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

I've been getting so many asks for go to

market help.

>> With AI, it's just intensified because

[music]

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.

>> I had Jenna Ael 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. 80% of customers buy to

avoid pain or reduce risk [music] 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 going to enable in the future, but

that's often really a sale that's going

to resonate with another founder.

Everybody else, particularly

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 [music] sold to will

increasingly actually differentiate a

company and [music] drive buying

decisions if products are only different

at the merger. [music] And so then you

really want to create a customer buying

journey that feels like very unique

experiences. [music]

>> Something I've heard from so many people

you've worked with is that your

superpower is building a sales or that

doesn't feel like a sales or to

engineers. 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 [music] of 10 engineers at

our company, it should take them 10

minutes to figure out you aren't a

product manager.

Today my guest is Gan Grosser. Gan was

chief product officer at Stripe where

she built their very early sales team

from the ground up. She's currently COO

at Versell where she oversees marketing,

sales, customer success, revenue ops,

and field engineering. 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 go to

market, the rise of the goto market

engineer and how this role is already

enabling her team to operate 10 [music]

times faster, a bunch of very specific

tactics to level up your go to market

skills, [music] a primer on

segmentation, how to think about your

goto market process like a product, her

favorite go to market tools, her hot

takes on PLG and sales comp and sales

hiring, [music]

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

Deiet for suggesting topics for this

conversation and Kelly Schaefer for the

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Jean Grosser after a short word from our

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>> Jean, thank you so much for being here

and welcome to the podcast.

>> Thanks for having me, Lenny. What I want

to get out of this conversation by the

end of this to basically have this

conversation be the thing that we send

people when they're like I want to get

better at go to market. I'm trying to

figure out what to do in market. We send

them this versus having to hire someone

for a lot of money and and usually they

can't find amazing people because

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 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 going to touch a customer or

make a dollar. Um, and actually my

remmit at Verscell 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

Verscell. 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 vend diagram

strategy where marketing is pursuing one

thing. It overlaps with what sales is

pursuing but not perfectly, which also

overlaps with what support is pursuing

but not perfectly. Examples of this

would be slightly different uh uh

slightly differing segmentation

frameworks etc. And so one of the things

I think you're going to want to see more

in this particular moment is that that

become a really integrated life cycle in

particular because I think we're going

to 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

going to 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 LTV five years on the

platform fully wallto-wall and you're

going to want to map that out and

orchestrate it the way you would think

about that within your own product.

>> Awesome. We're going to 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 a tech sales things like that.

Yeah, that's probably where most start

um you know is getting sales or frankly

just because 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 salesled

portions. So 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.

>> Awesome. So essentially it's like how

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?

>> Yep, absolutely.

>> What is 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

cell. 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

going to 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 customerfacing 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 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 going to 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 etc and then two

increasingly bringing AI um to bear as

well to rearchitect um your workflows um

and also So uh make it so it's easier to

have a personalized experience with

customers but do so at scale.

>> Amazing. Okay, let's follow the thread

on this uh go to market engineer.

>> Yeah.

>> So what was it like before and what are

what are these engineers doing at

companies?

>> So I think uh maybe like an interesting

story to tell. Uh when I when I was at

Stripe

uh we went to launch an outbound um SDR

function. uh so outbound prospecting and

Stripe always 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 going to get four.

So you know there's no way I was going

to 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

Rosland. Rosland is the scientist who

originally mapped uh DNA. And what this

was was 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 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 80% of it

will be fill-in- thelank 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.

[laughter]

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 Verscell

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 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

Salesoft 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 burcell 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- thelank mad

lips

>> I love the ambition of that project what

is this like eight years ago

>> yes it's such a I love the big thinking

there we're going to 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.

>> Well, the thing that's amazing about

that 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 named Ben

Salman um who went on to go to Zoom Info

and then actually recently just founded

a goto 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 GTM. You've got him

starting, you know, a totally AI native

GTM um company. And then, you know, here

I am at Rousell trying to do the same.

>> Okay. So, what's cool is this is an

emerging role and 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

customdesigned 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 GTMEN 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 the 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 will take a

while before we're able to really do

that in a very large enterprise there.

or 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 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

followup, the things that are a little

bit more, you know, wrote 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. 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 50 SDRs

as you described to do and now you could

do with a lot more. So it's a really

cool 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 this isn't

going to 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 a go to market engineer

and we have them shadow the 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 chatbt

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 work uh workflow and then

what we do is we let the agent make a

call so and 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 the time that we

feel confident that these will be

onbrand targeted etc. 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 etc.

