CRO Spotlight

During this episode of the CRO Spotlight show, Warren chats with Steve Schmidt who shares his experience as a Chief Revenue Officer (CRO) and discusses the importance of fully understanding how revenue functions within an organization.

Steve, shares his journey of becoming a CRO and how he learned to navigate the role through a baptism by fire in 2020. He emphasizes the significance of the CRO role and its various functions, including outbound and inbound motions, retention motion, and operational motion.

Steve believes that a CRO needs to be enabled by the CEO to cruise through the organization and be the right-hand person. He also stresses the importance of understanding the capital outlay for the tech stack, optimizing it, and measuring metrics like cost of acquisition (CAC) to drive revenue growth.

Key Takeaways:

  1. The CRO role is critical for an organization's revenue function and involves various functions like outbound and inbound motions, retention motion, and operational motion.
  2. The CEO needs to enable the CRO to navigate through the organization and understand the capital outlay for the tech stack to optimize revenue growth.
  3. Measuring metrics like CAC is crucial to understanding the economics of the business and making informed decisions to drive revenue growth.
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Are you a CRO looking for insights and ideas from your peers? Are you a Revenue Leader with aspirations to become a Chief Revenue Officer? Are you a CEO looking to appoint a CRO to scale your business?

Welcome to the CRO Spotlight podcast, a weekly show featuring insights from Chief Revenue Officers, B2B Revenue Leaders and CEOs. Hosted by Warren Zenna, Founder and CEO of The CRO Collective, the show goes deep behind the scenes with the people who have been there, done that and have seen the results. The CRO Spotlight Podcast is an open, free-form conversation that digs into real issues that Revenue Leaders and CROs grapple with everyday.

Warren Zenna: The CRO Spotlight Podcast.

Hi, I'm Warren Zena, founder and
CEO of the CRO Collective, and

welcome to the CRO Spotlight Podcast.

This podcast is for Chief Revenue
Officers, aspiring CROs and

CEOs who are looking to hire
or support a CRO to succeed.

To join me and my expert guests as
we debate, discuss and tackle today's

complex revenue growth challenges,
and provide practical insights

to help CROs succeed in the role.

We're really excited to have you
with us now, let's get to it.

All right, and welcome to this
episode of the CRO Spotlight Podcast.

I'm Warren Zenna, the c e o and
founder of the c r O Collective.

I'm not big.

New Year's resolutions.

I find the whole thing to be a little bit
silly, and that doesn't mean to say that

people that are into it are in any way.

I'm disparaging them.

I just personally never thought it really
worked for me, so I tend not to make 'em.

However, I was giving it some
thought, and here's what I, what I

think about this is sort of instead
of looking at the new year as, oh,

what am I gonna accomplish this year?

What am I get done this year?

A framework that may be helpful,
maybe try it on is maybe look at last

year and ask yourself two questions.

what did I do last year that
really didn't work, and what

did I do last year that did?

and see if you can make this year,
focus on the things that do work and

stop doing the things that don't work.

That instead of adding, adding new things
on, maybe removing stuff that you know

you shouldn't be doing or that aren't
effective, or wasting your time or habits

that you know you don't want to have and
remove them and just keep the good stuff.

If you keep the good stuff and
remove the bad stuff, you'd probably

see an uptick in performance even
if you don't add anything new.

I think we've dragged.

More by things than we are
because we're not doing enough.

So anyway, something to think about.

Um, and uh, you know, as I kicked
off in the year already, I've been

having a lot of conversations and
interesting trepidation about the market.

A lot of people are
taking very conservative.

Stance on how they're gonna hire.

I'm hearing a lot of people saying,
we're thinking a lot more about hiring

freelancers and part-timers as opposed
to adding people onto our W two s.

You know, these are cautionary things.

So much of this has to do with
externalities, which I'm not saying

externalities shouldn't be factors, but.

What I see, and I say it all the time,
is if you have a really buttoned up

revenue operation that's repeatable and
predictable, and you know what you need

to be looking for and you know who your
customer is, it gives you a lot more.

Ability to make decisions than
if you don't know that stuff.

And I think in the absence of knowing
that stuff, people rely on externalities

a lot more than they need to.

That's just my opinion.

So that being said, um,
really great to be back.

This year is gonna be great.

We have a lot going on and a lot
of great guests lined up and some

other exciting things happening.

So thanks again for listening.


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Warren Zenna: insightly.

And today I'm real excited to
have a guest on whom I've had the

pleasure of speaking to a lot.

We have connected through LinkedIn.

And um, this gentleman,
his name is Steve Sch.

He's a C R O and he's a
brilliant, brilliant man.

And you know, he shares a lot on LinkedIn
that I find really insightful and we've

had some really great conversations.

As a matter of fact, some of you may
recall earlier last year, we did a

great S D R debate and Steve was on it.

It was a real riot.

It was quite a , quite
a heated conversation.

Steve had the opportunity to weigh
in there and it was really great.

But, um, tell me a little bit about
Steve before I introduce him formally.

You know, Steve, uh, helped
launch and execute, uh, the

go-to-market strategy now, reach
for at and t and T-Mobile as well.

He was the founder and c e o of title.


Um, for a couple years.

Um, and so you know,
Steve has made some moves.

He's with Reggie AI now.

Um, I know AI is big on his mind.

Uh, go to market.

It's big on his mind.

