Jeanne DeWitt Grosser: How one GTM engineer replaced 10 SDRs

1. 0:00 – 5:26

   Introduction to Jeanne DeWitt Grosser

   1. LRLenny Rachitsky0:00

      I've been getting so many asks for go-to-market help.

   2. JGJeanne DeWitt Grosser0:03

      With AI, it's just intensified because you have 10 players pursuing the same market opportunity, and so your ability to actually bring the product to market, to differentiate yourself from the competition has become more strategically important than it was previously.

   3. LRLenny Rachitsky0:18

      I had Jen Abel on the podcast recently. One of her tips is you don't want to be focusing on, "Here's the pain and problem we're solving," and instead focus on, "Here's how you will be better than your competitors."

   4. JGJeanne DeWitt Grosser0:27

      80% of customers buy to avoid pain or reduce risk as opposed to increased upside, which is a good thing for startup founders to understand. We all love to talk about the art of the possible, everything we're going to enable in the future, but that's often really a sale that's going to resonate with another founder. For everybody else, particularly enterprises, you're avoiding the risk of not making your revenue target next quarter.

   5. LRLenny Rachitsky0:52

      I've heard a lot about how you think about go-to-market as a product.

   6. JGJeanne DeWitt Grosser0:55

      We buy a lot of things because of how we feel about them. The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the margin. And so then you really want to create a customer buying journey that feels like very unique experiences.

   7. LRLenny Rachitsky1:17

      Something I've heard from so many people you work with is that your superpower is building a sales org that doesn't feel like a sales org to engineers.

   8. JGJeanne DeWitt Grosser1:23

      The litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager.

   9. LRLenny Rachitsky1:36

      (instrumental music) Today my guest is Jeanne Grocer. Jeanne was chief product officer at Stripe, where she built their very early sales team from the ground up. She's currently COO at Vercel, where she oversees marketing, sales, customer success, revenue ops, and field engineering. Jeanne has built world-class go-to-market teams at multiple unicorns and has advised dozens of companies on doing the same. In our conversation, we go deep on what a world-class go-to-market team looks like, including what the heck is go-to-market, the rise of the go-to-market engineer and how this role is already enabling her team to operate 10 times faster, a bunch of very specific tactics to level up your go-to-market skills, a primer on segmentation, how to think about your go-to-market process like a product, her favorite go-to-market tools, her hot takes on PLG and sales comp and sales hiring, and so much more. If you are looking to get smart on the latest and greatest in go-to-market thinking, this episode is for you. A huge thank you to Claire Hughes Johnson, Kate Jensen, and James Diett for suggesting topics for this conversation, and Kelly Schaefer for the connection. 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 an entire year free of a ton of incredible products, including Devin, Lovable, Replit, Bolt, n8n, Linear, Superhuman, Descript, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Shape your HD, Mobinhand, Stripe, Atlas. Head on over to lennysnewsletter.com and click Product Pass. With that, I bring you Jeanne Grocer after a short word from our sponsors. 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 the 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. This episode is brought to you by Lovable. Not only are they the fastest-growing company in history, I use it regularly and I could not recommend it more highly. If you've ever had an idea for an app but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations, and deploy it to live domain. It's perfect for marketers spinning up tools, product managers prototyping new ideas, and founders launching their next business. Unlike no-code tools, Lovable isn't about static pages. It builds full apps with real functionality, and it's fast. What used to take weeks, months, or years you can now do over a weekend. So if you've been sitting on an idea, now is the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev.

2. 5:26 – 8:43

   Defining go-to-market

   1. LRLenny Rachitsky5:26

      (instrumental music) Jeanne, thank you so much for being here and welcome to the podcast.

   2. JGJeanne DeWitt Grosser5:32

      Thanks for having me, Lenny.

   3. LRLenny Rachitsky5:34

      What I wanted to get out of this conversation by the end of it is to basically have this conversation be the thing that we send people when they're like, "I want to get better go-to-market. I'm trying to figure out what to do in go-to-market." We send them this versus having to hire someone for a lot of money and... Right? And usually they can't find amazing people 'cause they're all snatched up.

   4. JGJeanne DeWitt Grosser5:50

      Yeah.

   5. LRLenny Rachitsky5:50

      So let me start with just the basics. When people hear the term go-to-market, what does that mean? What does that encompass?

   6. JGJeanne DeWitt Grosser5:57

      I think there are two answers to this. Often what people think of is sort of the t- tip of the spear of what drives revenue, which is marketing and sales. For me, I think of it as any...... function that is gonna touch a customer or make a dollar. Um, and actually, my remit at Vercel is that. So that includes marketing, sales, uh, all of your technical sales roles, like sales engineers, or, uh, post-sales platform architects is what we call them at Vercel, it's customer success, it's support, it's partnerships. And the reason I say that is, uh, my experience throughout my career has been that those functions often have this Venn diagram strategy, where marketing's pursuing one thing, it overlaps with what sales is pursuing, but not perfectly, which also overlaps with what support is pursuing, but not for- perfectly. Examples of this would be slightly differenting, uh, uh, slightly differing segmentation frameworks, et cetera. And so one of the things I think you're gonna wanna see more in this particular moment is that that become a really integrated life cycle. In particular, 'cause I think we're gonna see a lot of the functions of go-to-market get redefined. So we've gone through a period of, like, hyper-specialization in go-to-market. Uh, you know, depending on how you count them, there are, you know, I think somebody quoted, like, 17 different, uh, roles within go-to-market these days. And I hypothesize that a lot of those are gonna start to collapse. And so if you think of go-to-market more holistically, I think you can kind of go back to what are the jobs to be done from making a customer or prospect aware of, of your product, all the way through to, you know, high LTV, five years on the platform, fully wall-to-wall. And you're gonna wanna map that out and orchestrate it the way you would think about that within your own product.

   7. LRLenny Rachitsky7:54

      Awesome. We're gonna go through that whole cycle of go-to-market. But, so is it safe to say just for most companies that may, that are especially starting out, when they say go-to-market, that mostly is sales, and then there's marketing as a maybe a smaller fraction of that? And then as you become more advanced and grow, customer success plays into it, tech sales, things like that?

   8. JGJeanne DeWitt Grosser8:12

      Yeah, that's probably where most start-

   9. LRLenny Rachitsky8:14

      Cool.

   10. JGJeanne DeWitt Grosser8:14

       ... um, you know, is getting sales, or frankly, just 'cause a lot of companies also start PLG, you might actually start with marketing, and then you're layering in sales when it's time to do the sales-assisted and ultimately sales-led portions. So I, I think it can, depending on your product and your initial target market, it can either mean marketing or sales or a combination of those two.

   11. LRLenny Rachitsky8:33

       Awesome. So essentially, it's like h- the, the term go-to-market tells you what we're talking about. It's how do you take your product to market, get people aware of it, using it, sticking with it.

   12. JGJeanne DeWitt Grosser8:42

       Yep.

3. 8:43 – 11:23

   The evolution of go-to-market roles

   1. JGJeanne DeWitt Grosser8:43

      Absolutely.

   2. LRLenny Rachitsky8:44

      What has most changed in the world of go-to-market over the last few years? You've done this for a long time at Google, at Stripe you built up a sales team. Now you're doing that at Vercel. What's changed most in the skill and art of go-to-market?

   3. JGJeanne DeWitt Grosser8:55

      There are a number of things. So when consumption-based business models started, I think you saw go-to-market shift into being meaningfully more consultative, because often that first land was the very beginning of the journey and-

   4. LRLenny Rachitsky9:09

      Mm-hmm.

   5. JGJeanne DeWitt Grosser9:09

      ... represented a very small percent of what you were ultimately gonna do with that customer. And so you had to go from being transactional to a lot more relationship-based. You had to more deeply understand what that customer was trying to do, so you could align that ultimately to your product. I think that has, uh, played out that much more within AI, because right now everyone knows they need to change, but they don't necessarily know exactly what they need to change to. Whether that's their customer-facing product or their internal productivity and workflows. And so I think you're seeing a lot more of go-to-market orgs leaning into the art of the possible best practices, helping you actually think things through as if they were a consultant. And so one of the things you see, uh, you know, more of right now is forward-deployed engineering, which on some level is kind of a rebrand of professional services. (laughs) Um, but kind of not. And a big part of that is, hey, how do I actually get into your environment, ride alongside you, better understand what you're trying to do, and then help you actually bring the technology to life, and, and learn a lot along the way? Um, often, you're not only making that customer successful, but you're then taking all of that back to your product and engineering, uh, organization to figure out, okay, what was generalizable that we ought to build into our offering versus what is something that ultimately is gonna be more of a, a professional service in the fullness of time? So I think that has been a, a, a biggie is, is actually just, like, really getting embedded with your customer. And then unsurprisingly, um, I think bringing AI to bear on the sales process is another big one. And so you've seen the rise in probably the last, like, 18 to 24 months, um, of the go-to-market engineer, um, which, uh, you know, different, different folks define slightly differently, but it, it's kind of bringing, one, technical prowess to bear on go-to-market in general, so you can have a lot better tooling, data use, et cetera. And then, two, increasingly bringing AI, um, to bear as well, to re-architect, um, your workflows, um, and also, uh, make it so that it's easier to have a personalized experience with customers, but do so at

4. 11:23 – 14:21

   The rise of the go-to-market engineer

   1. JGJeanne DeWitt Grosser11:23

      scale.

   2. LRLenny Rachitsky11:23

      Amazing. Okay, let's follow this thread on this, uh, go-to-market engineer.

