting is our tool is not designed for sales that's why it's so interesting that's why it's guys that's why this is so cool when you talk about new use cases this delphi tool was originally designed to be a clone, a cool tool to clone.

45:00Clone Brian Halligan, clone Lenny, clone me. And they built all this cool functionality to be a clone. And to some extent, it's been architected as a support tool now. I don't know. The guys are coming that run Delphi. They're coming to Sastrano to explain how it all works under the hood. So if you really want to know, come to Sastrano because the guys that built RIA are coming. They're going to teach you how mine, Lenny's, and Brian Halligan's all work for real. You can ask all your questions. It's going to be super cool. But what's interesting is it was not designed for sales and yet it works pretty good for sales.

45:26So there may be guardrails in the tool. It's got a lot of stuff, but I don't, I think a sales tool would absolutely have guardrails, just like a CPU system. What ours doesn't, but it does have, you could absolutely add limitations. I forget where it is. We could show a demo. It has a version of guardrails where you can say, talk about certain things. Don't say certain things. Here are limits on certain things. And I think if we trained it and had a more complex pricing to be pretty easy to add, but we haven't added guardrails. and frankly i haven't seen it make it it made a couple goofy pricing mistakes that we fixed just by adding it but i haven't seen it make a lot which is probably pretty interesting as it is i'm just gonna keep asking the questions and some of them are repeats there has a question from alfonso you expect real customers are not going to be fast enough to follow the tech adoption cycle in ai that's a great question i'll give two different answers what we did we literally did a deep dive with mark benny our founder and ceo of salesforce it's our next podcast it's number 800 it's gonna be great and we talked a lot about this and what he he explained it was very bimodal at salesforce especially with asian force he said they have customers like lennar homes and singapore post i think he was just in singapore i'm like they're all in anything they can do on ai to automate Leonard Holmes and they're all in.

46:47But man, let me tell you, the enterprise is slow. He's like, overall, it's going to take a couple of years for enterprises to get there. One, both can be true, right? It can be segments. But the other thing is there's different types of AI. If you look at how we use it at Saster, we used to have Intercom years ago. It just replaced Intercom. So we always had chat, right? But our AI is, for us, it's 10 ,000 trillion billion. we would have intercom and people would create tickets and someone would check them once a month that's as bad as it gets now our ai answers thousands of them a month it's like a billion trillion better times better than someone never answering that so literally the fact that our chat bubble used to be intercom and is now our ai i don't think that's a lot of friction in the enterprise right so we may see a lot of enterprise uses in areas where there's low friction and areas where it's high friction going to mark's voice it may take years it may take years in areas that are high friction.

47:42Certainly folks are in a lot of regulated industries. Folks are of two mind on AI. There's a lot of spaces where it's slow, but it doesn't mean the areas that are easy to do aren't going to happen very fast in the enterprise. And that was my point as well. Yeah, I'm going to try and hit a few sales questions around time. So one from Shuresh, how does the role of sales enablement change in the era of AI? And it's, I think get ahead of it. In some ways, half of this presentation was sales enablement, wasn't it really? I just think I would, I don't know, but I would be all over this idea, especially for in-person selling, we're still going to learn.

48:22I do think AI is going to make in-person selling better because we're, but it's murkier to me exactly how the tools play out than when we're selling over Zoom, but be ahead of it. Be ahead of it because this Zoom AI is going to do 99 % of what we work really hard in sales enablement to get our team scaled up for. The way we train salespeople is going to be radically different. Our expectations are radically different. And I think maybe at a meta level, what I've also learned in the sports space, the way we're going to do QA, quality assurance, seeing how good reps are has already changed. I'm an investor in a company called Maestro QA, which is doing tens of millions for enterprise QA for contact center.

