GTM 151: AI-First GTM, Lean Teams, & Customer Obsession with Dennis Lyandres

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Dennis Lyandres is an Advisor with ICONiQ and a Board Member of Speedchain and CaptivateIQ. Dennis amassed incredible insights through his experience as the Chief Revenue Officer of Procore, where he helped grow the company from $10M to $900M+ in revenue and guided it through a successful IPO. At Procore, he led all customer-facing functions—Sales, Marketing, CS, RevOps, and BD. He’s now an investor, advisor, and board member to iconic B2B SaaS companies, and one of the most respected voices in GTM for vertical SaaS.

Discussed in this Episode:

• Why the Best SaaS Companies Align People, Product, and GTM into One Unified Strategy

• Using AI as a GTM Advantage Starts with a Crawl-Walk-Run Approach

• Scaling Multi-Product in Vertical SaaS Means Following the Money and the Pain

• GTM Leaders Win When They Speak Product and Co-Own Strategy with Engineering

• Customer Relationships Are Your Most Undervalued Strategic Growth Lever

• Your Top 5% of Talent Deserve a Purpose-Built Strategy to Maximize Impact

• Lean AI Teams Are Redefining What’s Possible with Just a Handful of Operators

If you missed GTM 150, check it out here: 80% of Exec Roles Aren’t Posted, Here’s How to Land Them Anyway with Andy Mowat

Highlights:

03:00 Dennis’s journey as the Chief Revenue Officer at Procore: from $10M to IPO

05:00 The “People, Product, GTM” triad and AI-native orgs

07:00 Why vertical SaaS startups need a talent strategy (and most companies lack one)

09:30 Multi-product GTM strategy explained via Procore and other verticals

13:00 How Go-To-Market teams can show up better for product teams

18:00 Building deep customer strategy across functions in a B2B startup

23:00 Price’s Law and the T30 program for top performers within a revenue organization

24:30 Lean AI startup: what it is and what it isn’t

30:00 Crawl-walk-run AI adoption in Go-To-Market teams

Guest Speaker Links (Dennis Lyandres):

• LinkedIn: https://www.linkedin.com/in/dlyandres/

• Speedchain: https://www.speedchain.com/

• ICONIQ: https://www.iconiqcapital.com/

Host Speaker Links (Sophie Buonassisi):

• LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/

• Newsletter: https://substack.com/@sophiebuonassisi

Where to find GTMnow (GTMfund’s media brand):

• Website: https://gtmnow.com/

• LinkedIn: https://www.linkedin.com/company/gtmnow/

• Twitter/X: https://x.com/GTMnow_

• YouTube: /@gtm_now

• The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

Sponsors: TriNet

Every early-stage founder is told to focus on product and growth. But behind every product launch and revenue milestone is a team – and building that team is one of the hardest and important parts of the journey.

“Build the team that builds the company.” – that is part of your go-to-market strategy responsible for growth. 

Hiring the right people, keeping them supported, and creating the infrastructure to help them thrive is critical. 

TriNet exists to make that easier. TriNet’s full suite of HR solutions is designed to support companies at critical inflection points – from early traction to scale.

Learn more at https://trinet.com/gtmnow

GTM 151 Episode Transcript

Dennis Lyandres: I‘ve come to believe that there are like these three pillars that when integrated and de-risked against each other create the greatest amount of magic and excellence. And that’s people. Product and Go-To-Market.

The very best companies, they have an actual people strategy. I walk in companies, got a product strategy, a fundraising strategy, but they don’t have a talent strategy for those of us that have seen tech shifts or studied them.

This one’s happening with more conviction and speed than anything any of us have seen. Don’t build for what you can do today because the world’s moving faster. Like you gotta think ahead on this stuff and you gotta play chestnut checkers because otherwise it just happenstance. If you do tactics and absence of strategy, probably not gonna get where you want to go.

You gotta. Follow the money and the pain. If you’re gonna have the most performant organizations on the planet, you’re gonna have the most performant people. And if you’re gonna work with and support those people, um, then these things matter. Customer drives everything in the organization. It drives employee engagement.

It’s the one person that can hire or fire you.

Sophie Buonassisi: Behind the scenes, it was a small group of people that were doing everything. I want

Dennis Lyandres: to know how this insane growth actually happened.

Sophie Buonassisi: Before we dive in today, a quick important message from our sponsor. Partner TriNet, a trusted HR provider to startups and scaling companies. Every early stage founder is told to focus on product and growth, but behind every product launch and revenue milestone is a team, and building that team is one of the hardest and most important parts of the journey.

Build the team that builds the company that is part of your Go-To-Market strategy, responsible for growth, hiring the right people, keeping them supported, and creating the infrastructure to help them thrive is critical. Try not exist to make that easier. TriNet’s Full suite of HR Solutions is designed to support companies at critical inflection points from early traction to scale.