   3. JGJeanne DeWitt Grosser11:27

      Yep.

   4. LRLenny Rachitsky11:28

      So what was it like before? And what are, what are these engineers doing at companies?

   5. JGJeanne DeWitt Grosser11:33

      So I think, uh, uh, maybe, like, an interesting story to tell, uh, when I, when I was at Stripe-... uh, we went to launch an outbound, um, uh, SDR function, uh, so outbound prospecting. And Stripe always lan- ran lean. Uh, the company, at that time, had an operating principle which was efficiency is leverage. And so if you looked at the sales organization I was running, most companies out there probably would have had 30 SDRs and I was gonna get four.

   6. LRLenny Rachitsky12:02

      (laughs)

   7. JGJeanne DeWitt Grosser12:03

      So, you know, there's no way I was gonna do the typical SDR, um, you know, approach and be successful. And so we thought to ourselves, "Okay, what can we do? We'll be super data-driven." And so we went and we started building Project Rosalind. Rosalind is the scientist who or- originally mapped, uh, DNA. And what this was, was ef- effectively a company universe. So you can think of this as like a massive database. Every row, uh, was a different company on the planet and every column was an attribute about that company that would help you sell to them, uh, in a more targeted fashion. So at Stripe, an example would be, like, knowing that their, um, their business model was a marketplace was super helpful 'cause that would mean you wanted to sell Stripe Connect versus vanilla payments. And so the goal was basically, hey, can we create a Mad Libs, you know, where I will come up with a sort of a, a pre-defined email template, but 80% of it will be fill-in-the-blank based on the different attributes, um, of that, that customer, right? So if they're this industry or this business model, then pull this customer reference, this value prop, you know, send it to this, um, uh, persona, not that. And we were trying to do this in 2017. And, uh, it was very hard and didn't actually totally work. (laughs) Um, our ability to, like, the false positive rate when... And we worked deeply with data science, like just, it just never really got there. And now that, we're literally redoing here at Vercel as we speak and it actually works, (laughs) um, and that's 'cause you can bring AI to bear on it. Um, and so what's different is we now... I have a data scientist, just like I did back in 2017, but I have a go-to-market engineer, um, whereas before I just had someone in systems that was helping me configure outreach or sales loft. And my go-to-market engineer is helping me build an agent, um, where we're coming up with, "Okay, well, what's the human workflow that you would have done and then how do you encode that, um, using Vercel workflows, as an example, (laughs) um, you know, in actual code that's both deterministic and, and less so," um, where an agent's going out and, and trying to replicate what a human might have done, um, to produce that fill-in-the-blank Mad Libs.

5. 14:21 – 15:28

   Implementing AI in sales processes

   1. JGJeanne DeWitt Grosser14:21

   2. LRLenny Rachitsky14:21

      I love the ambition of that project. What is this, like, eight years ago? (laughs)

   3. JGJeanne DeWitt Grosser14:25

      Yes.

   4. LRLenny Rachitsky14:25

      I- it's such a... I love the big thinking there. We're gonna map the entire universe of companies and then here's how we sell to them and then just... I'm trying to picture doing that without AI. It's, like, crazy to imagine trying that without AI and now it's, like, so much simpler. Can you imagine?

   5. JGJeanne DeWitt Grosser14:38

      Yeah. Well, the thing that's amazing about that, uh, just to geek out on it-

   6. LRLenny Rachitsky14:41

      Yeah.

   7. JGJeanne DeWitt Grosser14:41

      ... a s- a second, so, um, I, I was working on that with a bunch of folks at Stripe, um, on my team, obviously. I had a gentleman named Ben Salzman, um, who went on to go to ZoomInfo and then actually recently just founded a go-to-market startup that is basically sort of productizing that concept of a company universe and then layering AI on it, on top of it. And ultimately, his view is actually you'll, AI will get to the point that you won't have to do outbound prospecting because it will just sort of company and product match. Um, so it's, it's fun to sort of see back in 2017 some of the folks doing that now work at OpenAI, they work at Anthropic, they also are doing GTMEng. You've got him starting, you know, a totally AI native GTM, um, company and then, you know, here I am at a r- a Vercel

6. 15:28 – 23:47

   Optimizing sales with AI agents

   1. JGJeanne DeWitt Grosser15:28

      trying to do the same.

   2. LRLenny Rachitsky15:29

      Okay, so what's cool is this is an emerging role, an emerging skill-

   3. JGJeanne DeWitt Grosser15:33

      Yeah.

   4. LRLenny Rachitsky15:33

      ... that I don't think a lot of people have recognized is something that is happening.

   5. JGJeanne DeWitt Grosser15:37

      Yep.

   6. LRLenny Rachitsky15:37

      So one example I'm hearing of what this role does is they automate outbound emails, essentially, and outbound outreach. They figure out, they write workflows and agents that figure out, here's the company to go after, here's how we message them. Does that end up being kind of like an email that's custom-designed and written for this prospect?

   7. JGJeanne DeWitt Grosser15:54

      That's one version. So, so it's, it's broader than that really. Um, basically, the, the full remit of GTMEng will be to go through each of the different functions within go-to-market and break down all the different workflows that they do and then turn those into agents, um, where, you know, AI is better placed than a human, um, to do that task. So right now, we started with, uh, actually inbound and are now moving to outbound because, um, that workflow is most legible. And by legible, I mean you can basically write it down. It's relatively replicable, s- mostly deterministic, so it's more likely that AI will do it well. And we actually built the agent then we keep a human in the loop. But from there, we're starting to look at outbound, and with an outbound we're starting more at the lower end of the market where you tend to, you know, have slightly less customization 'cause there's a single decision-maker at the company, but I think it'll take a while before we're able to really do that in a very large enterprise. There, we might use an agent for research but maybe not all the way to actually send a message, and that's just within the prospecting function. So other places that we're looking at this would be, um, for install-based sales. So again, there it's a little bit more deterministic 'cause you've got awesome internal data on what a customer is and isn't using, what's the next best action, what's the thing they should get most value from, so that's where we're starting to map, "Hey, what does that ideal workflow look like?" But basically you want to get to a state where...... as long as I've been in sales, they, you know, release these annual reports that help us all benchmark ourselves re- relative to one another. And one of the stats is what percent of time do your sellers actually spend in front of customers. And, you know, for the 20 years I've been in sales, it's always been somewhere around 30 to 40%. So the minority of time is actually talking to other humans. And I think we're getting to a point where with layering in agents, ideally we finally get salespeople to a point where they're actually spending 70% of their time interacting with humans, and we can get the research, the follow-up, the things that are a little bit more, you know, rote and don't use the entirety of your human capacity, uh, done by an agent and then sort of unleash you to, uh, go deeper with your customers.

   8. LRLenny Rachitsky18:18

      I love that this is such a great example of where AI is contributing in a very meaningful high-ROI way, taking on all this work that people... Like, you had to hire, say, 50 SDRs, as you described, uh-

   9. JGJeanne DeWitt Grosser18:29

      Yep.

   10. LRLenny Rachitsky18:29

       ... to do, and now you could do it a lot more. So it's a really cool ar- example of leverage that AI, uh, gives you. One thing that I know a lot of people think about when they hear this is, "Okay, I'm going to get more of these really bad emails trying to pitch me on stuff and just, like, h- this isn't gonna work. I can tell this is AI." What have you learned about how to do this where people actually receive emails that actually convert and do well?

   11. JGJeanne DeWitt Grosser18:51

       Our processes all always have human in the loop. And, uh, so basically where we'll start is we take a go-to-market engineer, and we have them shadow the higher- highest-performing individual in that function. And so you can go, and you shadow an SDR, and you can see, "Oh, wow, they've got seven tabs open. They're looking up the, you know, person on LinkedIn. They're reading about the company. They're doing ChatGPT on this, or, you know, looking in this database to get these sets of attributes." Um, and so that's how you sort of inform the initial workfl- uh, workflow. And then what we do is we let the agent make a call. So in the specific example with, um, with inbound, right, you have to determine whether or not you think the lead is likely to be qualified, and then you have to determine what to say to it. And so we'll let the agent make those two calls. It ultimately then does some deep research, pulls in a bunch of information from our databases, and crafts a response. But we have a human review all of those and actually hit send. Now for us, we had 10 SDRs doing this inbound workflow, and now we just have one that is effectively QAing the agent. The other nine we deployed on outbound, so we got to move them up the value chain. At some point, I think we'll get to a place where we feel like, "Hey, you know, the, the human reviewer is, um, saying yes enough of, of the time that we feel confident that these will be on brand, targeted, et cetera." But right now, uh, we're still trying to train, um, the agent, and it, you know, it incorporates feedback on what we choose to reject, edit, et cetera.

   12. LRLenny Rachitsky20:31

       And you shared that it's already having a lot of impact. Like, you said you had, you said 10 SDRs, and now one can do the job of 10.

   13. JGJeanne DeWitt Grosser20:37

       Yes.

   14. LRLenny Rachitsky20:37

       Wow.

