What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)

Transcript from https://podmenti.com/t/5b8f46b91474f861

I've been getting so many ask for go to market help with AI it's just intensified because.
You have ten 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. I had Jenna Able 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.
eighty percent of customers buy to avoid
Pain or reduce risk as opposed to increase 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 gonna enable in the future, but that's often really a sale that's gonna resonate with another founder. Everybody else, Stigly Enterprises, you're avoiding the risk of not making
Your revenue target next quarter. I've heard a lot about how you think about go to market as a product. 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
Really wanna create a customer buying journey that feels like very unique experiences. Something I've heard from so many people you've worked with is that your superpower is building a sales org that doesn't feel like a sales org to engineers. The litmus test I have always given my sales team is if you're an account executive in my org and I put you in front.
Of ten engineers art our company, it should take them ten minutes to figure out you aren't a product manager.

Today my guest is Jean Grosser. Jean was chief business officer at Stripe, where she built their very early sales team from the ground up.
She's currently COO at Vercell.
Верші осі marketing, сел, кастомер сус, ревеню опс і філден.
Gene 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 Gooder Market.
the rise of the go-to market engineer, and how this role is already enabling her team to operate ten 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 Diet for suggesting topic for this conversation, and Kelly Schaefer for the connection.
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Gene, thank you so much for being here and welcome to the podcast.
Thanks for having me, Lenny.
What I wanna 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 wanna get better get a market. I'm trying to figure out what to do in Getter 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.
Yeah.
So let me start with just the basics.
When people hear the term go to market.
What does that mean? What does that encompass?
I 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 Verseal 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 Brelle.
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 f perfectly.
Examples of this would be slightly different to 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, because 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 and go to market. Uh, you know, depending on how you count them, there are, you know, I think somebody quoted like seventeen 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 prospect aware of
Of your product.
All the way through to you know high L T V 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.
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. Yeah, that's probably where most start.
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 d I think it can, depending on your product and your initial target market, it can either mean the marketing or sales or a combination of those two. Awesome. So essentially it's like ha 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, s using it, sticking with it.
Yeah.
Absolutely.
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 the first sales team, now you're doing that over sell. What's changed most in the skill and art of go to market?
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 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 with an 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 f 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 for deployed engineering.
which on some level is kind of a rebrand of professional services.
Um, but kinda 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 eighteen to twenty four 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's easier to have a personalized experience with
customers but do so at scale.
Amazing. Okay, let's follow the thread on this uh
You're a market engineer.
Yeah.
So what was it like before
And what is what are these engineers doing at companies? 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 la 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 thirty SDRs.
And I was gonna get four. So, you know, there's no way I was gonna do the typical SCR 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 Rosland.
Rosland is the scientist who uh originally mapped uh DNA.
And what this was was fem 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 in a more targeted fashion.
So at Stripe an example would be like knowing that they're um
their business model was a marketplace was super helpful because 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 uh sort of a
A predefined email template, but eighty percent of it will be fill in the blank.
Based on the different attributes 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
Persona not that.
We were trying to do this in twenty seventeen.
And uh it was very hard and didn't actually totally work. 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 Versailles as we speak, and it actually works.
Um, and that's because 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 twenty seventeen.
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 often.
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 using Brelle workflows as an example, 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 lips.
I love the ambition of that project. What is this like eight years ago? Yeah. 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 to imagine.
The thing that's amazing about that, uh, just to geek out on it a second. So um I I was working on that with a bunch of folks at Stripe, um on my team, obviously, and a gentleman Ben Salzman, um, who went on to go to Zoom Info and then actually recently just founded.
a go to market startup that is basically sort of productiz 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 twenty seventeen. Some of the folks doing that now work at Open AI, they work at Anthropic, they also are doing GTM. You've got him starting, you know, a totally AI native GTM um company. And then, you know, here I am at a a Russell trying to do the same.
Okay. So what's cool is this is an emerging role, an emerging skill that I don't think a lot of people have recognized as something that is happening. Yep. 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.