Learn more @ trinet.com slash GTMnow to see what’s possible for your business. That’s TriNet T-R-I-N-E t.com/ GTMnow. Now onto the episode. This episode is a special one, and you’ll learn tactical advice on scaling vertical SaaS companies. Just last week, we hosted GTM Fund’s first annual general meeting or a DM for short.

For new listeners, quick refresher. GTM Fund is an early stage B2B SaaS venture firm, and GTMnow is its media brand. The home of this podcast, GTM, now shares tactical go-to-market strategies, real stories, and proven frameworks from the top 1% of operators who have been there, done that alongside insights from the venture side.

At the A GM Annual general meeting, I hosted a session on scaling vertical SaaS with prolific leader Dennis Leaners. Dennis spent eight and a half years at Procore [00:03:00] where he helped grow the company from 10 million to over 900 million in revenue. And ultimately take it public on the New York Stock Exchange.

If you listen to any of the other executives at Procore, talk about the most important people in the room. You hear Dennis’s name, time and time again. His time there included serving as Chief Revenue Officer leaving all customer facing functions, sales, marketing, CS Rev, ops BD and procore.org. He’s now an active board member, advisor, investor, and works with iconic.

Maybe most importantly, if you get a chance to meet him, he is one of the kindest and most genuine people that you’ll meet in this industry. Enjoy the conversation.

Dennis Lyandres: Honestly, like this is such a special community and I find the content coming out of this place like I’m an avid listener. It’s like second to none.

So I must admit, if the content sucks, tell me it won’t be for a lack of effort because I think the bar is really high. So

Sophie Buonassisi: I love it. Shall shall do it. It feels inevitable. Not to start off with an AI question.

Dennis Lyandres: Okay, so

Sophie Buonassisi: when it comes to cross vertical software and ai, [00:04:00] what are you really advising founders on today?

Dennis Lyandres: Um, so. You know, I’ve spent quite a bit of time since Procore kind of advising across Iconics portfolio, doing independent work and trying to be a student of like what is uniquely valuable that ensures not only people win, but that they don’t lose, which I think is kind of like a different mindset, right?

And I know this sounds like world peace in everything, but I’ve come to believe that there are like these three pillars that when integrated and de-risked against each other create the greatest amount of magic and excellence. And that’s people. Product and Go-To-Market. And I know that sounds like World pc, like the dude is like, you know, just eat vegetables and train really hard and you’ll be great.

Like, so I promise I have a lot of tactical examples of like how these come together and can help you build a big business. And so for me, you know, like with speech in, in the room for example, like that’s a big thing we work on, which is like, hey, how are we gonna make sure that we’re exceptional, both in isolation.

Between people, product and Go-To-Market, and that they come together [00:05:00] in a one plus one is three way. And then, you know, I think there’s two schools of kind of AI transformations. I do both with folks that I work with. One is a more crawl, walk, run, and I can talk about that if you want. I. And the other is like, Nope, we’re just going all in.

And here’s what that looks like. And from a Go-To-Market perspective, you know, the crawl walk is like, Hey, do we use GPT and gong’s call coaching? And the we’re going all in is I’m just only gonna hire AI marketers, prompt engineers, and Go-To-Market engineers.

Sophie Buonassisi: Hmm. So are there things maybe then that the best companies or companies excelling that you’re working with are doing that maybe aren’t talked about enough?

You called out content earlier. It’s a lot of content out there. What are companies doing that might not be talked about through content or other mediums?

Dennis Lyandres: Um, so I mean, I think, let me offer a few and I’ll try to read the room and go where the room wants me to go. So like, please pay attention. Um, uh, but you know, I, I think that, you know, the, the, the very best companies, they have an actual people strategy.[00:06:00]

Like there’s real teeth to how they think about talent. They know are they building talent? Are they buying talent? Is it different in different organizations based on one reason or another? Our RD leader only wants super senior product people, but you know, for sales we want to build all our own talent.

LAR Nielsen style, we’re gonna hire SDRs, and then they’ve aligned how they invest in build the organization around it. I think that that like is probably the thing I see the least of. You know, I walk in, company’s got a product strategy, a fundraising strategy, but they don’t have a talent strategy. The talent strategy has a lot more things in it than that.

So that’s like illustrative. How are you gonna build an All star executive team, not just look at all star players in the executive ranks. You know, that’s another one. How do you drive mission, vision, values, and culture? Like it’s not squishy. It really matters. And it’s not like kombucha and coffee. So that’s another one.

And then, you know, an AI first talent strategy, like to intersect the prior question, like how are we actually gonna be an AI first company? I think that if you’re still wondering if it’s real and it’s a seminal shift, like stop wondering. And I also think like, please don’t build for what you [00:07:00] can do today because the world’s moving faster.

