We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)
Guests: Jason Lemkin
Full transcript · Read the full conversation in order, with its original context.
Contents1 chapter
§01Transcript · 00:00–1:42:07§01Transcript · 00:00–1:42:07
Used to have about 10 people full-time. Now you have 1.2 humans, 20 agents.
We have 10 desks that used to be go-to market people. They're all just labeled with our agents, Repli for Replit, Quali for Qualified, Arti for Artisan. Agentforce needs a nickname. Agents work all night and they work weekends and they work on Christmas. We're done with hiring humans in sales. We're done.
The business is doing very similarly to what it was when you had 10 humans.
If I had two more great humans that wanted to join, don't get me wrong, I would hire them tomorrow, but I'm not going to hire someone that after their third month in the job doesn't know what SaaStr does. I just can't do that. AI is replacing the jobs people don't want to do today, and it is displacing the midpack and the mediocre.
How do you see the future of the sales profession?
We should have $250,000 a year SDRs, but they'd be like ... At Vercel, they'd be managing 10 agents, not 10 people. The classic SDR junior kid that is hired out of college to send emails, we don't need them. Folks that qualify leads coming in, the contact mes that we see, we have no need for them today. They should be extinct next year.
Someone's listening to us like, "Oh man, my job is in trouble."
If you can go do this, you're hyper-employable.
Today, my guest is Jason Lemkin, founder and CEO of SaaStr, the world's largest community for B2B founders, and one of my absolute favorite sales and go-to market minds on the planet. Jason is not only deeply knowledgeable about everything sales, he's also extremely articulate and direct, and is also now personally going super deep on what AI can do for a sales org. He's transformed his own SaaStr sales team from around 10 SDRs and AEs to one full-time AE, a part-time chief of AI, named Amelia, and 20 AI agents. He is seeing the same performance from his AI team as he saw with his former human team, and he's just getting started. These are my favorite kinds of conversations because the guest is living in the future and comes here to show us what the future is like, where we're headed, and how we can get there ourselves, and also just how to avoid all the pitfalls that he had to deal with along the way. We cover all of the things that he has learned about where sales and go-to market is going in the AI age. He gives a bunch of advice for salespeople and the future of their careers, the future of the go-to market org, how to win as an AI startup right now, what tools he's finding most useful, what it took to shift a sales team, and so much more. This episode is going to get your mind spinning in the best way possible. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get 19 premium products for free for an entire year. Including a year free of Lovable, Replit, Bolt, N8N, Gamma, Linear, Devin, Posthog, Superhuman, Descript, Wspr Flow, Perplexity, Warp, Granola, Magic Patterns, Raycast, ChatPRD, Mobbin, and Stripe Atlas. Head on over to lennysnewsletter.com and click product pass. With that, I'd bring you Jason Lemkin after a short word from our sponsors. Today's episode is brought to you by DX, the developer intelligence platform designed by leading researchers. To thrive in the AI era, organizations need to adapt quickly, but many organization leaders struggle to answer pressing questions like, which tools are working? How are they being used? What's actually driving value? DX provides the data and insights that leaders need to navigate this shift. With DX, companies like Dropbox, Booking.com, Adyen, and Intercom get a deep understanding of how AI is providing value to their developers and what impact AI is having on engineering productivity. To learn more, visit DX's website at getdx.com/lenny. That's getdx.com/lenny. This episode is brought to you by v0 from Vercel. v0 is the web development assistant designed for professionals of all technical backgrounds. Whether you're a product manager, designer, or developer. Transform how you bring products to life. With v0, everybody can cook. Don't just show up to reviews with docs and ideas. Arrive with working prototypes that demonstrate real functionality. v0 drafts project plans, generates interactive interfaces, and builds full stack applications without writing a single line of code. And with features like AI and database integrations, screenshot import, and sync with GitHub, v0 helps reduce development bottlenecks and enhance collaboration between technical and non-technical team members. The result, faster iteration, and a shorter path from idea to implementation. Vercel built v0 for the builders who want to create at the moment of inspiration. If you can dream it, you can ship it. Visit vercel.com/lenny to get started. That's vercel.com/lenny. Jason, thank you so much for being here and welcome back to the podcast.
Lucky to be a super fan and then, to get to join, right? It's terrific to be on the other side.
So this is our second conversation. We did our last conversation a year and a half ago. I don't know if you know this, but it became a pretty legendary episode. It's something people continue to share and that conversation is around basically a deep dive into building your sales org. And a lot has changed for you and the world since then. Kauf AI, and what's happened is you've gone extremely deep on what AI enables for sales, for startups, for go-to market. And what I love about conversations like this is you're basically living in the future. And you're here to give us a glimpse of where things are heading and tell us how to avoid the wrong turns and just help us get there ourselves.
That I think I can do.
To start.
Yes.
Help us understand just the business you run, this SaaStr.
Yes.
What is it you sell? What is the business? What is it you do, Jason?
I'm still trying to figure it out, Lenny. Maybe you are too in some ways.
Yeah, that's true.
So I am a two-time founder who started writing a blog, my God, in 2012 about all the mistakes I made after I sold my startup to Adobe. We started doing a couple meetups. You've done meetups. Before anyone did this stuff, we did a big meetup in 2015, thousands of people came. Then we do 10,000 people a year at SaaStr Annual. I've actually also invested almost 200 million dollars, almost 10X lifetime, only into founders from the community. But the reason I don't know is what I ... Folks that are connected to our content, I'm just passionate about helping other founders see mistakes and make less of them. So anyhow, we're a large community. I do invest, but it turned into a business. There was no revenue in the beginning. I'm sure there was no revenue, Lenny in the beginning. And ours was less intentional, but we do do eight figures of revenue a year and it's work. That sounds great to do eight figures, but there's a lot of costs, especially on the event side. The media side has almost no cost. And it's work. We have a hundred sponsors. And as you know ... You have sponsors, but there's a certain level where it becomes a lot of work. Getting two folks to sponsor your podcast with a couple emails, no work. If you wanted to have four Lenny podcast, it just scales. So we have built our own go-to market team over time, and I've lived the frustrations. Folks have followed it. And then, maybe I'm rambling a little bit. The interesting thing, the aha moment that happened to us is going into May of this year, we had one AI agent in production called Delphi that we both use for digital Lenny and Digital Jason. Really interesting learnings. And we went into our 10,000 person event this year with a seven-figure budget and eight-figure top line. And two folks on the sales team who were paid high end of market. I have many flaws, but paying well and being loyal are not one of them. And two of them just quit at the event. They just quit on site. And this is like the third time I've done this, like the eighth team I've built, and I turned to Amelia, our chief AI officer, and I said, "We're done with hiring humans in sales. We're done. We are going to push the limits with agents. We're going to put..." Even if it doesn't quite work. And I knew from this Delphi, this general agent that it would sort of work because going into annual, this general agent, this Digital Jason closed a 70K sponsorship on its own. So when I saw that a horizontal agent, not trained for sales, not trained for GTM could close one deal, they're like, "Let's deploy a couple of these apps. We have time. And I just can't pay a junior SDR $150,000 a year to quit. I just can't ... criticize me, but I just couldn't do it one more time. I just couldn't do it one more." And I actually think this isn't ... When I talk to CEOs at leading AI companies, they kind of don't want to do it either. They want to have the smallest sales teams they can as much for cultural reasons. Even if Replit only goes from zero to 200, it could have been 220 with the smaller sales team. I think I'm just okay with it. So it's an enduring theme. But anyhow, so we pushed the limits. And now if you walk into SaaStr's office, it's kind of funny. We have 10 desks that used to be go-to market people. They're all just labeled with our agents, Repli for Replit, Quali for Qualified, Arti for Artisan. Agentforce needs a nickname. Maybe we can make one up with Salesforce. There's Amelia's corner office at one end. I'm in the back of the office and it's just agents. It's the quietest office. And net-net, Lenny, it's about, here's the Meta learning for when we're recording this. The net productivity is about the same. It's not better, it's not worse, but it's so much more efficient and it scales because software scales. And we can talk about what we've learned. I think it's important that it takes time to train these agents. They don't work out of the box. But when you dial them in, when you take your best person or your best script and you train an agent with your best person and best script, that agent can start to become a version of your best salesperson, your best person. And that's what we've learned and how to perfect it. And I just think because ... and criticize me, you or anyone watching or listening, maybe it's not cool. I didn't want to hire my 28th rep that was going to quit, but I just couldn't do it one more time in the age of AI. I'm like, "It's time to go to the bleeding edge and just see what we can push the limits here."
Okay. I love all the directions we're already heading. Okay. So just to help people totally understand what your business is, basically these people are selling sponsors for your conferences.
They're selling two things because it's just relevant to the deep dive. They're selling sponsorships, which average about 70 to 80K. And then, they're also selling tickets, which is the high volume for ... This is like the self-serve version. They're selling tickets that are anywhere from a couple of hundred bucks to if you're a VC that comes the night before, could be two grand. No gifts for VCs that decide the night before. Founders that decide early get at about 20% of cost. And it's work to sell these tickets. And so, you can just post an email like you do and you probably fill up Lenny Summit, but if you want to max it out, you got to do work. You got to do drip campaigns. You got to reach out to people. You have to reactivate folks that came to Lenny's Summit three years ago, but you want them back because they're good people and that just requires work. And as your base scales, you have how many people subscribe to Lenny's newsletter now? 1.2 million or something.
1.2 million, roughly.
Okay. How many of those is a human willing to reach out to? Approaching nons.
20,000. Yeah.
Imagine you hired a 21-year-old SDR fresh out of junior college and said, here's my list, 1.2 million people, start calling them. I want them to come to Lenny's Summit. But anyhow, so we have this low end version, which is tickets, which is four or five million a year. And then, we have this higher end sales cycle and they're very different and actually they have different agents. And then, we have a different agent to get people to come back, lapse people. So we have lapsed, high end and low end agents, and they have different workflows. And we actually use different vendors for now. For now, we use different vendors.
Okay. And so previously before this future world, how many SDRs did you have? How many salespeople in this house?
We would have two to three SDRs and up to five AEs.
Okay. So like eight, nine people full-time working on SaaStr to bring in sponsors and to bring in tickets.
Yes. Although ... Yes, a lot of it is inbound and renewals, but yes, to manage that business, to manage the sales side of that business.
Yeah, you mean, manage on it and be successful.
Yeah, go-to market. Let's call it eight to nine and go-to market. Now we have 1.2.
1.2-
Humans.
1.2 humans.
And 20 agents, AI agents.
What is a 0.2 human?
Amelia, who's our chief AI officer who runs everything. She spends 20% of her time managing the agents, orchestrating the agents.