>> 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. 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 a single

GTM engineer. He spent maybe 25 30% on

his time of his time on this. Uh, it was

6 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 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 night time 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 shifted 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

offunnel row work.

>> Yeah.

>> I don't want to get into whole like jobs

AI discussion, but uh there's always

been this talk about AI SDRs basically

replacing SDRs. It feels like that's 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 a steer

a lot more leverage and obviously you

still need people running the show. T

thoughts there just like do you think AI

will replace all this at some point and

then I don't know you don't need

salespeople.

>> 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 be at

multiple layers in an org chart. You've

got to pick between business lines. You

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." It was

more, okay, that's where you are forced

to start. But I think the average STR

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 the forcing

function of working your way up the

totem pole.

>> Awesome. Since a lot of people listening

to this aren't sales people, 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

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 typically have

two types of an STR. 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, eg small business,

mid-market, enterprise, etc. 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

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 derisk the fact that they're

probably migrating from something. So

much more complicated um coordination

effort to sell. 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?

>> 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

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 last couple years but

actually sales is is more than that it's

a skill just like writing code as a

skill or building a financial model as 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, etc. 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 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. 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 going to

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 sale versus if you can say hey I

now have an ICP here or ideal customer

profile eg 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 SAS

applications right something like that

um then they're probably ready to hand

over the reigns. Uh and then what

founders have to remember is to actually

hand over the reigns. 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 want to 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 going to resonate, where are you

getting, you know, stock as you scale,

etc.

>> To close the loop on the go to market

engineer, what's the profile of the

ideal go to market engineer, maybe your

first

>> what we have found works really well is

somebody who uh does have go to market

experience. So at Verscell, our first

three go to market engineers were

actually sales engineers. So Verscell

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 GTME 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 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 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 model the lead agent

off, you know, our best person, but our

best person who has two years of sales

experience. So, it actually is important

to understand the art and the science of

sales and how you bring best practice to

bear. So, either you've done it and so

you know some best practice or you're

going to 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 sales people

to do something completely different and

move closer to engineering.

>> Yeah, I I mean, we're having a lot of

fun with it at uh at Rurell in

particular. We basically get to be

customer zero. So everything that we're

building with agents, we're building on

Versell's AI cloud. So you know these

agents are now have multiple steps that

they go through. So we're using

Verscell'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. I could

tell the the fun that you guys are

having just the way you describe it.

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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

goto market stack that you love that

you'd recommend?

>> Well, so I'm going to 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, 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 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. Um, so we

take all of our gong transcripts and we

dump them um into an agent called the

dealbot. And that dealbot then can do a

bunch of things. So the first thing we

had it do was uh 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

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 versell uh which

actually is very easily quantifiable.

It's one of the things I love about

selling this product but we got to

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 dealbot And now

the dealbot is running in real time and

we basically feed insights into Slack.

Versel 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?

We're like I I have never seen an

iteration velocity like exists now in my

career. My 20 plus 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 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 process, so you should not have

them. And you know, by the next week,

we're going to add content to our

objection handling to guide. We're going

to add content to a discovery guide.

We're going to 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.

>> Jean, you're blowing my mind in so many

ways. This just sounds so fun and just

like you guys are going to 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. This is

the whole promise of the eye. is going

to 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 aber so you know we have

an AI cloud so people use that to put AI

native features into their customerf

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 I

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 sea 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 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

los 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? Here's how to make a

really good bot for sales.

>> Yes. Um, so actually that's the second

half of my answer that I forgot to uh

forgot. That's perfect.

>> 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 rifted 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 it's you know for better for

worse for Brcell but that uh that lead

agent which runs full stack on Verscell

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 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 90 plus%

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 nent, 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 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 think that's partially true. And I

think because you also have 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 because everyone's got an AI

mandate. You kind of 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 going to 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 because 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 will worth 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 know

they sit on Versel. So, shout out

Versel, but just uh anything that you

point people to to like are these SDR

these GTM engineers, they're former

salespeople. Are they learning to code?

Are they bip coding these agents? How

does that

>> 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

Verscell 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 need it. Um so so we're just sort of

building it from the ground up um here

because 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 build builders

that are somewhere between fully

wizzywig um almost like drag and drop 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 GTME

team at Verscell can build these agents

so easily is because the Verscell

platform is making it that easy to use

our, you know, framework defined

infrastructure and get that agent onto

into production very rapidly.

>> What a neat unfair advantage you all

have to do this.

