Reverse-Engineering the AI Buyer — Aliisa Rosenthal, Acrew Capital

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>> Hi everyone. My name is Alyssa and I

joined a little research lab called

OpenAI a little over four years ago.

When I joined it was

you know a couple million in revenue. We

had a self-serve API. We had some

developers who found it and swiped a

credit card and started building.

Over the next few years I helped grow

the organization to several hundred

people, grow our revenue to several

billion on the enterprise side and and

launched multiple products. So I really

had the opportunity to be at the

bleeding edge of bringing this somewhat

alien technology to organizations from

startups to massive enterprises and I'm

going to share a little bit about what I

learned along the way.

So I think most organizations typically

have said okay, I'm ready to build out

my go-to-market organization. I'm going

to hire a bunch of sales people. I'm

going to hire RevOps. I'm going to hire

sales engineers and I'm going to build

out my sales organization and then I'm

going to figure out where the

bottlenecks are and I'm going to add AI

or I'm going to add automation to figure

out how to scale this thing.

My current advice to founders is do the

opposite. So start with what you can

automate. Start with there's so many

tools available now in 2026 for a modern

go-to-market or sales organization that

have never been available before which

really turns the entire playbook on its

head. And you'll find that a lot of

traditional sales leaders are very used

to coming in and hiring a really big

team and augmenting everything with

humans, bringing in sales operations,

sales engineers, lots of sales people,

BDRs, SDRs. You can do so much of this

through an automated approach now. So my

my advice to founders is build the

machine first before you build the team.

Figure out what you can automate. Figure

out where the bottlenecks are and what's

broken and then add humans on top of

that to get through those bottlenecks.

So, just a story about how this played

out at OpenAI. So, we launched ChatGPT

in the end of 2022. When we launched it,

we had no enterprise features

whatsoever. And I got bombarded with

organizations saying, "Hey, everyone in

my company is using ChatGPT. Can I get

SSO? Can I get an NDA? Can I get an

invoice?" I had none of these things. I

had no enterprise features whatsoever.

Uh so, over the next few months, I

begged and begged and begged our

technical team, "Can we build an

enterprise version of this product and

we build some enterprise features?" And

finally, 9 months later, we got

approval. Now, over that 9-month time,

the companies that had been the loudest,

the companies that had gotten to me,

were the bigger companies, were the

large enterprises. So, I thought, "Okay,

we should go out and build a really

high-end product for all these

enterprises that want to use us." So, we

added every bell and whistle. We made it

lightning fast. It was a very expensive

product that we shipped. We went up

market. We went way up market right out

the gate. And, you know, we did fine. We

We did pretty well. Um, you know, and

and I think for most companies we did

great. Uh but after about a quarter, we

said, "Well, we should probably also

offer a self-serve version. Not everyone

wants to opt into this heavy sales

process and start with these really high

price points." So, then we released our

self-serve motion in January of 2024, so

about

4 months after our enterprise version,

and it just completely cannibalized our

enterprise business. Uh it grew so much

faster. It turns out most people just

didn't want to talk to a salesperson,

and our mid-market SMB sort of

self-serve business was much higher

growth than our and then our heavy

enterprise business. So, it frustrated

the sales reps cuz now they had to

compete with self-serve. It sort of

cannibalized the customer base. They

sometimes they preferred to just

move into the cheaper self-serve option.

And so, that was a really valuable

lesson. We should have launched with

self-serve first, listen to feedback

from our customers and what we they

weren't getting from the self-serve

product, and then figured out how to add

build a more expensive enterprise

offering, and then hire the team to sell

it. So, we did it all backwards. Was a

really really valuable learning

experience, and from there we decided

not to do that again. For every other

product we launched at OpenAI, we made

sure to to do it self-serve first, learn

where we needed to tack on humans and

add them.

Uh the other thing I'll mention, and uh

you know, uh if Everett's still here,

nice uh shout-out to him. We used Clay

at OpenAI, and it was really really

useful for us. So, in the beginning, we

were just completely overwhelmed with

inbound, which I know sounds like such a

champagne problem, but it was me and

four sales sales reps, and we were

getting, you know, 10,000 inbound a day.