For those of us that have seen tech shifts or studied them, this one’s happening with more conviction and speed than anything any of us have seen. I think pretty much everyone agrees on that. Where are we gonna be five years from now? I don’t know. But it’s 12, 18 months out. And if you’re not building for that today, good luck.

And that is a very, very heavy lift on the talent side.

Sophie Buonassisi: That makes sense. And what about if we shift towards thinking multi-product, what are some of the strategies towards going multi-product for vertical SaaS companies? I.

Dennis Lyandres: Have a strategy and actually I come back to strategy. Yeah, yeah. Well, no, I mean, I think that like, if you have, this is one of these things, right?

People are like, just gimme the tactics. And I’m like, okay, well, but if you do tactics in absence of strategy, probably not gonna get where you want to go. And if you are, it’s, it’s gonna be more luck than it is like absolute wielded into existence. And I know what, why and how it happened. Look on the multi-product side, especially for vertical software, I think everyone thinks they’re kind of unique in a snowflake.

And what I’ve come to see, and I do a ton of work [00:08:00] in vertical and ai, healthcare, legal, fin services, construction, it’s more the same than dissimilar, specifically around the sense that most folks are gonna start with one part of the value chain, right? And then they’re going to expend who they sell to, so what stakeholders they kind of sell to, and they’re gonna eventually kind of fork out of that workflow.

Build features and eventually build that into products. And so like, let me use Procore as an example, but I’ll give you a couple of others to illustrate how consistent it’s, so how many people have done any construction or know anything about construction? Just so I can.

Sophie Buonassisi: That’s a good number.

Dennis Lyandres: Yeah, that’s a good, okay, so I’ll, I’ll talk really fast through this.

You have an owner, that’s me building a house. You have a general contractor. They’re the ones who coordinate and orchestrate all the work. You have specialty contractors or subtrades. These are the people, your plumber, your electrician, et cetera. They actually do the work. Yeah. There’s more folks in the ecosystem.

Architects forget about ’em for right now. Right. So you know, Procore, we started selling to the general contractor. You can look at public literature in 2014, and we called out, we wanted to build a financial product. We [00:09:00] called out, we wanted to sell to owners. We also called out, we wanted to sell to specialty contractors, and we did all these things, right?

But we started with general contractor and we started with project management, like docs drawings. But what happens, I’m building a home. I’m the general contractor, I’m working off a drawing, and all of a sudden now my drawing, I see that I gotta change something. Ah, you know what change means? Change money.

Yeah, change order. So now I’m building essentially a feature. That is starting to fork into this financial strategy, right? So that I can eventually have a financial product right now Who’s gonna approve that? Change order? The owner. The owner. So some of the stuff is old as time in enterprise software.

Follow the money. Follow the pain, right? So who do you think’s got the money and the most amount of pain in a construction project? By the way, for Procore, it’s, you know, JP Morgan’s headquarters and it’s Jamon Diamond who does a weekly update on it, right? So like the stakes are very high, it’s them. So we’re starting to think through, okay, we have [00:10:00] an existing place we’re gonna be able to build as we go, right?

And we’re gonna be able to start to follow the money and the pain healthcare, right? Same thing, right? You go to the providers, right? And then there are these insurers. At some point you’re gonna want to build a workflow that might connect from a provider. Let’s say it’s a prior authorization who’s had this crappy experience, right?

You go in physical pen and paper, fill out a form, then they’re like, ah, you gotta go see a specialist, but we gotta get approval, et cetera. That goes up to the insurer. Then there’s a nuance here that in most of the industries, there are hybrids, which can be a great wedge in the door for Go-To-Market because you still gotta sell and you still gotta prove it out.

So in construction, there are these owner operators, right? So there are really big Fortune 10 companies. They build data centers. They have their own general contractors. There are real estate developers. They do their own general contracting. There are general contractors. They self-perform their own electrical work.

Healthcare, same thing. They’re providers. They’re called payviders, they take it at risk, [00:11:00] right? Food business. I do some work in food and agriculture, same thing. There are some farmers that go all the way to distribution. There are distributors that go all the way to retail, right? And so I think when you think about multi-product to my headline on like people product, Go-To-Market, kind of be intentional around it.

Like you gotta think ahead on this stuff and you gotta play chestnut checkers because otherwise it’s just happenstance, right? And I think we, you know, if it gets there, we’ll talk about like how can Go-To-Market folks show up better for product? With the headline that like, usually they don’t, right? Like this is one of those ways that you can show up really well as an executive leadership team is like have an actual strategy and with Go-To-Market, be able to make your own luck.

Because if you sell to a payer or you sell to a provider and there are pay providers, you can usually bridge that gap. ’cause you have some feature function. I give you more examples, right? There’s firms in this area, they sell to PTs, physical therapists, well they want to go after chiros. Are there shops that do PT and Cairo?