Okay.
Which is something I think people don't-
Let's get into that.
They talk about, but they don't actually understand what that means.
Yeah. Okay. I definitely want to spend time there. Okay. So you used to have about 10 people full-time. Now you have 1.2 humans and you said 20 agents.
20 agents. Yeah.
Okay. And what you're describing is the business is doing very similarly to what it was when you had 10 humans. Now you have 20 agents, the business doing the same.
Yeah. Now listen, if I had two more great humans that wanted to join, don't get me wrong, and this is true of every fast-forward startup, I would hire them tomorrow. Okay? And if you go to Vercel, if you go to Replit, if you go to ... They're all going to tell you the same. I was literally in London, we were just at our abundant event with Maggie, who's in the leadership of OpenAI, she said they just can't hire enough enterprise reps now. But what it is replacing are the mid-pack and below. The ones that don't really understand what Linear does. The ones that don't really know what a pull request is or exactly how Replit works, the AI can do better, not than the best, right? So I would love to have more humans, but I'm not going to hire someone that after their third month in the job doesn't know what SaaStr does. I just can't do that one more time. And I don't think you need to ... This is the thing, AI is replacing the jobs people don't want to do today, and it is displacing the mid-pack and the mediocre. Their jobs are at risk. They are at risk. The best humans, it is true that they will get superpowers from AI, but I'm not sure the rest will. It's a cautionary to ... but I would love to have more than one ... but at the end of the day, 1.2 humans is ... plus 20 AI agents is doing about what 10 human GTM did.
Okay. I want to spend time on the different agents you've built, but first of all, just kind of zooming out, having gone through this experience, how do you see the world of go-to market changing next year in the coming years?
All the plays work. It's the playbooks that are kind of broken in the age of AI. All the plays work. Outbound still works. Webinars still works. Podcasts still work. Okay? Events still work. All this stuff works. All this stuff works. Why is ElevenLabs out doing a roadshow, right? It works. Why do they go on Lenny's podcast? It works. So the plays all work. It's just the playbooks are broken because for folks that aren't in the age of AI, growth has decelerated so much that nothing seems to work. It's working. It just works so much worse than 2021, but the play still work. They don't have enough ROI. There's not enough budget for old school SaaS from 2021. The ones that are blowing up, the Vercels, the Replits, the ElevenLabs, they have so much demand, so much demand that they're still running the plays, but they're doing them differently. They're doing them from a hyper PLG focus because there's so much demand. And they're often picking and choosing which prospects to contact. So for example, Bolt is probably a distant number three behind Replit and Lovable, right? But one of my old sales guys run sales there. And I talked to them when they went from zero to 50 million in six months. He's like, "We honestly just have so many leads. Half our job is picking which ones to respond to." And he also is like," we closed a seven figure deal we stole from Lovable because no one called them back at Lovable. So your traditional B2B SaaS company, even ones at billions of revenue, even the HubSpots and all of them, they don't have so many great leads, they don't call them back. So that is a different world, not easy, different world. And then this world where nothing seems to be working, it's just because the demand has evaporated. So both ends have an incentive in 2026 to push the limits for AI for go-to market. The ones that are hyper-growing can't touch everybody. They can't do everything. Not everyone like Vercel will build their own internally. We can talk about why most folks should not build. They should buy. For the same reasons it's always been true in software, we can talk about it. At the low end, you still need humans, but ruthless efficiency is going to be the name of the game for 2026. So anything where AI works, the demand is inexhaustible. So everyone is either looking for more efficiency or they just can't service the massive amount of inbound they have.q And so maybe that doesn't totally answer your question or I got a little bit off track, but that's how the world's changing. When we first did this, which wasn't that long ago, in a way, pre the AI explosion, all B2B companies were kind of the same. They grew at somewhat different rates, some blew up faster like a Samsara, some took longer like a UiPath, but come on, they all kind of grew the same way for the same ACV, for the same deal size. Now, just like in venture and everything else, it's wildly bifurcated, right? You've got the low end, which is all about price increases and forcing things onto the base. And at the high end, we have something we've never seen since 2020, which is everyone in the market at once. Everyone in the market at once. This is something that people don't understand. Why are these companies doing so well? Why are they blowing up? Because it's not just at the software ... We love this stuff, Lenny, all these new tools, we love them. But it's not one law firm looking at Harvey. It's everyone. It's everyone. It's not a few folks looking at video on the internet. It's everyone trying to make video on the internet.
Because there's a lot of push from the top of like, we need to adopt AI, we need to be more productive-
Now, everyone, not the traditional ... The traditional metric was in most categories, three to 5% of prospects would be in market a year. So you'd send a trillion emails and you'd do cold calls and you'd hope maybe 2026 was the time they were willing to dump Salesforce for your new product. So add all that up, 5%. And many categories work north of 50% in market. So that just totally changes ... the plays still work. Showing up in person, actually knowing what the hell you're selling, knowing how to get through procurement, all of those that work. But other than these weird windows, artificial windows in 2020, we've never had so many people in market at once.
And this is for AI products specifically or beyond that?
Yeah, that have massive ROI.
Yeah. Productivity.
I need to bring a Vibecode tool into my company, Lenny. Okay, go out and do the work, compare Replit, Lovable, and whoever else and buy one. Okay? Why are Harvey and the others and the Goro are doing ... I mean, they're great tools, but everyone is like, we need to automate how we review contracts and documents with AI now. They want a leader and they're going to do it. And that will slow down. Not everybody can be in market every year. It's an exhausting enterprise. So this is a version of the AI bubble that will end and we will revert in some ways to old school, but when everybody is in market, it just changes how you run the whole thing. So the fastest growing ones and the slowest growing ones both have incentives to use AI here, just for different reasons.
How about the sales profession specifically? Are SDRs going to be replaced fully AEs? How do you see the future of the sales profession?
The classic SDR junior kid that is hired out of college to send emails and respond to inbound emails and maybe get back to them later that day or the next day, we don't need them. We're not going to need most of them. SDRs that knock on doors in a lot of industries aren't going to be displaced. The email-based cadence SDR will be 90% displaced by AI next year. People have different nomenclature. I call BDRs, folks that qualify leads coming in, the contact needs that we see. We have no need for them today. They should be extinct next year. There is no reason in the age of AI. I have Hit contact me, wait a day or two for a 21-year-old that doesn't know what Linear does to say, "Hey, what do you do? How much are you willing to pay me? Maybe I'll set up a call with Lenny later this week." There is no need to do that with AI. Our AI alone, one of our agent fully qualifies everybody on the website, so they don't even know they're being qualified and just sets up the meeting with the salesperson. So this email-based SDR and this human qualifying leads, which is not good for the customer. It doesn't feel good to be qualified, does it? They will be mostly extinct next year. I'm guessing with your ... Now the AE, the classic human doing the sales, most of the tools aren't there yet for the most part. I think 70% of their jobs will be safe by the end of next year, but I think it will decline to 40 or 50. I don't think there's any reason what we're seeing in other categories, a great agent can't close a deal too. If there's not a lot to negotiate on price and the agent knows the product better than a human, at least for folks like you and me, I mean, do you like to talk to a human in sales?
Sometimes. I'd rather just chat with a really smart AI.
Yeah. So that's all in progress now, but the classic ... And the tough part, and a lot of folks ask this question, Lenny, they say, "Okay, Jason, I see that in your data. How are we going to build the sales profession if there's no entry level jobs in SDRs and AEs?" And that's a Meta question across all of AI. We're already seeing AI concentrate strength in sort of mid-tier folks, isn't it? And we're already seeing lots of folks cut back on entry level hires, Shopify's and others aside, where they'd rather have the six or seven-year-old engineer that's a cursor machine rather than train some kid. It's just more efficient today. I'm sure you see that across a lot of folks you talk to. It's going to happen in sales too. So the folks that know how to manage an agent, work with an agent, the folks that know their product for real, they're going to become more valuable and the rest are going to become less valuable.
It's interesting because I'm an investor in a bunch of startups, as are you, and I'm actually seeing a lot of asks for go-to market people, salespeople. Do you think this is kind of a temporary because there's so much demand they're like, "Oh, we need people to help." And then, this will start to become more AI over time or are they just looking for these really senior people that you're talking about?
Well, listen, whether you're managing humans or orchestrating agents, you need leadership. We've yet to produce an autonomous CEO. I know folks talk about how ... on Twitter that AI will replace the CEO, but I don't know that that's literal as much as figurative, right? So we're still going to need the C-suite. We're still going to need VPs. I mean, it's become so much work to manage a million leads, right? A half a million leads. So we need these leaders whether ... The question is, and I've seen your call out there and I saw your tweet on it. The question is, how many of the folks that had the current playbooks are the right folks for the future? I'm thinking maybe 20% of the folks I talk to. 20 are still panicking about AI and I'll tell you how to be in the 20% if you want to know, but I think very few like the Jeanne from Vercel are going to make the jump, so we'll see. There will be huge organizations, right? Like Denise just went from Slack and Salesforce after 14 years to be CRO of OpenAI. She's working going to be pretty high level, right? So she may not need to know how to implement the agents, but most of the folks your companies want to hire, I would just make sure that they really want to roll up their sleeves and do the job of 2026, 2027, right? Just because they worked at Slack does not necessarily mean they have the skills at your startup.
You said that you had some tips for folks to actually be this 20%. If someone's listening to this like, "Oh man, my job is in trouble. What should I focus on?"