   15. JGJeanne DeWitt Grosser20:38

       Um, yeah, and we... So before we did that move, I mean, the other thing that's just incredible about this is the person who built the lead agent was a single GTM engineer. He spent maybe 25, 30% on his time, of his time on this. Uh, it was six weeks before we felt confident going from 10 to one. So it wasn't like this was a multi-quarter process. It actually moved super quickly. Um, so, uh, and then, again now, we just sort of keep that agent manager (laughs) sort of working with the agent to get it to a point where we say, "Hey, we're ready to roll." Um, and actually throughout the process, we also tracked all of the KPIs that you typically would hold an SDR accountable to. So we were looking at our lead to opportunity conversion rate. We're looking at the number of touches it takes, the time to convert. Uh, and basically what we were able to do is hold that lead to opportunity conversion rate flat, um, so the agent is as good as our humans were, but it's actually condensed the number of touches it takes to convert, because it's so much quicker at responding relative to leads inevitably sitting in the queue or coming in at nighttime and no one, you know, can get to it, that, that type of deal. Um, so, uh, that's sort of, you know, when we knew it was, uh, ready to pull nine people off and shift them into outbound.

   16. LRLenny Rachitsky21:56

       That's incredible. Okay, that's interesting. So you shipped them to outbound. What I love about this is this SDR that is now doing this is, as you said, doing the things they enjoy more. They're talking to customers more. They're not doing all this kind of top-of-funnel rote work.

   17. JGJeanne DeWitt Grosser22:09

       Yeah.

   18. LRLenny Rachitsky22:10

       I don't want to get into a whole, like, jobs AI discussion, but, uh, there's always been this talk about, uh, AI SDRs basically replacing SDRs. It feels like that's the one thing where everyone's like, "This is 100% going to be AI in the future." Uh, what I'm hearing here is it gives one SDR a lot more leverage, and obviously you still need people running the show. Uh, ta- thoughts there, just, like, do you think AI will replace all this at some point and then y- I don't know, (laughs) you don't need salespeople?

   19. JGJeanne DeWitt Grosser22:31

       (laughs) I think on prospecting, it can replace a fair amount, because the average SDR wasn't doing overly sophisticated research in the first place. Um, so where I, I think the last part to go, as I mentioned, will be in deep enterprise prospecting, where, you know, you can up- be at multiple layers in an org chart. You've got to pick between business lines. You've got to triangulate those. Um, but, uh, I, I do think for the things that are more repetitive that often don't take that much time to learn and get ramped, AI will be good at that. And in my view, no one, like, graduated from college and was like, "Yes, I just went to college for four years to become an SDR." (laughs) It was more, okay, that's where you are forced to start. But I think the average SDR could have gone straight into outbound or straight into an SMB closing role.Uh, and so basically what we're just doing is shifting folks into something that uses more of their full capacity right out of the gates, rather than sort of the, uh, you know, the forcing function of working your

7. 23:47 – 26:04

   Defining sales roles: SDRs and AEs

   1. JGJeanne DeWitt Grosser23:47

      way up the totem pole.

   2. LRLenny Rachitsky23:48

      Awesome. Since a lot of people listening to this aren't salespeople, don't have a lot of background in sales, we've used this term SDR. There's also the term AE. Can you just help people understand what is an SDR? What do they do? What's an AE, and then what's kind of the role of Bob?

   3. JGJeanne DeWitt Grosser24:01

      Sure. So SDR is typically in charge of generating pipeline. So they're meant to talk to prospective customers and, uh, get them to a point where it is worth investing time to run them through a sales process. So you te- te- typically have two types of an SDR. You have an inbound one, so this is where people come to your website, they fill out contact sales. They'll be the first call, uh, to make sure that it's actually worth a more expensive account executive to go and run a sales process. Or you then have outbound. So this is where when you want to grow faster than your inbound demand, they will go out and at this point, you probably have a point of view on where you think you have product market fit. And so they will target that part of the market and try to drum up interest from folks who weren't otherwise raising their hand saying, "I'd like to talk to you." So that's sales development, basically pipeline generation. Account executives are closers. So it's their job to take somebody from, "Okay, hey, I'm interested in learning about your solution. I have a legitimate problem. I potentially could make a decision," to, "I now believe that your product is the best in the market and for me, and I'm willing to pay for it." And then account executives, depending on, uh, the segments that your company sells into, e.g. small business, mid-market, enterprise, et cetera, they may work their way up the food chain from selling to a smaller company like an SMB or a startup. Those tend to be a little bit more of a transactional sale. You often have a single decision-maker to then going into a mid-market or a cr- commercial role where now maybe you have an economic buyer, like somebody in finance, and a technical buyer, like somebody in engineering, to getting into enterprise where, you know, you now have procurement and you have committees, and 10 people have to weigh in, and, um, you know, you've got to help them figure out how to de-risk the fact that they're probably migrating from something, so much more complicated, um, coordination

8. 26:04 – 29:04

   When to hire a GTM engineer

   1. JGJeanne DeWitt Grosser26:04

      effort to sell.

   2. LRLenny Rachitsky26:05

      That was extremely helpful. So SDR, pipeline generation, AE, closer. Such a simple way of thinking about it. Okay, this is great. Uh, going back to the GDM engineer, a few questions for people that may want to try this at their company. What scale do you think it makes sense to start hiring for this role, having someone automate the go-to-market process?

   3. JGJeanne DeWitt Grosser26:25

      What's interesting about this is it will force companies to be more rigorous about their sales process early. So often startups when they go from founder-led sales to say, "I'm going to have my first salesperson," whether that's an actual, you know, account executive who has prior sales experience or your general athlete, wicked smart, who's going to go figure it out, you know, often founders will just say, "Okay, sales is showing up and talking to people." Isn't, you know, isn't that what I just did for the (laughs) last couple years? But actually, sales is, is more than that. It's a skill, just like writing code is a skill or building a financial model is a skill. It's about discovery, so asking all the right questions that help you, uh, identify challenges and pain, willingness to pay, um, you know, et cetera. Uh, and then going through a process to handle those objections and showcase, you know, where you add enough value such that somebody ultimately wants to hand over some money. So often, you know, startups will get, particularly ones with strong product market fit, to pretty significant scale without really having a replicable process. And you can't really apply go-to-market engineering unless you actually have a point of view on what best practice should look like. And so I think basically this is going to force folks to have more of a playbook out of the gates. What's working? What's not? Can I document it? Do I have content for the different parts of the sales process? And then, you know, once you do that, which, you know, maybe 10 people is a good size and scale for that, ostensibly, you know, a GTM engineer can come in and turn that into an agent. You could also argue that if, you know, you're a founder who wants to bring in a general athlete profile, and that person is technically minded, that you could have a hybrid AE GTM engineer who figures out what their best practice is and then tries to turn that into an agent, you know, that's riding alongside them and making them more effective as well. So, um, you know, I, I don't know that I have a point of view yet on what's the optimal size and scale, but I forever have given founders the advice that, uh, it's, you often want to bring in revenue operations, which is basically the analytical arm of sales, earlier than you think, because having data, having process is actually what gives you insights as a founder into what is and isn't working. And so I would argue just like it's a good idea to have that sooner than later, increasingly it'll probably be a good idea to have GTM engine and be looking to bring agents to bear on your process, uh,

9. 29:04 – 30:50

   Hiring and scaling sales teams

   1. JGJeanne DeWitt Grosser29:04

      at the outset.

   2. LRLenny Rachitsky29:05

      While we're on this topic, just a quick tangent. The advice for hiring your first salesperson that I usually hear is, wait until you're around a million in ARR. When you have a repeatable process, you can teach someone. Any- anything there? Is that- does that seem right? What would you- what would you recommend?

   3. JGJeanne DeWitt Grosser29:18

      Yeah, I think that seems about right. Um, I do think, uh, as a founder, you wanna stay deeply connected to customers and get it to a scale and get it to a point where, you know, you use the word, there's some repeatability there. I think that's one of the things that not all founders get right, is founders are incredible salespeople, right? They convince some VC angel investors to fork over a bunch of money, so clearly they're gonna inspire people to buy. But if you're getting to a million in ARR and the set of customers you have look nothing like one another, you still have very much like an evangelist sale, very much founder led sale. Versus if you can say, "Hey, I now have an ICP here, or ideal customer profile," e.g. something you can write down, you know, "We are good. Uh, our product fits with, uh, startups with less than 100 employees who are typically building SaaS applications." Right? Something like that. Um, then you're probably ready to hand over the reins. Uh, and then what founders have to remember is to actually hand over the reins. (laughs) So, you know, you've got to enable the person who comes in. What is it that, you know, you're doing effectively? What's your content? What are the discovery questions you're asking? How are you handling objections? Um, so you can transition that knowledge. But also don't hand them over entirely, right? You wanna stay connected to the customer because you still have a fair amount of R&D to do to figure out where are you- you know, where is a product next gonna resonate? Where are you getting, you know, stock as you scale,

10. 30:50 – 34:24

    The ideal go-to-market engineer

    1. JGJeanne DeWitt Grosser30:50

       et cetera.

    2. LRLenny Rachitsky30:51

       To close the loop on the go-to-market engineer, what's the profile of the ideal go-to-market engineer? Maybe you're first.

    3. JGJeanne DeWitt Grosser30:57

       What we have found works really well is somebody who, uh, does have go-to-market experience. So at Vercel, our first three go-to-market engineers were actually sales engineers. So Vercel hires very technical, uh, sales engineers. All of them were front end developers before they decided they wanted to get into sales. And so we just said, "Hey, three of you, congrats. You're now founding members of our GTM eng team." Uh, and the thing that works well there is, uh, you know, you do understand aspects of, uh, what is good GTM, uh, what does a process look like. It's been really interesting actually, um, so the gentleman who runs GTM eng for me, um, we were going through, you know, this- this lead agent and QA-ing it. Uh, and, you know, so I'm going and I'm looking at some of the responses that we've ultimately, uh, had- had the lead j- agent send and realized, "Oh, I wouldn't have sent that. Um, and that's because I have 20 years of sales experience and we modeled the lead agent off, you know, our best person, but our best person who has two years of ex- sales experience." So it actually is important to understand the art and the science of sales and how you bring breast- best practice to bear. So either you've done it and so you know some best practice, or you're gonna geek out on sales, read a bunch of books, learn a thing or two, um, you know, and- and try to incorporate some of those into- into your agent development.