Yeah, more of these hybrids. Right. So I think with multi-product, like, well, I say all [00:12:00] that to be like, look, you gotta follow the money and the pain. You gotta understand the workflows and extend. And if those workflows extend through the value chain or the stakeholders or the ecosystem, like that’s ultimately how you’re gonna own the whole vertical and create unique value.

Sophie Buonassisi: Okay. Now that Curiosity’s peaked from the headline, you gotta tell us about how Go-To-Market leaders can show up better for product.

Dennis Lyandres: Well, I mean, so how many folks are Go-To-Market versus CEOs in here? Let’s do Go-To-Market first. Okay. And CEOs. Okay, so like, look, let me just feel out the room, room and sort of See, that wasn’t a trick question, by the way.

Sometimes it’s like every CEO e is a Go-To-Market. It’s like, no, no. It wasn’t one of those. How many of you could articulate Henry Ford’s thinking that you don’t ask the customer what they want, or Steve Jobs thinking? Can you argue that side? By the way, I don’t actually really agree with this, especially in enterprise software, but how many of you could extremely proficiently and with conviction make that argument.

These are some of the starting points, right? Which [00:13:00] is like, you gotta seek to understand, you gotta be able to speak the language of product. Why is it so gospel in product? And you know, I use product to talk about engineering, product design. You know that whole genre, right? Why is it that they’re like the way you build great software as you ship shitty software?

Can you argue their side for why they don’t have a good release schedule? I’ll give you an example where I saw someone do this really, really well, which is in 2012, I bought a Tesla and one week later they shipped a new model. I was like, what the heck? By the way, LAR was just about me. I was driving like the world’s shittiest, like 2004 Chevy Impala.

Lived in San Francisco, was broke down like all heck. And I went from this like Impala where the wheels were falling off, like literally to like a brand new Tesla model S, and then a week later a new one came out. And I went back to the sales rep and he was beyond our message. He’s like, listen, you know, sir, I, I, I really apologize, but like the thing we are absolutely most committed to is always being the leader in technology.

And that car you just bought last week, other than the one we just rolled out this week, is still by a [00:14:00] mile, the best fricking car out there. And the reason it’s the best car is because when we have a new feature, a new function, we ship it. And it gets to market faster and we develop it and we build against it.

And we’re not gonna be like the old car companies where they wait and they roll 50 things out and then a bunch of things are wrong. And then you gotta wait three years still, or two years for the model to mature, right? So these are the kinds of conversations and or understandings you need to have. And if you’re looking for like a tactical example, like Deon and I had this right, where I’m like, Deon, you gotta walk me through why?

You gotta appreciate the product’s, pretty much never gonna work. And he is like, what are you talking about, dude? Like you suck. Like what do you mean? I’m like, here’s the reality. If you’re always building product and you’re always expanding the use cases and the workloads and the stakeholders and the folks that you can sell to, it’s never gonna fully be there.

So you actually have to have a perpetual state between product and Go-To-Market, oversimplified product work, great. Go-To-Market, can suck, product doesn’t work, great. Go-To-Market. Both work together, like $50 billion market cap business, [00:15:00] right? But they’re never in sync at the same time. Right, and it’s also not as easy to build product as you think.

So like for DePauw, like we had this conversation like, look, it takes three to seven years to build world class software. It’s faster than ever today, but even if you’re committing 50, 80% of your code through Cursor, replicate or Bolt, it’s still years to get world class enterprise software. So what do you do in the interim?

Sit around or figure out how you can actually show up. Awesome for product. There’s a whole set of tactics that can underlay the seek to understand, build a relationship, argue their side. But that’s really the starting point that truthfully. Seldom I go in a room, they’re like, oh god, dude, this is like, I don’t need to talk about that.

I already could talk to you about it. And I think that just tactically, there are things like, you know, we had a shadow program between, uh, pre-sales and uh, engineering. And it was hilarious, right? Because the engineers were like, okay, hold on. Crisis. Who are these posers who get to have engineering in their title?

Why? Why these are not engineers. They don’t code shit. All they [00:16:00] do is whine and complain. Right. And you know, the sales engineers were like, dude, it’s not that. I told ’em to build the button. Like build the button, dude. It can’t be that hard to build a button. My buddy in his basement built a button in two days.

Right. Well, what ended up happening, right, they sought to understand and learn each other’s side. The engineers were like on some customer calls and they’re like, dude, your job sucks. You get the crap kicked outta you. Oh my God. I had no idea they’re that frustrated with it. Honestly. Like I just thought they were kind of being whiny, but like that seems like a really bad business process.