It's going to sound simple. It will work and almost nobody is doing this. Pick a tool, an agent, an agentic tool to solve one of your problems. It doesn't almost ... Just one that's the most painful or the one that's most acute. It could be support, it could be SDR, it could be inbound qualification. Pick one, pick a leading vendor. I don't care which one it is. We can talk about how to pick a vendor, but pick a leading vendor that treats you well, that you like, and do it yourself. Train the agent, ingest the data, do the iterations, understand how this damn thing works. Okay? The folks that are lost today have never done it. We literally ... we've turned it into a consulting shop, Lenny. It's kind of crazy. I don't know what I think about it, but we literally just did a job. Amelia, our chief AI officer and Mia, she drove it. We did a call with a public B2B company worth well over 10 billion that you would think is an AI leader, okay? And we did a call with their team and they're like, "We want to figure out this AI SDR stuff." We're like, "Great. We think we're just going to buy this tool and just give it to our SDRs to figure it out on their own." One, no chance. Two, we asked them, "How much of this have you done yourself? Have you done it yourself?" And it was just crickets on this call of 20 people. No one had done it theirself. So they thought they could take an untrained agent with no training and just magically give it to a bunch of young 20-year-old SDRs and this magically would sell on its own. It doesn't work that way. So the way all these agents work is there's a lot of jargon, which is intimidating, ingestion, orchestration, training. It's not that hard, guys. It's just different. It's the same B2B stuff we've been doing for over a decade. You go to a website, you give it a URL of your website, you give it a URL of what your Wiki is, you give it a URL of your training docs. Maybe you upload your prospectus, you upload a few documents, it ingests the data and ingesting means it uploads. It means it processes the data and it does some other stuff that you don't really need to know, some ragging, some vectoring. It really doesn't matter. You upload some stuff and it kind of knows it and isn't great at it. And then ideally, it will turn it into questions. ... great at it. And then ideally it will turn it into questions. And you answer these questions and the more you answer and train it, training is just answering questions and getting better and better. So first you upload a bunch of your stuff, then you spend hours training it, often with the help of a vendor, someone called the Forward Deployed Engineer, which is a scary term, it means someone's going to help you do this. You upload your stuff, you try to get it right, and then you basically have to make sure it's right. QA, testing. And every day when that AI SDR sends out emails and do practice emails, they will say some dumb things. Maybe it's hallucinations, it really doesn't matter what the technical term is, and you correct it. And if you do this for 30 days, then every day you spend an hour or two correcting those mistakes. By the 30th day, it's going to be pretty good. Anyone can do this that has been in B2B or SaaS. Anyone can do what I just described. It is not that different than other things we've done. It's just sequenced differently. But nobody does this. Everyone's panicked. And if you can go do this, pick any tool, pick Agentforce, pick Qualified, pick Artisan, pick whatever you want, if you can go do this and get it live into production, you're hyper employable. All the companies you talked about, the GTM person, they will hire you. You could magically be their chief agentic GTM officer because almost anyone can do this if they want to. It's just going to take a month of your time and it might take you 50 or 60 hours plus qualifying the vendor. And in the old days, when we first did our podcast, you'd hire an agency and disappear. That's how you do this stuff. The agencies don't know how to do this. You've got to do it yourself. But if you do, man, you will rock. You will just rock and you will learn. And you will learn the limits and you will learn the agent can... what it can do and where it can't do. And then you will learn how to do the next one. So we're pretty far on Agentforce, which is Salesforce's one, which Marc talks a lot about, but we're probably one of the only organizations of our size on it. I will tell you a cheat code, which is pretty interesting. We had three of these agents working for sales. After training it and learning it and spending months time to learn it, we got it down to one prompt. And prompt is another almost intimidating word. A string of text that describes what you want this thing to do. We took that prompt and gave it to Agentforce. Then the day was pretty good. If you can do one of these, it'll be really hard. It'll be brutal. Then the second one will be easier. And then you're going to be like the master of the universe in AI if you can do it yourself. But if you're waiting for people on your team to do it, if you're waiting for an agency to do it, I think you're going to be out of a job. Everyone comes to us as experts. We're only experts because we did it 20 times.
I think what might be helpful here actually is to do a tour, kind of a quick tour of the agents that you've built and what they do, which ones have been most impactful. And then as you do that, what products you use, what powers these agents that you like and maybe don't like.
If anyone goes to SaaStr.ai/agents, you'll see everything we built. It's all bulleted out. You can copy us and I'll walk you through it. But two caveats are things at the top. I built a lot of stuff in Replit. We can talk about it for fun. I'm a top 1% user. I love it. None of the GTM stuff we built ourselves. Don't build it yourself. You're not Vercel. You don't have a full-time, wicked awesome engineer that wants to build this. Could all this stuff be built yourself? It's the same idea of building your own Notion. You could do it, but don't do it. These products are expensive. They're not so expensive it's worth... and then maintaining. The pace of innovation is so fast. Even if you can hire someone to build it internally, it will become obsolete if you're not careful in a couple months. We've built a lot of stuff. We could talk about... I built a calculator to do startup calculations, been used 800,000 times in 90 days.
For valuation, right?
Yeah, for valuations. I built a pitch deck reviewer that's reviewed almost 3,000 pitch decks. Lots of fun stuff, but none of the GTM stuff we built ourselves. None of it. Just a caveat, don't build it yourself, unless you're Vercel, unless you have a reason. That was a great pod. It was wonderful. Don't do it. Don't do that yourself.
Basically, unless you have awesome go-to-market engineers.
And they really want to do it. They really are chomping at the bit to do it. Don't do it. So I started... and this is not where other folks would start, but there's some learnings. I started, there's an app called Delphi, which makes digital clones. You used it for the Lenny Bot a long time ago. I saw you do-
Lennybot.com.
What's that? Yeah, Lennybot.com.
Lennybot.com. Yeah, check it out.
I saw it a long time ago. It was interesting, but it didn't click. And then Brian Halligan, who's the founder and chairman of HubSpot, did one too. They're Sequoia backed, and he was working at Sequoia, so he helped them early on. And then I kind of had a magic moment, and this is the way it works in AI, when I saw the combination of the two. People should love Lenny Bot because if folks haven't tried it, try it. It is ingested, I know a scary term for some, it is ingested every single interview you've ever done. Every word of content you've written. And it can combine them all together. It can combine the Vercel story and what you did with Dylan at Figma, and it can synthesize the knowledge, and it's pretty good. It's pretty good. What I liked about Brian's better than yours, though, was that it was Brian. And Lenny Bot is kind of Lenny, but it's also kind of all your guests. I think that's the superpower of it, right?
That's the way I think about it. It's not just my intelligence. It's the lessons of every single person I've had on this podcast.
So it's great, but I thought, "Hey, maybe I could finally do one that's in between the two." I've been a founder and I've written 10,000 pieces of content. So that's a little bit like Brian, but I have more than Brian. And I'm not Lenny in terms of productivity, but I've got a lot of voices. So I'm like, "I'll try it." I used Delphi. I instantly broke it because I had too much data to ingest. It took about a week to get going and it worked. And it's just like you. Some people spend hours a day on Digital Jason in another browser and they don't do what they do with Lenny, but they'll ask about their sales woes and what to do with their sales team and they'll upload LinkedIns and ask if they should hire people. And then a curious thing happened, which is that because we do these events, people started to use it for questions for the events. "Hey, how do I get a refund? Hey, can I get a discount? Hey, where is the San Mateo County Fairgrounds?" So Jason Live is really in the San Francisco Bay Area. "Who's speaking?" There's endless questions. And we used to use PreFin Intercom, and we're so busy, we would answer two weeks later. It was worst support ever. And the agent just started doing support on its own. And then it did this thing where it sold sponsorship on its own. So one place to start if you haven't started is in support. And you don't have to buy Sierra and you don't have to buy DecaCon necessarily and you don't have to buy Fin, but one potential place to start is can you do great 24/7 support? Can you? Most apps can't. In fact, some of the worst offenders are AI leaders. They have no support at all on their website. So that's one place to start. And then the next place we started... so for us, the login for the next place we started is, "Hey, we want to try Outbound." Because we don't have 1.2,000,000 names like you have, but we have 400,000 and we have data on them. So we wanted to say, "Hey, come back to our SaaStr event." So we didn't know what to use. And I'll tell you some learning. So we picked a YC company called Artisan. They've gone from nothing to $10,000,000 this year. We picked them, but this is important why. They were a sponsor at SaaStr, we didn't know, and they offered to help us the most. This is the critical insight. We didn't know if Artisan was the... I have opinions now. We hadn't deployed it, but another vendor, the CRO argued with us. He said, "I need $100K upfront before I help you." Another one said they were scared of SaaStr. They didn't want bad PR if it failed. Fair.
Yeah. A certain company [inaudible 00:33:43].
"We don't want to be your first." And Artisan said, "We'll do it." And we had nothing. And here's the interesting thing about agentic stuff, it's like support. If you have nothing, it doesn't have to change the world. If you're literally doing nothing and you start to do something that's high ROI, you're going to get return. So we did that one. We trained it. It's great. We did about 60,000 emails, saw pretty high rates. Then we said, "Well, we'll try inbound. We don't want to have this depressing experience where a salesperson quits and it's two weeks later until they talk to..." So we used this vendor called Qualified, which was founded by the ex CMO of Salesforce that does a lot now, but mostly focused on Qualified stuff. That immediately worked. We had someone at 11:00 PM on Saturday night that wanted to sponsor and they sponsored and it worked and it worked great. But again, they helped us.
And this is an agent that is emailing with prospect selling them on a sponsorship.
Well, it's literally, if you go to SaaStrAnnual.com, and anyone should buy a product like this, it doesn't have to be Qualified, and the bubble, the intercom-like bubble, is tuned to qualifying inbound prospects. Folks that say, "Hey, I want to sponsor Lenny's podcast." "Sorry, we're sold out through 2028, but if you want to be on the wait list, sign up here." Or even better for us, it would qualify folks out that weren't a good fit. It would save so much time, and it would do it 24 hours, then it would just set up the meeting. So the reason that was a great second one was because no one was willing to do that. No human was willing to pick up the phone and talk to these people. So it was such low-hanging fruit. But the key to the first two, and if you're going to pick an agent, is they offered to help the most. At the end of the day, Lenny, these are all running on Claude 4. They're all basically using a bunch of APIs mashed together. That's not new to software, mashing a bunch of APIs under the hood. But deep down, I don't want to trigger anybody, many of these, the leaders in AI GTM, they're more similar than different. They're more similar than different under the hood. It doesn't mean the features are parity. So because you have to train them, because it takes a month, the world's best software with no help training you is not one 99% of people should buy. In the old days, we would qualify the best software. We would make a matrix and we would do their thing and we would compare features and do it. You've got to do another column, which is your Forward Deployed Engineer or solution architect or your SE and talk to them and say, "Who is going to help me?" And before you write a check, get on the phone with Lenny and see if Lenny's really going to do deployment. And if Lenny rocks and the other vendor is better and won't help you, don't do it. And that's why we've had so much success is the first two we did, yeah, they were startups, so they worked harder, but Artisan and Qualified just did the work with us. And we're not stupid, but it was work. We needed help. And so that's what I learned is, you have this partner, the FDE and the vendor, and a lot of them actually might not take your business if they don't think they can help you. The best ones turn away a lot of business today, which is interesting. An interesting learning from this for folks is a lot of folks say, and they would say it to you if you use these, Lenny, they say, "You have too much data. SaaStr is not like us. We're a startup, we're tiny. You have 400,000 people in your database. Lenny has 1.2,000,000. I only have 300 customers or 200 customers." What I've learned is that's wrong. If you have 300 customers, how many folks have come to your website ever? 30,000. How many leads do you have? How many folks in your database? How many folks have you tried to reach out before? More than a human's doing. And all of a sudden they have aha moment. "How many folks do you have in your HubSpot? How many folks do you have in your CRM?" They look it up. 31,000. "Okay. How many folks do you have talking to them? Zero." You don't need the scale of numbers that you and I have to make these agents work. You need a little bit of scale and you need a little bit of traffic, but not as much as you think. So all the learnings, we have a lot of folks that honestly, they don't want to do the work. They're like, "Well, SaaStr has a lot of scale. They have a lot of years." It's not true. And it turns out to also be true with the training. I'm sure you've seen it with Lenny Bot. I thought having 12 years of content made the difference. Nah. It's having a couple months of really good content and a long tail beyond that, but you don't need as deep training and as much as you think. You just need a bit to be really good. So anyone that has any scale whatsoever, even a couple million of revenue and up, can benefit from these products. So we did horizontal general bot, got us to a certain place. Then we did SDR for outbound, then we did inbound, and then we did Agentforce really early with Salesforce. And we didn't know what to do with Agentforce at first, but we decided we would reactivate the folks that sales decide was not worth their time. Folks that reached out to sales, and this is true at every startup. We even just talked about some of the AI leaders where a human says, "You know what? I don't think this is enough commission. I'm kind of busy. I got a $4,000,000 deal with Meta going." We just took Agentforce just on those and we trained it on very similar prompt. It had 70% response rate. Those are people that were dying to interact with us. 70% is so good. And this is something humans were not willing to... it wasn't worth their time. And I know this sounds critical and maybe I'm going to trigger some sales folks, but the reality is if you're in a lead-rich environment, and I think that there's lead-rich and lead-poor environments for even big companies but startups. There's not enough, but eventually you become lead-rich. Reps just don't follow up with a lot of them. It's just human nature. Even you. I bet more folks want to sponsor the newsletter than you can let in, right? Do you pick up the phone with all of them?