    4. LRLenny Rachitsky32:28

       That is really interesting. So come from the sales side, now from the engineering side, and I imagine this is such a cool opportunity for salespeople to do something completely different and move closer to engineering.

    5. JGJeanne DeWitt Grosser32:38

       Yeah. Uh, I mean, we're having a lot of fun with it at, uh, at Vercel in particular, we basically get to be customer zero. So everything that we're building with agents, we're building on Vercel's AI cloud. So, you know, these agents are now have multiple steps that they go through. So we're using Vercel's, uh, workflow SDK and, um, workflow offering. We, um, you know, use the AI gateway to call the different models that we use to do deep research, um, or, uh, other enrichment that we do. Uh, so for us it's- it's great 'cause we basically sort of bang on everything the engineering team is- is building and get to go be a discerning customer before we actually get it out the door to real customers. (laughs)

    6. LRLenny Rachitsky33:23

       What a fun time to be alive.

    7. JGJeanne DeWitt Grosser33:24

       Yes.

    8. LRLenny Rachitsky33:24

       I could- I could tell the- the fun that you guys are having just from the way you describe it.

    9. JGJeanne DeWitt Grosser33:29

       (laughs)

    10. LRLenny Rachitsky33:29

        Stripe handles the massive scale and complexity of many of the world's fastest growing enterprises, including 78% of the Forbes AI50 and more than half of the Fortune 100. Enterprises like Atlassian, Figma, and Urban Outfitters use Stripe to create fully branded and customized checkout pages with access to more than 125 global payment methods. There's a reason I've had more leaders from Stripe on this podcast than any other company. They know how to build great products that scale and that people love. And Stripe is a lot more than payments. They've also got a category leading billing solution and a highly optimized checkout experience built specifically to increase your checkout conversion. Join the ranks of industry leaders like Salesforce, OpenAI, and Pepsi that are using Stripe to grow faster and to grow the world's GDP. Learn how Stripe can help your business grow at stripe.com.

11. 34:24 – 40:39

    The go-to-market tool stack

    1. LRLenny Rachitsky34:24

       Zooming out a little bit, in terms of you mentioned tools, some tools that you use. I'm curious just what are kind of the state of the art tools within the go-to-market stack that you love, that you'd recommend?

    2. JGJeanne DeWitt Grosser34:33

       Well, so I'm gonna have an interesting answer to this. Um, uh, so I'll give you one, and it's not state of the art per se, although that- I don't- don't mean that dis- uh, disparagingly, it's just that it's been around for- for a while now and- and a lot of folks use it, but I think Gong has gotten just meaningfully more interesting in the last year. Um, and then second half of my question, I will get into I think the calculus on build verse buy is changing. So, all right, Gong. Uh, Gong is incredible because you can run agents against it now. (laughs) Um, so we take all of our Gong transcripts and we dump 'em, um, into an agent called the Deal Bot, and that Deal Bot then can do a bunch of things. So the first thing we had it do was a lost, a lost opportunity review. So we had just finished Q2. We had, you know, a list of our top losses for the quarter, sorted by deal size, and we ran it against that and, uh, it was incredibly interesting. So the biggest loss that quarter, uh, according to the account executive, was lost on price. And when you ran the agent over every Slack interaction, every email, every Gong call, it said, "Actually, you lost because you never really got in touch with the economic buyer. And when you talked to somebody about ROI and total cost of ownership, it was clear from their reaction that they didn't really buy your math." And so really the reason we lost was an inability to demonstrate value, um, which, you know, upon reflection, I've got work to do to build out how we quantify the value of Vercel, uh, which actually is very easily quantifiable. It's one of the things I love about selling this product, but we gotta codify that for the go-to-market team. Um, so that was incredibly interesting, and now we run it against all of our lost opportunities and actually do a much better job of categorizing why it was we really, really lost and then either feeding that back into the engineering team or back into marketing, sales leadership on, "Hey, where are we falling short in the sales process?" And so that was awesome, but then we were like, "Well, it's not very fun to lose." (laughs) "So why don't we pull that forward?" And so we went from Lost Bot to Deal Bot, and now the Deal Bot is running in real time and we basically feed insights into Slack. Vercel is incredibly heavy users of Slack, so we have a channel for every single customer, either opportunity or existing one, and so now we're feeding insights into that Slack channel, which is, you know, "Hey, you're this far into the sales process and you haven't talked to an economic buyer. You should think about that." Or, "Hey, you just got off that call with an economic buyer, it didn't sound like it went that, that, that well. You know, here are some things to consider and how you might follow up." And, uh, last thing before I pause, the other thing that's really interesting and how we're, we're using this too is, you know, we are in this moment, right, where, like, I, I have never seen an iteration velocity like exists now in my career, my 20 plus cr- year career has all been in tech. Um, and so for go-to-market teams, that's really hard. If you are launching something every other day, the ability to be enabled on that is actually quite challenging. And so this, uh, bot agent, um, is now also letting us, where we're starting to go with it, is we'll release something, we'll do our best to enable the team, then we'll go run the agent across, uh, calls, interactions, and we'll diagnose where we did a bad job of dis- uh, objection handling, where we're getting stuck, and then at the end of the week, we can have a huddle and say, "Okay, what are all the places that our agent would suggest we aren't selling effectively?" And then almost like an engineering team, we'll now run sprints, which is, like, those are just bugs. They're bugs in your go-to-market (laughs) process, so you should not have them. And, you know, by the next week, we're gonna add content to our objection handling to guide, we're gonna add content to our discovery guide, we're gonna figure out something we need to change about our demo, so on and so forth. So that's early, that's a little bit of a preview, um, but, but that's where we're talking about taking things right now within our, our go-to-market org.

    3. LRLenny Rachitsky39:00

       Jean, you're blowing my mind-

    4. JGJeanne DeWitt Grosser39:01

       (laughs)

    5. LRLenny Rachitsky39:01

       ... in so many ways. This just sounds so fun and just, uh, like, you guys are gonna win is what I'm feeling when I hear all this, uh, incredible. What I love about this is this AI tool, this agent you built, sees things that humans were not seeing. The fact that you were surprised of just, like, this is a completely different conclusion is such a big deal.

    6. JGJeanne DeWitt Grosser39:21

       Yeah.

    7. LRLenny Rachitsky39:21

       This is the whole promise of AI. It's gonna do things that we aren't even thinking about or capable of.

    8. JGJeanne DeWitt Grosser39:26

       It is. Uh, we had a really interesting... One of the things we're doing, um, at Vercel so, you know, we have an A- AI cloud, so people use that to put AI native features into their customer-facing applications, but they're also using it to build internal applications to improve productivity or outcomes. And we are talking to a very large airline, and that airline, uh, obviously gets tons and tons of support queries. So, uh, of course they would want to go apply AI to, "Hey, how can we have AI answer these so that our cost to support goes down?" Sort of the obvious thing. But the more interesting conversation was actually, um, with, uh, one of the C-level executives who said, "We also actually transcribe every single one of those support calls. And so what I really wanna know is why are they calling and how do I make it so that fewer people call the next week?" Um, and so again, this is now with AI, you can rapidly go through all of that content and actually be able to much more quickly than having a, a human, you know, in your CRM sort of pick some status why it was that folks were calling the airline this week and, and what, if anything, you can do to make it less the case

12. 40:39 – 44:34

    Advice on building a great sales bot

    1. JGJeanne DeWitt Grosser40:39

       next week.

    2. LRLenny Rachitsky40:39

       I imagine many people hearing this are like, "I need one of these Deal Bots and Lost Bots." Uh, these are all internal products that you all built.

    3. JGJeanne DeWitt Grosser40:46

       Yes.

    4. LRLenny Rachitsky40:47

       Is there anything that you've learned about...... making them this good, any tips you can share of here's how to make a really good bot for sales?

    5. JGJeanne DeWitt Grosser40:54

       Yes. Um, so actually that's the second ha- half of my answer-

    6. LRLenny Rachitsky40:58

       Mm-hmm.

    7. JGJeanne DeWitt Grosser40:58

       ... that I forgot to, uh, forgot. (laughs)

    8. LRLenny Rachitsky41:00

       No, that's perfect.

    9. JGJeanne DeWitt Grosser41:00

       Which is sort of like build versus buy calculus. Um, so I think one of our learnings is that it's not that hard to build these agents, and they aren't that expensive either. So, you know, I mentioned with the lead agent, um, that was a six-week process with one human, a third of his time. Uh, that Dealbot, the LostBot version was like two days. Um, like basically we riffed on it, he had it 40 hours later. Um, you know, now we're continuing to refine it for, for the other things I mentioned. Um, and, and what's also interesting about them is they, uh, uh, it's, you know, for better or for worse for Vercel, but that, uh, that lead agent which runs full stack on Vercel will cost us about $1,000 to run for the entire year. So if you remember, I told you we had 10 people in the SDR function, so I'm pr- I'm paying well over a million dollars for that from a salary perspective. I got that down to one, and then behind that I have a lead agent that costs 1,000 bucks. Um, (laughs) so that's like a, you know, 90-plus percent reduction in total cost there. Um, so, and, you know, there are a lot, there's lots of software for, for agents on, on, um, out there right now and I think one of the things we're learning is because this whole space is so nascent, often your own esoteric context, you know, your content, your workflow is really key to unlocking the power of the agent. And so I think there's real value in experimenting with your own internal agent development. We may ultimately end up on, you know, better integrated agent platforms in the fullness of time, um, or we may find that the CIO increasingly goes from a procurer of software to a builder of software and you'll have an AI, AI internal platform with 1,000 agents running across your org, I'm not really sure yet. Um, but I certainly think, um, there's value in trying it yourself because you may find that it's meaningfully eas- easier than you think, um, and you get returns pretty quickly.

