Shift & Thrive: CEO Insights on Driving Change

S&T_Cheryl Jordan-Aguilera
===

[00:00:00]

Natalie Nathanson: Welcome to

another special edition

episode on Shift and Thrive as

part of our

go-to-market

miniseries. If you're a CEO, or business leader wondering how your go-to-market

strategy

needs

to evolve right

now

to

meet today's

market realities,

this

episode is for you.

Today's guest

is a go-to-market strategist

with 25 years of expertise

across sales, marketing, and corporate strategy.

With

a depth of focus in

[00:01:00] the market

research and data analytics fields. She has led critical

initiatives in areas including sales enablement and product commercialization,

Consistently

driving revenue growth, and

enhancing operational efficiency. She recently took

on a new role as head of growth and strategy at

Official AI, where she's helping

shape the company's direction at the intersection of AI and business innovation.

Cheryl Jordan Aguilera, welcome to the show. I.

Cheryl Jordan-Aguilera: Yeah. Thank you. Thanks for

having me.

Natalie Nathanson: It's

great

to have

you and you

know, you've had such a

dynamic career across go to market and I know you've worked in early stage startups

and more

mature environments,

And one of the things that

you know,

really stood out, uh, when we spoke previously was kinda

how you've built these like full revenue ecosystems.

And

one

of the

stories that caught my attention was your time at Gut Check

And that you were there

during a period of major transformation and that the work you did really helped lay the groundwork for, uh, some of the company's future success. So

can you

take us

through that chapter, [00:02:00]

you know, what were the business challenges that

you were solving and then, you know,

how did

you go about

evolving the go-to market?

Cheryl Jordan-Aguilera: Sure. Um, yeah, so a gut check is definitely,

um, holds a dear place

in my heart. It was the, um, a great four years, um, and joining

as

employee

probably 30 or 40 something,

um,

on a trajectory

to have, you know, over 200 employees.

Um,

I joined

as an individual contributor on the sales team to, to lead, um, sales for

gut check, um, on

the West Coast.

And, you

know, quickly moved

up into

the leadership of the organization just because I had, um, so much experience in market

research and technology and how those two,

um, work

together for large brands. And, um, as we were building, um. Kind of the, the ecosystem to support, um, those initiatives at GutCheck. Uh, with bringing on new [00:03:00] clients, um, really addressing their business needs, um, wowing them

with

the insights

that GutCheck could provide

that

were both

quantitative and qualitative in nature, which was very unique at

the time

to be able to

do both at

once.

Um,

you know, we found

that we needed to start building out more, um, customer support, account management functions in addition to the straight selling.

Um, it was really important to

our model to really take care of our clients,

make sure

we were answering the right kinds of questions, and then where necessary Conti continue to, um, dig into different questions

that

arise.

From your research projects and the insights that you learn. 'cause sometimes you, you learn more and then all of a sudden that produces more questions. Um,

so we

did build out, um, quite a, a large team eventually. So, you know, it consisted of, um, a sales organization with probably [00:04:00] like 10 to 20 people at any given time.

Um, and then an account management team of about the same

size,

um,

really taking the aftermarket, um, like

nurturing and care approach

to

helping those clients continue to work with us.

So, um,

yeah, it was definitely where I, I learned the hard way, um, with

how to

build out the right infrastructure to support this type of, um,

technology

software sale with a service

component to

it.

Natalie Nathanson: What would

you say were the, you know, biggest kind

of keys to

success, and whether those were things that

kinda went right in the process or didn't, but you learned from it. Are there kind of a few

things

that come to mind?

Cheryl Jordan-Aguilera: Yeah. Um, I think one of the

cornerstones of why

Gut Check was so successful,

um, is because

they

hired

not only for your, um,

technical and professional,

um,

experience and expertise,

[00:05:00] Um, but they really wanted to hire people

who were cultural fits for the organization.

And so they had this motto called the give a Shit Index, or How gassy are you? Um, and

that's something that stuck with me

in, in my hiring

practices now because I often find myself looking at

how, um, you know, how technical. Technically successful

or

professional, someone is, but then I'm also looking a layer deeper to

say, Hey,

is this gonna match with

the organization

and the, the vibe we're going with?

And maybe

it's 'cause I'm on the West

Coast and these

things matter more to

us.