I replied to all of them and then we just tell them we're full, but yeah.
Yeah. But you see the point, right? Even your scale, you see the point, right?
Yeah. Yeah, it gets challenging.
And let's imagine all of a sudden you had six months of inventory available. I bet if you spooled up an agent and emailed all those folks back automatically, you'd fill up the docket, right?
Mm-hmm.
So anyone can do these sorts of... you think you can't, unless you're so small that you have sufficient humans to talk with every potential lead, every person that touches your website, every person that clicks with anything, you can benefit from AI. So that was kind of our journey. And then we've done a lot of other niche stuff. I'll tell you at the end where we are today, maybe this is almost too much learning, is we're at the point where maybe we can't do one more. Because right now, when we did Delphi in the beginning, when I copied you with Delphi, even me, I spent almost an hour a day training it in the beginning because when we started to use it for support, it had an initial... it started telling people the wrong dates, and we could talk about why. So I had to fix it and it made some mistakes. And so when people started to use it, I had to spend an hour each morning firing up Delphi, reviewing the issues and answering them. I don't have to do it anymore. It's well-trained. We have so many agents going and so many emails that Amelia has to spend 10 to 15 hours a week reviewing the outputs. And it's exhausting because agents work all night and they work weekends and they work on Christmas. It's a big issue. Being the orchestrator or the chief AI person is not a good job for lazy people because the agents never sleep. So it is so much time now to manage these 20. This is just interesting. I don't know when we're going to do the 21st. We may be full. And for folks that are startups, this is a reason to go harder because everyone was in market this year and it's going to keep happening, but business process change remains an issue for business software. Business process change at the end of the day, and so many founders get this wrong, and 99% of sales folks, they don't care about business process change. Salesforce, they just want to get their commission. It doesn't really matter what you pay for an app for a customer as long as it's fair. It's all the work to change the way you do your business. And so we're at the point where we're overloaded. And so just be aware, if you're a startup or even Salesforce or HubSpot, maybe close those deals in the next 12 months, because the window may close where people say, "Listen, that's the coolest agent I've ever seen. I'm exhausted from the last five. I had to do five last year. I just literally cannot bring one more app into my enterprise." And so that's going to be a headwind that today everything seems like it has tailwinds. Everything's on fire, but people are going to get exhausted for having so many agents. Exhausted.
Man, okay. There's so much to learn from in what you just shared. Something I definitely want to ask about, as people hear this, agents sending off emails, agents talking to your clients, I get a ton of emails that are terrible.
Yes.
What have you learned about making these outbound emails good and not just noise? How do you make these conversations high quality?
It's a really, really, really good question. Maybe the two biggest learnings. Take your best person on your sales team, your best marketer you have, take their email copy and use that as the template for your AI. Everyone in 2024 said these products didn't work. There were two reasons they didn't work. It was before Claude 4. Replit didn't work. Lovable didn't exist. Gamma didn't really work before 2025, right before Claude. The LMs reached this point where they would work for these use cases. So that was one threshold. The other thing that happened in 2024 is the vendors kind of lied and said, "Just turn the product on. It'll get you revenue. No need to train it, no need to do anything. We'll just do everything as this magic AI savant." It's not the way it works this way. What you do is an agent will be successful in go-to-market and sales today if you take what works for your best person, train... I know this seems like a scary term, but it's not. Upload that text. Train the agent on it and let it iterate an A/B test from that. Agents are really good at A/B testing. They're really good at creating variants. Ask Claude for a variant of your best email. Say, "Give me three versions of my best email." They'll be pretty good. That's all the agent has to do is take your best email you ever sent and stick it through an API. I'm making it sound simpler than it is, but not by too much. So train it and then what it'll do and then give it some data sources. And the data source could be as simple as Salesforce. And then if it has any data on Lenny, it can pull data and it can lightly personalize that email. And even better, a lot of these products track all the visitors to your website. So they can see what's happened and they use other APIs and so they can personalize your emails more. And so what ends up happening is the emails that the AI's write are pretty good. If you're getting terrible emails, it's a poorly trained product from a bad vendor. You should be getting emails when you get them and you're like, "This isn't as good as Jason said on Lenny's podcast, but it's pretty good." That's what AI can do today. And the magic is if a human isn't even doing that or if your mediocre humans are worse. And I'll tell you, one of the first lessons I learned when my last startup was acquired by Adobe, Sam Blond was one of our sales leaders, then he became CRO of Brex and others. We inherited a bunch of reps from Adobe. We didn't ask for them. And he's like, "My God, I never read everyone's emails before. These are the worst emails I've ever read." So the AI can do better than that. The AI can do better than that. And so you just train it on your best and it'll be pretty good. You just haven't seen a well-trained agent. And then what I learned, and then another question folks ask is, "Okay, Jason, that email was pretty good. It wasn't as great as you said on stage, but it was pretty good." But do you tell people it's an AI or do you hide it? And what we learned from sending hundreds of thousands is it doesn't matter. We're in an age where people don't really care as long as the email adds value and they know they're going to get an instant response. We've tried both. We've tried to say, "Hey, it's Digital Amelia or Digital Jason." We've tried to fake it. And what we've learned is now we just send it. We just send it and no one cares. Especially founders will get an email back, they'll be like, "Haha, I can tell this is an AI, but it's pretty good. Can I do a meeting?" That kind of says it all, doesn't it?
Mm-hmm.
So we're creating issues as excuses to not do the work.
Your point about how human salespeople's emails are not great already is really powerful because all we're looking at is these okay emails from AI and you're saying, "Okay, but humans, they're not actually that much better if you actually look at them."
My God, they're not. Listen, the best outbound emails you've ever gotten. For example, I know you've done a bunch of investments. A lot of them are inbound to you. They want Lenny involved, right?
That's right.
Some of them are just so good you can't believe it, right? A few.
Yeah.
But a lot of them aren't, right?
Right. Mm-hmm.
So the best founders and the best sales execs and the best SDRs will spend two hours researching an email. "Okay, who exactly at IBM should I reach out to? Who else exactly is a competitor that's using them? Exactly what was the ROI?" They'll give you a perfect story. If you get the world's best story, here's your competitor, here's how they use it, here's exactly when they bought, here's the ROI, here's the case study, that's a great email. How many 21-year-old SDRs do that? No, they use an automation tool, whether it's Outreach or Gong or Salesloft or MixMax or an AI-based, but they do no work. It's not going to be that great. It's not going to be that great. So that's why people get a little confused. The bar for good enough for AI GTM, it's not as high as we think. It's just a facsimile of your best person reproduced as best we can. It's going to beat your mid-pack person. It's going to beat the person that literally knows nothing about your product.
Is this an opportunity for humans to continue to thrive, this layer of much better emails? This came up when we had Jen Abel on the podcast. I asked her, "What tools do you use? What do you use?" She's like, "Nothing. I just write it out artisanally." And it works really well because everyone's sending AI emails. Is this just where go-to-market salespeople still can exist, this much better email, or is that also going to go away?
Look, if you have a high-performing human team hunting high dollar value logos, and this is classic stuff, Lenny and I and Jen are in a conference room, we put a whiteboard of the 50 best folks that we want to sponsor Lenny's podcast. There's only 50 and we write Notion and we write Linear and we write Replit. There's only 50. And we're all trying to sell them these new sponsorships. They're half a million bucks for two years. Take it or leave it. We divide them up and we say, "Lenny's best at this, Jason's best as Jen," and we each take 15 or 17. Dude, no need for AI there, is there? Agreed. No need for AI today.
Because ROI is really high.