Uh, he's just got a lot of wisdom.

He's got a lot of
experience under his belt.

So Steve, thank you so
much for being here today.


Steven Schmidt: Warren.

I appreciate it.

Two things I pulled out of your intro.

I was in the meditative state,
just doing some reflection.

Addition by subtraction, um, was
like the theme for this year.

So that resonates big time.


And then in the absence of
facts, you have faith, right?

And, and I think as a C R
O , there, you said it, right?

And when rev ops is strong,
you have facts, you have data.

And when you don't, you have faith,
which can get you, you know, the,

he might get you a little bit there.

But as a c o role, I, the one
thing I learned is, is certainly

not about your skillsets anymore.

It is about truly understanding how
revenue functions in the organization.

and, um, baptism by fire back in
2020 for me, um, is when I first

had a chance to get into that role.

Warren and I, um, I knew very little,
very little, was a good sales guy, right?

Could sell a lot and was always
promoted by, by that default mechanism.

And I think the fifth time I
was promoted, maybe when my mid

thirties, I started to underst.

, you know, I was like a, you know,
sales leader and so I understood a

little bit of the revenue function,
but I still didn't care, right?

I was still really kind of a
worried about my quota or my team's

quota and didn't look past that.


So I got my start in 2020.

Um, it's actually the story
like title began because, I

mean, I sat down with my wife.

and I was hellbent on doing
something in the consulting arena,

but I, I knew of fractional rev
op, I knew of fractional CROs.

I just didn't know how to do it.

And I quite frankly weren't, I didn't
know if I was skilled enough to pick up

the phone and call somebody and say, Hey,
I want to be your fractional anything.

Um, you named, uh, T-Mobile, right?

I came from the IT and the
telco space space brief stint

at, um, outreach in 2017.

Ended up in rehab shortly after that.

Hence the brief.

. Best thing that could
ever happen to me though.

Dip the toes in the SAS
water for seven months.


and you get a lack of a better term
addicted, which sounds counterintuitive

when I'm talking about recovery,
but like that it got in my blood.

So when I got out and had the wits
about me, I, I, I wanted to get into

software and funny enough, when I
decided to get my first job, I ended up.

Uh, getting hired by a
guy in the March of 2020.

And as you recall, that
was when Covid hit.


And, um, he said, congrats, you just
got promoted from consultant to C R O.

He said, we're gonna sell p p e,
we're not gonna sell, um, video

equipment that's AI driven from China.

And I said, wait a second.

That's not my background.

What are we doing this for?

And they own five manufacturing
facilities in China.

, they said, let's advertise it.

And we did.

And that was where the first 160 million
of revenue driven from Title had.

Now, I mean, it's funny, I took the
headline down, um, not because people,

you know, I got some grief about
it here and there, but truly, you

know, I was title my bank account.

My L l C was title.

I was one person as a 10 99.

I needed the name for it.

And so I thought, okay, and we
went out and hired 56 people.

Yeah, we spun up a big s d
r team and, and really ran a

predictable revenue abound motion.

Not too complicated.

Uh, but I think in that, in that
timeframe, we were the only ones who

sprinted out of the gates, day one in the
PPE shortage, who knew how to handle it.

with a true background of, call
it a revenue machine, versus

let's make some deals mm-hmm.

And, um, that allowed us to get
very creative in our outreach.

And hospitals answer the phone, um, a
lot, especially when they need something.

So, um, it was not shooting fish in
a barrel as the adage goes, but it

was very much a, an understanding on
how rapid revenue growth and margins

and understanding operating costs
and, and really the return really

the first time it fell on me and.

That was a really interesting time.

I was commissioned only by the way.

Warren Zenna: Wow.


So it was trial by fire every day.


So let's talk about this role, right?

This C r O role.


So what, what you think of a chief
revenue officer in your world?

What do you, how would you
describe it to someone?

Let's say like you're,
like your grandmother.

Like what does a CRO do in your

Steven Schmidt: perspective?

Make sure that the piggy bank
is always full of ironed.

Bills and make sure you have
a couple $2 bills in there

that you hold on for a while.

Um, just making sure that everything
is in order, that the money coming

in is healthy and that you're getting
the right kind of money versus.

money that could leave you soon
cuz you wanna hold onto that money

that's going to mature over time.

I e good customers.

So I would say that my job is, and it got
confused and I will tell you that even

five years ago, I didn't know, I thought
it was like a new name for the cfo.

F o mm-hmm.

. Um, interesting.


Warren Zenna: so cfo, F O, you
thought it was like a financial sort.

focused role.

Steven Schmidt: Yeah.

The first time I heard,
I saw the term, right?

Cause I wasn't in the SaaS space, but
Matt Millon, who was my boss at T-Mobile,

you know, he, he went over to outreach
and I saw revenue, which wasn't being

tossed around at all like it is now.

We just called it sales, right?


And, um, I was like, well,
what is that as Matta C F O?

And someone was, no, it's
uh, it's the same thing.

It's just like an inflated
VP of sales title.


And, and so of course that's
what the mass population thought.


And so I thought the same thing.

I thought, oh, That's just a way to
promote 'em and give 'em a c title.

Revenue sounds fancy,
but man, was I wrong?

Uh, the outbound motion, the
inbound motion, the retention

motion, the operational motion all
falls into you as well as timely

payments from your customers and,
and really good implementations.