That's one version. So so it's it's broader than that, really. Um basically the the full remit of GTMN 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, mostly deterministic. So it's more likely that AI will do it well.
And we actually built the agent and 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 because 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 because 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 r 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 twenty years I've been in sales, it's always been somewhere around three to forty percent. 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 seventy percent 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 unleas you to uh go deeper with your customers.
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 that you had to hire, say, fifty SDRs, as you described.
Uh to do and now you could do with a lot more. So it's a really cool uh example of leverage that AI
All right.
Gives you
one thing that I know a lot of people think about when they hear this is okay, I'm gonna get more of these really bad emails trying to pitch me on stuff and just like 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.
our processes all always have human in the loop
And uh so basically where we'll start is
We take it go to market engineer.
And we have them shadow the high highest performing individual.
And not 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 chat GPT on this, they're, you know, looking in this database to get these sets of attributes. Um
And so that's how you sort of inform the initial workflow uh workflow.
And then what we do is we let the agent make a call. So
In the specific example of 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 in it, you know, it incorporates feedback on what we choose to reject, edit, et cetera.
And you shared that it's already having a lot of impact. Like you said you had you said ten STRs and now one can do the job of ten.
Yes.
Wow. 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 single GTM engineer.
He spent
maybe twenty five, thirty percent on his time.
Of his time on this. Uh it was six weeks before we felt confident going from ten 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 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. That's incredible. Okay, that's interesting. So you shift 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 kinda top of funnel
Wrote work.
Yeah.
I don't wanna get into 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 one thing where everyone's like, This is a hundred percent gonna be AI in the future.
Uh, what I'm hearing here is it gives one A S TR a lot more leverage and obviously you still need people running the show. Uh thoughts there, just like do you think AI will replace all this at some point and then you I don't know. You don't need salespeople. I think on
prospecting
It can replace a fair amount.
Because the average
Естіар 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 be at multiple layers in an org chart. You've got to pick between business lines, you gotta 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.
It was more okay, that's where you are forced to start.
But I think the average S Cr could have gone straight into outbound or straight into an S B 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 the forcing function of working your way up the Totem pole.
Awesome.
Since a lot of people listening to this aren't salespeople, don't have a lot of background in sales, we've
Use this term S D R 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 kinda the role above?
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 t t 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.
That'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 wanna 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 S B 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 cur 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 ten 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 effort to sell.
That was extremely helpful. So
S DR 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.
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 gonna have my first
Sales person, whether that's an actual, you know, accounting executive who has prior sales experience, or you're a general athlete wick and smart, who's gonna 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 last couple of years?
But actually sales is is more than that as a skill, just like writing code as 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 gonna 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 ten 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've forever have given founders the advice that
Uh it's uh you often want to bring in revenue operations, which is basically the analytic 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 at the outset.
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?
Yeah, I think that seems about right. Um I do think uh as a founder, you want to 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 convinced a 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 and 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 a hundred 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 rates. So, you know, you 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 the product next gonna resonate? Where are you getting, you know, stock as you scale, et cetera.
To close the loop on the go to market engineer, what's the profile
of the ideal go to market engineer may be your first.
What we have found works really well is somebody who uh does have go to market experience. So at Versailles, 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 Engine 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 GTMN for me
Um we were going through, you know, this this lead agent.
And QAing 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 agents send.
And realized.
Oh.
I wouldn't have sent that.
Um, and that's because I have twenty 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 sal 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.
That is really interesting. So
Come from the sales side, not 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.
Yeah.
I I mean we're having a lot of fun with that at uh
at Rosselle in particular, we basically get to be customer zero.
So everything that we're building with agents we're building on Brussels AI cloud.
So, you know, these agents are now have multiple steps that they go through. So we're using Vercell'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 because 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. What a fun time to be alive. Yeah, I could tell if the the the fun that you guys are having just from the way you describe it.
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Zooming in 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?
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 uh th I don't don't mean not to stere
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, gone.