Yeah, and we're great. The three of us, we're different. The three of us are really different. It's going to crush and we don't need any... Maybe one of us will take our emails and run it through Claude real quick just to make it better. Or what I do is I do it for more research. I write the world's best email and then I say, "Claude, how could I make this better?" Do a little research, it will still be better. So that's an AI boost Jen should be doing. I love Jen, but she should at least be making it better. But for our 45, 50 best ones, we don't need it. What if it's 5,000? Her approach just doesn't work. So yes, a lot of the stuff we're talking about lends itself to higher-volume sales, but as everyone gets bigger, it's all higher volume. There's just so much volume as you scale. Yes, if you're tiny and you have three prospects and you're just getting into Y Combinator, maybe you don't need these tools, but we graduate out of that more quickly. And the bespoke thing for Jen, I think, will work for high dollar value enterprise, but outside of that, I don't know, man. You just can't touch enough people. Humans can't touch enough people. And humans don't want to do the work. They don't want to talk to the mediocre leads. I'll tell you an example. When I was in London, I wanted to buy a $10,000 product and I'm literally in London and we're doing SaaS one. I don't have any time. I get confused with the time zones, Lenny. I don't know if you do. I don't even know what time it is in the Bay Area. So I just emailed this rep, it's the end of the year. I'm like, "Just send me the contract. I want to buy it." But I have two questions. I have two questions I want answered. And I told them these two questions and they weren't even about price. Took him three days to get back to me and he introduced me to someone else on his team. It wasn't worth his time. 10 grand wasn't enough because there's not enough commission for him. So he introduced someone else to me and the other guy said, "I can't answer your questions unless you'll get on the phone." And I said, "I'm in London. I'm traveling." Ordinarily, I would've ended this, but it's a journey. I'm like, "If you answer my two questions, I will buy your product for 10K." He's like, "I need to get on the phone." AI's better than that. This is not Jen's and the whiteboard's thing of doing it. Even if Jen's process is right, AI can fill all the gaps. What about all the sponsors, the leads we didn't follow up with that we got a 70% response rate? The Jens are a diamond in the rough, whatever the expression is. There's not that many of them. There's not that many of them. I love her and I love what she says and I agree with 99% of it, but here's a related point. Most of us don't have the hottest brands and we don't have the most elite CROs running them, so we end up settling for not the best sales team. That's the truth. 99% of the best sales reps want to work just with the hottest brands. And the minute your star fades just a little bit, they immediately want to jump to the next one. There's a lot of reasons why. Bear in mind, 99% of the world cannot attract a team of Jens for better. It's just practical. Even I can't. Lenny, you're so great, but even a lot of folks that would want to go work for you if you wanted to hire someone, they'd be like, "Well, I love the... But what do I have to do? I've got to sell newsletter spon... No, no, no, no, No, no, no, no. I want to be CRO at Lovable. I love Lenny, but is that really going to get me there?" Right?
Yeah.
AI can beat those. AI can beat those. But AI can't beat the enterprise thing. I have no idea how AI is going to do in person sales. Someone smarter than me is going to have to answer that. You have such a huge audience, Lenny, but I still think most of your folks are in tech and doing tech sales. Tech is the largest segment of our economy and growing. So for the most part, these tools will work for tech sales. Tech sales is over the Zoom, over the phone, over email. We should knock on more doors. We should do more in person. All the data I've ever collected shows everything closes at a higher rate if you go in person. It's just not. But in tech, it's basically as much automation as we can get away with in GTM.
What I think might be helpful is just let me zoom out for a second and describe what you've gone through here. I love this visual you had of the desks of the sales folks in your office where you had inbound SDRs, you had outbound SDRs, maybe a support person.
And three or four AEs, account executives.
Okay. And three or four AEs who take these leads and then close the deal. And so now, just instead of humans, there's an agent doing each of these jobs.
Yes.
They have this outbound agent that's just sending emails, trying to find potential leads. An inbound agent that's talking to people that are interested, trying to get them more excited. And then is there an AE agent or... I forget how that works.
No, that's what I'm still learning. We have one full-time AE plus 20% of Amelia's time, so it's 1.2, doing what five or six AEs do.
I see. So basically-
No SDR, BDRs.
Got it. So basically all the top of funnels is AI.
Yes.
And there's one human now that takes all the great stuff and just closes the deals, negotiates pricing, things like that.
Yeah. Maybe 1.2 just to say it, but yeah, let's call it 1.2.
Yeah. So that's where I wanted to go. So Amelia, so that feels really important. Just somebody, not necessarily full-time, but just staying on top of these agents, watching the emails, making sure quality's high, making sure they're running correctly. Talk about just how important that part is to this whole operation.
It's critical. It's critical. And people are posting on LinkedIn that they want to hire these GTM engineers or... I don't think that role exists today. I worry when I see these roles. I think today, and listen, if we get together in 18 months, we'll update this because the world's changing so fast. I think today, 95% of 100, you've got to promote someone internally. It's got to be a nerd, someone that likes marketing and sales and is quant. A lot of B2C people are frankly good at this stuff because in B2C, sales and marketing are kind of the same thing. But someone that's a nerd that loves to sit in front of data for a couple hours a day and route data and manage these agents. And they could come out of product, they could come out of marketing, but maybe they could come out of RevOps, but they better be nerdy. Odds, they come out of regular sales approach zero. So I would find someone on my team that raises their hand and says, "I've already done this. I've already written 10 apps in Replit and I love Vercel and I did this and I've already tried these ones on my own. Can I please manage these for you?" And then have them be your chief orchestration officer. But it is a new skillset. It really is. And ultimately, finding someone that's going to spend an hour to two a day to manage these agents is the new frontier for us to figure out. They operate autonomously, but not without constant oversight and iteration. That's the confusing part. And if you just buy one of these products and disappear, you will have zero ROI. So maybe too long of an answer, but that's critical. And I just think, unfortunately, you have to grow this resource at home today. You have to. Even between Vercel that basically grew the resource at home. We're not all Vercel, but I just haven't seen it. Everyone's hosting for this job, but we need veterans. We don't have veterans yet. And going back earlier in the conversation, if that is you, you're going to be super employable next year. You're going to have so many job offers, you're not going to know what to... You're going to have to beat them off.
And when you think of... Is Amelia, would you describe her as a go to-market engineer or is that a different role, would you call her chief AE officer?
I would say now, yeah.
Okay, cool.
But she knows the product's cold. Cold. She knows how all the quirks work, how all the agents work. And this is a complicated issue, but an interesting one. If you're running multiple agents, okay, someone's got to segment which of the base the agents are working with, or they're going to have tons of conflict. You need someone smart enough and any really nerdy demand gen marketer that loves data can do this, but you've got to segment your base. Otherwise, it just becomes a mess. There are no people on X and the internet talk about these master agents that can manage agents that can manage agents. We're not there yet, okay? Maybe. I'm excited for it, but we're not there yet. So just even figuring out how to segment your base so you can do inbound, retargeting, remarketing, new marketing. So that is complicated. But most badass marketers can't understand that. They're already doing A/B testing, segmenting their bases. This is not new, is it?
No.
No. Yeah.
Yeah.
But turning it on with zero work is a F. It's just no chance.
This episode is brought to you by Datadog, now home to Eppo, the leading experimentation and feature flagging platform. Product managers at the world's best companies use Datadog. The same platform their engineers rely on every day to connect product insights to product issues like bugs, UX friction, and business impact. It starts with product analytics, where PMs can watch replays, review funnels, dive into retention, and explore their growth metrics. Where other tools stop, Datadog goes even further. It helps you actually diagnose the impact of funnel drop-offs and bugs and UX friction. Once you know where to focus, experiments prove what works. I saw this firsthand when I was at Airbnb where our experimentation platform was critical for analyzing what worked and where things went wrong. And the same team that built experimentation at Airbnb built Eppo. Datadog then lets you go beyond the numbers with session replay. Watch exactly how users interact with heat maps and scroll maps to truly understand their behavior. And all of this is powered by feature flags that are tied to real-time data so that you can roll out safely, target precisely and learn continuously. Datadog is more than engineering metrics. It's where great product teams learn faster, fix smarter, and ship with confidence. Request a demo at datadoghq.com/lenny. That's datadoghq.com/lenny. I'm looking back at some notes I took as you were talking of just advice for each function almost of how to be successful in this future that you're seeing. So I'll try to summarize briefly. So your advice for salespeople is use the agents, build one yourself, try to train it, help it run, run alongside you so that you understand these tools and be the person within the sales organization.
For leadership, I advise that.
For leaders.
I don't know that if your average SDR or junior salesperson is going to get budget for their own agent. If they do run with it. The problem, Lenny, is that all these agents that work today, they have forward deployed engineers, they have training. So they're all like 50 grand and up. 50 grand, 80 grand. I mean, people pay more, don't get me wrong. But kind of the entry level point for these is like 50 grand plus 25K for the FDE or 75. Even Clay I think starts at 100K a year. So if you're a bigger organization, that's cheaper than a human, right? It's a tall. But there are no $99 a month products, which has a lot of it. They're trying and I think it's going to come. They don't auto train yet particularly well. And so I don't know that junior folks are going to have access to 100K budget, unfortunately. So that advice is for the VPs, the folks that are worried. A lot of them are worried that I'm obsolete, that I'm obsolete, that I'm not going to get that role at Vercel or OpenAI. So keep going. The advice for the junior folks is to embrace it. Whatever tools your organization is using, become the best person at working with that agent and you'll automatically get more efficient. Yeah. Is it annoying that you walk into work and the agent set up four calls for you and maybe you only wanted to do two of them? Embrace it. Embrace it because you'll be twice as productive. I was literally talking yesterday. There's a company I'm on the board of called owner.com, which is kind of like AI for restaurants are crossing 100 million and revenue going really quickly. It's got a hundred folks on the sales team Kyle does. With AI, he's targeting three to five million in revenue per rep. Three to five million. Honestly, if this was three or four years ago for a similar company, it would be three to 500K. That's an order of magnitude more efficiency. Still a hundred reps, right? A hundred reps. He's going to need more to hit the number for next year, but three to five million per rep. So if you're that guy that can work with those tools, you become more valuable. But if you fight it, if you don't want to do that extra meeting, if you fight it, there's another tool we use for RevOps. There's two we use. One's called Momentum. One's called Attention. They're both great. They're very similar. And what it does is every single thing a human does is automatically tracked in your CRM instantly, real time. There have been tools that have done some of this before, but literally everything. And when we rolled it out and it happened with a few other folks I know, one of the folks on that old team quit that day. Quit the day we rolled out the AI RevOps. You know why? Hadn't done anything in 30 days. The gig was up.
Oh, wow.
Every day he would show up to our standup and he said, "Yeah, I'm doing outbound and I'm really working on that deal with Vercel and nothing would close." And then we said, "Oh," and he quit that day. So my point is he didn't lean into it, right? Lean into it. Now you're going to have total transparency on your day. Granola is a side example for everything, but AI is going to track everything you do. If you want to fight it, if you want to fight the future, good luck to you, but embrace it and you will leap ahead of your peers that aren't embracing this. Embrace all the transparency, all the leads, all the work it makes you do, because you can't close 10 times as much doing the same amount of work, can you?
Nope.
We do more work with AI. I'm working the hardest I've ever worked. With all these agents and all the output they create, and Amelia does a lot of it, but even I am working the hardest, but it's better, but it's not less work. It's more work. The agents are so productive, you have to keep up. So sorry to interrupt. For the managers, buy an agent, deploy it yourself. Don't have someone else do it. Do everything from training to ingestion to orchestration. And those terms will be less scary to you. For the junior folks, be the guy, the gal, the person that loves these tools and that is the first person to embrace whatever it is. Don't fight it.