Seems really shitty for them. Their days are really hard. Right. And then for the, the sales engineers, they’re like, decompiling code’s really hard. Apparently there’s like bogs and maintenance we have to do too. So like we can’t just yell at all hundred engineers to build my button. And so I think look as it relates to like Go-To-Market, and I think you could broaden this, this exercise, which is like a lot of CROs or Go-To-Market leaders fail because they don’t know how to go up and out and solve the [00:17:00] company’s hardest problems.

They don’t understand how to sit with the CFO and talk about rule of 40 or rule of X and gross margin and you know, the drivers of that and they don’t understand when the comp services, how it impacts that. But I, I think that the most important things in a technology company are product and distribution.

Right. And again, they have an interplay off each other. So when it’s like, what don’t I see that I advise founders is I actually have a strategy for this. As you’re going more multi-product, how does Go-To-Market show up exceptionally well for you? And I mean, the truth is, if you have the world’s best reference customers, right?

And you have exceptional product, you have some extra room on Go-To-Market. Like you might be just lighting money on fire. Don’t do that. Put it back into product. Into the product. That sucks. ’cause it’ll get better faster if you invest in it. Does that answer your question? That sure does. I have more, but I feel like I should cut myself off.

Sophie Buonassisi: That was perfect. And you mentioned customer, I’d love to hear your perspective on customer overall and how that’s maybe an unexploited strategic lever for SaaS companies.

Dennis Lyandres:[00:18:00] Yeah, you always ask really good questions. So you know, I think that in my study of like what did Procore do well that I’ve kind of tried to bring to other companies I work with.

I find this integration of people, product and Go-To-Market. All oriented around the customer is like magic. And it’s not just the account, like it’s actually the humans inside of that organization. And so to me, like I think customer is like one of the things you should be the absolute most strategic about that people usually aren’t like, what do I mean by that?

I think there’s broadly two ways you win with a customer. And I’ll give you a framework if it’s helpful, but I, I think that when you do big enterprise deals, there’s four wins. There’s a technical win, there’s a political win, there’s a legal win, there’s a commercial win, and you can build a strategy around each of them.

They’re not all equally important, right? We get where I’m going win politically so that you win. Technically, you shouldn’t then lose the deal on legal and commercial. And so as it relates within customer, right? I think customer drives [00:19:00] everything in the organization. It drives employee engagement. It’s the one person that can hire or fire you.

I said on boards, we can fire the CEO. We pretty much never do that, right? ’cause then what the heck did you invest in in a venture-backed company? So really the only person that can fire people around this joint is the customer. The customer is also how everything else great in the company happens. And I think people really underappreciate this and they’re like, oh yeah, customer, you know, it’s how I get my, you know, next dollar of revenue.

And you’re like, yeah, cool. It’s also how you’re gonna sell the next product. It’s also how you get the next deal. It’s also when you put engineers in front of a customer, it’s how they get an employee engagement. What about fundraising? I mean, come on. Every single public and private market investor is gonna do customer calls.

So when you look at technical and political as those two things which oversimplified, consider political, Go-To-Market and consider it relationship management and consider that relationship management, a mix of donuts. ’cause I think that stuff works and you can actually codify that and be intentional about it.

But also you have to be uniquely valuable to folks and anyone who’s doing AI stuff [00:20:00] right now, like, let me assure you, like the customers want to understand what the heck else you are seeing and showing face really matters. So I think even in s and b, you can scale, look at toast, you can scale being in person.

And so to me, when I think about customer, like go on and on about the whys, but the oversimplified is like, do you know your most valuable customers? Right. They’re valuable not just because of current and future revenue, but also their strategic visibility and importance to the market from a multi-product perspective, from a persona perspective.

Is this person really matter in the industry? Do they know how to drive change, et cetera, and that you really try to ladder up a strategy to have a unique, unfair advantage, both on the technology side as well, on the relationship or the political side. And you truthfully exploit that asset very strategically.

And then you know, tactically, you know, ways you would know you’re doing this is, I know my most important reference customers and I’ve made sure they say exactly what needs to get said to the marketplace to get the next 20 deals. [00:21:00] Spoiler alert, that’s usually, I didn’t think I should move urgently. I thought there was too much noise in the market and this solution.

Didn’t have a why now effect. I didn’t think I could trust these humans, et cetera, et cetera. Right? But are they actually saying those things when you walk in, does every executive leadership team member have one or two deep personal relationships with customers, right? If you’re gonna go raise capital, are you gonna get fed back from the customer?

Every single question the VC or the public market analyst asked, those are like indications that you have built an intentional, exceptional customer strategy.

Sophie Buonassisi: I never knew the donut playbook was gonna make such an appearance today.

Dennis Lyandres: You know, it’s actually like a seminal kinda meta thing if you, if you will, which is, if you study relationships, then you realize breaking bread is like as old, you know, it’s biblical.