And so I, I'm also a big fan of rolling
CX a hundred percent up through,

and I believe that Chris Walker's
theory that revenue should report

as one organization isn't wrong.

Warren Zenna: I'm in.

You know how I feel.

I do.

So that's interesting.


So, and you're correct on some,
some things you said, of course.

But, uh, even though I know that I've
been banging this drum and other people

have too, I mean, it's not just me, but,
you know, I'm, I'm sure of a loud voice

and very focused voice on this topic.

I think the c r o role is coming
in more into focus over the last

couple of years than I've seen it.

However, the knee jerk is, let's take
our VP of sales and promote him or her.

give this person a c title many times
to keep them, to retain them, right?


, uh, because by promoting
them, they'll stick around.

They'll get a title they
like, so everyone's happy.

And then the other
thing is sometimes it's.

Private equity or VC wants a C R O
role on the Rolodex or whatever you

call it, the, the rosters who kind of
create a patina of, you know, we have,

you know, mature revenue ownership.

. Mm-hmm.

, whether or not the role is deployed
correctly or not, sort of seems to

be secondary to the title and what it
represents to outsiders, and I think

that's the big miss and I'd curious to
know what your thoughts are on mm-hmm.

what's the way that you think that
companies need to sort of recalibrate

that so that like you, it doesn't sort
of like become a C by accident and all of

a sudden now you have to deal with stuff
as opposed to being more prepared for it?

I think the CRO

Steven Schmidt: role is less shortsighted
by a long shot than a any head

of sales role, simply because it.

even if it's a bad hire, right?

And if there's eight to 13 months
or whatever, um, the statistics

are currently heading into 2023.

Um, it isn't, uh, it isn't the role
that's gonna come in and make immediate

impact in one area right there.

There's gonna be immediate focus
areas that have the lowest hanging

fruit or the biggest opportunity,
or it's bleeding the most.

and I think CROs, if you think about like,
let's just use 12 months of square number.

The first three months, you're trying
to understand the environment, right?

You might get to execute
for, call it three or four.

And in that example, the last three
or four months are typically very

toxic relationships to the C E O.

A lot of arguing, number, why things
aren't happening the right way and.

out goes the cro and they go
on to go hire another one.

When really that function that they wanted
to drive was more of a sales function.


We need more outbound, we
need more top of funnel.

Okay, well that falls within the
CROs realm, but it's one thing.

It doesn't mean that saving money
on non-used SAS components won't

make you more money than getting
some more top of the funnel.

So that might be the most
critical thing to drive through.

Rev ops or sales ops is a, a
really thorough understanding of

the capital outlay for tech stack.

. And is it being optimized?

I mean, if you save 500 bucks
a person a month and you have

50 sellers, you do the math.

To me that sounds like a pretty big win.


. Um, that's the margin on a nice new
enterprise logo in a lot of cases.

So that's the function where I
think when you're fully enabled,

and that'll use the word enablement.

Cause I think A C E O needs to enable a
cro r o to be able to go and, and kind

of cruise through the organization.

And really be the right hand person to
the CEO E o, where a lot of times they

see it as a battle where a CEO maybe has
that founder ego and they bring in a c o.

Cause like you said, Warren,
the board said we want that.

And the ceo, CEO might say,
well I don't want that.


Cuz this is my show and I don't like all
the inspection work that's being done.


Warren Zenna: So I'm in the
middle of a lot of these

conversations with people mm-hmm.

and I'm seeing so many of these
scenarios where, what happens.

Is someone's looking to move into
the C-suite or they want a C R O

role, and there's two scenarios.

One is they're gonna be promoted into
the role in their current company

or they're gonna go, you know,
leave and go find one elsewhere.

So in the case where you're being
promoted, you know, you obviously

have the benefit of having a lot
more data cuz you work there.

So you know, all the bodies
are buried, so to speak.


and it sort of become, the shift
that's required because if people in

the company perceive you as a head
of sales and then you all of a sudden

have a CRO role, you know how it is.

People are reluctant to want
to view you differently.

They want to keep you in the bucket
that they're comfortable with, and

they're gonna continue to engage with
you in the manner that they've been

used to, and you have to create a.

Perception of yourself in within
an organization and change the

scope of your role all of a sudden.


You know, you are focusing specifically
on just one channel and now, Magically

within a week of this new promotion.

Now you're talking about managing
multiple channels that weren't

previously per year purview.


, if you don't have the support
of your CEO O to do that,

it's probably not gonna work.



Steven Schmidt: Yeah.

And if you're, if you're CEOs
part the issue, I'm seeing

the, the, um, cac, right?

I mean is the, the most infamous
term in sort of how companies

are evaluating themselves.

And I think that also, . You know, I've
seen bootstrapped companies really, they

start to measure cac, but you're measuring
it so early on, Warren, that, I mean,

as you grow the model of, of progression
through funding naturally as CAC really

inflated at first and then getting to
a targeted CAC number in time, right?

Because you're gonna bring
on a lot of costs at first.

Like there's a lot of companies right
now, early stage call it series A

companies that have a five and a half
year payback period for a customer, right?


But if a bootstrap founder reads an
article on CAC on LinkedIn and goes the

next day and goes, wait a second, our CACs
$60,000, you're fired, doesn't understand

the economics of how this thing plays out.

And that's probably what I see more
than anything is a lot of CEOs are

so eager to still grow, even in this
macro economy where they haven't

really buckled down and said in a more
mature path, where you see a lot of the

progression of companies that I really.