I mean, it was just the most staggering

problem to deal with this tidal wave of

inbound. And, you know, if I could go

back in time, there's so much I would

have done differently. I would have,

first of all, added way more fields to

our sign-up form, like phone number,

because eventually when we did catch up

and we built all the automation and we

figured out how to handle these leads, I

didn't have a lot of information to go

follow up with people. So, add a very

in-depth sales form. It can be optional,

but if people are willing to give you

their phone number, you should get it,

cuz at some point you might want to call

them or have AI call them. Um so, gather

as much info as you can. Try to respond

to everyone, and I I you know, I wish I

would have done this, at least just sent

some email out saying, "Hey, we hear

you. We don't have our enterprise

product ready yet. You're on our

waitlist. You're on our list. Tell us

XYZ about what you're looking for." Just

some sort of automated email campaign to

make them feel like we cared. Because

when we finally did launch our

enterprise product 9 months later,

almost every company went out and talked

to you said, "Well, you never got back

to me." And I went out and I brought

Microsoft Copilot. Um so, that was a

that was a really hard lesson.

Um and then similarly on outbound, uh

you know, there's lots of great tools

out there now. Clay is one of them. I

hear really great things about Nooks. Uh

there are really wonderful tools to

start researching, sequencing, dialing,

and automate as much as the outbound

pipeline gen as you can, so your reps

can focus on the qualified leads and the

high value conversations.

So, this is my biggest advice to any

company starting to build their

go-to-market motion is just make it easy

on your buyers.

Uh don't give them homework. Don't make

them go and fill out a form or if you

can avoid it, integrate something

without you hand-holding them through

that. Never say, "Hey, go do these five

things and then come back to me." or "Go

ask this person about this and come back

to me." You do as much of the work for

them. You hand-hold them through that.

Maybe that means you have to set up

hackathons and come in their office and

do it with them in person. Um maybe that

means you have to set up some sort of

Zoom session and do it live with them.

But, whatever you do, don't send your

buyer away to do something and wait for

them to come back because you lose total

control of the sales cycle and it makes

everything take longer.

Secondly, remove as much friction as you

can in the buying process. Fewer options

is better on pricing. Make the paperwork

easy and fast. Make the approval flow as

manageable as possible. We've already

talked about investing in self-service,

doing that up front before you add on

humans. And the other thing I'll hammer

home is to avoid pilots at all cost. Um

and this is something that comes up when

I talk to founders a lot is they say,

"We are stuck in pilot hell. We've got

all of these pilots going on. None of

them are converting. They're so much

work." Or if they do convert, it just I

have to run an entire sales process all

over again. I sell the pilot. I invest

really heavily in managing the pilot.

And then I have to start all over again

from scratch once the pilot I get a yes

to move forward on the sales cycle. So,

use pilots sparingly. They should be not

the default, but the option for your

most valuable,

uh highest paying, biggest revenue

opportunities. Now, how do you get out

of a pilot? Because every customer will

ask you for one. They'll say, "I need to

try this out. I need a POC. It's part of

our process. I need to validate this

works in my environment. It meets my

needs. We have, you know, all of these

things we need to validate and check

on." Just remember, as soon as you give

someone access to your product, you're

giving away a lot of power and leverage

in the deal cycle. So, there's lots of

ways to get around these objections

without a pilot. You can introduce them

to another customer. You can do an eval

on on part of their data. You can do a

demo with their custom data and you do

it over Zoom rather than handing them

access to it. You can give them an

opt-out clause. It's not something you

do when you're a giant company, but when

you're a startup, you can get away with

these things. So, sign a contract, you

have 90 days to opt out if it doesn't

meet your needs, and that shifts the

onus of trying out the product and

validating it uh onto them cuz the the

clock is ticking on them now. Uh so, it

gives you a lot more control over the

deal. And then another one I like to do

is I say, "Well, our normal uh contracts

are 3 years, but we'll do a 1-year POC

with you." So, there's all kinds of ways

to sort of negotiate your way around a

POC without putting tons of resources

and getting stuck in them.

The other thing is security. Security is

where deals tend to stall out and die

over time. Uh there's a lot you can

automate now. There's so many wonderful

tools on the market to build these trust

portals where, you know, companies can

come in and they can auto sign an NDA.

They can self-serve for your pen test

and security documentation. There's AI

products that can auto fill out your

security questionnaires. So, automate a

as much as the security as you can, and

most companies will tell you, "Oh, I

need to get on a call. I need to talk

for 2 hours." Push back on that. You

know, push them towards your trust

portal and then make them come to you

and say, "Here, you know, here's what I

couldn't find. Here's what wasn't

available. Here's why I need a call."

And try to automate security because a

lot of it really can be automated now,

which is really really uh speeds up the

sales cycle.

Um so, another thing we learned, another

expensive story, and this goes back to

sort of building the Porsche before the

Prius, is we built this this really

high-end product, this enterprise

product, and we set the price really

high. We set it initially ChatGPT

Enterprise was $60 per user per month.