And then you realize that like you can actually like manufacture that situation. And again, even in SMB, because I don’t only work with big enterprise organizations and I’m kind of stage agnostic, I [00:22:00] work with, you know, companies, hundreds of millions of revenue. I work with some that are pre-revenue. In every single one of those situations, like showing up and breaking bread matters.

And by the way, if you wanna qualify your pipeline, right, for those of you and Go-To-Market, engagement is the best way to look at pipe quality. So if you all go and reach out to all these people that are closing this month and they don’t respond real fast to you, you should worry. If you do the opposite and you reach out to all these folks and 50 different people respond and they’ll meet with you and they’re open and authentic and they wanna break bread, that’s probably a better sign.

Sophie Buonassisi: Excellent.

Dennis Lyandres: Food works.

Sophie Buonassisi: Yes, food. Food works well. We’ll have food shortly, but I do have to ask you, you know, you came on the podcast last year. We were fortunate to have you on, and an idea that you shared on there that really resonated with leaders, both in our audience and ecosystem, was prices law, which is the notion that it’s actually a small percentage of people driving a disproportionate amount of impact in an organization.

So that fundamentally in itself shifts hiring, and now we’ve got AI that is also fundamentally shifting, hiring [00:23:00] with greater leverage. How do you see that intersection of prices, law and ai, and how does that impact the way founders and Go-To-Market leaders think about hiring?

Dennis Lyandres: So how many folks are familiar with this lean AI startup concept?

If anyone want to try to define it. I’m working with a couple of these so I could try, but I’m still learning more than I’m teaching.

Audience Member: Okay. Nick Trying to do more with less, higher and higher revenue for ft. Be AI native all the way across the board, all their processes.

Dennis Lyandres: Yeah, so more with less AI native.

It’s, it’s a sort of can you know in the most extreme it’s can one employee company build a billion dollar revenue business? I see this in, in isolation, working exceptionally well. So I have some organizations where we’re doing AI first marketing and there’s three AI marketers, one for product marketing, one for community, one for demand gen, and they’re doing the work of 30 or 50 marketers and they’re doing a really good job.

Now the contrast with this is to say they’re [00:24:00] burnt is not true, but they’re definitely crispy. Um, it’s really hard and there’s a whole new level of like shit show and crazy that you’re like, ah, what are we dealing with now? But look, I think to your question is if your strategy is going to be Lean ai, and I have some companies that are 10 employees and they’re spinning off the biggest insurers in the country doing massive deals, and their revenue per FT is like nothing I’ve ever seen in that regard.

I don’t think Prices Law works anymore. I. I actually think it’s an entirely different talent strategy. It creates an entirely different set of advantages. So like I do not like remote work. I think relationships matter. I think you need to be in person, especially if you’re early in the career and leadership needs to be there.

So like you just need to be in the office. Sorry. Right. Um, but these lean AI companies, a lot of the times it’s 10 people who work together at like Facebook or whatever and they know each other exceptionally well, like. Gone to college, their kids play with each other. Like they can be remote. They already have the relationship, they have the trust, right?

And so I think they just [00:25:00] fundamentally operate differently. And in the lean ai, my hypothesis prices law doesn’t work. By the way, the prices law. If I give a little, how many people are familiar with that? Because I think when I talked about it, people were like, no. Okay, so let me try to repeat it. I’ll give the colorful story of how I came to learn of it, which is please.

Uh, my mentors are like, you know, like Lars Nielsen is, is one of ’em who’s in the room. John McMahon is another who created medic, you know, incubated, snowflake, et cetera. Like that. That’s the profile of mentors. I have. I’m spoiler riches. And I remember pretty much calling all of them in like complete crisis to be honest.

And Lars is CB of this moment. He was like, dude, you’re all right. I’m like, yeah, I’m fine. But like, basically I had scaled an organization and it had, you know, it was like, it scaled it from like 200 people and we were 200 people. There were like 15 people. They did like half the work in the company. Like truthfully, they just disproportionately mattered.

They got all the work, everything they touched came back great and somehow like they just kept being able to take more things. And then we were like a thousand people and I was like this number scaled to like [00:26:00] 50. Like I am an entirely failed leader. Like it was my job to set strategy higher and put the right people in the right roles.

I failed miserably. And then every single one of my mentors was like, oh dude, that’s just how it goes. That’s just like nature. I’m like, it can’t be nature. And I came across this thing called crisis law, which is a social psychology concept, and it basically says half the work is done by the square root of the number of employees.

So that’s what Sophie’s talking about. That’s what I talked about on the podcast. I think you can codify that into a talent strategy. If you want me to connect some of the dots here, which is you should have a strategy for your. You know, if you’re a thousand employees, what’s your T 30 strategy? By the way, Steve Jobs had this at Apple, right?

So like, these programs have existed, this has like been scaled out exceptionally. Can

Sophie Buonassisi: you help explain a T 30 for anyone unfamiliar?