Uh, Gong is incredible because you can run agents against it now. 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 uh lost.
uh lost opportunity review.
So we had just finished Q two.
We had, you know, a list of our top losses for the quarter sort of 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 gone 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 Brelle.
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're like, Well, it's not very fun to lose. 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.
Verse 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. Didn't sound like it went that that that well. You know, here's 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 twenty 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 h 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 d 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 will now run sprints, which is like those are just bugs. They're bugs in your go to market 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 a 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.
Gene, you're blowing my mind 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 uh incredible.
What I love about this is this AI tool, this agent you build 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.
This is the whole promise of the I it's gonna do things we aren't even thinking about or capable of.
It is. I we had a really interesting one of the things we're doing, um at Bristol, 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 want to 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 next week.
I imagine many people hearing this are like I need one of these deal bots and last bots.
Uh these are all internal products that you all built.
Yes.
Is there anything that you've learned about
making them this good. Any tips you can share over here is how to make a really good bot for sales.
Yes. Um so actually that's the second ha half of my answer that I forgot to
Uh forgot. Which is sort of like bill 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 deal bot, the lost bot version was like two days. Um like basically we rift on it, he had it 40 hours later. Um, you know, now we're continuing to refine it for the 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 Brelle, but that uh
That lead agent, which runs full stack on Brusselle, will cost us about a thousand dollars.
to run for the entire year.
So if you remember
I told you we had 10 people in the SDR function, so I'm 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 a thousand bucks.
Um, so that's like a, you know.
Name the
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 a thousand 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.
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.
I I think that's partially true. And I think because you also have you all these tools proliferating right now, you get into the perennial problem where
You wind up with twenty of them.
uh to do you know the
twenty 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 because 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.
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 twenty 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 the shelf.
Are there any platforms or tools you want to shout out that allow you to build these agents so quickly? I'm I know they sit on Vercelle, so shout out Verse.
But just uh anything that you point people to to like are these SDR these uh uh GTM engineers, they're former salespeople, are they learning to code or are they bypoding these agents? How do they so our sales engineers uh 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 Versailles.
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 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 will builders that are somewhere between fully WYSIWYG, um, almost like drag and drop, um, and a little bit more more code forward. Um, so you got a bunch uh out there along those lines.
But uh, you know, I I I do think we've sort of found like one of one of the reasons actually the GTM Engine team at Versal can build these agents so easily is because
the Verse platform is making it that easy to use our you know framework to find infrastructure and get that agent onto into production really very rapidly.
What a neat unfair advantage you all have to do this. 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 Verseau builds Verselle with Versailles.
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 better.
Along these lines, something that's already come across a lot in the way that you describe the stuff is
I've heard a lot about how you think about go to market as a product.
A lot of people as any 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?
Yeah, I've always um so I had this realization um probably a little over a decade ago in my career. Um, so my first job out of college was working on Gmail in two thousand four.
So Gmail launched on April first. I joined on June first.
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 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.
Ah 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 engaging 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.
I'm 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 diagram. 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 we would do.
Um
So uh that's sort of how I think about build and go to market like a product.
is basically you need to go through from the first time you become aware of 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.
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?
Yeah, another principle we really developed this um at Stripe Two and I I brought it to to Versailles was
Just the idea of adding value at any touch point.
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 Verseal is um
We uh 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 your interest and you 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.
Awesome. So
What I'm hearing here is uh when you say think of it like a product, it'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
prospects perspective, how do we make every step of that journey awesome?
continue them down that journey.
Yeah.
Yeah, how do you make it be an experience rather than a transaction?
Or is it just like feel like sales coming at you trying to sell you stuff?
Yeah. Okay.
Uh staying along this track of being staying tactical.
Uh
I wanna 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 to be more successful.
And getting people to pay attention to their stuff to
Buy their stuff.
Uh I mean one I would sort of say uh dovetails of where I just uh 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 s 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 setup.
Uh a great example of this, um, this is f from Stripe was
You know, Stripe was excellent at marketplaces. Most, you know, Lift, 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'em all. And so when you then would go and sell a marketplace and you know say, Oh yeah, we've got docs, go check'em out.