    10. LRLenny Rachitsky43:10

        So what I'm hearing here is that you're finding that there are not tools out there to plug and play, the alpha is essentially in building your own stuff.

    11. JGJeanne DeWitt Grosser43:18

        I think that's partially true, and I think because you also have y- all these tools proliferating right now, you get into the perennial problem where you wind up with 20 of them, uh, to do, you know, the 20 jobs to be done basically, rather than an integrated platform that's doing all of them. Uh, I'm hearing this a lot actually when I'm talking to customers right now where their biggest issue, uh, in deploying AI is actually just getting through procurement. And it's sort of 'cause everyone's got an AI mandate, you kinda have a blank check. Uh, I recently heard the term of instead of ARR it's ERR, which is experimental run rate revenue. (laughs) Which is to say, you know, everyone's out there sort of, "Hey, we're gonna give this thing a go for a year and then TBD on whether or not, you know, we keep it." But, you know, basically you're having to procure 20 different things 'cause most things are getting off the ground and so, you know, they're solving something relatively narrow and that'll change in the fullness of time. But I do think there's an opportunity to figure out, hey, where do I likely have a more specific workflow, you know, internally? For that it might be well worth building your own agent, and then maybe for the things that are a little bit more generalizable, you go get something off

13. 44:34 – 46:37

    Vercel’s unfair advantage

    1. JGJeanne DeWitt Grosser44:34

       the shelf.

    2. LRLenny Rachitsky44:34

       Are there any platforms or tools that you wanna shout out that allow you to build these agents so quickly? I'm, I know they sit on Vercel, so shout out Vercel, but just, uh, anything that you point people to, to... Like are these SDR, these, uh, uh, GTM engineers, they're former salespeople-

    3. JGJeanne DeWitt Grosser44:48

       Yeah.

    4. LRLenny Rachitsky44:48

       ... are they learning to code? Are they vibe coding these agents? How does that work?

    5. JGJeanne DeWitt Grosser44:51

       Uh, well the, so our sales engineers all have, uh, CS degrees, so they, they were engineers, um, uh, in a sales capacity, so they're writing code and actually these agents they're building directly on Vercel. Um, so you get the AI Gateway, that lets you, you know, call different models. Um, you have a sandbox if you're running untrusted code, you've got, uh, workflows that let you build the process, you've got Fluid Compute which lets you, um, really efficiently use compute when you only need it. Um, so, so we're just sort of building it from the ground up, um, here, 'cause again, it's not that hard. Now, you do need to write code for that. Um, certainly there are a lot of vibe coding tools out there that also give you more, um, kind of workflow wil- builders that are somewhere between fully WYSIWYG, um, almost like drag and drop, (laughs) um, and a little bit more, more code forward. Um, so you've got a bunch, uh, out there along those lines, but, uh, you know, I, I do think we've sort of found like one of, one of the reasons actually the GTM eng team at Vercel can build these agents so easily is because the Vercel platform is making it that easy to use our, you know, framework-defined infrastructure and get that agent onto, into production re- very rapidly.

    6. LRLenny Rachitsky46:11

       What a neat unfair advantage y'all have to do this stuff.

    7. JGJeanne DeWitt Grosser46:13

       Yes, it is, it is fun to like... Uh, I mean, I, I do think this company is better than any I've seen at eating its own dog, dog food, um, and just everyone is constantly, we say Vercel builds Vercel with Vercel, so you're just always looking for ways to, hey, how can we use our product to go do what we need to do and as a result either understand then what a customer would want or what's missing from our product that we could go make

14. 46:37 – 47:04

    Go-to-market as a product

    1. JGJeanne DeWitt Grosser46:37

       better?

    2. LRLenny Rachitsky46:37

       Along these lines, something that's already come across a lot in the way that you describe this stuff is I've heard a lot about how you think about go-to-market as a product. A lot of people listening to this, as I've said, are product builders, so I think this is a really, uh, nice way of thinking about go-to-market. Uh, I'm guessing you've already talked about elements of this, but just what's a way to think about go-to-market as a product?

    3. JGJeanne DeWitt Grosser46:56

       Yeah, I've always, um... So I had this realization, um, probably a little over a decade ago in my career. Um, so

15. 47:04 – 52:38

    Innovative sales tactics at Stripe

    1. JGJeanne DeWitt Grosser47:04

       my first job out of college was working on Gmail in 2004. So Gmail launched on April 1st, I joined on June 1st. And, uh, as I'm sure you'll remember as well, Gmail was this incredible innovation, uh, you know, massive JavaScript application that didn't really exist at the time, and it had this gig of storage. It was a full year before Yahoo Mail caught up, and even longer before Hotmail and others did, right? So that, that was the level of, like, technical differentiation between, you know, Gmail and the next best. And a decade later, I, you know, you had cloud, uh, computing enabling folks to do stuff that you never would have been able to do previously, and so I kind of felt like, "Uh-huh, like software's starting to commoditize a little bit." Um, and so, uh, you know, when, when that happens, when technical differentiation kind of narrows, what are other things that will differentiate you? Um, and, you know, sort of thinking outside of tech, like, we buy a lot of things because of how we feel about them. Um, and so I started to develop this thesis that, um, actually, the experience that you have of being sold to will increasingly actually, uh, differentiate a company and, uh, drive buying decisions if, uh, products are, are only different at the margin. Uh, and so if, if you believe that, then you really want to create a customer buying journey that feels like very unique experiences. And so we did a lot of this at Stripe, and now we're looking to replicate this here, but an example of one of the things I think we did really nicely at Stripe was, you know, a lot of companies' sales, sort of the first call after you're qualified, you know, we've decided you're worth engagi- engaging in the sales process, is discovery, which is basically, let me ask you a lot of questions to try to under- uncover pain, figure out where buying power lies, et cetera. And so that is kind of boring sometimes for a customer. You're basically being quizzed, um, often on the phone. Uh, and so what we started to do at Stripe was, that first session was a whiteboarding session, and we would actually get together and have you, you know, draw your architecture, um, for payments, um, and all the other things that were under the hood to enable you to take money and drive customer outcomes. And through that, we would learn a ton about, you know, what was in your stack, what we were gonna have to compete with, displace, where value lied. But the customer also learned a lot themselves, because in many cases, they'd never drawn their architecture di- diagram. And so they left that meeting with an asset and a sense of like, wow, this is a really collaborative person who's, like, deeply interested in helping me, like, you know, develop a mental model for how to think about this. Um, you know, and then we had other things that we would, we would do. Um, so, uh, that's sort of how I think about building go-to-market like a product, is basically you need to go through from the first time you become aware that the company exists to, again, that sort of five-year, heavily retained, wall-to-wall customer, a set of experiences. And those experiences can feel transactional, flat, boring, or they can feel very human, personalized, and unique. Um, and so, you know, we try to go map those out and figure out how do you, you know, bring the product to bear, make it really human, um, and, and hopefully that, uh, creates a customer for life in the end.

    2. LRLenny Rachitsky50:37

       I love that whiteboarding example. Are there any other examples of what you've done to make it actually work really well in this way?

    3. JGJeanne DeWitt Grosser50:43

       Yeah, another principle, we really developed this, um, at Stripe too, and I, I, I brought it to, to Vercel, was just the idea of adding value at any touchpoint, regardless of whether or not that customer bought. Because even if customers don't buy, you often find that if you miss them on that buying cycle, three or four years later when they're in another buying cycle, they do come back. You know, I was at Stripe for nine years, and so I saw the number of customers that we lost, and then half a decade later, here they are and they bought. So, um, uh, that, that was sort of another one. So, you know, examples of this that we're doing at Vercel is, um, we, uh, y- you can... There's great data on the internet, um, that helps people understand the performance of their website, and how fast, uh, your website is, um, actually impacts SEO, and SEO impacts AEO, and everybody's thinking about AEO right now. Um, and so, you know, one of the things we try to do when we reach out is actually give folks insight immediately into how they're performing on an absolute basis, how they're performing relative to peers. So ideally, you know, that piques their interest and they want to learn more from us. Um, but even if it doesn't, you still have insights that you may or may not have been aware of, um, that maybe make you contemplate whether or not you've got the optimal setup.

    4. LRLenny Rachitsky52:07

       Awesome. So what I'm hearing here is, uh, when you say think of it like a product, that's basically a product person thinks about the experience of their product at every step of the journey, here's the flow, step one, two, three, four, five, how do we make every step awesome, keep them going along that journey. And so what you think about is just, from the prospect's perspective, how do we make every step of that journey awesome, continue them down that journey?

    5. JGJeanne DeWitt Grosser52:30

       Yeah. Yeah, how do you make it be an experience rather than a transaction?

    6. LRLenny Rachitsky52:35

       Whereas just, like, feel like sales coming at you, trying to sell you stuff.