I'll, I'll give an example of one
of probably 10 scratch pad, right?


kind of quietly out there growing
really quietly in the background.

ORMs another one, right?

Picking up customers over
time, but not racing towards a

hundred million exit next year.

Nor do they have the tam
that supports that yet.

And so I think that there is so much
out there now because it's still

new, uh, that really, that opens up
a conversation where, , there can

be a lot more room for understanding
things like that, like cac, right?

Which is a good c r o metric to, to,
to look at versus a EP of sales who

can support one of the functions of.

the cost of acquisition, but doesn't
own the whole cost, because now A C R O

has to look at what channel am I getting
the outputs through, and if it's, or

you know, if it's demand and I'm putting
a lot of money into paid, now I'm, I'm

responsible to say, let's reallocate
that money and find a better channel.


, VP of sales didn't do that in the past.

You have five sellers and one
doesn't work out, you replace 'em.

Right now you're trying to get
80% of your team to hit quota,

and so you're, you're also.

Likely not to get any training
from your company, Warren.


And so things like what you are doing
and you know, people who are awesome,

like Mary Grothy outta Denver, who
really support sort of, you know,

various movements of CROs, whether
it's at Pavilion or working with you

or working with various groups, is
that's really the only area they can get

education on CROs, cuz they're probably
not gonna get her from their c E O.

If it's a first time C role.


Warren Zenna: Agreed.

And thank you for including me
in those, with those people.

Of course.

So here's the way I look at it is, and
you're a hundred percent correct, is that,

and what we're trying to do here, aside
from supporting Chief Revenue Officers, is

to support CEOs so that they do have the,
the tools needed to support their CROs.

I, mm-hmm.

, you know, I sort of weirdly, I mean,
it's been weird analogy, but I sort

of look at it like your first child,
you, you don't know what you're doing.

You know, you're making it up.

I mean, you read a lot of books
and you know, you have some kind

of maybe empirical knowledge of
what it think, you think raising

a kid's like, but you don't know.

Cause you never had one.

So that first one is the Guinea
pig and it's always the third or

fourth kid if you have a lot of 'em,
that they get the best upbringing.

Cuz you figured it all out, you realize
you don't really gotta pay as much

attention to 'em as you thought you did.

They, they're just fine, you know?


And, and you know, and it, it's
sort of like, um, uh, CEO's

first c o is a crash test.

for the company.

So I, I say this, I said this to
a customer, my mind, client of

mine yesterday is, you know, do
you want to be a crash desk dummy?

How do you sort of ensure that they
don't just take a look at the, you

know, skull fractures that you have
after a year and say, all right,

well we should probably buckle 'em in
better this time, next time around.

That kind of thing.


And, um, that's part of the job,
as you said already, you made

it really like articulated it.

It's a complex job.


, and it has so many components.

It's financial, it's data
management, it's people management,

it's operational management.

It's strategic, you know, I mean, very
specifically sort of talented people

thrive in this role because they have
a talent stack that's a combination of

art and science, and most people are
kind of built either one or the other.

And the other one too is, uh, you know,
having the resources and the flexibility

of knowing your profile types, that
when you take the job, you're in a

position to say, okay, well I'm more
of a scientist than I am an artist,

so I need to hire people that can kind
of compensate for my lack of artistry,

which is perfectly appropriate, right?

It's fine.

You're not gonna find someone
who's magical unicorn.

It's gonna be places that they need
support, but how do you put that team

together to make sure that that person
gets the right resource allocation?

And talent that they need.


. And these are tough things because
like you said, you've never

given enough runway do this job.

There's no way.

I mean, they want results fast.

And even that three month window that
you mentioned to try and just learn

what's going on, that's hard to do
because to dig into the data, , it

takes more than three months.

So you get a superficial
understanding of what's going on.

So you don't really work
from, um, the truth.

You're working from an opinion
or an assessment of, of things.


So what do you, what, what would
you suggest then, let's say

you're thinking about a C E O.

. Mm-hmm.

, who right now listening to
this is thinking about hiring

their first c o mm-hmm.

. What might be a way that you think A C
E O would best suit themselves to ensure

that that hire, which is expensive mm-hmm.

and risky be, is

Steven Schmidt: successful?

I would model a company I admire
and call that person up and

I'd say, how did you do it?

And because I, I've learned that
intuition, especially with people, and I

use people because we're people, right.

And so, um, you're, you're probably not
gonna hire somebody you don't know or.

. I mean, that would be weird.

I mean, I don't see a lot of
CROs hired off of a LinkedIn job

posting, I'll put it that way.


. Um, now I, I wish, I wish there was, I
guess, because that'd be a better way to

make sure everybody's being taken care of.

But you're, it's a trust thing.

And I think the trust thing is the
thing that people look at today and

go, okay, now I've got the trust.

But they're not looking at the
skill set and saying, oh, pardon

me, Warren's more of a scientist.

Steve is more of an artist.

Hey, they're both.

What do we need?


And then who do we need to
surround that person with?

I am more of an artist, right?

I'm the Sierra who will go down to
the trenches and focus on messaging.

Um, because I believe in that and
that's where I, I know the most, Warren.

So like your New Year's resolution,
like I run to the thing I know

the most and love the most.