Awesome. Okay. For founders in startups, what I'm hearing is be that forward deployed engineer, have that person, that sales engineer that's sitting there helping companies. This is basically an opportunity to compete with bigger players where you're actually there helping them set things up. All the companies you mentioned, none of them are big companies. They're all startups, which is really interesting.
It is true. I will say it is working with Salesforce the way we are. It's the way I haven't worked with Salesforce since it was the first product I bought, I mean, 20 years ago, dude. When I bought Salesforce 20 years ago, I got everything that was hands-on. I bought two seats. I remember back in the day talking to my rep, I'm like, "Don't talk to me. You don't have time. You work at Salesforce. I'm buying two seats." It's like, "No, no, no. This is what we do. I'm here for you. I'm going to help you get your app on the app exchange. We're going to do all of it." And that went away. It's back. And Marc's got 2,000 folks doing this at Salesforce now. So we have a forward deployed engineer. I'm not even sure it makes economic sense. And maybe in two years, someone like you or I would not get an FDE, but the big companies are figuring it out. But yes, pick a vendor that will make you a success with an FDE. And people throw this term out, but again, it's just someone that's going to make sure you get trained and onboarded with your product for real. But yeah, so startups have a motivation to do this in a way that maybe some of the incumbents really are still figuring out, right?
Which is a big opportunity for startups to actually do this. And this actually resonates very closely to what Jen suggested for startups, which is sell services initially, just like do work for them, solve their problem, not with software to get things started, to grow that into a massive contract with them that is software.
You mean being landed, expand, start with a smaller deal and grow it?
No, a person sitting there doing this work with them, essentially what you're describing. Don't just like, "We have software, go try using it." It's like we will have someone on our team helping you figure this out and maybe there's not even software yet to do all these things, but we'll have them do it for you. And then the software will take on more and more of that work over time.
I think that's always been great advice. And startups have always been great at this. In the early days, the CEO does it is doing support and CEO's onboarding you. I think what's different today is the agent will fail without training and onboarding this product. It will fail. It will never work. So it becomes an imperative if you want to win. This term's been bandied about too much, but you need a team of humans, we can call them forward deployed engineers that make 100% sure that when the agent is turned on, it's awesome. That's your job as a founder. Make sure it's awesome. Versus in the old days, even when I built one of the first e-signature services that was so easy to use, we'd have some customers take them two years to go live, big customers. That's just not okay in the age of AI. Right?
Yeah. And these forward deployed engineers, is that just another name for sales engineer or is that a different sort of background?
It can be. And I think all this nomenclature is confusing, man. All this orchestration and ingestion. I think Palantir is obviously the single most successful public B2B company at the moment. Maybe Databricks and a few others will beat them in the next wave of IPOs, but their idea for forward deployed engineers is similar, but these are nine figure deals. Most of us aren't doing $100 million deals. So the idea that you'll have Garry Tan and an army of folks out in the office for six months getting the software to work, that sort of inspires the idea, but it's really, sure, it could be a sales engineer or solution architect. But the difference is the SEs that a lot of us worked with in the days were resources. And often, there was also a classic resource of like eight sales reps to one SE. So the eight reps, there'd be a pod and one SE would be responsible and you'd kind of have to fight to get Jason or Lenny's time to help the eight reps. This is inverted. The FDE is number one job is to make the customer a success. Okay? I was literally the other day doing a presentation in an AI leader that closed a $3 million deal. The FDE did it all himself. Sales wasn't even involved in the deal. They went on site, they got the deployment going, they tuned it everything. All sales did was manage it through the procurement process. Okay? That's pretty different than a guy answering some questions for the humans. So it is a combination of customer success and SE or whatever, but it is really... I mean, frankly, it's just being a classic consultant that gets the product done on day one, on day one. That's the difference is that when you go live, it works. When you go live, it works. And it's a fancy name for a bunch of folks on your team that when it goes live, the AI agent actually works. So you have 100% success rate instead of like the 5% rate of 2024. So those people, but they do need to be technical. I don't know if they need to be engineers. It can really vary based on... I love it when they're like mediocre engineers that are in love with the product. That's my favorite type of FDE. They don't really want to code much anymore, but they did code and they just love your product. But I don't think it can be someone with no product chops, but all different folks can work, but they've got to know the product cold. But yeah, startups, I mean, the term is thrown around. You need four folks that will just make sure that on go live, the product works, your agentic product works. That's what you need.
I think what might be useful to close out this conversation is to go through what are the things that are changing, like maybe a handful of things that are changed that are now going to be different in the world of sales go-to-market, and what are a few things that are just going to stay the same?
Yeah, let's go through it. Obviously, support is the first one to have changed. It's our obviously permanently changed with AI. Whatever vendor you look at, 50 to 80% of support is done by AI. And we don't always think about support as GTM, but it is. It's the start of a customer journey. It's very important to the customer journey. So if you're skeptical, go look at... Support has changed permanently. So that train's left the station. Really, as we record this, not much has changed in sales. I mean, I do think the stuff we've talked about is the bleeding edge. I do think the classic cadence-based SDR running campaigns through a tool, him or herself, will be mostly extinct with 12 months. There is no reason AI can't do a better job than that role. The classic qualifier, qualifying inbound leads, which is a crappy experience for customers, should be similarly extinct within mostly extinct in 12 months. The rest, we're going to wait and see. I think what we do know for reps, for sales reps, everyone wants to be even more efficient in the next 12 months. There's a lot of reasons people want to be... Again, at the bottom end, it's cost, it's profitability pressures. At the high end, it's cultural. We just don't want 200 reps running around Vercel or Replit that don't know what the product does. Just the company owner, three to five million per rep is a lot different than three to 500,000. So you have to adjust as a rep. Every AI leader can't hire enough reps like we talked about, but you're going to have to adjust to being geometrically, if not exponentially more productive with help from AI. So you have to embrace these tools for real. And a lot of folks, a lot of old school GTM leaders are like, "AI isn't going to hurt sales reps. It's just going to give them superpowers." The best ones, yes. The mediocre are just going to be more mediocre. So I think the AE is what we will always have salespeople, but being a people person is not enough anymore. You know how you can tell a mediocre salesperson, Lenny?
Yeah.
You ask them what they're really good at. I'm a people person, Lenny. You know how good I am, Lenny? I'm on text with 10 of my best customers. I'm a people person. What are the toughest technical objections you have at your product? What? What? They don't know, but they're a people person. This is like golf 3.0. It's not enough. It's insufficient. So people are becoming obsolete in sales. Field sales, no idea how AI is going to impact that if you're out in the field. I mean, the enterprise leaders are hiring more field salespeople than ever. Salesforce is hiring more than ever and knocking on doors still works, man. So don't know the answers there. But the office worker and the work from home worker, AI is going to take as much of your job or make you as much better as it can and you got to embrace it. So that's, I would say, from support to knocking on doors, we're going to go from 80% to 0% from AI.
What about phone calls?
It's a great question and we should have hit it. Obviously, there's plenty of robocall and regulatory issues around it. Certainly a lot of startups are breaking the rules anyway. I would say this, listen, there's phone calls and there's even SMS. There's limits to how much SMS you can automate. A lot of old school businesses don't even check emails. I mean, you're working on the shop floor. So those are unanswered questions. People are breaking the rules. OpenAI still breaks the rules. Now it's licensing Disney content. It used to just borrow Disney content. We will see. So I don't know the answers to that. I think in Europe, it'll certainly be much lower than in the US, but startups are going to push the limits. They're going to push the limits on what we can do with AI calls, AI enhanced, whether a human's kind of on the line, but AI is doing all the work, maybe that's legal, right? Getting more consent for SMS than we typically get. So to think that the typical barriers to robocalling and SMS that startups aren't going to bend the rules in the age of AI, I'm dubious. But it's a good question. It's harder to do. The one thing I will add is, and it's a good objection to all of this, and I'd love to get Jen's thoughts too. But if you talk to the startups you'd invest in, Lenny, fewer of them are good at outbound phone calls than you'd think. We had many of the heads of revenue at Rippling, speak at SaaStr, the old CRO worked on my team and others. They were late to develop cold calling because we never did it back in the day. The CRO was on my team. So we had to bring in someone that had worked with Sam Blond at Brex who had done it. It is a real art to pick up the phone and close business. It is a specialized skill. And so if that's your specialized skill and there's no way for AI to benefit, so be it. But I don't think for most tech calls that that is as impactful as we pretend it is. I don't think most of the startups you and I work with and most of the folks listen to this do not close the majority of their revenue with cold human cold calls. It is a craft that works, but man, you got to be good at it.
Yeah, this line somewhere that if you can close on a text message, AI can close it.
Yes. It is. I'm being facetious in the sense that people say that I think have weaker relationships with customers. This is why people have weaker relationships with their customers than they think. Yeah. And if it's so easy to close the deal on a text message, and we've done hundreds of thousands of these and folks don't mind if it's an AI, if it's a good AI, why won't it close it on the text message? AI can be people too. It really can't. If you don't believe me, folks, go to Lennybot. Is that the old lennybot.com?
Lennybot.com.
If you don't think AI can be people, people spend hours on Lennybot, don't they?
Yeah. And the best part is you could talk to Lennybot with voice. There's a voice feature that sounds exactly like me. It's unbelievable.
Yeah. And a meta reason to go use Lennybot, go in with a learn in mind, don't go and bias. You will find that AI can be people people. People spend hours. Who are our best therapists today as we record this? ChatGPT is our best therapist on planet Earth. It's a people person. I mean, it sounds silly, but if that is your best defense in sales that you're a people person, the sands are sinking beneath you right now. It's not enough of a skill. People person is great when people buy enterprise software that's going to take two years to roll out and they have no idea how it works and it's a hope and a prayer. When you expect the agent to work during the pilot before the big check comes, people person is insufficient. Terrific. Tell me the person that's going to launch my agent, train it and get into production for me before I even pay you. This is the dream. Maybe this is one of the biggest changes of all. When I talk with Marc Benioff, and Salesforce is the biggest, right? It's 44 billion. It's the biggest ship to turn. He's like, "The number one thing I envy in Palantir, one is their high deal sizes." He made that joke in all the media and all the press. But the other thing is, he said, "I wish I could. I can't today. I wish every Salesforce customer now could go live before they pay." That is so different from how we've been trained in many ways to almost rip off the customer, to get them to buy the product, first try to avoid a pilot, then have the smallest pilot we can, then roll it out over years to different people. AI has upped the bar in terms of what customers expect. And that's why the best ones are blowing up because the ROI is so high. And so you've got to deliver the ROI before the document is e-signed today. People that haven't fully embraced that are at public companies growing 8%. They're still trying to play games.