    7. JGJeanne DeWitt Grosser52:37

       Yeah.

16. 52:38 – 1:00:37

    Effective go-to-market tactics

    1. JGJeanne DeWitt Grosser52:38

    2. LRLenny Rachitsky52:38

       Okay. Uh, staying along this track of being... staying tactical, uh, I want to go even further there. So what are just some go-to-market tactics that you find really effective these days for people trying to just be more successful in getting people to pay attention to their stuff, to buy their stuff?

    3. JGJeanne DeWitt Grosser52:56

       Uh...... uh, I mean, one, I would sort of say, uh, dovetails with where I just ended, but is, what are the unique insights that you can bring to bear, um, about your product or, you know, how that, that customer may be in a suboptimal state. So, I do think investing in, in data to tease that out is, is one thing. I think the other thing, this is, is straightforward, but often, um, not done enough is like, a lot of good companies invest in docs. Um, you know, good thing to do, and, but they, they stop there. And particularly, if you're selling into a slightly larger company, doing things like, um, you know, AWS calls it well-architected guides, um, or blueprints, uh, a lot of customers, particularly larger ones, really want to know the best practice for how exactly to implement your product in, with their particular set up. Uh, a great example of this, um, this is from Stripe, was, you know, Stripe was excellent at marketplaces. Most, you know, Lyft, Instacart, DoorDash, they were all on Stripe. Um, and so Stripe definitely knew the best way to set up payments for a marketplace because we'd seen them all. (laughs) And so when you then would go and sell a marketplace and, you know, say, "Oh yeah, we've got docs, go check them out," they didn't like that, right? 'Cause they're like, "Hey, every marketplace runs on Stripe. I don't wanna look at generic docs, I want you to tell me what's the best way to set up payments for a marketplace." Um, and so, I think that's another key thing to be doing, um, particularly as you move past that sort of solo developer, startup founder as potentially a target, uh, audience. Um, and then, I don't know if this is a tactic per se, um, but I do think just a good reminder for founders in particular who, um, are still in that maybe founder led sales moment, is just the value of really good discovery. Uh, I often find founders are so in- you know, so excited about, uh, talking about their product or, you know, you ask one question, and now they've got a hook of like, "Oh, I can fix that for you." But, uh, excellent salespeople typically, uh, will talk well under half the time in, uh, a conversation, because they're out asking questions, probing, often helping a customer, uh, arrive at conclusions on their own. And so learning how to, you know, do five whys, go deep, rather than immediately going into problem solving mode, you know, if they ask a question, you respond. Often they ask a question, you should ask a question about the question and then respond, right? So learning to be great at that I, I think differentiates people.

    4. LRLenny Rachitsky55:43

       So last tip, I think this is something a lot of, and I bet everyone could learn, is just listen more and talk less.

    5. JGJeanne DeWitt Grosser55:48

       Yep.

    6. LRLenny Rachitsky55:49

       On that first piece of advice, this kind of sharing unique insights and how you're suboptimal, is there an example you could share of how you did that? Maybe a story of just how you convinced someone you were selling Stripe or Vercel, like, "Hey," or something, "You sh- you're missing. Here's how this could help you become much better."

    7. JGJeanne DeWitt Grosser56:04

       Uh, so with Vercel, the, um, sort of, uh, is g- giving an example, but I'll make it more specific. So, um, you know, the performance point, you can go and look at core web vitals. Um, and so we can actually see the different things, um, within their site that are fast, uh, or, you know, load correctly, et cetera. So, uh, that, we then... So anyone can go look that up. But what we can do is actually then help with benchmarking relative to peers. Um, so that's been, um, a big one that we've gone out and done. The other one that, uh, we spent some good time on is just around helping customers understand w- uh, MCP servers and when it would make sense to use one. Um, so I think, you know, those are all the rage, but often people don't know how to contemplate them within their own product. So that was, uh, another one that, that we've gone pretty deep on. And then related to the first one is, um, AEO, answer engine optimization. Uh, it's actually, you know, somewhat tangential to Vercel, right? So we drive performance, performance drives SEO, SEO is an input into AEO. Uh, but we have spent a ton of time, um, i- sharing insights on AEO because we ourselves focus deeply on it and think we understand it better than many. And so again, as part of just building a trusted relationship, you know, folks may go from those AMAs or that content, um, into, "Okay, great. You learned, you taught me a lot, and therefore I want Vercel to help me with performance." Um, but in many cases they actually now are just like, "This is a company that seems insightful, seems like one I can learn from, and now I'm gonna pay a little bit more attention to them," and over the fullness of time maybe, you know, they see something that triggers them to decide, "Now is the time I wanna go investigate that aspect of Vercel."

    8. LRLenny Rachitsky57:55

       Awesome. So what I'm hearing here in, in many ways, and this resonates, I had, uh, Jen Abel on the podcast recently, and it was all about sales skills and how to sell.

    9. JGJeanne DeWitt Grosser58:02

       Nice.

    10. LRLenny Rachitsky58:02

        And o- one of her tips is, you don't wanna be focusing on, "Here's the pain and problem we're solving," and instead focus on, "Here's how you will be better than your competitors. Here's a big, uh, gap and alpha that you can achieve if you use, say, Vercel." So here's like, "You, you're missing out on the speed and you're gonna get screwed in AEO," and all these things. "Here's, like, how you can architect your entire payments art system to be top tier." Does that resonate?

    11. JGJeanne DeWitt Grosser58:27

        Yeah. It, uh, there's... I, I was told this stat, it's round numbers so I, I can't imagine it's entirely accurate but, um, you know, basically that, um, customers, 80% of customers buy to avoid pain or reduce risk as opposed to the other one out of five to increase upside, which is a good thing, again, for startup founders to understand. So, you know, we all love to talk about art of the possible, you know, uh, everything we're gonna enable in the future, it's very exciting, everyone's visionaries, right? But, um, that's often really a sale that's gonna resonate with another founder. (laughs) ... um, and for everybody else, uh, it, you know, it, particularly enterprises, you're avoiding the risk of not making your revenue target next quarter, uh, the risk of having a comp- you know, being outdone by the competition, the risk of having brand damage, et cetera. And so, it's really hard actually for, uh, many startups to make that pivot 'cause it, it feels off-brand, but it does actually drive more buying behavior, is setting up a little bit of that concern that either I might not be well-positioned or again, through good question asking, I know exactly where I'm not well-positioned and you can help me de-risk that.

    12. LRLenny Rachitsky59:53

        That is such a, an important stat you shared. This has come up actually, uh, before on this podcast that buying, people are buying in large part to reduce risks, to basically not hurt themselves in their career and not hurt the company. Like, that's a bigger factor in the buying decision than, "I have this problem I need to solve," and, "Okay, thank you. This solving..." And the way April Dunford came on the podcast and talked about this of just like, like it's such a massive career bet. We are gonna bring in product X and it's gonna become... Like Stripe, let's say. Let's not talk about Vercel-

    13. JGJeanne DeWitt Grosser1:00:23

        (laughs)

    14. LRLenny Rachitsky1:00:23

        ... but let's say Stripe. We're gonna adopt Stripe. That's like a huge decision. Every... If it doesn't go well, your career is hurt, your manager's gonna be mad at you, it's gonna set your company back.

    15. JGJeanne DeWitt Grosser1:00:32

        Yeah.

    16. LRLenny Rachitsky1:00:32

        So a lot of the buying decision, as you've said, is I just don't wanna screw this up.

    17. JGJeanne DeWitt Grosser1:00:36

        Right. Absolutely.

17. 1:00:37 – 1:09:31

    Segmentation strategies

    1. JGJeanne DeWitt Grosser1:00:37

    2. LRLenny Rachitsky1:00:37

       Okay. Along the line of tactics, something that I know you're a big fan of and, uh, help people think about is segmentation.

    3. JGJeanne DeWitt Grosser1:00:45

       Yes.

    4. LRLenny Rachitsky1:00:45

       This is something a lot of founders struggle with. They know, okay, I need to figure out my segmentation strategy and here we're going after. Can you just kinda give us a primer on segmentation, what people should know about why this is important, and then how they might approach this?

    5. JGJeanne DeWitt Grosser1:00:58

       Yeah. So segmentation is basically how do you carve up the world of companies that exist on the planet, uh, to reason about them where they buy differently. So I'll give, um, I'll give examples from, from Stripe and Vercel to bring this home. So a ver- very typical company segmentation is small, medium, large. That's a rational way to do things. Uh, small, you often have a single decision maker, medium, you know, a small team, and large, it's complex, it's a committee, et cetera. Um, so the buying process does change across SMB mid-market enterprise. Um, but if you stop there, uh, you are likely missing, okay, but what are the things within your offering that also change the way something gets sold? So at Stripe, um, there, there were two ways we further cut the business. Way one was, so, eh, think of segmentation as, as a graph. So X axis was size. Um, so small, medium, large. Y axis was growth potential, and that was important for Stripe because it was a consumption-based business. So if you were gonna grow at 200% year on year, you were more valuable to Stripe than if you were gonna grow at 8% year on year. And so we wanted to spend more time, spend more money, um, going after the 200% growers than the 8%. So that was one that informed your strategy on who you targeted. And then for Stripe the other thing that we cut it was business model. So are you a B2B? Are you B2C? Are you B2B2B, e.g. a platform, or B2B2C, e.g. a marketplace? And why is that relevant? Well, if you're B2B, you are gonna need business payments, right? Credit card was useful for a PLG function, uh, or PLG sale, but you are gonna need ACH, wires, et cetera, and you probably had a recurring business, so you are gonna want Stripe Billing. You know, if you were B2C, that's consumer, so you're gonna want consumer payments. Apple Pay is super important. If you were in the, like, the platform or the marketplace, you were gonna buy our Connect product. Um, so it helped us basically then craft, uh, a more targeted and replicable sales. Vercel sort of similar deal. So small, medium, large buying compl- uh, complexity. We also do the same thing on growth potential 'cause we are similarly a consumption-based business. But for us, um, a couple other things. On, uh, the X axis we layer in, uh, Promote, which is, uh, one of the things that is observable is, um, traffic, site traffic on the internet. So Google publishes a CrUX score, which is basically, they have a bunch of data in Chrome, and so they know that Lenny's site gets, you know, a million X the amount-

    6. LRLenny Rachitsky1:03:48

       Millions.