They didn't like that, right? Cause they're like, Hey, every marketplace runs on Stripe. I don't want to 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 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.
It's 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 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 a 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 Ys go deep rather than immediately going into problem solving mode. You know, if they ask a question, you respond.
Often if 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.
So the last tip, I think there's something a lot of I bet everyone could learn is just listen more and talk less. Yep.
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
convince someone you're selling striper or sell like care something you sh you're missing here's how this could help you become much better.
So with Fell 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
At 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've spent some good time on is just around helping
Customers understand
uh MCP servers and when it would make sense to use one. Um, so I think, you know, those are all the range, 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 is actually, you know, somewhat tangential to Rassal, right? So we drive performance, performance drives SEO, SEO is an input into AEO.
Uh, but we have spent a ton of time um uh 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 learn you taught me a lot, and therefore I want Verse to help me with performance.
Um, but in many cases they actually now are just like this is a company that seems insightful. It 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's the time I wanna go.
investigate that aspect of her cell. Awesome. So what I'm hearing here in in many ways, and this resonates, I had uh Jenna Able on the podcast recently and was all about sales skills and how to sell. Nice. And 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
Yeah.
And alpha that you can
achieve if you use say Vercell. 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?
Yeah, it uh there's I I was told the stat. It's round numbers, so I'm I can't imagine it's entirely accurate, but
Um, you know, basically that um customers, eighty percent 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 the 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.
Um and for everybody else, uh uh, you know, it particularly enterprises.
you're avoiding
the risk of not making your revenue target next quarter.
uh the risk of having uh 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 because it it feels off brand.
But it does actually drive more buying behaviour.
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.
That is such uh an important stat you shared. This has come up actually uh before in this podcast.
That buying
People are buying in large part.
to reduce risk to basically not
hurt themselves in their career, 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 in 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 our cell, 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.
Yeah. So a lot of the buying decision, as you've said, is
I just don't want to screw this up.
Right.
Absolutely.
Okay.
Along the line of tactic, something that I know you're a big fan of and uh help people think about is segmentation.
Yes.
This is something a lot of founders struggle with. They know, okay, I need to figure out my segmentation strategy and here are we're going after.
Can you just kinda give us a primer on segmentation, what people should know about why this is important and how they might approach this?
Yep. 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 Brussel to bring this home.
So a very 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
Uh stripe.
Um there there were two ways we further cut the business.
Way one was so think of segmentation as as a graph. So x axis was size.
Um so small, medium, large.
why access was growth potential.
And that was important for Stripe because it was a consumption based business. So if you were gonna grow at two hundred percent year on year, you were more valuable to Stripe than if you were gonna grow at eight percent year on year.
And so we wanted to spend more time, spend more money, um, going after the two hundred percent growers than the eight percent.
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 B to B?
Are you B to C?
Are you B to B to B e G a platform or B to B to C?
e g marketplace.
And why is that relevant? Well, if you're B to B, you were gonna need business
Payments, right? Credit card was useful for a PLG function, uh, PLG sale, but you were gonna need ACH wires, et cetera.
And you probably had a recurring business, so you were gonna want straight billing.
You know, if you were B to C, 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.
We're sell sort of similar deals. So small, medium, large.
buying comp uh complexity. We also do the same thing on growth potential, because 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 site gets, you know, a million X the amount volume that uh Jean 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. Versal's gonna make more money, and so we wanna promote you.
So
great example of this, uh, would be Open AI.
OpenAI, I forget these days how many uh employees it has. Let's say it's three thousand. 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 top twenty five traffic site on the internet.
So for us, that's gonna push them 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 uh listing pages and product description pages, and you got an order management system as the backend.
super different from a crypto company where, you know, you might be running soup to nuts eight uh on AWS.
And so again, that helps us start to then have a really different uh buying content.
For you.
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
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
uh correlated with they are likely to be great potential customers. Yep.