And, and like for example, like discovery
and disco doesn't mean I'm bad at it

or doesn't mean I'm bad at teaching it.

It just means that that's my area of.

I'm, I'm okay being up
above average at that.

, I don't wake up and listen to podcasts
about the perfect discovery call

because I'd rather hire somebody to
make sure that that's happening well,

or making sure you're hiring, you know,
somebody in rev op that can support

the structure of operating a person.

Uh, a great discovery call, like when
I onboarded here at Reggie, it was very

apparent they wanted that disco demo
done In 52 minutes, you got 13 minutes

for disco, 12 minutes on V1 of the demo.

16 minutes on b2 and then about
seven minutes for conversation.

I was blown away at how they had
that scientifically nailed out in

such an early stage company and,
and the why behind that one, right?


, which is, okay, so regardless of what
you are addicted to from your disco demo

standpoint of it needs to be one or both
combined, they've realized that that

shortens a sales cycle and eliminates
a, a, a nice to have, which Reggie is

perceived as a nice to have, right?


from getting two weeks of
space between the next meeting

because it's sure to flop then.


And they did a great job of recognizing
that, keep the momentum up early.

And I think that was the
first time I can say the last.

two decades I've seen that done.

It doesn't mean it doesn't
happen at other companies, but

that's a revenue function, right?

You're preserving the investment
of the hour block of time that

you could be doing anything else
with your team and that customer.

And when you really like to isolate
it down, then your, the CRM goes,

well, what is a qualified customer?

And they're gonna look at you,
Warren and go, what do you think?


. And you'll say, well,
how have you done it?


and they'll say, geez,
Warren, I don't know.

Like the deal stages are all over and,
and, and so you'll start from scratch,

but you're in the middle of a war.


Trying to pick up the pieces and
show people what you can do with

somebody else's dead bodies.

It's not the best place to be.

So I think what I would do is
articulate very strongly that for

the first three months, I'm not
gonna judge you on any performance.

You need to show up.

I'm gonna judge you on your
ability to report back to me the

current state of all business.

You have 90 days to do it, good luck.

And then the next 90 days I'm gonna
say, okay, what do you want to change?

What are the first three things that
we can actually agree on tackling?

And then I'm gonna judge you on how
well you execute that the next 90 days.


. And I would like say that first year
you're really earning the next 90 days

by doing the simple things, if you have
the right pairing and the understanding.

And so that's what I would do because
now you sort of are looking at

seasons in Mary growth's words versus.

A forever thing where if Warren
can't get it by month four,

we gotta get somebody else.

And then each season you might
say, well they did terrible

and two, but really good.

And two, we should probably work on
improving that one area higher around it.

But gosh darn it, let's
not crush this momentum.

It's been nine months.

The team likes him or her.

And so that's the kind of momentum
that I think the, you know, when you're

looking at the burn rates, they're not
including the damage that that quick

hire and Unhi does to an organization.

Millions of dollars.


It's a big, big

Warren Zenna: hire.

It is.

It's not just the amount of money you're
gonna spend on this person, it's also the

implications of the outcomes that you want
this person to produce for the business.

So, you know, if you add all
that stuff up, you know it's

millions of dollars in many cases.


And uh, I like the formula you laid out.

I think it's, it's, it's a smart kind
of framework, which is there's sort

of a discovery phase and then there's
sort of a, a visionary planning

phase and there's an execution phase.

and, and I, I think that it's,
that, it's that initial 90 to, I'd

say 90 to 180 days that I think
the Cro o's future is determined.


You know, the, uh, intestinal fortitude
of A C E O that allows their c to

have that amount of time to do the
due diligence without pulling them

out of that and saying, all right,
I need you to get in the trenches.

I, this is enough already.

Yeah, yeah.

It's pretty much over at that
point, because now you're, you're,

you're essentially being told, all
right, you know, I, I really can't.

I can't afford the time to give you the
amount of intelligence that you need.

I need you to get in the trenches
because I'm, I'm, I'm getting

screwed here by my by board.

You know, when that happens, it,
it, it, it's an indicator that

the CEO sort of maybe had a loose
understanding of what was necessary,

but didn't have the fortitude to
stick through it and have your back.

I think the relationship between the C
and a CEO is so critically important.

It's almost to the point where
if, um, and I tell this to all my

clients, if you're interviewing
for a CRO role, e getting to know.

How your c e o thinks and what
the relationship you're gonna have

is gonna tell you every single
thing you need to know about how

the next first year is gonna go.

And you can ask about 12 questions
that will get you pretty much

the best answers you can get.

And you'll know whether or not this is
gonna be either a, a ruck, a bumpy ride,

or you've got someone who's got your back.

. Mm-hmm.

. And then you get investors involved,
you know, whom have their own agendas

and a lot of control, you know?


Is it a board led company?

Is it a product led company?

Is it a founder led company?

Is it a visionary led company?

I mean, these are all important
questions cuz the CRO is gonna be, uh,

so more affected by that than anybody.


. So these are critical things.

So I wanna switch gears for a
sec cuz um, you know, uh, you,

you've made some recent switches.

I know you're working in the AI space.


I'm really curious to know
what your thoughts are on that.

I mean, I, I know we're really
moving to a different topic, but

I'm fascinated because the amount
of stuff I'm seeing about AI, and

I've always been interested in it.

I, I think it's just mm-hmm.