But, um, that's, but that's where I learned it from

and I just thought that Gassy Index was, um,

one

of the

things that really made that organization successful. Um,

Natalie Nathanson: I like that. I think, um,

it makes me

think of, uh, an EOS

like entrepreneurs

operating

system. They

have GWC,

the

like get it wants it,

capacity to do it as

like the three levers for, you know, not specific to sales in that case, but across the organization [00:06:00] looking

at your

employees. And I think

sometimes things like, you know, alignment to values can feel like lip service.

Um, but it really is

so critical Both in the hiring process, but then

kind of over

time making sure that people are kind of evolving as a company evolves and

uh, you know, all of that.

Cheryl Jordan-Aguilera: Absolutely.

Absolutely. And

that organization was a, a lot, it was more than like just showing up every day and like punching the clock. It was a lot more about being invested in, um, and, and

believing in what we were doing.

And so,

um, that was definitely

the foundation for, um,

a successful, you know, go-to market organization.

Natalie Nathanson: Were there any kind of challenges or resistance to

kinda the approach you were

looking to roll

out? Or was it really kind

of all hands on deck? We just need to kinda find

all

the right people and lots of them.

Cheryl Jordan-Aguilera: Um,

yeah, I think.

Overall, because everyone

had a mindset that was,

[00:07:00] um,

like shared success.

There was a lot of collaboration and problem solving together, um, which I think contributed to the success. Um, and there's always kind of a push and

pull between different

departments and

so, you know, sales and marketing kind of push and

pull against

each other.

And

then so do sales and then like account management depending on how organizations are working together.

So there's definitely some negotiation about who owned

what and which

process. And,

um, but what I liked about it is that we ironed

it all out and like created, um, playbooks

so

that teams were really clear on what their role was, um, what the expectations were and what success looked like, and then

how the other

team

had

the same

thing, but how they

complimented each

other and really kept the, the client.

As

the focus. And

that was really what our goal was, to keep the client as a focus. So, um, there, so there was a lot of collaboration, but there was [00:08:00] also some, I would

say, healthy

pushback in places

as

we, we got the balance. Right.

Natalie Nathanson: Yeah. Makes sense.

I'm curious if there's, you know, anything you would approach differently today if you were kind of faced with the same situation.

Cheryl Jordan-Aguilera: Um, you know,

I think

there's, as

you continue to age, you get, um, more mature in your thinking and you have that many more experiences that lets you, um, stay a little bit more even

keel and like think

through things more rather than react. And I think as I look back, um, I was so like, passionate about what we were doing

that I

think,

um, I was a little intense at

times

and maybe that wasn't.

To

the benefit of everyone else. And so I think

now I,

there's a more of a calmness that I can

come to the table

with that's like, okay, well let's think

through this.

We don't have to be, you know, emotionally invested to

the nth degree

and like, and

react[00:09:00]

overreact. And so I think these days, um, I would approach things with more curiosity rather than judgment.

Natalie Nathanson: Yep. Yep.

I think it, it certainly a case Swear. Like

we, we all learned those kind of lessons over the years. I think you made me think of an example when I was,

uh,

building a new sales enablement function

in an organization

from

the ground up. And I was just

so excited by

the initiative and what I was doing, um,

that I think now back

on it, like,

you know, a

couple decades later of what it must

have felt like for

the salespeople as

recipients of

it.

And like,

yes, There

was a lot of great content in there

and all of that, but I was not sufficiently putting myself in the shoes of the salesperson

and everything else that was coming at them and, you know, the expectations and, and

all of that. So I think that's, uh, definitely an a, an important lesson to learn over the years.

Cheryl Jordan-Aguilera: Yeah.

Yeah. And it's hard to put

yourself in the, the frontline sales

role,

um, if you haven't been in it or

haven't been in it for a while. 'cause I, I've definitely had that [00:10:00] experience where I worked, um, on sales enablement, and I thought I understood completely what it was like to stand in someone's

shoes.

But, um,

there's always things to learn. So I guess it keeps us humble.

Natalie Nathanson: Yes.

I, I

am a big advocate of the concept of like the

rotation programs and at small

companies. It doesn't have to be formal,

but like, especially coming from the marketing world,

that every marketer should have some experience, exposure

to selling in a way that

you don't get if you've only kind

of sat squarely in the marketing realm.

It

just makes you such a better

marketer.

Cheryl Jordan-Aguilera: Yes,

I completely agree with that because it, it kind of strips away. Some of the fluff

to

get to some of the practical, like rubber hits the road

needs

that, um, that if you understand as a marketer, a sales loves you.

Natalie Nathanson: Yes.