Now, we were really the first ones on

the market, and we didn't know what

pricing was going going

Uh so, we we basically priced it

according to how expensive it was for us

to serve it. And then all the other

products came out on the market, Copilot

and Gemini and Anthropic at a much lower

price point. And we realized we had set

the price too high.

So, we eventually went and we did lower

the price. And what we did, we changed

the model to basically a license fee a

bare fee to use the product and then

move to usage base. And then we just saw

a the barrier to entry went down. So, we

had so many more companies signing

licenses and signing contracts with us.

And then usage went up over time as more

as we started the barrier to entry went

down. Because when it was $60 per month,

organizations would come in and say,

well, I'm only buying this for a subset

of my team or only for my developers or

only for my investors. I'm not going to

buy buy it for my whole company. It's

too expensive. But once we lowered the

threshold, it spread like wildfire.

Everyone started using it and it was a

much better pricing model that we

learned the hard way. I know over time

now seats are out. This this has become

common knowledge. We learned it the hard

way. And I also know that now usage is

also getting pushed back as company push

back on as companies are seeing cost of

usage skyrocket. There's easy ways

around this. So, you could for example,

cap. You can say, hey, we have a

dashboard. You can cap your spend per

month. Most companies don't end up using

that, but they like to know that it's

there. You can cap certain employees

spend. But people like the idea that

it's a low barrier to entry. People can

use it. If they're using it, ideally

they're getting value out of it. And

then there's ways to handle the

objections of what if the cost spirals

out of control.

All right. So, we've talked about

building the machine. When do you hire

the humans? When do you start bringing

on sales people? Sales people are

expensive.

You know, they're that's a big hire.

They're they're you know, how do you

know when the time is right? It's

basically when you're starting to hit

you've gone as far as you can in your

sales process and you're really having a

lot of companies saying, I just need to

talk to somebody whether it's I need a

demo. I just need to look someone in the

eye and build the trust here. And you're

going to have that as you start to move

up market naturally. Bigger companies

are going to want to look shake the

hands of a human and have a conversation

with them. On that note, I will say

avoid the pull-up market as long as you

can resist it because once you get a big

customer, they'll come and they'll say,

"I can spend a million dollars, 10

million dollars with you." And it's very

tempting to want orient your whole

business around that. They will take so

many of your resources. As soon as you

have this enterprise customer, they will

take so many of your legal, security,

product, engineering, sales resources.

So, you want to be really, really picky

about who those first big enterprise

partners are. Eventually, you're going

to need, most likely, not everyone, but

eventually you most likely are going to

need some humans to help have these

conversations.

So, who do you hire? You hire someone

who is AI native, who really gets AI,

who lives it, who can authentically sell

it because they're really bought into

it. This is not a reseller right now,

but this is more and more becoming the

norm with sellers, with account

executives. Uh you want them to practice

what they preach, you want them to be

efficient, you want them to be bought

into the culture of your organization.

Why do you need them? I'm calling this

the revenge of the steak dinner. As more

and more of this becomes automated, as

you have the automated outbound, the

automated demo, the automated security

checklist, more and more companies are

craving in-person times with humans. So,

conferences, conference booths work

really well, dinners work really well.

And they're, by the way, not that

expensive to set up a dinner with some

buyers, some customers, some prospects.

It's a very effective tool, and you do

still at this at this moment in time

need humans to run those dinners.

Uh so, let's talk a little bit about

hiring sales people and how you pay

them. Um this comes up a lot at OpenAI.

We were notorious because we still have

not given out comp plans. Um it was not

necessarily my intention to wait this

long. I just kind of kept kicking the

can down the road and saying,

"Eventually, I'll pay commission." And

then we just the team got bigger and it

got harder and harder. I do think OpenAI

is finally about to put in commission.

Uh but we we made a we made it really

far without any comp plans. I would not

necessarily say that is the right path

for every company to follow. I think

OpenAI could get away with that because

of the equity packages and the way the

company was increasing in value, but in

general, it's really hard to hire the

best enterprise sellers in the market if

you don't pay a variable. That said, you

can get away with it for your first few

hires. Those first few sales hires are

usually wired a little bit differently.

They're there to build the company.

They're there for the equity. They want

to roll up their sleeves. They want to

contribute. They're not necessarily as

motivated just by commission and by a

W-2. So, you can get away with it really

for the first two or three sales hires.

Eventually, you're going to want to hire

kind of more coin-operated enterprise

sellers. They're very motivated by the

cash compensation, and so eventually

you'll need to put in a comp plan. So,

just I get this question a lot, so I

just wanted to put it out there on how

to think about building out comp plans.