Dennis Lyandres: Yeah. I mean these are the, so if, if you’re willing to play ball with this hypothesis of prices law, right then in an organization of a hundred people, let’s use that. ’cause I like small, simple numbers.

That’s 10 people. [00:27:00] An organization of a thousand, that’s 30. So what is the program for those 10 people? And I would submit to you, there are some common ingredients that you should just make sure there. One, they need to know each other. All the best people know all the best people. You can actually manufacture that, right?

Two, they need to have outsized relationships with the senior leaders. So spoiler alert, a lot of people try to hire Procore folks and they’re like, is this person exceptional? I’m like, do they know me? And the CEO. If they do, they’re probably on that program. If they don’t, uh, maybe I miss them. I make mistakes all the time, but maybe not.

And so, you know, the, the relationships matter. They solve the hardest problems in the company. And yes, I think you give them f you screw you compensation. So good luck hiring any of these people because their holding power is out of market with anything you’d be able to offer them. Right? And they have relationships with leadership.

So these are the kinds of programs. Steve Jobs was famous for skipping levels, so it didn’t matter if you were a director or vp, you were the most important people in the company and he brought you together on a regular cadence to solve the [00:28:00] hardest problems. And I believe, I’m not sure of this, the iPhone came out of that.

So, and I’ve, countless other examples. Most of the companies that I work with have built one of these programs.

Sophie Buonassisi: Incredible. So if anyone wants to pick Dennis’s Brain on Price’s law and these kind of programs, you’ll be around during happy hour, I believe. Yeah. Yeah. I’d say Vera, Steven, Kevin Dennis is also an incredible person to chat about vertical on.

And I do have to ask you one more question, Dennis.

Dennis Lyandres: Yeah. Did I answer though the AI for crisis law, kind of lean ai, et cetera?

Sophie Buonassisi: Oh, no. Yeah, yeah, yeah. Jordan’s leaning in. We’re waiting. Well,

Dennis Lyandres: well, so, so I think this goes back to like, you have to align things to the strategy. And that’s why, like, I struggle with these sometimes because without being able to go from vision, strategy, execution, and outcomes, and I know those sound jargony, but I swear I have teeth behind each of them.

Like, I think you missed the mark. And so if your strategy is lean ai. We’re gonna get to a hundred million in revenue with seven humans. Prices law does not apply. [00:29:00] You’re playing a very different game. And it is that, which is you’re just trying to be uniquely gifted at how you use AI to drive an unreasonable amount of productivity.

And by the way, the dirty secret, ’cause I’ve talked to a lot of these organizations is they use a ton of contractors and there’s still a lot of mechanical turk going on in all these places. Right. Did that come up earlier or something? Outsource. Yeah. Um, if you are not gonna do that, and if you’re wondering in general, I tell companies be pragmatic and take a hybrid approach.

So you can test a lean AI strategy in something like marketing, but you still need humans. You just want the best humans and you wanna enable, um. With the best tools. So in the non lean AI strategy, how AI is impacting it is, I think you, you pick one or two kind of approaches. You’re either like, scorch earth, it’s a revolution.

Nothing evolutionary, I’m going there, you’re either in or out. Here’s how I’ll measure it. And you know, that’s like one way to do it. I have some companies doing that. My general advice, and I don’t know [00:30:00] if you wanna call it boiler frog slowly, but is a crawl, walk, run approach that then gets you to that same end state.

The crawl is, if you’re a C-suite leader, you better be sharing examples of how you use GPT Rock Claude for pretty much everything you do, right? The walk, you know, so from a crawl, walk, run is, you probably have existing technology that has tried to embed AI into it, and oftentimes at no cost. Gong’s a great example of this for us, on the Go-To-Market side, I work with some incredible Go-To-Market organizations.

The leadership team is exceptional. And gong outperforms those frontline managers 85% of the time in call coaching. Right? And so you should be using that right. Then the third is take really critical business initiatives and solve them in an AI native way. An example of that is, you know, pipe generation, if you’re still using, you know, yesterday’s technology stack to find leads and engage them like.

Your competition should be stoked, right? And so you can [00:31:00] take one or two very critical initiatives and you can do them in a totally different way. Then if you’ve done all that, then I think you’re ready to just go all in on AI first. The question I probably get asked the most, and I was at an event recently in Palo Alto Network, CEO said it with the.

A level of simplicity. I was like, ah, I guess that is the thing, which is he was like, Hey, what do you do if like employees aren’t, you know, doing the AI thing? And he is like, ah, I either teach the old dog new tricks or I get a new dog. That’s it. Right? And so I think you can build training and development that’ll teach you with a lot of clarity, our folks gonna be able to evolve and adapt to this AI world.

So those are the two extremes. As I see you’re an existing org and you want to go through the AI transformation, that’s how I’ve been doing it. Or you want to go lean AI or kind of scorch earth revolution, you could tell that’s not my recommendation ’cause of the words I used against it. And in which case I, I think you take a, you know, kind of in or out right away.