Uh, I,

you know, I also think about the, the common language and, you know, marketers

can have the frustration of, you know, why isn't sales following up diligently on all of my [00:11:00] leads? But then

from the sales

hat,

it's, well,

maybe they weren't necessarily good leads to begin with. And so it's one of those cases where there's often no, uh, right

or wrong, but each person's

coming from

their own purview.

And once

you can see the other person's perspective,

you have more understanding, more empathy, and

ultimately can work better together.

Cheryl Jordan-Aguilera: I completely agree,

and I've been fortunate now to work

on both

sides of that sales and marketing fence. Um, and I have a lot more empathy for both

sides and a lot more understanding

of what's driving certain behaviors.

And those behaviors are what

drive sales and marketing crazy about each other. Um, so that was insightful when

I pieced that together

and I was like, aha, okay, I get this now

Natalie Nathanson: For sure. Yes.

[00:12:00]

Natalie Nathanson: Um, you

know, I wanna talk

about a different

kind of transformation.

So, shifting gears a bit, uh, but talk about, uh,

m and a activity

And maybe an

example where

things didn't go quite as smoothly in an environment that you were in. Um, I think, I've

had my own

experiences with, uh, kinda m and a and,

you know,

what could go right, what could go wrong, uh, but can you share, you know, what

that was for you and kinda what you learned from that

process?

Cheryl Jordan-Aguilera: Yeah. Yeah. So following my time at Gut Check, um, I wanted to stay

on the cutting

edge of. [00:13:00] Uh, you know, innovation. 'cause that's the part of market research that always, um, interested

me

the most. Like, what new thing can we use or a new insight that can help drive

business effectively. And so

I joined a startup that was

also

doing, um, kind

of a mix of quantitative and qualitative research, but it was in more of a, um, agile, um, manner and a little bit more self-service.

And so I joined, um, a startup, you know, as employee

10,

um, and really worked on this

partic

potential product and then started, um, helping to build out the sales and marketing functions of how we would position this in the market. And

at six months

into it, um, this company was acquired by,

um, one of

the largest

market research firms in the

country.

Um.

That merger and acquisition experience [00:14:00] taught me a lot. Um,

if

I could go back in time, I would have been a lot more, um, opinionated and

forceful about some

of my recommendations. Um, but I don't think I believed in my voice at that point. Um,

and

I thought, oh,

people

know better than me. They'll, they know what to do.

They've done this a lot

and turns

out, um.

I did

know better and some

of my suggestions would've

made a much bigger difference to how the product ended up working. So essentially,

um, this really cool product was

acquired and then

we were left alone for the first year

and

then kind of forced

integration with the rest of the products in the following years.

Um, but nobody had a strategy for how all these different acquired products could work together. And so that was when, um,

I took the opportunity

to

get more involved in like a corporate

strategy role, um, [00:15:00] because I had a strong sense of how these different products could work together to create an amazing ecosystem for

customers.

Um.

And there were some really, there were good things that came out of those, those opportunities for me personally, just getting to, to work

in different organizations

within the, the company. Um, but for the actual product that I had come on board with and then entered this company with, um, that product was eventually discontinued.

Um, and

I

still think that was

a shame

because there was so much potential, um, that was there. Um, we just

didn't have

the buy-in of the larger organization. And then that's kind of where I look back at times when I could have been more, um,

emphatic about some

suggestions, um, but

more importantly, built a better business case for why a different approach might be more effective.

So that was [00:16:00] definitely a learning experience.

Natalie Nathanson: I'm curious to ask like,

what was

the reason that

the company had made the acquisition and like, why didn't they do something with it

right away? I wanted to unpack that a bit.

Cheryl Jordan-Aguilera: Yeah, so, um, the, the company, the small company that I was at, was part of

a collective of small companies.

And so that collective got purchased and I think, um, there were reasons

with each co, with each small company's

products

of what they thought they could do together. Um, but some of the other products

were more developed,

um,

and had been more mature in

their

selling strategies and in their product

development. Like

they'd been

around for like eight or 10 years.

So they

naturally,

um, took on more of the,

the leadership role, um, among the product development organization. And then that left

some of the,

the newer just getting started products like the one I was working

on. Um.[00:17:00]

Kind of

left

behind. And

I should also say the, the founder of that company left after the acquisition.

And so, um, I think that that leadership vacuum needed to be filled. Um, and I, I should have

stepped up more than I did.

Natalie Nathanson: Yep. Hindsight's always

2020. Um,

you know, I think part of the reason I ask the

question is I,

I do see a lot of, uh, cases where, you know, there's much to be desired with kind of the, the go to market side of, of an acquisition. And, um, I find

often,

you know,

marketing is

brought in late. The go to market

strategy is thought of,

uh, a bit late,

And

it's easy for things to get lost in the shuffle.