Simpler is better, but have upside for

out-performers.

Um so, I love this slide. I saw this

early in my career in sales, and I just

think it's um it's a really great

reminder of what you're actually

selling. You're not selling your tool.

You're not selling your product. You're

selling what that tool or that product

does to your champion or your buyer. And

this is where I do think humans are

still very helpful. They're very good at

value selling, and I think AI does still

have some ways to go on value selling.

So, until we totally crack that, I do

think we're going to need those steak

dinners, and we're going to need those

humans to sell value.

All right. So, that's me. You can grab a

one-pager of this with that QR code. Um

also really easy to find on LinkedIn.

I'm the only one with my crazy spelling

of a name with A L I I S A. Feel free to

reach out if you have questions, and it

looks like I have a couple minutes for

Q&A here.

>> Okay. How First question right here.

>> Yeah, I uh

Can you hear me?

>> I can.

>> Okay. Yeah, I was just curious about um

you talked about the POCs and pilots

should be the exception, but then

there's also the self-serve first

motion. How do you reconcile that?

Because

you know, the POC or pilot then becomes

just do they get help when they go off

and do self-serve?

And they need your help to be

successful.

>> Great question. I am sort of thinking of

PLG, so people coming and self-serving

and just using your product is very

different from a POC, which is usually a

contracted period of time where they

have access to your product and they

have support and resources from your

team and you're giving them sort of

services and support along the way. So,

you're right. That is access like

self-serve access to your product is

totally fine and great and you can stage

gate that or limit that with

um consumption,

uh time box it, um or um

uh feature gate it and those are all

really valid ways to have people sort of

build a natural PLG funnel into your

product. When I talk about POCs, I'm I'm

specifically referring to more handheld

services uh oriented POCs that require a

sales engineer or salesperson to sort of

supervise.

>> Hey Alyssa Roy. Um

quick question on forward deployed

engineers. How do you think about them

fitting into the sales cycle?

>> Yeah. I mean, in an ideal world, we

wouldn't need them. Uh eventually,

hopefully we get continual learning and

these models can just figure out the

inner organization and how to just

immediately become smart. Uh I do think

for now, the thing with a forward

deployed engineer is on the one hand,

they're expensive, they're hard to hire.

I think there's something like 55,000

job wrecks for forward deployed

engineers right now and about 5,000

people who know how to do that job. So,

they're hard to hire. If they're you

know, they're you're getting more and

more of them available.

The positive is they make the product

really sticky cuz once you've invested

in that sort of services element of

we're going to have someone come and

help you uh integrate the product, your

customer is unlikely to go anywhere soon

because they feel like they've got a

customized tool that works uniquely for

them. So, I would say obviously the in

an ideal world, your product works

without the forward deployed engineering

uh cuz they are very hard to get right

now, but the the positive is then you

have a you have a sticky customer who's

with you for a long time. So, if you can

if you can find good forward deployed

engineers, they they certainly do pay

dividends.

>> Hi Alyssa. Um

for startup working on like their first

10 customers, would you go like the clay

route or would you do something else?

>> Uh I'm sorry, when you say the clay

route, what do you mean specifically?

>> Like using something like clay for

automated outbound.

>> Got it. No, your first 10 customers are

going to be different. Um they're going

to be really more design partners. Um

and they're going to need to be much

more handheld. So, I I'm talking a

little bit more when you're beyond the

first sort of design partners and you

have some product market fit and you're

starting to scale the organization. For

those first partners, you want to be

very particular and picky about who you

choose. On the one hand, it's it's sort

of a gift to a company to let them be

your design partner. There's exclusivity

to it, there's scarcity to it. They

really help give you a lot of feedback

on your product, but you want someone

who's going to work well with you, who's

going to understand this is

realistically where my product is. This

is where my enterprise features are. Um

so, you want to be thoughtful about who

those first few customers are. One

tactic I love to do on the design

partner side is go to a company that has

a great logo, but work on like their

internal product or some sort of product

that's not their main production, so

that they're willing to take a little

bit more risks with you and bypass some

security processes, but then you get the

logo on your site and you can go to

companies and say, "Hey, I work with

this company." And it opens the door to

potentially sign a bigger agreement with

that company over time.

And I think we're at time here. Sorry.

Ideally, they're relationships you

already have, either companies you've

worked with or your investors are

introducing you or they're you know,

friends at at companies cuz you want

these to be very friendly uh uh

uh processes and experiments in the

beginning.

Great. All right. Thank you.

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