>> Yes, it is. It is fun to like I mean I I

do think this company is better than any

I've seen at eating its own dog food. Um

and just everyone is constantly we say

Verscell builds Verscell with Verscell.

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 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?

>> 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 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 huh like software is 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 wortha engaging in 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, etc. 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 going to 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. 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 and 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 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-all 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 2 and I

brought it to to Verscell 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 Verscell 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 piqus 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 1 2 3 4 5. 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.

>> Yeah. Yeah. How do you make it be an

experience rather than a transaction

>> versus 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 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 to be more successful in

getting people to pay attention to their

stuff to buy their stuff? Uh I mean one

I would sort of say uh dubtales 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

setup. Uh, a great example of this, um,

this is from Stripe was, you know,

Stripe was excellent at marketplaces.

Most, you know, Lyft, Instacart, Door

Dash, 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. 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? Because 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-ledd

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 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 W's,

go deep, rather than immediately going

into problemsolving 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 something

a lot of I bet everyone could learn is

just listen more and talk less.

>> Yeah.

>> 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 versus

sell care. Something you you're missing.

Here's how this could help you become

much better. So with versell the um sort

of is 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 etc. 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

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 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 is actually you know

somewhat tangential to Versell right so

we drive performance performance drives

SEO SEO is an input into AEO uh but we

have spent a ton of time um 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 ship. 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 Versel 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 going to 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 want to go investigate

that aspect of Versell.

>> Awesome. So, what I'm hearing here in

many ways, and this resonates, I had

Jenna Ael on the podcast recently, and

it was all about sales skills and how to

sell. Nice.

>> And 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. Here's a big gap

and alpha that you can achieve if you

use say Versel. So, here's like you

you're missing out on speed and you're

going to get screwed in AO 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 this

stat. It's round numbers so 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 the art of the possible you

know uh everything we're going to enable

in the future. It's very exciting.

Everyone's visionaries, right? But, um,

that's often really a sale that's going

to resonate with another founder. Um,

and for everybody else, uh, you know, it

particularly enterprises, you're

avoiding the risk of not making your

revenue target next quarter, uh, the

risk of having comp, you know, being

outdone by the competition, the risk of

having brand damage, etc. 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 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 derisk that.

>> That is such an important stat you

shared. This has come up actually 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

then 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

going to bring in product X and it's

going to become like Stripe let's say

let's not talk about her cell but let's

say Stripe we're going to adopt Stripe

Right. That's like a huge decision. If

it doesn't go well, your career is hurt.

Your manager is going to be mad at you.

It's going to 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 tactics,

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 we're going after. Can you just

kind of give us a primer on

segmentation? what people should know

about why this is important and how they

might approach this.

>> 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 Burcell 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, etc. 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 think of segmentation as as a

graph. So x-axis was size um so small,

medium, large. Yaxis was growth

potential and that was important for

Stripe because it was a consumptionbased

business. So if you were going to grow

at 200% yearon-year, you were more

valuable to Stripe than if you were

going to 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 B to C? Are

you B2B T2B? Eg a platform or B2B TOC eg

marketplace. And why is that relevant?

Well, if you're B2B, you are going to

need business payments, right? credit

card was useful for a PLG function, uh,

PLG sale, but you were going to need a

wires, etc. And you probably had a

recurring business, so you were going to

want Stripe billing. You know, if you

were B toC, that's consumer, so you're

going to want consumer payments. Apple

Pay is super important. If you were in

the like the platform or the

marketplace, you were going to buy our

connect product. Um, so it helped us

basically then craft uh a more targeted

and replicable sales or sell sort of

similar deal. So small, medium, large

buying 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's

site gets you know a millionx the amount

volume that Jean's site does.

>> Um and so um basically if you're a small

company but you have super high traffic

that's going to be more complex is going

to make more money and so we want to

promote you. So great example of this uh

would be OpenAI. Open AI 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 going

to 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

going to push them in our enterprise

because we need to go uh you know lean

in with a much uh you know a 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 going to be a very

different sale. We're going to have to

you actually use different language. You

talk about product uh listing pages and

product description pages and you've got

an order management system as the back

end. Super different from a crypto

company where, you know, you might be

running soup to nuts 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

>> y

>> uh correlated with they are likely to be

great potential customers.

>> Y

>> do you recommend using this uh xyaxis as

the approach versus something else like

a spreadsheet with like five columns

like I don't know how do you start?

there's probably something to be said

for X and Y like I do think size is

going to play into most buying decisions

and then these days there 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

Burcell 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 man Obby 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

xanty about a customer to know this

person's likely to pay us $100,000

versus a million those that's probably

going to 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 going to be super

important. Um because what you pay for

cell is correlated with your traffic.