Cheryl Jordan-Aguilera: Absolutely. And, you know, I think there has to

be

an.

somebody,

um,

involved with the, the product marketing that there's a curiosity

to, like,

how do all these

things work? How

can they work together? Um, and I, [00:18:00] I think that

when you throw

everybody in the deep end together, um, and there's not enough guidance for that, then you're kind of at the, the will of, um, different

people's experiences

and what their knowledge is. And if that's limited in

the space

that you work in, then that's a disadvantage.

And yeah.

Lesson Right. I

Natalie Nathanson: think, you know, the lack of

maybe knowledge

on the go-to market side or if you're acquiring for the team or the technology like the technical

team or the

technology, it's easy to forget

about the,

the go-to market side. And so then,

you know, been in situations where, you know, the,

the

announcements are ready to be made out to the public, but yet no one has thought about the customer communication plan or,

um, you know, what is your new combined message?

What

is your new competitive landscape? And so it can feel like a real missed opportunity, right? Just

like I say, you only get to be new once you only get to launch

once and make these announcements

once.

And so [00:19:00] really like,

putting all of your strategic, uh, efforts into what is the best way to communicate that externally and work

through kind of the internal

backend

systems and all of that.

Cheryl Jordan-Aguilera: And

I, I think

also as a, a small startup company, um, we needed to be cautious about, um, not over promising and under-delivering. And we, we did a good job of talking about what our technology could

do and how

it could

help, um,

to the sales

organization. And then they did a great job of pitching it to their

clients.

But then, um, that

kind of overwhelmed a very small team.

And it's,

it's, it's like totally Murphy's

law of what, what happens with

these things where you go out and like sell, sell, sell, and we'll figure it out later.

And,

um, that's

never sat well with me in this use case is

why,

because

it's nothing worse to me than, um, promising capabilities or insights to somebody and then not being able to

follow through on it.[00:20:00]

Um,

Natalie Nathanson: right.

I mean, someone's left holding the bag, right?

It's like you

can say,

you know, too much demand

is a good problem to have.

Yes and no. Right?

Cheryl Jordan-Aguilera: Yeah. Devil's in to deal with that yeah. Yeah. And your brand

Natalie Nathanson: suffers, and then future

customers or

prospects are

harder to

come by.

you know, has a real ripple effect.

Cheryl Jordan-Aguilera: Yes it is.

Natalie Nathanson: so Cheryl,

I'd love to shift gears a bit, and I know you've been very

involved in kind of building and scaling, go to market infrastructure. We've talked about that a bit.

Um,

but

would love to maybe hear, uh, you know, in your current environment, um, being kind of an AI native or AI first company.

Does it look

any

different on

kind of the back

end of things than

in other environments?

And, you know, if so, how?

Cheryl Jordan-Aguilera: Yes. Um, it's

fascinating to

be an,

an AI first organization

and, and

we're part of,

um,

a collection

of

startups working with,

um.

Puget

Sound, [00:21:00] or

sorry, pioneer Square Labs

getting my

Seattle references off.

Um,

and so we

work

side by

side with other startups that are also AI first. And so that's,

um, really interesting

for everybody

learning from

each other.

It produces a very like

collegial environment when

we learn something, um, or find something that's helpful, like

sharing that knowledge amongst all of the teams.

Um, one of the things that's very different in this organization for me is that, um, a lot of our communication isn't

on email.

Um, it's not,

you know, with. You know, shared Google drives or, you know, OneDrive Holdings, um, it's a lot more real time. And so,

um, before

joining Official AI, I had never heard of or used, um, notion, and that that particular software has been

a

game changer [00:22:00] for me in terms of

updating,

um, my work style and how I collaborate with my teams.

Um,

because

Natalie Nathanson: can

you give us some examples of how you're using Notion and kinda the different

impact that's having versus

Cheryl Jordan-Aguilera: yeah. yeah. I think in the past I would've communicated specific ideas in like

a PowerPoint. Or a Google Slides format, um, and like walked people through,

a very traditional

and

what I would even call old school now. Um, because a

notion, um, it's more of a living, breathing document

where,

um, you're, you can enable it to allow edits from

teammates. Um, it can be kind of a brainstorming area, but it can also be

a place

where you finalize, um,

your

materials and make it, um, publicly available to your team or, you know, a subset of the team.