49:01And this space is nothing like it was 18 months ago because 18, 24 months ago, they have big customers, huge e-commerce customers. And 24 months ago, these customers would have thousands of human reps and all the QA was basically manual, right? Now for their biggest customers, 30 to 40 % of the reps are AIs, but the AIs make mistakes. We talked about guard roles. We talked about issues. So the whole way we do QA has radically changed. The same thing's going to happen in sales enablement. We're going to have to create, not only is AI going to make our sales reps better at many things, but we're going to have to check it very differently than just randomly listening to gongs, which is the classic way, right?

49:35And testing, like we're going to need to screen every single thing through AI and what that means and how we're going to QAM and how we're going to judge them is going to, it's going to change. I don't have all the answers, but you want to be at the, you want to be at the leading edge here because the, just like QA is for eight, I don't think the space is going to be the same in 24 months. It's going to be radically different. Okay. Next question on sales is from Luis. I know you and Sam talked about this a couple of weeks ago, but when, and you talked about this earlier, so for folks who joined late, but when do you see AI actually replacing the SDR function?

50:09I purposely, that's one I didn't write about because I don't know. I don't know. We did a survey, I don't know, six or eight months ago on SAS. We got thousands of responses. Have have you ever made an S has an AI SDR ever worked for you? And almost everyone said no. And even the folks that said, yes, it worked. They're like a generated pipeline, but no deals closed. Okay. But that was a while ago, folks, that was six months, six months ago. We didn't have an AI six months ago, this full duplex thing of digital Brian and Jason talking wasn't possible. The world's changed so much. So I'm actually a super fan of the AI SDR.

50:42Now I'm super excited. It's just, I don't think it's going to be the way we thought about it in 2024. Okay. In 2024, everyone's like, okay, let's automate sales often outreach, right? That's what we're going to do. We're just going to take this well-known paradigm and people building cadence and let's have an AI build a cadence. And I still think there's a role for that. And those tools are great because if nothing else, those tools make the emails more professional. There's no question that when you run SDR content through AI, yeah, can you smell it and see it when you see it, but sure, but That's sure better than terrible copy.

51:14But the idea that an AISDR on its own can close business was a bridge too far, right? I don't know. But what does make sense to me, and so I don't know, and that's why I didn't touch into this. And we're going to have a bunch of the vendors at Sastra Annual, and let's ask all of them where it's going, because I am bullish on this space. Because if you step back for a minute, I think we expected the wrong things and expected too much from AISDRs. Let's step back for a minute. If you take an AI that's already just as good as what Saster's own AI has, and you thoughtfully develop your target accounts, and you thoughtfully make sure the communications are tailored to them, and the AI then make sure they're all followed up properly.

51:55The AI makes sure they all get the right case studies. The AI makes sure they're all invited to your weekly webinar. The AI makes sure they all come to the right customer dinner in the right city because the AEs don't. And they make sure that when you're doing the dinner in Austin, everyone in Austin is invited. And they make sure that they're all invited because you're a platinum sponsor to Sastranial. You can invite 50 customers that they're all in your VIP room at Sastranial. Why can't the AI make that high quality outbound better? You know, this at the edge of ABM, it's got to make it much better.

52:21It's got to make it. ABM has never delivered what we've hoped it has been, but it's always worked. So I don't know if where AI sales off outreach goes. I don't know. but making the human 50 times better, I think is achievable today. So I'm excited to see where it goes. I just don't know that expecting an AI to bring you 10 million of revenue because you pay them$199 a month is realistic today. These other things are. But I was skeptical like many of you were six months ago. I am not. I'm all in on the AI star today. I just don't think it's going to be the 20, it's going to look, I don't think it's going to be anything like the 2024 version.

53:01Yep. Two related questions. What do you suggest using AI for to complement specifically founder-led sales?

53:14Listen, what we will see as tools evolve, I think the reality is there's, let's simplify sales at the early stage. There's outbound. There's get into deals. there's been middlers there's closing and there's follow-up okay founders almost universally are best at stage two they're great middlers they're great middlers because they know the product cold they know the why they can commit to the future if there's a product app the founder can commit to solving it in a way nobody else can and customers love to talk to the ceo they love to talk to the founders so they're great middlers there's like everyone gets energized talking to Mark Benioff at that scale.