, it's hit a sort of a, a crescendo
recently with Jack Chief, P T T P,

which I've been playing around with.

um, I, you know, I know
all the hype is there.

I understand that people like shiny new
things, but you know, I am seeing some

really clever stuff being done with
it, and it's only gonna accelerate.

So I'm just curious to know, like, where
you are in your workings and even maybe

in the role of a Chief Revenue Officer.

What is, yeah, I don't know.

What, what are you prognosticate here
that AI is gonna play in the role

of revenue operations going forward?


Steven Schmidt: I see a lot of
funding going to it right now, which

is, um, always exciting to know as
we're, um, Reporting better news

on the current inflation rate and
the recession and things like that.

It's, it's, it's nice to see that, you
know, companies are still getting funded

every day, um, especially in the AI
space and, and there's no secret, right.

We all can feel the
untapped potential of this.


Is, um, in, in Bostonian words,
it is a fever pitch and, um, . I

think most people are as scared of
it as they are enlightened by it.

I had a demo this morning with a
gentleman from India, very smart guy,

very great company, awesome product.

And I said, here is what
I did to prep for you.

And I brought up the personality ai, and
then I talked about how that parlays into

the personalization and, and what it said
was so, so good that I even stopped.

And I just said, I'm gonna be honest,
this is the best generated first

line of a cold email I've ever seen.

Reggie put out and he goes, yeah,
this is, he goes, I don't know

how they would know that about me.

And he's in the AI space.

And, and then we got into talking
about like, so there's all this,

this information out there, right?

Wikipedia is 0.06% of it that's
available in the open AI architecture,

which is now gonna be Microsoft if
I understand everything correctly.

Um, what's really interesting
to me is you or I today, Warren

could, if we wanted to go.

Start conditioning our own AI library.

Just go to open AI and
you buy some credits.

And I did it the other day and I was
like, okay, I don't know what I'm doing.

I'll never learn that, by the way.

But I was curious, I think in the
function that it will serve primarily

in sales is you're gonna see a lot
of what you see right now, which

is, you know, messaging, finance.

You know, can I find the easiest
thing and populate it for you

in a short amount of time?

And that's gonna be enough
of the magic factor chat.

G P T four will be released, which is,
um, something like a hundred thousand

times bigger than chat G p T three.

And that's I think, when people are
going to be wowed because people who are

prepping for that release now mm-hmm.

are giving them chat, g p t three,
and they're, they're enamored and

they're going, wait a second, we
haven't shown you anything yet.

Like the ability for me to be able to
spin up a picture of Warren drinking a cup

of coffee next to his car in his drive.

at 7 42 in the morning with a pensive
look and generating an image like that.

That's when it gets interesting.

And that's when it quite frankly
gets, uh, very frightening too,

because now you're looking at how
do you protect that information?

And I'm glad to see some of
the regulations out there and

it'll be interesting to see
how this plays out in sales.

But I know in the news they're
pushing, for example, if AI generated

something, they will need to highlight
that text and be very clear that

this was AI and this was a person.

So you start to understand.

AI opinions by lack of
understanding and versus human

because it can be very confusing.

Now as it relates to sales, I think
that um, there are not budgets today

created for AI Warren, and as you
know, um, there's probably a lot of c

cvs and VPs running their boss going,
we've gotta have this right now.

We've gotta have this tool.

It's gonna change the way we do business.

And fundamentally, we all
know that that's not true.

Gong, which is one of the most
impressive software suites out.

was a must have for me three years ago.

I said, this is gonna change
the way we fundamentally do

one-on-ones in funnel reviews.

Two weeks later, I was so busy I
forgot that that was a function

that I wanted to do because I
couldn't fit into my workflow.

I didn't have the rev op to support that
function, and we probably invested, you

know, 30, $40,000 in a software that
truly we never got the value out of.

Not because it doesn't have it.

but because we couldn't extract it,
and I always just remind myself, unless

the organization's able to extract the
value, time to value, especially in

today's economy, and that's a great
CRO term, is you better be damn quick.

It better not be a, oh, just wait
Warren, it takes four to six months.

You want to implement something that
can save you money as quickly as

it can make you money, and I think
that's where AI is gonna have the

biggest advantage is, Hey, I could
replace with this, this, with that.

and particularly in the SD R model
today, you know, you're using headcount

and a predictable model in a lot of
shops still knowing that I could have

the power to upload and personalize
a thousand emails in an hour and make

AI voice calls and only queue up my
best callers, which nobody's talking

about, that which is gonna be the real
kick in the face for a lot of people.


Because it's really good.

I can now automate from a rev op
and I could have a very successful a

hundred million company with a very.

, call it top of funnel, human
flesh staff department.

And I could have rev ops running
the majority of that motion.

And Conversica gave us all a preview
of that about three years ago.

That's what I deployed in the p e, is we
were just weaving in virtual agents and

doing handoffs to the reps if and when
certain words were picked up with AI to

say, this warrants me introducing Warren
because he can answer your question.

And so we looked like about 600
reps when we really had, you know,


because we are weaving in
all these virtual agents.

So I think that we'll see that and now
people who want to post about what is

or isn't a good cold-call opener will
have to find something else to post

Warren Zenna: about.

Yeah, you're right about that.

It is something to post about.


You know, we made a couple good
points here I wanna chat about.

It's really interesting.

So one is workflow cuz
it's so true, right?