Um, and so

I think, you

know, having something that's always available,

always accessible to people, [00:23:00] um, allows us

to make changes in

real time. And so it speeds up

The conversation

and it

speeds up our, um. Go to market pace, um, just because

we're able

to discuss and move through conversations at a, a quicker pace.

Um,

the thing that's also been

interesting for me

is how much, um, how many decisions, um,

and information we share through

Slack.

Um, because I've come from some more

recently, some more traditional environments where

we would've been using teams. It would've been, um, just a more structured

process, especially being in a bigger company.

Um, and so Slack has been, um,

game changer for

me

just

in.

You know,

moving, having the ability to move

faster,

but then also being able to look

back in conversations

and find

documents,

[00:24:00] um, that people shared in certain channels.

And, you

know, not having to guess at where in a,

a program

file it's saved on who's

hard drive

or whatever.

Um,

so yeah, so, so some of those are, um, I think.

Just

like a day in the life. Um, tools that help us do things faster. There's a advisor at PSL, um, pioneer Square Labs,

Greg

Gottesman,

and his

challenge to the organization has been,

you know, before you

start anything, ask yourself how can AI help me? And if you're not using AI to

help you

in everything you do every day, you're gonna get left behind.

And that advice really

stuck with me

when I started with this organization. And it's definitely changed,

um, how

I work and what questions, you know, I ask AI and how I use it to help me

structure

different

arguments [00:25:00] or, um, think about frameworks

for setting

things

up.

Natalie Nathanson: yeah,

I love that question. And I would say we,

uh,

embody a similar kind of mindset at, at my organization. Uh,

Um,

it was a little bit of

a

kind of

cultural

shift

or like there's some change management involved in getting that to be, uh, the default.

But

because I think we do need to kind of continue to look at

different ways of working and, and,

all of that. Um, the nice thing about some

of the tools that you're,

uh,

sharing

is they also continue to add in new AI

features.

Right?

So even

like Slack, I know

we're getting

some new

AI capabilities rolled out in,

you know, our

version, uh, I think this week or next week.

Um, And so it's both

kind of your own

AI use

based on

your role and what

you already have, and then always staying on top of kind of

the new features coming out and do you use them?

How

do you use them? So it's, it's

a,

a

moving target, but in a, in an

exciting

and impactful

way.

Cheryl Jordan-Aguilera: Exactly. [00:26:00] Exactly. And it's fun to be working in a, a team that's very collaborative and um, shares the learnings and so it doesn't feel as overwhelming as it can if you feel like it's all up to you to figure out ai.

'cause it's a big world. Um, and so It's great to be working with other people

who have curiosity

about that, um, and are trying different things and aren't, aren't afraid,

um, to be curious and.

experiment a little bit. And that was one of the things that I, I learned through a course I took last year at MIT, um, about AI and business strategy.

Um, great foundational

class for understanding AI

and the different facets of it.

Um, but it also, um, helped

me to

understand more of the, the iterations and the

process

that you go through

Leveraging AI because it enables

you to ask

questions early and often and

make adjustments

constantly.

Natalie Nathanson: [00:27:00] I'm curious, just while you're talking about the MIT course,

were there any kind of frameworks that

stand out to you

that came

up there? Kinda any kind of key takeaways that you think

would be helpful for

other executives to hear?

Cheryl Jordan-Aguilera: Um,

yeah, I think the, the big

takeaway

for me was like, don't be afraid of ai. Um, it, it's really about

Um, and getting

questions answered for yourself,

And that for me was what I was trying to get to the bottom of because I felt like

everyone was trying to tell me what AI could do for me or why I should should be using ai.

But I felt like there were a lot of different

definitions of

AI and I was like,

how

are LLMs and robotics like

related? How

are those both

AI

and there's all these different, um.

Categories

that you

don't realize are part of this, what we call AI now. And some of these subcategories have been around for a

long time,

and [00:28:00] especially somebody, you know, working in, in data science and in, you know, mass

data analysis.

Um, there was a lot of like

AI

that we'd been using for the last 10 years. It just hadn't categorized it like that. So

learning. About the

categorization

of these different,

um, areas and then how they can work together.

Um, and just like

continuing to, um,

pursue that

curiosity rather than having fear

about, oh my gosh,

it's changing everything.

Um,

it reminds me

a lot of when I first got started in the

industry back in 2000 with

the.com boom, um, and I worked

in a, in

a startup organization

in Silicon Valley and, um, we were the

early days of user experience on the internet. And so we were having people go to like gap.com and put the red turtleneck sweater into the shopping basket and tell me about this experience.