53:58And don't be intimidated because you have six people in your company. The customers will love to talk to you because you care so much about their problems and you care about them. Typically founders deeply care about their customers in a way that Zoom doesn't care about me. Nothing personal. Eric Wan's one of the greatest founders of our generation, but the Zoom around, they don't care about me, but you care about your customers. So we're good at the beginning, in the middle. We vary on our other stage. And most of us as founders were just dead awful at follow-up. Follow-up requires a lot of process, a lot of task management.

54:30And so I think AI is going to automate all the follow-up in the founder-led sales. I think it will help us with the opener if we use these next generation tools properly, and we don't expect to do everything. It's going to help us with the opener. It's not going to help too much with the middler, but our AI will join us. I don't know if it'll help with the close, but for routine deals, you know what we'll do? Let's say your founder-led sales working on a two or three K deal, it may just follow up with you and close the deal on its own. And it will absolutely make your follow-up either in the pipe or after the deal closed, like a hundred times better because all founders are terrible at follow-up.

55:02They're all terrible at it. Yep. You're too busy. The founder, it's not that founders can't do sales or business. The problem is they don't have 50 hours a week to just do sales or business development or marketing. That's why they're really good at the relationship building, but all the follow-up sales, marketing, and business development. They're terrible. That's why founders, beyond this, business development partnerships, founders screwed up the most because they build a great relationship with Mark Benioff or Toby at Shopify. But then there's 100 people at Shopify you have to work with on the deal and they fail.

55:39AI is going to help with all of this. I'll try and squeeze in one, maybe two last questions. How do you deal with... with, I think that's the question is, how do you deal with people disagreeing with your AI? I think AI is great for that. Do we have seen it in our 30th? We do see people argue. Yeah, we do. And I think it's great because I will tell you my learning. I did. If you'd asked me this question 45 days, I couldn't have answered it. Our AI is so patient. It's so patient and it will hear your complaint and it will, and it knows that you're being aggro. It knows it and it deflects it and it answers it and it'll answer it simply and then it'll say, you're right but, and it'll say, I hear you and then if you want, it'll ask, can I go into deeper?

56:31Can I explain? It'll try to explain things in more detail and other ways to you until it wears you down with its honesty of your answer and then people just end the chat. But that is better than 99.9 % of humans can handle. So I think it's wonderful. I wouldn't have known 45 days. I think it's wonderful. Awesome. And they do. They do. Yep. The last ones are really just, it's funny, the AI note takers are giving us the key takeaways from the meeting, which one of them was to attend after. And the other one, for it to be how AI can help improve your sales enablement and quality assurance, which is a little bit funny.

57:08the maybe last question here hold on let me just one second how it's a good i think it's a good last question how often do you see the ai getting either hung up or losing a customer if it can't answer honestly never i know i haven't seen this thing guys this is why i made this presentation never never i've never seen listen we're just we didn't mean just to be a sales tool right listen do amelia's been at sassar for seven years all of our we have hundreds of sponsors they all know her they all trust her they'd all rather talk to amelia than the ai 40 of the time not actually not most of the time because they just want a question answered they'd actually rather talk to the ai but they but 40 they'd rather talk to her but but no sorry what was the question again i got a little bit distracted yeah how often do we lose deals or customers in the ai never never and now listen now okay i'm being a little facetious it handles everything well now where i guess in theory if you had a very if you were selling a fungible commodity and aggressive where our ai is not we're going to work on this after sas turn away a little bit of time okay when it literally does a handoff to sales it is not a sales tool so it is not it what it doesn't do is immediately reach out to Mona and get her on the phone that second when you need to go to a human.