What are some other things that you think are going to change that people may not be thinking about that's going to change the way we do sales in the next couple years?
Net net, we're going to need more sales and go-to-market professionals than ever because the winners are growing so quickly that even if they're more efficient, they will need more human beings than ever. We'd have to put together a spreadsheet to see the crossover point. Obviously, many folks are shrinking headcount. Microsoft's already said they're past peak employee. They're never going to be bigger. We're seeing this all across the companies we work with. They want to be as lean as they can, but AI is such a huge part of our economy already. And it's such a force of nature. And everyone eventually goes enterprise. Everyone eventually has a sales team. Everyone eventually does it. It's happening faster. ElevenLabs, 50% of their sales is through enterprise now. I mean, I don't know everybody. The fact that Vercel just added Jeanne means they're going more enterprise by definition. I think Replit just added a sales team a couple months ago for real, and now they've added another CRO. So they got to a hundred and something million with no traditional sales team, but at a billion, it's going to be flooded with salespeople. So if you get great at this stuff, if you go buy an agent today, when you listen to this and deploy it yourself and do the hard work and train it and ingest it and iterate it every day and get ahead of it and then get two agents and then three and then four, you may become more valuable, have a better experience in ETM. And I believe, I hope, actually be better paid. I've talked about that we should have $250,000 a year SDRs, but they'd be like at Vercel, they'd be managing 10 agents, not 10 people. Then they're worth 250 grand. For sell, they'd be managing 10 agents, not 10 people. Then they're worth 250 grand, instead of 80 grand or 90 grand. It's not that much, is it? So, there is a great world coming. These are the best of times, aren't they, Lenny, for product and business? It's not evenly distributed. So, if you have those skills, even though we're not going to need these SDRs and even though not going to be BDRs, even though we can get rid of half of AEs, the amount of revenue and growth in AI leaders is so phenomenal, right? And not just at the startups, at the Google Clouds, at everywhere. Azure, they're hiring so many humans that net-net, it's a positive for the profession, but not for the way we've done it in the past. You're at risk.
That is really interesting that we're still hiring. And this is what I've seen too, just like everyone's hiring salespeople, go-to-market people. Do you think there's going to be this peak in the next couple years of just, okay, now that AI is doing more and more of this, or is it just hard to predict because who knows how big AI gets, how big these companies get?
I mean, IT's over a trillion dollars, and it's accelerating. AI is increasing the amount. Gartner says next year will be the fastest acceleration of money deployed into IT and software in a decade. It's reaccelerated. Can that last forever? No. Eventually we consume 100% of the global GDP. There's no money left to buy. There are some limits. But I don't think you and I and anyone, any of the millions of people that follow you, I don't think we got to think too much more than three to 40 years out here. It's too much. There's too much change. If you become a master of the universe in AI, you will be hyper employable the next two to three years. And if you stay with a learner's mind, that will just compound. And so, you will have a job that I think is far more interesting, even if more tiring than we used to have. But the days of working 20 hours a week and phoning it in and getting a few deals, I think that was a great time. Even you had a little bit of that. I think you're working harder than you used to, aren't you?
I am, I am.
I mean, the classic Lenny vibe at 100,000 subscribers was, leave me alone. I take a lot of vacations. I do some good work. I mean, it's still part of your vibe, but I think you're working harder.
I'm working incredibly hard. I am. The original idea was create this chill newsletter life. I'm just going to write a newsletter once a week. Life's going to be good. And it's just hard to pass up on really cool opportunities and do more, help it grow bigger. I couldn't resist. So, yeah, I'm working and that should be hard.
And that should be all of us though. If you're not feeling what you said or even a version of what I said, then you're not living the AI dream today. It is more work. It should be tiring. Even if it's better in some ways, it is just more work. But this is the most exciting time of our lifetimes to be in software. I mean, good God. I can't even code Lenny, and I've built 12 apps on Replit in the last 150 days used by a million times. I've been waiting 10 years for some of these folks to build some of these apps. I just did it myself, right? I literally, just when I was in London, I built a whole app where you can practice selling Harvey, Cursor, Replit, and ChatGPT Enterprise, and it works. This wasn't even possible at the start of the year, was it? So, these are magical times. And the fact that we can run an eight figure business with three people and 20 agents, it's like, get excited or go join one of these really slow growing... My advice is pick one of two paths today. Either be working harder like even you and I are. We don't have to. Or honestly, I will say the truth is there are a thousand unicorns born in 2021. 800 of them are growing pretty slowly. We'll never IPO, may not have an exit, but they're okay with 8% or 15% growth. If you don't want to be on the journey we talked about, I'm not judging. I get it. We're humans, right? We have families. Not all of us are obsessed. I think I'm obsessed. I think you've become more obsessed. If that's not you, join something more slow growing. They still need people. Not as many, they still need people. But I would pick a lane for next year. Don't pretend that there's this middle path going to start because it don't exist in GTM. And I don't think it exists in product or engineering either.
I love just how excited you are about this. Just like you could tell on Twitter just how fun this is for you, just learning and sharing. And I love that you're sharing it, but I think it's just a symptom of you're just so excited about what's happening and what you're learning and it's just like you can't help but share it. I'm in the same way. I'm just like, "Oh shit, I go to this really cool thing. I got to tweet about it."
It is just magical that our ability to build things that we couldn't build before or build in ways and paces, and it's accelerating. I mean, we could talk about it forever, but even for me, I picked Replit because Twitter told me to, I could have picked another tool. I'm not an investor and I'm not even biased, but I'm in the top 1%.
Just to double down what you said, you're top 1% user of Replit?
Yeah.
Wow.
Yeah.
I love that.
So, it really didn't work well when I started about 170 days ago. Then a V2 came out and it got better. The hallucinations went away. And then this is just like you got to get excited about. Folks may not know this and other tools. When V3 came out, I don't know, 45 days ago, now it has agents talking to agents. So, what happens is, and again, I can't really code. So, when I have an issue and I'm trying to figure out how to do something, the agent calls in an architect or another agent and they debate and argue with it and they come up with the right answer. The first time this happened, I just fell out of my chair. Not only is it magical, I mean, great, you can do a prompt and build a crappy app that doesn't work. Now, 150 days later, you have agents debating how to build better code with each other and you don't even need to know how to code. The only greater time is going to be next year, right? I've been waiting. I've been waiting, right? And just the things that you can build today. And I mean, you know this, but other folks, I mean, that's me building without being able to code. The other captain obvious thing, why are folks so productive on all these tools? I mean, every bit of open source software in the world is in these tools. If you want to build something that's been built before, it's so easy. The novel stuff's really hard, right? It's not any easier, but man, it's just these are great. And so, for GTM, for sales, it's a couple beats behind. And there's probably a bunch of reasons for it. Some of it is, I think ironically is just where founders are interested. So, marketing is behind sales for AI. AI, SGR has exploded. I don't really know why. I invested in a couple of pre-AI tools. I invested in Salesloft, which was sold for two and a half billion. It was like the last deal of the 2020 ones, like the seed investment. No one wanted to be in that category. Now everyone in the world wants to build an AI, SDR, AIR, CRM. But marketing is slower just because people don't really want to build the cursor for marketing. People say they do, but it will get there. But the innovation will just accelerate. It's just going to accelerate. So, don't be a skeptic on this stuff. If you're not as excited as me, then here's my last bit of advice on this for folks. If you don't feel what I feel, here's my advice over the holidays. When you have a quiet moment when you're having your mold wine or your hot chocolate or whatever, fire up your browser, do it incognito, go to your app and do everything with a fresh Gmail address. Try support. See how your support is. Try to contact sales. Sign up for the newsletter. Do everything. Try your product. If you do this quietly, your heart, you're going to cry about some of the things you've seen. You're going to cry how bad your support is. You're going to cry how long it takes sales to get back to you. You're going to cry about a couple things. Pick the thing that makes you cry the most over your mold wine and go buy that agent and fix it. And then you will have the passion that we have. I always counsel people to do this. It just wasn't as actionable before AI. You just get lost. You forget about the onboarding workflow and you forget about support and you forget how bad contact me and you're so lost in the strategic. So, you got it once a year, ideally once a quarter, just do this Incognito mode test. And even for Lenny's newsletter, I bet we can find some part you forgot to touch.
Nope.
No, you disagree?
It's not going to happen. I'm just joking.
You'd be like, "Oh my God, I can't believe I didn't touch that since I launched the Substack. It doesn't even go to the right. That place gets a 404."
I'm going to do this over the holiday. Usually, the advice would've been, "Okay, email your product manager and tell them you found all these bugs." What you're saying here is no, find an agent to take care of this in the future, make this a much better experience for everyone always.
Yeah. Yeah. And if it's the one that makes you cry, it may motivate you to do it.
Yeah. And it's not like you have to publish it to production. It's not like you have to have your CEO approve this thing. It's just like, show them what you might be able to do. Here's what I did over the weekend. Maybe we should explore doing this thing with our site.
Yeah, the jaw is just my job.
Yeah.
Yeah.
Oh, man. Jason, I feel like I could chat with you for hours, but I think this is a good point to wrap things up. Is there anything that you wanted to share or is there anything you want to leave listeners with?
One last thing maybe that comes up that I've learned that are on people's minds and we can't break is a lot of folks are concerned, "Hey, this will unpack people's jobs. What do I do? Okay, I did what you said. I did the incognito mode. I'm going to bring in this agent, this sales agent or this support agent. I've tried, I've even did it, but I'm worried I'm going to get pushback and people are going to lose their jobs." I don't have the perfect answer to this one, but I think be honest about it, be honest that for the best people, it will make them more productive. For the best people, it will be even fun. For the best people, they will be better at their job. And if it is a threat to some of the folks on the team, the future is coming anyway. We might as well embrace it. So, it's just when I hear, I would be positive about it. I would explain it helps the best people, but I don't think dancing around it is the right answer in your organization. It will result in change. And if some jobs change from one role to the other, that's life in the age of AI. Don't hide it. I don't think it helps.
I love that in your case and in Jeanne's case at Vercel, it's not like you let anyone go. In your case, the SDRs quit. And in her case, she moved them from, I believe, from inbound to outbound or outbound to inbound. She just reshuffled them to do to have higher impact somewhere else.