And [00:29:00] I remember.

Lots

of learnings around

how people

will make small purchases online, but they're never gonna buy furniture, cars,

houses,

never gonna buy

that off the internet, you know? And then look where we are years later.

Um, but there

was a genuine fear from people about how different the world was gonna be, uh, with that technology available.

And I, I feel like, um, uh, what we're doing with AI now is that next

big

leap.

Um, just like

the.com boom in the, in 2000 was a leap. This is that next really game

shifting leap

that we're going through. And so it's,

you

can see it happening. And so it's better to be a part of it and have knowledge around it

than like be scared of it and just like, wish

it away.

'cause I see people doing both things.

Natalie Nathanson: Yep. Oh, it's amazing how

much has changed

in

those,

uh, the things that we

thought were, uh, not going to happen [00:30:00] or not realistic.

Cheryl Jordan-Aguilera: Absolutely.

Natalie Nathanson: and now they're just people. Yeah. I know Plenty

Cheryl Jordan-Aguilera: of people now have bought several

houses online cars then they just get delivered to your house.

You don't have to go deal with anybody.

Like, it's just the advances that happen,

um, are amazing. And I

think once

people get their arms around the AI

world a little

bit more

and see how it can be used for good, um, and how it can

be used ethically, um, because there's plenty

of AI companies like

mine that

feels strongly about those values and I wanna see those carry on in this next phase.

Um,

I think we can work with

AI in a

really positive way

to help people. And it doesn't have to be a big scary

like demon.

Natalie Nathanson: I'm curious for the type of, uh, clients that your organization works with, what kind of, uh, like, I guess like psychographic profiles, do you see, is it like still very much the early adopters? Is it ones

that are very like AI forward?

Just [00:31:00] kinda

walk me through, Uh,

kind of the profile.

Cheryl Jordan-Aguilera: Yeah.

Yeah.

I

would

say, um, what everyone has in

common is that they are

early adopters, so they're not afraid to go first. And I think a lot of people, um, uh.

Uh,

trying

to dip their toe into ai. They're interested, but

then they're

afraid to be the one to go first.

And so there's a lot of education, um,

with our sales process, um, about helping people understand, um, the

importance of,

um, managing

their name, image, and likeness, and using

official

AI as, um, you know, a patented technology that protects them. And so there's a lot of traction in, um, athletics and, um, with celebrities who have a, you

know, a famous likeness that

they wanna maintain control over.

Um, but there, it's also important

for

regular folks, [00:32:00] um, like all of us at official AI have our own vaults.

and in

our vaults we have,

um, the blueprint. And so

the blueprint is what allows us to produce, um, images and videos.

Of all of us doing

anything we can dream of,

um, with

ethical parameters, of course.

Um, and so

this is very intriguing, uh, for people who, um, want to be able to monetize themselves, um, either while they're playing a sport or participating in,

um, film, um, or afterwards.

Natalie Nathanson: it's so interesting.

I think we're gonna see some

very different use cases out there than what we've ever seen before because of

some of these

capabilities.

Cheryl Jordan-Aguilera: Yeah,

It's, um, one of the

reasons I joined, um, was because

of the, the patented technology, um, that our CEO Dave Siegfried, um, had worked on and created. Um, [00:33:00] and that ability

to. Really

track

usage

and understand how to protect people. Um, he has a background in music, the music industry and some, um, providence technology that, um, enables that security and that safety.

And so, um, being able to do that for people in this bold new world is a great thing to be

part of because

you see all the horror stories every day about, um,

People taking

over, you know, or using Scarlett Johansson's voice or, um, taping, taking over somebody's, um, likeness and having them

say things that they would've never said or go

to places they never have been, like this

fake influencer

at Wimbledon and stuff.

And

those types of things, um,

aren't possible within our system because

when you've registered, um, yourself, then you get to say how it

is your

name, image, and [00:34:00] likeness is used. Um, and so you get to say if it's used

for a brand purpose or if it's used for

anything you can imagine, um, you have control over that.

And then it's watermarked with our official ai, um, logo. And so, you know, we dream of a day where, um, AI images.

Are

out there, but it's transparent to all of us as users that it is ai because we believe that, um, AI can still be authentic, even if it is synthetic, if that makes sense. So yes. yes. it's a,

Natalie Nathanson: it's a nuance, but it's such an important

nuance.

I mean, so my,

uh, company works a lot in

the cybersecurity

industry and like the. Clients in the identity space.