58:29Okay. That is what tools like gorgeous do. Like they will immediately ask if the AI can't solve the problem and support, it will immediately find a human. So that is a gap. And while I can tell you that it does a great job answering all the questions, maybe we lost a deal because it sent it to, to email and it, and we didn't write the connection absolutely could have happened, but I haven't seen a single bad experience, not one for the prospect, not one. And I can tell you, man, in the early, we have a really good sales team today, but over the years, we've had some really literally terrible experiences with sales, right?

59:02We almost lost one of our, a partner of us that has spent over$2 million with Saster over 10 years. And they said they would never work with someone that used to be on our sales team ever again. It was such a horrible experience. And it would never work with them. And they churned. We had to get them back. And you're just never going to have that with AI. You don't want to think that's true. But I got to be honest with you, when sales folks leave, when they get angry, when they struggle, when they have a dumb boss, it's sad what people say and do. And sometimes they don't even realize it. And the AA never does that.

59:33The AA never threatens you. It never says if you don't sign today, you can't come to Sastra Annual. It never says we're only going to allow your competitor to come and not you if you don't sign this minute to get their commission. It don't do those things. and don't do that. Maybe that works here and there, right? For an individual rep, like being super aggro can work to get their commission. I don't think it's good for the brand of the company though, is it, when that happens? When that happens? And maybe the meta question I'll leave you, I put this, I did this poll on Saster. Let me see if I can pull it up and then we could break.

1:00:03Let's see. And maybe this is the last meta point. And I did the survey. It's kind of wildly on Saster. I'll try to find the link and then we can edit. How many folks, how many sales, folks said their competitors lie to win deals. 93%, 93%. This may be a profound change from AI. We can train the AI to lie a little bit, but if you think of all this bad behavior that happens in sales, right? I mean, deal rippling, come on. The AI is not going to do that shit. Okay. Terrible. And a lot of folks think this deal rippling thing is crazy. I don't think it's crazy. I think it's just like a little bit more extreme than what happens all the time.

1:00:44I think it's just a little more extreme. And AI never does this. AI always treats the customer with respect. And I think if you're building a brand, if you're building something generational, you want to treat your customers. We, none of us treat customers with enough respect. I love sales. Sasser is all about sales, but for sales, it's about the deal. It's about getting the deal signed and getting their commission. For the customer, this is the one thing we forget. It is, this is business process change. This is changing how I run my business. This is not just the 29 bucks or 29 ,000 bucks. The money does not really matter to the customer at the end of the day, as long as it's fair.

1:01:16It's so much more work to deploy a new tool or a new business process. So I just want to be treated well. And AI is going to mean we're going to treat our customers better. So thanks for the time, everybody. We'll keep doing this and we'll do a bunch of deep dives like this in just a couple of weeks at Sastre Annual. Awesome. See everybody IRL there.

1:01:40All right, everybody in SaaS, this is it. The biggest, most action-packed SaaS and AI event of the year. SaaS, your annual 2025. It's coming this May. Yes, this May. Three full days, 10 ,000 SaaS, AI, and cloud leaders, and more tactical, no-fluff content than you'll find everywhere else. Hundreds of workshops, thousands of brain dates, and one-on-ones. If you want to scale faster to 10 million, 50 million, 100 million, 300 million ARN beyond, You need the right playbooks, the right relationships, the right connections, and the right people in your corner. And Saster Annual is where it happens.

1:02:12We'll have hundreds of legendary speakers from companies and CEOs from Snowflake, HubSpot, OpenAI, Canva, and more. We'll have more networking than you can handle. You'll meet your next VC, your co-founder, the next biggest deal. I was just talking with a founder that closed a$450 ,000 deal just the month after Saster Annual last year. and we'll have a new AI demo and pitch stage where hundreds of you will be able to do quick pitches of your hottest new AI feature or product and a chance to win up to 5 million in VC funding from Mayfield. Apply right on sasterannual.com to pitch your AI startup.

1:02:46So don't wait. Grab your tickets now at sasterannual.com and if you want, use my code Jason100, Jason100 to save$100 before prices go up again. That's Jason100 at sasterannual.com. See you in May, May 13th through 15th in the SFA.

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