Do you recommend using this uh
X Y axis as the approach versus something else just like a spreadsheet with like five columns. Like I I don't know. How do you start?
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 Brussels 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 thirty 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 revenu.
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 a hundred thousand dollars versus a million.
those that 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 because
what you pay or sell is correlated with your traffic.
And then workload type was super important as well.
Um, so uh you know, and for for Russell when we did that it was really interesting.
Um because
You know, we saw
Wow, like we have a a lot of penetration and ecom.
Not not that surprising, actually, uh, given that
We you know, drive highly performant sites and e com having a super fast performant 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 have 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 migrating 200 line or um two million lines of code, you know, to Brelle, 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 because 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.
Okay. So essentially you're doing kind of this regression analysis on what's working and then here's the attributes that are most correlated with
Success.
Uh something I always recommend when founders ask me for how do I figure out my C P 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 series A company with that's engelead, that's the marketplace.
Something like that. That feel like a good like just rule of thumb.
I think like beyond three, I like, you know, it's that's getting pretty detailed and reasonably speaking, you're not gonna cut like you you have five sellers, so you're when you're gonna put one cellar in five different 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
Lotta 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 and every new hire's first week, one of our company values is KYC, or 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.
Okay, this is a great segue to uh there's a couple other things I want to talk about. One is something I've heard from so many people you work with is that you're amazing at building a 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's suggested asked 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?
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 ten engineers at our company.
It should take them ten 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 twenty 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 um you know, uh market an opportunity in the market.
So
Uh I think I think those things have helped. 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 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.
Well ask for all these features. Yes. 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.
Yeah, you want a sales
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 no's. 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 that 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.
I love that. Okay. So another quote uh from Claire Hughes Johnson, former podcast guest. Wow. Amazing sales leader. Uh worked with you at Stripe.
She said something along these lines, but a little different. That Gina'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 a
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.
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 the market that is well commercialised.
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 gotta 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 nable the
the insights I'm getting from talking to customers constantly.
to have the company strategy be more effective.
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 gotta go P L Get the only way to win now. It's impossible to do sales. There's no
uh the futures PLG. It feels like that's gone away in in large part. Obviously still companies grow through PLG and work through PLG.
What's just kinda 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?
I 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 Two Thousand 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 art 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 sellers growth. It was a big driver of stripes growth. The thing that folks get wrong is um it does typically have a ceiling.
So people are
uh generally not going to, you know, go s give it give you a million dollars via 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 gotta 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.
So essentially every company ends up having to build a sales org. Some start product led and then at sales, some just start sales and
And and have it from the beginning.
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 S B, 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 hundred billion dollar company that's PLG only. Yeah, like it just feels like a big like you're l losing you're leaving money on the table, even if you are growing really fast. I know Lasian was uh a long time PLG company, but
Uh
But eventually uh succumbed out enough. That's the right way to put it. Okay. Um you mentioned pricing.
I know you have strong opinions on pricing and pricing strategy. What's just like a couple of tips that you might share with someone thinking about how to price their product?
Uh yeah. So I uh uh kinda got a theme, but uh I think the first thing is like
You gotta think 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 drive 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, because you'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.
Uh like a good example at Strape, we launched Stripe Billings years ago. Um, it had a premium strategy because that's what you do.
And then we sort of looked at it and we're like, you know, it actually integrating strength building takes a little bit of work. So if you do that, you're probably gonna stay. And so we killed that killed that uh killed the free t trial to zero downside.
Uh so you know that's that's another one. Um at Brusselle we've been going through that transition where
You know, were consumption based
uh business model ultimately.
But for at the outset, we basically kind of bundled that into what looked like a SAS 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 at a pro ski.
And if you looked at the enterprise skew.
It's called Enterprise for a reason. Enterpr it's meant to be sold to an enterprise.
And actually um
About half of the folks on Enterprise Skew were startups.
Which suggests that there's stuff in enterprise skew 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. So, you know, so now that's like really driven a lot of growth in our PLG funnel, which is awesome for startups because it l super efficient. They they can just buy things, they want that. It's awesome for us because you don't have to have a human intermediate that.