Ultimately the more tools we get, they're
only as good as our ability to fit

them into what we're doing, you know?


Ultimately, I think these
things find their sort.

place in the system, but
it takes a long time.

People are mm-hmm.

, it's hard to bake new things in.

So I think that the friction is always
gonna be how do we get what we're doing

to be baked into a process so that it
becomes, you know, necessary or required.


, um, to your point that you said
after that, which is that it, it

helps to, quickly and expand.

I think that's gonna be something that's
going to be very attractive to companies

whom right now are saying, boy, if I can
make my 20 people look like a hundred

people that sign me up for that because
I don't, I can't afford a hundred people.


So there is gonna be a sort of
efficiency play, but my concern around

this, and I'm having a lot of, that's
why we even had the SDR debate that

we had last year in the first place.


is, you know, these tools
sort of become just.

Enablers of spam fests, you know?


, I mean, if I know that I have a machine
that can crank out more emails and posts

and stuff, well then I'm gonna send more
emails and posts, and the customer seems

to be the last person we think about
in relation to these tools, because

ultimately they're gonna be the ones who
are gonna be the, uh, recipients of even.

Distracting messages, you know, and Okay.

I mean, maybe they may end up, end
up being more effective or more,

more, more persuasive, which, okay.

But I, I'm sure like you, the amount
of inbound I get on a day-to-day

basis is overwhelming at this point.

And yeah, um, so much of it is
wrong, even if it's well-written.

It's just not well targeted.

I don't know.

, the organization formulated that I was
the correct person to send this to.

It seems random at best.

I got lumped into some general mm-hmm.

profile or segment.

How is, you know, this not going
to just become another, another?

Farm, you know, or sort of manufacturing
plant for just more and more and

more overwhelming communications.


to the point where customers just tune out
and say, I don't want any of this anymore.

I'm gonna turn off my notifications.

I'm not gonna read my emails anymore.

And these tools would just become sort
of dead because the consumers had enough.


Steven Schmidt: Wow.

Great question.

I've got an answer, at least my
opinion is, I think what we're not

talking about, and you said it, the
customer, is how can we now give

buyers the same sort of advantage in.

In that buying cycle as we're trying
to give the sellers and, and, and what

that looks like, I don't know, but
it might look like something where

I would be able to know, as with
the advancements of AI tech, really

what Warren wants and needs, but.

What he's not, what he, you
know, I, I would want to know

a pro full profile on you.

So, so I would know that if my
message is gonna fall in deaf

ears, like why even send it?


So whatever that looks like, I think
it's gonna give preferential treatment

to kind of shut that valve off and
open up only those things that you're

interested in, which will of course
open up a whole new ad channel.

And nobody's really talking in
sales about the ability to, to,

to deliver, add revenue when
you're parsing people's language.

And we're also not talking Warren about.

You've got chat g PT four
out there and all that stuff.

But every time Warren's typing in
something or saying something or doing

something, it's learning you and you
are a collection of the big body.

But a real good AI tool pays as
much of attention to learning you

with machine learning as it does
to the generalized population.

And it marries the two up.

And that's where nobody's able to,
you know, and, and this is where I.

, you know, I'm not an engineer by the way,
but no company's able to deliver that yet.

So if Warren opened a company and
you've got your little neural network

of, call it open ai, and then you've
got the big pool of it, you can say,

Hey, um, Johnny Sales guy, I'm gonna
learn you and what you would say, and

I'm just talking about messaging here.

And then we're gonna pull the best
stuff that is said to those people

and now we're gonna meld those up
and that's gonna be your best shot.

Like, that's about where AI is
on the tipping point right now.

Preferential treatment for buyers.

Call it like, I would love to know
if you have a budget for something.


And, and most good sellers
would say, well, I mean, why

would you want to know a budget?

Because you can create
it if it's good enough.

Well, you're right, but
I'd still want to know.


, I'd still want to know and then want
to know your contract cycles and you

know, if you're with a competitor, if
you're for another year and a half.

And so as AI can feed me more
of that, I don't need to even go

outbound when it doesn't make sense.

And the outbound function
today, Warren, what?

We have people.

We have people email and now we're
seeing a lot of, you know, mostly

terrible content on LinkedIn.


That people are trying to push out there.

Good for them.

But I mean, we're not there yet
where they're, you know, they're all

using chat, G p T, it's terrible.

Lots of one through 10 lists right now,
, you know, um, where I believe that that

function and where AI can be enabled the
best is doing research on your customers.

Well, that would

Warren Zenna: be great.

I, I couldn't agree more.

And actually hearing you say
that is actually interesting to.

because I tend to, I don't
know, maybe I'm cynical.

I tend to think about these things as
just being other ways for people to

manufacture more content, but, mm-hmm.

man, if, if you could have an ai, real
ai, you're not fake, but a real true

learning engine that starts to say, make,
how do you say, correlations between so

types of conditions and certain types of
actions and certain types of behaviors

and certain types of outcomes over time.

Points me in a direction to say, here
are the seven people that you should talk

to today because they fit the profile
of the mindset and the psychological

profile and their current circumstances,
et cetera, that indicate that they'd

have a higher propensity for hearing
this specific message in this way.

Steven Schmidt: That would be incredible.


Imagine how much that would cost.


Warren Zenna: Yeah.

Well, it would be worth a lot.

I mean, if it worked.



I mean, I, but I, I could
see how it could work.