I think that's a really important point. This is another thing that I think the media creates too much drama on. I mean, AI has led to some layoffs, but even though most of the ones we read, it's just a justification to do layoffs. It's just a reason to blame it on it. What's a much bigger issue is that people just won't be backfilled with humans. We will use AI to backfill. That's what we did. We didn't fire. I've never fired anyone my whole career other than for inappropriate conduct a few times that you fired today for that stuff. But pretty much I've never fired anyone that didn't do something inappropriate. When they go, this time we just said, now it's the agents, right? And so, that's a much bigger force of nature than some random layoffs, which probably aren't really new to AI, right? It's probably not because you brought in 20 agents in 2025. It's probably because you just want to downsize anyway, and this is the excuse. So, it's probably less of a threat to you than you think AI. But what it does mean is if you don't want to embrace it, Lenny, maybe don't leave your current job. Yeah.
I was just going to say...
Maybe don't leave your current job.
Because the new place might not be hiring for this role.
Yeah. God, I have a sales exec who I love. I've known for many years and he went from a 100K job, then almost an 800K job, then down to a 200K job, then left that one because he didn't like it and now he can't get a job at all. He's back in school. So, maybe stay.
There we go.
We all maybe stay. No shame in staying, is there?
Yeah. I like that. Well, with that, Jason, we have reached our very exciting lighting round. This is your second time going through a lightning round, so I'll make it quick. First question, what are a couple books you often find yourself recommending to other people?
I was recently asked to write a forward for a book from one of the revenue leaders I have the most respect for in the world. I read a little bit of it. I couldn't do it because as good as it was, it was dated. It wasn't current enough in AI. I don't know what we said at this... It might've been before we started the pod. The plays all work, but the playbooks don't really work as well. So, many of these GTM books are playbooks, especially folks selling courses and stuff, but they're playbooks. Run from the playbooks, embrace the plays. And so, read all these go to-market and sales books and take great items from them, which was always the goal from a book. Pick two or three things out of it. But I think I'm waiting for the next level of books and GTM and 2026 because everything I've read, it's just too backwards looking. So, just be a skeptic. Grab the plays, but don't adopt the playbook. I just
Had the head of growth from Lovable, Elena Verna on the podcast. She had the same advice. Then all these playbooks that she's used over the last 20 years in growth just don't work anymore at AI companies. Next question. Do you have a favorite recent movie or TV show that you have really enjoyed?
What's this one called? What's it called? Pluribus? Is that what it's called?
Pluribus, yeah.
Okay.
I've been watching that.
So, it's a good show. This is what I realized is why you should be excited about AI and GTM is Pluribus because in Pluribus, there's like a hive mind, right? All the people accept 11 people or 13 people. They're all connected. People don't get this. This is why right now, the whole point when we're doing this, maybe we'll do a third one if I'm lucky. The whole point is just get your AI agents to be almost as good as humans, but working 24/7 and at scale, that's pretty good. If it can do 10 or 100 times more work, 24/7, as pretty good as your human, that's a resource you don't even have today. It's not that complicated. When AI really is the hive mind, when it can share all of the data across all of your agents and knows everything that happens, then humans are at risk in GTM. They're going to be so much better when they're the hive mind. Right now, our hive, and there's a bit of a Renaissance for Salesforce as a CRM. There's a bunch of reasons, even though it's old, it's founded in the '90s, it has become the hub for these AI GTM agents. They all plug in. So, Salesforce has become the database for all these. So, that's a little hint of the Pluribus hive mind. But when all these agents can talk with each other for real and share all their GTM data and all the customer data and everything on the next time we do it, the 3.8 million people that read Lenny's and all the agents can share data together, I don't mean to turn Pluribus into an AI GTM show, but there's my connection, but it's pretty good, right?
I get it. I get it. Oh man, that show's so good. I feel like every episode, I get these pushes from Apple TV of like, there's a new episode of Pluribus. I'm like, "I can't wait to go watch that." Each episode ends in like, oh, I can't wait to see what happens next. Okay. Is there a favorite product you've recently discovered that you really love, like an app or a gadget or clothing?
Maybe not in the last two weeks. I'll just give a small one just for GTM one.
Yeah, that's okay.
Because everyone's about Sora this and all of this and video and I love it. I get it. But there is an app called Reve. It used to be Revar. It's for imaging. And the folks that build it built their own image LLMs on their own. And the reason I bring this up, I use it every single day is because it can do a lot of cool things with a prompt, right? But if you want to do cool stuff for marketing, if you want to create a great image, I have a CMMO buying my product doing this. I don't know a tool that is better for that kind of stuff. That stuff that we used to torture, we used to fire up Canva and try to create things or even worse, wait four days for someone to do it for you. This is one of my cheat sheets. I have a couple tools that I use that people don't get, but now it's app.reveai. It changed its name. But it's just a simple prompt to go to it, type in whatever image you want to make. And for a lot of the boring B2B stuff we like to do, I find it's the best.
And it's Reve.com?
Yeah. Reve.com.
I'm looking at it right now. Capybara delivering matcha through a quite must garden.
App.reve.com.
Yeah, sweet.
Oh, you're making the image, you said?
I'm just like, they're giving me examples here while I'm on the website here. Yeah, this is great. And you're saying this is better than Nano Banana and all these other...
For this use case. You and I, we just want to do...
For marketing images?
I want to do a thumb. I want an image for my article. My niche thing, content I just want to do. I've got to do it. I just don't think there's anything better for this use case. Sweet. I use it two or three times a day and I use all this stuff.
Okay. The alpha, more alpha to share with the audience. Okay, two more questions. Do you have a favorite life motto that you often find yourself coming back to in work or in life that you often maybe even share with other people?
I'll just tell you one in the weird time we're at. This is probably your best startup. Just talking yesterday with a friend of mine, startup just raised 20 million from a top two or three VC. Founder just quit the next day. Just on the call the other day, yesterday, CEO of a company at 250 million, just quit. No success or no anyone to join a hot AI startup. Maybe, maybe, maybe. Most of the time, there are times and places to just quit when you have customers, when you have a million or two million or five or 10 million in revenue. But we often think it's easier to get back, to get back to that 10 million of revenue, to get back to 100 happy customers or 200 pap. It might seem easier to quit in the age of AI, but I'd rather take those 500 happy customers, build that badass AI product and sell it to 500 happy customers and go off to find them from scratch. Go off to find that 10 or 20 million. I literally had a third conversation with the founder just crossing a hundred million that wanted to leave and do a robotic startup after 10 years. I'm like, "I get it, man, but you have nine figures of equity in this company. Maybe go to the next level." So, there's so much going on. They're decelerating, accelerating. I just usually think the best startup for founders, not necessarily for everybody else, is the one you're already working at. And if you're not happy, turn that into your hot AI startup. Here's the thing. It's not too late, Lenny. Sometimes it feels like it's too late on social media. Maybe it's too late to build the next ChatGPT on the cheap. Okay. But for most stuff, it's not too late. It's still so early. We don't even have great AI marketing tools. We're really early on these AI SDRs. The markets have not hardened. The LLMs are getting so much better. Dude, if you want it's not too late. So, the best startup you're ever going to have probably is the one you're working at today. Don't quit. Don't quit if you have happy customers. Maybe that's how it is. Don't quit if you have happy customers. They'll buy more from you.
I love advice like that that's empowering and optimistic and destresses people, I think, in a lot of ways. So, that is great. Final question. So, how many SaaStr have you done at this point? How many years have SaaStr have there been?
Good God. We did some meetups. You know that, right? And then we did the first bigger one in 2015. So, 2016, we did take a break in 2020, but we did in 2021. We're the only event in the Bay Area in 2021. So, is that 12 of them? 12 years? It's a long time, man.
And then how many talks have there been across those would you say total?
I know we've done seven in Europe. So, 12 in the US and seven in Europe.
So, about 20. Okay, 20 events.
Twenty bigger events. Yeah. I don't know. The annual one, probably if you count the smaller ones, 300. So, 3,000, 4,000 over the years.
So, then here's the question. What's your favorite talk across all those events? Is the one you're like, "Oh, this one really stood out. This is one I always share with people"? One that you think you'd want people to check out if they were to check out one talk across all SaaStr.
It's interesting. It's like a lot of things in B2B. Everything was pretty much the same for 10 years, and then all of a sudden everything's out of date, right? If you wanted to watch an older one, not that old, but old in internet AI time that I think will change the way you think. Watch the one I did with Ben Chestnut right after they got acquired. Because that's a magical time. It's called Everything That Breaks On The Way to One Billion. It's only got 23,000 views. That's nothing for Lenny, but for me, that's pretty good. Okay. And it's a moment in time right after he sold a billion-dollar company where he talks about how the deal almost fell apart, where he challenges almost every B2B metric we know. Running a profitable business at that scale, not really caring about CLTV and CAC or any of these things, what really matters for customers. Is MailChimp as cutting edge as it was today? Maybe not. But that's one when I look at it because everything's the same. We don't really get challenged in the way we think everyone's talking their book. You're so good at getting people to not talk their book, but that one I think is a great one. And then if people wanted to watch a GTM one, just some favorite ones, we do this one. It's a recent one. Because these guys were on my team, Matt Plank who's CRO of Rippling did one with Sam Blond who was then CRO of Brex. It's called Rippling Secrets to Hypergrowth. It sounds like a commercial for Rippling, which is okay, right? But because Sam was, they worked together and now Sam's on the board and all, they have a fluency of two CROs who are honest and have a Lenny style learner's mindset. This one on the revenue playbook from Rippling, it's a 14 for GTM.
I just had Matt MacInnis on the podcast, former COO, now CPO At Rippling. So, that would be a good combo of those two. Jason, I don't know if you know this, but you're the perfect podcast guest because you have such deep experience in the space that you just have answers to everything I ask. Plus, you're now just living in this future that we're all heading towards and you're like hands-on telling us, here's how the future will be and here's how it works and here's how you can get there and here's what you shouldn't do and here's what we'll bring. So, I'm just so thankful that you're here sharing all this advice with us. I'm excited for many more podcast conversations. So, thanks for doing this.
All right, Lenny, you're the best. I'm just a super fan. I'm lucky to be here. So, thank you.
Let me just ask you, how can listeners be useful to you as a closing question?
The fun thing for me, we have two websites, SaaStr.com and SaaStr.ai. Just go to SaaStr.ai and just play with the tools we built. Play with the valuation calculator we talked about. Play with the AI VC, play with any of our tools and just have fun and share any feedback because I've waited 10 years to build tools for the SaaStr community. Now I want to build like 20. So, on the side, we've talked about tools you should go buy, but building your own stuff's pretty fun too. So, try our tools and give me kind, but critical feedback, but with some kindness.
Okay. And that's S-A-A-S-T-R.ai?
.ai. Yeah, I'm still trying to figure out the AI versus the com. We got an SEO issue, so I can't really move it over, but...
It looks great. It works, it works. It's shorter too.
It is shorter.
Jason, thank you so much for being here.
All right, Lenny, you're the best.
Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.