    7. JGJeanne DeWitt Grosser1:03:48

       ... volume that, uh, Jean's site does. Um, and so, um, basically, if you're a small company but you have super high traffic, that's gonna be more complex, Vercel's gonna make more money, and so we wanna promote you. So great example of this, uh, would be OpenAI. OpenAI, I forget these days how many, uh, employees it has. Let's say it's 3,000. It's probably more than that at this point. But, so that's gonna put it in, uh, the mid-market at most companies. But they're a top 25 traffic site on the internet. So for us, that's gonna push 'em in our enterprise because we need to go, uh, you know, lean in with a much, uh, you know, uh, uh, more in-depth sales process. And then the other thing we layer on is, uh, workload type. So if you are an e-commerce company, that's gonna be a very different sale. We're gonna have to... You actually use different language. You talk about product li- uh, listing pages and product description pages, and you've got an order management system as the backend. Super different from a crypto company where, you know, you might be running soup to nuts A- uh, on AWS. And so again, that helps us start to then have a really different, uh, buying content for you.

    8. LRLenny Rachitsky1:05:03

       Okay. This is awesome. So essentially what you do is you break up this universe, going back to your original story at Stripe, into, uh, to help you sort essentially which companies are most likely to buy your product, and what you're coming up with is these attributes that are-

    9. JGJeanne DeWitt Grosser1:05:17

       Yep.

    10. LRLenny Rachitsky1:05:18

        ... uh, correlated with they are likely to be great potential customers.

    11. JGJeanne DeWitt Grosser1:05:22

        Yep.

    12. LRLenny Rachitsky1:05:22

        Do you recommend using this, uh, X,Y axis as the approach versus something else, so like a spreadsheet with, like, five columns? Like, I, I don't know. How do you start?

    13. JGJeanne DeWitt Grosser1:05:31

        There's probably something to be said for the X and Y. Like, I do think size is gonna play into most buying decisions. And then these days, there's, is a fair amount of, you know, consumption, um, happening, so there'll be aspects of this that I think are somewhat universal. But I think, uh, basically, like, when I came to Vercel 'cause it was a new product market, product offering for me, it's a new market, I had a lot to learn, but this is one of the first things I did in the first 30 days. Um, and so basically, I sat down, uh, with the gentleman, Abi, who leads data science here, and, uh, you know, said, "Okay. What, what drives revenue?" So what are, what are the things that you can look at ex ante about a customer to know this person's likely to pay us $100,000 versus a million? Those, that's probably gonna be part of a segmentation framework. And then similarly, okay, uh, where can we, how, how, what attributes would we look for to cluster where we seem to be winning repeatedly? And that was how we ultimately got at, okay, CrUX Rank is gonna be super important, um, 'cause what you pay Vercel is correlated with your traffic, and then workload type was super important as well. Um, so, uh, you know, and for, for Vercel, when we did that, it was really interesting, um, because, you know, we saw, wow, like, we have, uh, a lot of penetration in e-comm. Not, not that surprising actually, uh, given that we, you know, drive highly performant sites in e-comm. Having a super fast performance site really matters. Um, but, you know, at the time, if you looked at, as an example, an enterprise SaaS companies, uh, we didn't have a lot of penetration, um, even though you would've thought, okay, front end cloud, very developer-oriented, of course software companies would be on us. Um, but in enterprise, most of those companies built that SaaS offering before Vercel existed. And so, you know, migrating 200 li- or, um, two million lines of code, you know, to Vercel, that, that's a big lift, right? Um, so it helped us really understand, where are we winning, where are we not? You know, and now, uh, as an example, like, uh, in, within SaaS companies and enterprise, we're actually seeing a lot of interest in the AI cloud 'cause those are some of the earlier adopters of, Hey, let's add AI native functionality to our existing SaaS app. Um, and so again, it helps us figure out what to target where.

    14. LRLenny Rachitsky1:07:55

        Okay. So essentially, you're doing kind of this regression analysis on what's-

    15. JGJeanne DeWitt Grosser1:07:58

        (laughs)

    16. LRLenny Rachitsky1:07:58

        ... working and then here's the attributes that are most correlated with-

    17. JGJeanne DeWitt Grosser1:08:00

        Yeah, totally.

    18. LRLenny Rachitsky1:08:01

        ... success. Uh, something I always recommend when founders ask me for, "How do I figure out my CP? How do I figure out where to focus?" I, my heuristic is just think of three attributes that narrow them down. So it's like-

    19. JGJeanne DeWitt Grosser1:08:12

        Yep.

    20. LRLenny Rachitsky1:08:12

        ... Series A company with, that's eng-led, that's a marketplace-

    21. JGJeanne DeWitt Grosser1:08:15

        Yep.

    22. LRLenny Rachitsky1:08:15

        ... something like that. That feel like a good, like, just rule of thumb just to start?

    23. JGJeanne DeWitt Grosser1:08:18

        Yeah. I think, like, beyond three, uh, like, you know-

    24. LRLenny Rachitsky1:08:21

        Mm-hmm.

    25. JGJeanne DeWitt Grosser1:08:21

        ... I would s- that's getting pretty detailed. And reasonably speaking, you're not gonna cut, like, y- y- you have five sellers, so you're, what, you're gonna put one seller in five different-

    26. LRLenny Rachitsky1:08:29

        Mm-hmm.

    27. JGJeanne DeWitt Grosser1:08:30

        ... segments? So I, I do think three is something you can reason about. The other thing I'll say on this topic that I think is really important is a lot of times folks think segmentation is a go-to-market thing. I really think it's a company thing. So when you join Vercel, um, I actually deliver in every new hire's first week, one of our company values is KYC, know your customer, um, and I deliver the KYC sec- section, um, and, uh, you know, talk through our segmentation framework, how our customer base maps into those segments, because it's really important as, you know, those new product managers leave the room that when they're building something, they think to themselves, "Okay, I'm building a new backend product. Who is this targeted at? Is it targeted at an enterprise or, um, or a startup?" Um, you know, basically, "Do I have a point of view on where I'm trying to win and why?" Um, and if you're doing that out of the gates, then it's mar- much easier to then go speak the same language with the go-to-market org and figure out, okay, how are we gonna take that to market in line with the other motions that we, we have in play?

18. 1:09:31 – 1:14:00

    Building a sales org that engineers love

    1. JGJeanne DeWitt Grosser1:09:31

    2. LRLenny Rachitsky1:09:31

       Okay. This is a great segue to, uh, there's a couple other things I wanna talk about. One is, something I've heard from so many people you work with is that you are amazing at building a s- go-to-market org that works really well with product and engineering, so I'll read this quote from your former colleague, Kate Jensen. She said that your superpower is building a sales org that doesn't feel like a sales org to engineers. So the question she suggests I ask, just like, what does it take to do that? What are the ingredients to building a sales org that engineers and product teams really like working with?

    3. JGJeanne DeWitt Grosser1:09:59

       The litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager. And what I'm trying to get across is you need to have incredible product depth. And, uh, the reason for that is twofold. One, it gives you credibility with the product and engineering org, and two, I also believe that the best go-to-market orgs on the planet are equal parts revenue driving and R&D. And the reason I emphasize the latter is if you think about a product management organization, you know, you may have a UXR team, you know, out doing research, product managers certainly should be out talking to customers. Well, if I have a 20-person sales team, think of the number of customers that we talk to in a week. And so if we can do an excellent job of translating all of that, uh, feedback into signal and then feeding that into the roadmap, um, you know, we can be actually an extension of the product management org. Um, but that takes being really good at discerning signal from noise, understanding when something is an objection that should be overcome versus a m-, you know, a, a market, an opportunity in the market.... so, uh, I think, I think those things have helped.

    4. LRLenny Rachitsky1:11:27

       I just love this. As a, uh, product manager, maybe former product manager, I don't know what the hell I am these days, uh-

    5. JGJeanne DeWitt Grosser1:11:33

       (laughs)

    6. LRLenny Rachitsky1:11:33

       ... I just love the idea of the salesperson, like, you not knowing the difference between a product manager and a salesperson. The most classic challenge is sales orgs will ask for all these features-

    7. JGJeanne DeWitt Grosser1:11:43

       Yes.

    8. LRLenny Rachitsky1:11:43

       ... and PMs are constantly having to push back and think about, does this fit into everything? So it feels like that's a big part of this, is to understand that deeply.