Like there is just

so much happening

there and you know, so much demand to kind of rethink and, and

think through all this works. Both the

technologies and just the, the safeguards.

Cheryl Jordan-Aguilera: Yes. Yes.

And we love that there's [00:35:00] companies out there,

um, trying

to find all

the fraudulent, fraudulent

use cases. Um, 'cause that's definitely necessary. And then we're trying to

kind of

a proactive compliment to that,

um, with being

able to.

Mark

images and video from the beginning is, yes, this is ai, but it's,

it's also, um,

consented by the person in the the image or video.

Natalie Nathanson: Exactly,

exactly. You know, we're talking a lot about, you know, how much has changed.

I'm curious to ask you if

there are any, like go-to market beliefs or

practices that you feel are, you know, outdated these days and,

and

you

know, what

should replace it?

Cheryl Jordan-Aguilera: Yes.

So I

think I've been around long enough that I've experienced, um, a couple of different types of

sales cultures

and, um,

one that I

consistently have

seen over the years, especially in technology sales, is this whole Glengarry Glen Ross.[00:36:00]

Um.

You

know, coffee is for closers stuff.

And

while I appreciate

the, the

sentiment that, you know, everyone should always be selling,

um, I,

I've started to really steer away from, um, that

kind of, I guess a do

or dime mentality and like, you're, you're, you're only good if you've only

sold

this much and,

um, in this

amount of time.

And I think it depends on what your widget is that you're selling. Um, and I've tended towards more consultative environments where it's not about how many widgets you sell, it's about problems that you're solving. And so it's, it does require a change in mindset about what success looks like.

Um,

and I personally believe that salespeople, um.

Succeed

when they listen more.

I

think there's

a habit and probably a [00:37:00] stereotype out there that a lot of salespeople, they just talk at you and they don't really care what you think or what you have to say. And I've always tried to coach my teams to be curious, ask questions, understand, um, the pain point, understand the issue that someone's trying to solve, and then put your thinking

hat on

and say, okay, amongst the products and the services we offer, how can we help them with this issue?

Um, and I also have a philosophy that, you

know, people

buy from people they like. And so if you're genuinely interested and curious and wanting to help somebody

succeed,

nine times outta

10, that's gonna

take you

farther than, um, kind of this rigid old school. Stick versus a carrot mentality. And so that's one of the things that I've definitely evolved away from.

And that's not to say that we don't hold people accountable

for

goals and successes. There's definitely [00:38:00] ways that that's measured. Um, but we

just go

about it in, um, I'd, I'd say a more, I don't wanna, I don't know if

it's compassionate,

but to me it's a smarter way because you're, um,

asking people

and

you're hiring the kind of people who wanna be problem solvers

and

helpers.

Um, so it's just a different, a different take on it. And again, it does depend on like what your widget is that you're selling. 'cause

this does,

this philosophy doesn't always work with

everything. Um, but the places that I tend to

gravitate towards

are the places where this type of model works.

Natalie Nathanson: Yeah. Yeah, I've certainly had that kind of experience. You know, when you talk about listening, I think there's the, um,

the,

you know, you're talking about kind of the prospects, right? And listening for the pain points and be able to bring the right

solution to

the table.

I think

there's also

the element

around,

uh, internal feedback.

Right. And who, who else

do you listen to kind of internally[00:39:00]

in the organization? We've certainly

had the

experience

with,

you know, some of the more,

I'd say like old school, uh, sales leaders that don't

necessarily wanna take.

kind of ideas or

directions from,

from marketing

and in A landscape.

I think

where a

lot is

changing, marketing has a certain purview on

how do you look

at the competitive landscape, how

do you kind of take

in

feedback from kinda

the

market at large?

Um,

and you

know, compare

the kind of relationships that

are kind

of more collaborative and the ones that aren't. And we see like a very measurable difference

in kinda

the success of those functions.

Cheryl Jordan-Aguilera: I

completely agree. And so I, I've had the,

um, privilege of being to

sit in a couple times in organizations where I'm responsible for sales and for marketing like I am right now.

Um, and there it's, it really, it always highlights for me the importance of both, but how they're, they're,

really driving

some different [00:40:00] outcomes,

but

in a sup, in a supportive way of each other. And so, um,

I find myself on a

daily basis, like I put on my marketer

hat and

say, okay, these are the things that we need to accomplish for the brand or for, um,

customers

in a, a certain,

like more of a global thinking way.