And then you fundamentally change [00:32:00] every workload and every way you do it. Just again, be mindful for every reaction is invert reactions, and it is just a different kind of crazy and chaos. It, it’s not like some nirvana, at least not that I’ve seen.

Sophie Buonassisi: Got it. Hopefully that helped. And just for time’s sake, we won’t be doing questions, but anyone can find Dennis during the happy hour.

I do have one last question, a little birdie named Max might have me to find out, but Max recently shared how, and kind of came out and shared that he’s been struggling with a serious illness and thankfully he’s on the rebound. He looks great. He’s back on his workout game as we all saw, and he’s taking notes.

So we wanna know from you. What’s the, what’s the latest, what’s in vogue for the workout regime? What’s your workout regime? Max was writing notes

Dennis Lyandres: with it, first off. I mean, I’m in awe of Max. I’m taking notes from him. Max’s a lot more Jack than me. So you know, like how, how much? I won’t go too long. I have like three minutes on this.

’cause I feel like if I just answer your question, I at least what ridiculous stuff am I doing? It [00:33:00] will have missed the context of the other things that I’m just gonna be. Sad with my positioning.

Sophie Buonassisi: We got three minutes. We all worked out, so we all, we’re all curious now. Okay.

Dennis Lyandres: Okay. Three minutes. Yeah, so I’ll, I’ll maybe start with the ridiculous and then I’ll back into the why.

At my hotel earlier this week, I was using occlusion or restricted blood flow training. Has anyone done that? I think a tourniquet around your limbs. Very well regarded Cleveland Clinic, Mayo Clinic, top strength coaches in the world. I had a altitude mask on to mimic kind of high altitude training. It doesn’t do exactly what altitude does other than for the respiratory system.

1. And if I can, I cold plunge before that to drive additional kind of hormone health and abil and additional ability to handle stimulus. Because heat is actually what Denigrates performance. And any of you that have tried to run in the desert know that you perform less than you do when you run. I. In cool climate.

So I think that is some of the ridiculous that B was asking about. If I back in

Sophie Buonassisi: the now this makes sense.

Dennis Lyandres: Yeah, yeah, yeah, yeah. I, I actually sent him the occlusion cuffs to try, I [00:34:00] think they’re with Daniel. This is why I’m like, dude, do we have to talk about this? I, so, so, but, but look, let, let me go more to the why, which is my obsession is.

Kind of organizational performance, which ultimately all comes down to human performance. And I do think that like, who cares what I did at Procore? The world’s so different. So if I can’t show countless examples of being a wonderful advisor, I’m not a good advisor. It doesn’t mean if I was a good operator.

And in the same regard, like I think if you want to care deeply about people, which I think is like the underpinning of being a great leader. Then, you know, you wanna set them up to find ways to sustain health and hypergrowth. I did not do that while I was at Procore. I yo yoed a lot, I had a lot of challenges.

So I’ve since been on a journey to really appreciate the same way I have in the advising world. You know, people product Go-To-Market oriented around customer centricity. Is like most people actually agree on all the health pillars, believe it or not, right? It’s eating, it’s sleeping, it’s community, it’s relationships, it’s stress management, it’s breath work, it’s meditation.

Then you go to the next one and people agree on [00:35:00] them. But then the biggest blocker, and this is what I try to specialize in, it’s like lemme help you figure out the problem is things like time. So I now have found, and then, you know, I have a lot of orthopedic issues. So some of the like occlusion training is really joint friendly.

And so for me, I’ve tried to just lead from the front on like, how do I stack and integrate these things because I sucked at it in many other parts of my life, and I don’t wanna make excuses. I. And if you’re gonna have the most performant organizations on the planet, you’re gonna have the most performant people.

And if you’re gonna work with and support those people, then these things matter. So I’ve just been going pillar by pillar, nutrition, sleep, you name it, and where you can stack ’em. So I have some sleep apnea. So I’ve been doing all this work that drives a lot of respiratory training while still getting cardio, while still getting strength training.

’cause I haven’t had a lot of time. All right. That’s my ridiculousness. I’ve done,

I do eat donuts, just so that’s why I don’t look like Max.

Sophie Buonassisi:[00:36:00] There we go. If you need to sell to Dennis, we know donuts still works. Well, thank you for joining us. Dennis is one of the my iconic leaders in vertical SaaS. Super lucky to have him on stage. Thank you for your time.

I hope you enjoyed this special edition episode. More information from the A GM, like the State of Venture in 2025 can be found as a newsletter edition on the GTMnow website or substack. You can check it out and subscribe for future updates on GTMnow dot com. That’s GTM and ow.com. Thanks for tuning in Means the World and see you next week.