    9. JGJeanne DeWitt Grosser1:11:51

       Yeah, you want a sales, uh, you want a sales org that can think like a general manager, so, you know, that's not just trying to get deals done, but is trying to help build a business, and so again, knows when to say no, knows when to objection handle versus knows, "Hey, I've actually heard this on the last three calls, and I, I do think this would be a really big unlock that would make us more competitive, you know, would be something net new that nobody's doing." So, um, you know, I think that takes looking for a profile that both has sales skills but also is gonna think with, you know, that product mindset.

    10. LRLenny Rachitsky1:12:29

        I love that. Okay, so another quote, uh, from Claire Hughes Johnson, former podcast guest-

    11. JGJeanne DeWitt Grosser1:12:34

        Oh, wow.

    12. LRLenny Rachitsky1:12:35

        ... amazing sales leader, uh, worked with you at Stripe. She said something along these lines, but a little different, that "Jeanna's probably the best go-to-market person at connecting with product and engineering, deeply understanding the product and providing the most valuable input to her counterparts of any I've ever seen." It sounds like just another ingredient here is just sales feeling like a real partner to product engineering, actually not just being like, "Hey, do these things for me," but actually feeling like a partner.

    13. JGJeanne DeWitt Grosser1:13:00

        You know, ultimately, company strategy is, is basically product strategy meets go-to-market strategy, right? Um, and so I spend... I guess as a go-to-market leader, I'm constantly trying to figure out, you know, how do I make more money more efficiently? And you typically do that by having a winning product in a market that is well commercialized. And so that means that I, I really lean into thinking about product strategy and thinking about pricing strategy, um, because if those two things are optimal, you're, you know, you're gonna win more often, and there'll be less friction, um, in it. Um, and so that's sort of where you've got to put, as a revenue leader, like a GM hat on, um, and not just think, how do I sell? But actually, how do I, uh, how do I enable the, the insights I'm getting from talking to customers constantly to have the company strategy be more effective?

19. 1:14:00 – 1:16:44

    Thoughts on PLG and pricing

    1. JGJeanne DeWitt Grosser1:14:00

    2. LRLenny Rachitsky1:14:00

       Speaking of product, going in a slightly different direction, PLG, product-led growth, was, it felt like it was very hot for a while, where everyone's like, "You got to go PLG. That's the only way to win now. It's impossible to do sales. There's no, uh, the future's PLG." It feels like that's gone away in, in large part. Obviously, still companies grow through PLG and work through PLG, but just kind of your thoughts on PLG and when does it make sense for a company these days to s- actually think this is how they will grow for a while?

    3. JGJeanne DeWitt Grosser1:14:27

       Uh, I think a lot... PLG is, makes sense for a lot of companies at the outset, un- unless you are very explicitly building a product for enterprise, um, so Sierra as an example, right? Like, they are very clearly going after Global 2000 or, you know, some- something close to that. So PLG is not going to be overly useful to them because they are trying to win eight-figure deals from day one. But for a lot of products, um, folks are targeting a startup a- audience at the outset, and then they're adding more functionality so that they can ultimately continue to scale up market. So I think PLG is still super relevant. It's a, it's a major driver of Vercel's growth. It was a big driver of, of Stripe's growth. The thing that folks get wrong is, um, it does typically have a ceiling. So people are n- uh, generally not going to, you know, go s- give a- give you a million dollars via a self-serve flow. So at some point, um, if you want to sustain growth rates, you're gonna have to have your deal sizes get bigger and bigger. And where I, I think folks get stuck is, uh, waiting too long on PLG because it does take a while to build a replicable sales process and a sales process which often you're getting fed by inbound at the beginning, and then you've got to add outbound. It, it takes a while, actually, to turn outbound into a predictable engine. So I think where you see companies hit walls is just when they don't add the sales portion of it soon enough.

    4. LRLenny Rachitsky1:16:00

       So essentially, every company ends up having to build a sales org. Some start product-led and then add sales. Some just start sales and, and, and have it from the beginning.

    5. JGJeanne DeWitt Grosser1:16:09

       Yeah, I would, I would agree. There are, um, you know, there are probably some good examples of, like, large vertical SaaS platforms that are, are SMB, but even they wind up with like a, you know, velocity sales team. So, um, yeah, I don't, I don't know that I can think of, like, a $100 billion company that's PLG only. (laughs)

    6. LRLenny Rachitsky1:16:30

       Yeah, like, it just feels like a big... like you're lo- losing... you're leaving money on the table, even if you are growing really fast.

    7. JGJeanne DeWitt Grosser1:16:35

       Yeah.

    8. LRLenny Rachitsky1:16:35

       I know Atlassian was, uh, a long time PLG company, but, uh, but eventually, uh, succumbed, I don't know if that's the right way to put it.

    9. JGJeanne DeWitt Grosser1:16:42

       (laughs)

    10. LRLenny Rachitsky1:16:42

        Okay, um, you mentioned pricing.

20. 1:16:44 – 1:19:24

    Sales compensation and hiring

    1. LRLenny Rachitsky1:16:44

       I know you have strong opinions on pricing and pricing strategy. What's just, like, a couple tips you might share with someone thinking about how to price their product?

    2. JGJeanne DeWitt Grosser1:16:52

       Uh, yeah, so (laughs) I, uh... Uh, this is k- kind of the theme, but, uh, I think the first thing is, like, you got to think ab- about pricing like a product. Um, so it's another one where, um, it, it actually really matters how you choose to pi- price a product. Um, do you really understand where customers are going to derive value? Do you really understand where you incur costs? And are you doing a smart job of aligning those things? You know, you've got lots of examples of companies grossly underpricing, um, 'cause they're sort of afraid to charge for the value that you actually provide. I think there are a lot of examples where people default to including a freemium strategy without that actually being a strategy.... a, like, a good example at Stripe, we launched Stripe Billing s- years ago. Um, it had a freemium strategy because that's what you do. And then we sort of looked at it and we're like, e- you know, a- actually integrating Stripe Billing takes a little bit of work. (laughs) So if you do that, you're probably gonna stay. And so we killed that, k- killed that, uh, killed the free t- trial to zero downside. Uh, so, you know, that's, that's another one. Um, at Vercel, we've been going through that transition where, you know, we're a consumption-based, uh, business model ultimately, but for, at the outset, we basically kind of bundled that into what looked like a SaaS-like price. And, you know, as we've added a lot more functionality, that, that wasn't working anymore. Um, and so we did an unbundling, um, and right now actually, we, we did a pretty substantial pricing change in, in August where we have an enterprise and a pro SKU. And if you looked at the enterprise SKU, it's called enterprise for a reason. Enterpri- it's meant to be sold to an enterprise. And actually, um, about half of the folks on the enterprise SKU were startups, which suggests that there's stuff in the enterprise SKU (laughs) that a startup really wants. So we kicked a lot of that stuff out of the enterprise SKU and made it so you could buy it self-serve online. And what do you know? People are. (laughs) So, you know, so now that's, like, really driven a lot of growth in our PLG funnel, which is awesome for startups 'cause it l- it's super efficient. They c- they can just buy things, they want that. It's awesome for us 'cause you don't have to have a human intermediate that. So, you know, getting all of these knobs really tuned, uh, is a, a key to both a great customer experience and optimal revenue outcomes.

21. 1:19:24 – 1:22:22

    Lightning round and final thoughts

    1. JGJeanne DeWitt Grosser1:19:24

    2. LRLenny Rachitsky1:19:24

       Maybe just one more question before we get to our very exciting lightning round. Let's give you a combo question. Uh, I hear you have a hot take on kind of sales comp, how to comp salespeople that's different from other people, and also who to hire when you're hiring folks in sales. Can you just talk about your takes there?

    3. JGJeanne DeWitt Grosser1:19:41

       I struggle with sales comp because, um, uh, you know, it's all about pay for performance, which I'm obviously a, a fan of. Um, but it is, um ... it makes your organization less flexible, 'cause you basically have to decide 12 months in advance, these are things I value. Um, and particularly in this moment, that could be different. Um, as a great example of this, uh, when, you know, we wrote the sales plans for this year at Vercel, the AI Cloud did not exist. (laughs) We were selling our front end cloud and we were selling v0 and, you know, introduced the AI Cloud halfway through the year. Now, we had all sorts of good ways to still incentivize that. Um, but, um, you know, I, I think, um, you want to be able to be innovative and pivot and, um, you know, when you have a well-designed sales plan, um, uh, or, you know, a very structured sales plan, that c- that can be challenging. So that's, that's a little bit of, of my hot take, is just I'm trying to figure out how do you have the upside of sales of, you know, motivates people. It's a quantitative function, which is great, but also the flexibility to change your mind, because I think a lot of companies right now are having a hard time doing annual planning. So, so that's one. Um, on profiles, I have always valued what, uh, just sort of a diversified portfolio. Um, so I, I strongly believe that sales is a skill. And so you want salespeople with actual sales experience in your organization. But I think there's value in pairing them with, um, more non-traditional backgrounds, in particular in consulting or a banking, um, you know, background. Those folks are really good at, uh, you know, more quantitative and analyst political aspects of sales, so getting into that consultative, you know, part which I think we talked about at the, at the outset. Um, and so I find that when you mix these together, uh, the sort of, you know, consultant, banker profile realizes, "Oh, wait a minute. Sales is, is a skill and I didn't really have it." (laughs) Um, and so they go learn from, you know, your, uh, your account executives with that background, and then your AEs learn more about, "Okay, how do I think about a PnL? How can I talk to a CFO?" You know, "How do I present a, a TCO analysis more effectively?" Um, and so it just creates a much richer learning environment where people are bouncing ideas off each other.

Episode duration: 1:26:01