And then there's a more of

a, a day-to-day specific hat I put on for sales. Like, okay,

we need to be talking to this many people

and have this many meetings so that we're moving this

many deals through the pipeline. Um, and. It reminds me of how important

that, marketing, um,

layer in

that role

is in laying the groundwork for sales.

Um, it makes sales life

so much

easier when there's a strong brand in the marketplace. Um, there's really clear value and differentiation,

um, that sales can then build

on in conversations and [00:41:00] because it's hard to, to do sales without

the marketing and,

um, they're, they both need to thrive and achieve their goals.

Um,

but they are,

they're

definitely different,

but complimentary

Natalie Nathanson: right

Cheryl Jordan-Aguilera: the right atmosphere. said. I'm curious

Natalie Nathanson: to ask, um, you know, under kind of a CEO's leadership

and maybe

a CEO that doesn't. Come from sales or marketing, maybe doesn't appreciate all of the, uh,

I

guess, nuances that need to go into it. Or

if they do come from one

background and not the other,

are there things you would

advise

CEOs

to be

thinking about

of

how to

kinda strike

that right balance on the

relationship between

sales and

marketing,

alignment of goals, um, anything that kind of should

come from the top.

Cheryl Jordan-Aguilera: yeah, I think it's important that

the, the

top really, um,

Acknowledges

the importance,

um,

of both sales and marketing.

Um, I think

in

product-led [00:42:00] organizations,

it

can be really easy,

um, to overlook

those groups as

not being as important as

the product development

or the engineering team.

Um,

and while the engineering team's critical to the success of any

startup,

um,

You you need people to understand what your company and your product's about and you know, what's in it

for them.

Why would they wanna

subscribe

to or,

or buy your product? And that's the key role that sales and marketing play. Um, I think what I have learned over the years is to

put

everything

in, um,

a business case situation. So if we invest X amount in this type of marketing, we

expect this to

translate into this much,

um, sales opportunity,

which

then

should be this many

deals Using kind of the math side of things.

Um, I personally subscribe to more of like an art and

a

science

of, of[00:43:00]

forecasting. Um, and

I think

earlier on in my career,

um, I would've

relied more on

it just makes sense. How are you not seeing this? Like, of

course you

need to talk about

your brand and then like what we can do with these products to help people.

Like why isn't this.

landing?

Um, and

I've learned over the years, well, the business case around, that's really important because if, if someone hasn't sat on that side of

sales and marketing,

um, they really,

they don't understand

what's possible.

And

so you have to walk people through it. Just like I need to be walked through

engineering and development

things sometimes.

Well, you have to build this first before you can add on these bells and whistles that you're saying are important to this client. Like, we hear you, but this infrastructure has to be in place first. And that's, I see the same thing with sales and marketing. It's like, okay,

I

see you guys

wanting us to sell X, Y, or Z, but we have to tell the bigger story

and

lay a, a brand [00:44:00] foundation before we can do some of these other things.

And so it's just learning how to talk to

everybody in your organization. 'cause people

definitely show up with their own

perspectives and especially when they've,

they're experts in them and

they've been working at it

a long time.

Um, you know, there's a, a respect for that. And

then a,

okay, let me help

you step

back from this and look at the bigger picture and this is why

we would recommend this, that, or the other.

Natalie Nathanson: I think that is very well said,

and, uh,

because of that, I think a great place for us to wrap up the conversation,

uh, on

such a great note. So thank you so much, uh, Cheryl for everything that you've

shared with us.

Cheryl Jordan-Aguilera: Yeah. Thanks

for having me, Natalie. This was fun.

Natalie Nathanson: people want to

get in touch with you,

what's the best way to reach you?

Cheryl Jordan-Aguilera: Um, great question.

Um,

best way

to, to reach me is probably on LinkedIn, um, Cheryl Jordan Aguilera. I'm

the only

one, so you should be able to find me and then find our company official ai.

Oh

Natalie Nathanson: thank you too to

everybody listening. I know I [00:45:00] loved hearing

about

so much of what

Cheryl shared and our discussion around,

uh, the m and a lessons learned,

uh, AI

usage and what that's looking like,

uh, in today's world, uh, some of the outdated sales leadership mindsets and how do we kinda work through that and support our companies as best as possible.

So, if today's episode gave you any valuable insights,

and I'm sure that it did. Please

share this with

a CEO founder or go-to-market leader in your network. It's these kinds of conversations that help us all scale smarter, build stronger, and create resilient go-to-market engines. So thank

you again, Cheryl,

and

this has been another fantastic conversation on Shift and Thrive.

I'll see you all next

time.

[00:46:00]