So, you know, getting all of these knobs really tuned, uh, is a uh key to both a great customer experience and optimal revenue outcomes.
Maybe just one more question before we get to our very exciting lightning round. Give me 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.
You can just talk about your takes there.
I struggle with sales comp because um
uh, you know, it's all about pay for performance, which I'm obviously uh a fan of, um, but it is
Um
Yeah.
M makes your organization less flexible.
'Cause you basically have to decide twelve 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 Versailles, the AI cloud did not exist.
We were selling our front end cloud and we were selling V zero and you know introduced the AI cloud halfway through the year.
Now
We had all sorts of good ways to still incentivise 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 that can be challenging.
So
That's that's a little bit of
Of my hot take і 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 I just sort of a diversified portfolio. Um, so I I strongly believe that sales is a skill.
And so you want sales people with actual sales experience in your organization.
But I think there's value in pairing them with um
more non traditional backgrounds, in particular consulting or banking, um
You know, background.
those folks are really good at uh, you know, more quantitative and analytical aspects of sales. So getting into that consultative, you know, part, which I think we talked about at the
At the outset.
Um 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. 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 P L, how can I talk to a CFO
you know, how do I present uh a T CL analysis more effectively?
Um and so just creates a much richer learning environment where people are bouncing ideas off each other.
That is awesome. I love that strategy.
Okay.
Final question, just is there anything else you wanted to share, anything else you want to leave listeners with before we get to our very exciting lightning round?
Oh man, um I feel like we've been very thorough. I think so too. Yeah, I'm gonna you you've stumped me on that one. Okay, that's the goal. With that, Gene, we reached our very exciting lightning round. I'm gonna make it very quick because I know you gotta run.
Uh I'm gonna ask you just two questions. Okay.
One is uh I'm gonna skip to
Your life motto.
Do you have a favorite life motto that you often come back to find useful in worker in life?
I do. Um I I actually have found that I'm known for saying a handful of things um that I didn't necessarily realize it, but when you leave an organization, people tend to, you know, tell you what stuck with them. But there is one that I think I'm I'm known for saying
Growing up my mom always said to me when the going gets tough, the tough get going.
And um I you know, in sales you're always gonna have a quarter when you're not on pace.
And so that's one that I feel like I pull on um
Not infrequently.
because uh you know there's in my view there's another another version of this my mom also would always says was where there's a will, there's a way.
So, you know, I think you can always choose to find a path forward, even when that's not
Uh super clear.
Mm-hmm.
Okay, last question.
Uh, I read that you were a very competitive diver in college early on.
Uh, I'm just curious if there's something you learned from that experience that you brought with you that helps you be as successful as you've become.
Um, well, I mean, first of all, I should say I was I was uh generally coming in like third place out of three on my team. So uh I you know I I managed managed to to do it in college, but uh that that was the extent of that career. Um so I do think so diving is a precision sport and it is a repetitive sport.
And it's also a sport where uh when you land flat on your back.
And literally as you are swimming to the side of the pool, like welts are forming on it.
You uh
Always 100% of the time will be forced to immediately get back on the diving board and do that exact same dive again.
And so I think that has a lot of stuff that's transferable um to to work and to sales.
So you know, for me, I I just have an obsession with excellence.
And within sales, sales is about replicability. How do you drive predictable outcomes? Um, you know, how excellent are you at your ability to forecast? Um, and so I think I bring that to bear within sales a lot.
Um and then similarly, like you get a lot of nose in sales. Um, and so you know, I I
Another phrase that uh a sales guru said to me once uh or in a training was Yeses are great, no's are great, maybe'll kill you.
And so how do you get really comfortable that no is a great thing and that just gave you data and now you can go do something with it.
This is a really uh
in inspiring and uh empowering way to end the conversation.
Jean, thank you so much for being here.
Thanks so much for having me, Lenny. It was a lot of fun.
By everyone.
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