And then workload type was super

important as well. Um so uh you know and

for for Brazelle when we did that it was

really interesting um because you know

we saw wow like we have a lot of

penetration and ecom not not that

surprising actually uh given that we you

know drive highly performant sites and

ecom having a super fast performance

site really matters um but you know at

the time if you looked at as an example

in enterprise SAS companies uh we didn't

have a lot 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 SAS offering before

Verscell existed. And so, you know,

migrating 200 or two million lines of

code, you know, to Verscell, 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 SAS

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 SAS 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 CP? How do I figure out where to

focus? I my heristic is just think of

three attributes that narrow them down.

So it's like series A company with

that's angelled that's a marketplace

something like that. I feel like a good

like just rule of thumb just to start.

>> I think like beyond three I like you

know that's getting pretty detailed and

reasonably speaking you're not going to

cut like you have five sellers so you're

going to put one seller 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 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

Verscell um I actually deliver and every

new hire's first week one of our company

values is KYC know your customer. Um and

I deliver the KYC SE 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

back-end 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 much

much easier to then speak the same

language with the go to market org and

figure out okay how are we going to 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've worked with

is that you are 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 or

that doesn't feel like a sales or to

engineers. So the question she suggested

asked just like what does it take to do

that? What are the ingredients to

building a sales or 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 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 road map, 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, you know, a a market

an opportunity in the market. So, uh, I

think I think those things have helped.

>> I just love this as a 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 ask for all these

features. Yes. NPMs 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 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 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 going to think

with, you know, that product mindset.

>> I love that. Okay, so another quote uh

from Claire Hughes Johnson, former

podcast guest, amazing sales leader. I

worked with you at Stripe. She said

something along these lines, but a

little different. That Gina is 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.

[snorts] 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.

>> 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

goto 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 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 going to win more often and

there'll be less friction um in it. Um,

and so that's sort of where you 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 how do I

enable 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 productle

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 is 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 kind of your thoughts on PLG and

when does it make sense for a company

these days to 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 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 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 Versell'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

generally not going to, you know, go

give a give you a million dollars via

self-s served flow. So at some point,

um, if you want to sustain growth rates,

you're going to 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 got to add

outbound. 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

productled 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 SAS

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 hundred

billion dollar company that's PLG only.

Yeah, like it just feels like a big like

you're losing you're leaving money on

the table even if you are growing really

fast. I know Lastian was a long time PLG

company but uh but eventually uh to calm

down I don't know if 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 tips you might share

with someone thinking about how to price

their product?

>> Uh yeah. So I uh this kind of the theme

but uh I think the first thing is like

you got to think about pricing like a

product. Um so it's another one where um

it it actually really matters how you

choose to 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 premium strategy without

that actually being a strategy. Uh like

a good example at Stripe, we launched

Stripe billing 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 actually integrating

straight building takes a little bit of

work. So if you do that you're probably

going to stay and so we killed that

killed that uh killed the free trial to

zero downside. Uh so you know that's

that's another one. Um, at Verscell,

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 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 skew. And if you

looked at the enterprise skew, it's

called enterprise for a reason.

Enterprise

and actually um about half of the folks

on the enterprise skew were startups,

which suggests that there's stuff in the

enterprise skew that a startup really

wants. So we kicked a lot of that stuff

out of the enterprise skew and made it

so you could buy it self-s 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 let it's

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 a key to both a great customer

experience and optimal revenue outcomes.

S maybe just one more question before we

get to our very exciting lightning

round. It's going to be a combo

question. Uh I hear you have a hot take

on kind of sales comp, how to comp sales

people 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?

>> 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 it makes your

organization less flexible because 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 Verscell the AI

cloud did not exist. we were selling our

front-end cloud and we were selling

vzero and you know introduce 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 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 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 a consulting or a 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, 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 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 a TCO 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 going to You stumped me on

that one.

>> Okay, that's the goal. With that, Gan,

we reached our very exciting lightning

round. I'm going to make it very quick

because I know you got to 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 work or 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 going to 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.

>> I love these. 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, um, 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 is 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 forbing

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 nos in

sales. Um, and so, you know, I another

phrase that a sales guru said to me once

uh or in a training was yeses are great,

nos are great, may will 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 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.

>> Bye, everyone.

Thank you so much for listening. If you

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