I mean, we have enough
data, we just don't use it.

Well, that's the problem too.

But you know, if the data is being
analyzed properly and you have a big

enough organization where you're talking
to enough people with enough historical

data to show some trends in the way
that people respond to things and

enough customer, customers to do so.


, um, if I had a tool that gave me a
dashboard every morning, I logged

into it and it basically said,
all right, you know, based on.

Events, psychological, you know?


conditions, situations,
circumstances, mindsets, roles.

Timing is that, that we've
formulated as like the sort of

recipe for the right conversations.

Here's your dashboard of the eight
people that you need to engage with

today that have fall into that.


. And here's the way that you
should engage with them.

And we're gonna give you some
suggestions as to things you could say.


. And you know, we think the right
channel would be this channel.

It should be done through this one.

Cuz this person didn't this time of day.

LinkedIn, a lot.

This one loves Twitter.

This person opened a lot of emails.

I mean, man, that's.

Phenomenally cool, right?


And it might feel really natural to
the person on the or other end, right?

They just get a good message
in a place that they like, that

they're thinking about, and they're
like, whoa, you're really smart.

How did you know I was looking for this
right now in this channel, in this manner?

In that

Steven Schmidt: tone, let me give you
an example of this quick Warren, that,

that would, if AI could do what this
did, and I, I don't doubt that it didn't.

There's a guy who used to be a client
of ours at title, and he was stuck in,

uh, Florida with his family, with the.


And he posted about it on LinkedIn.

It was like, Hey, I'm gonna make
the most of it, you know, da da da.

Just a real generic post about like his
picture is kids in him at Disneyland.

Three hours later he got a phone call
from a jet company that said, we heard

you and your family are stuck in Florida.

So they knew he was a C E O.

They knew his company was making a decent
amount of money cause they said, we're

gonna come and get you and fly you home.

, they're gonna give him
the pitch on the way home.

I mean, they know he has his wife
with him and she's probably the

real decision maker of course.

And they know that they have about
three and a half hours going back to

Fargo that they can sell him on doing.


You know, asking him a
lot of good discovery

Warren Zenna: questions, stuff
'em full of crunchy peanuts

and just get 'em going at that

Steven Schmidt: point.


And I don't know if AI parsed that out
or someone who's just doing really good

research or timing, but like that he

Warren Zenna: said a form of ai.

I mean, it's what we're saying.

it's brilliant.

I mean, obviously that's
really very hyper-targeted.

You're right.

I mean, there has to be someone
whom is worth a flight, right?

Who knows how much that costs because that
person has the potential to be somebody

who can, you know, 10 care flight.


So that's a, that's a big cac, right?

If it works, but someone's
calculated that that's the way to do.

You know, it's no different than trying
to get someone in the seat of a car.

I worked at a lot of work in the
automotive industry for many, many years

in that marketing, and the whole idea
there, as you probably know, is you

just gotta get people to sit in the car.


. right?

When they drive the car.

It's like you've got a certain kinda
level of, um, uh, hypno, hypnotic,

you know, relationship with that
person's experience behind the wheel

of that car that they're about as
close to consideration as possible now.


Because it's not just
a picture or a video.


. So getting people to come in and
do test drives is the objective.

Cause they, they.

that that's lot in reams of data that
when people come in and you know, they

get up off their ass, they actually
leave the house, they go to a dealer,

they sit behind the wheel of a car.

I mean, that's someone who's
obviously seriously looking to buy.


. Now, granted, they may go to Toyota, they
may go across the street and go to Honda.

They may go across the
street and go to Mazda.

Doesn't matter.

It's just that they
figured out the same thing.

, right?

You gotta get someone to come
in and sit down inside the car.

So if again, you can identify that
activity that you know, makes that

sort of transition to a buyer and
you can predict it through numerous.

Factors through an AI platform
really quickly, maybe even look out

ahead into the future and say, eh,
this person may not be right now.


, but the trajectory of this person based
on x y factors indicates that in four

months or five months, this person will
be ready to have this conversation.



So anyway, I, I, we can go on
and on and on cause I'm kind

of a wonky nerd for this stuff.

But yeah, before we sign off, you're
kind of moving towards the end here.

I liked a little bit more about
like what you're doing right now.

And how people can kind of work with
you and what are you helping them with

and what are some ways they can get
in touch with you so that they can

benefit from your, your experience

Steven Schmidt: today.

Thanks, Warren.

Uh, I'm the commercial head of
commercial Revenue at Reggie, so I

oversee right now our largest segment
of revenue, which is through agency

Warren Zenna: channels.

And Reggie, Reggie, I'm sorry, is

Steven Schmidt: Oh,, sorry.



And we are a, uh, we are a tool that
allows you to write better emails,

develop better cadences, all with ai.

So we.

Develop a cadence or a sequence in
two to three minutes, and probably

right now it's taking you at a
minimum two to three hours, or like

most people, two to three weeks.

So we look at your persona, the problem
or pain you're solving, and then the

value proposition behind that, and try and
really balance relevance to the persona.

and then the ability to personalize it
to the person and allow SDRs and full

cycle sellers and marketers to go out
and really try and be hyper specific.


. And that's what we're doing.

And the interesting part about that
space, I'll end that little advertisement

with this is the reason I picked
up the phone called Matt Millon.

in November while we talk, you
know, once a month as friends.

Anyways, just catching up.

I was a customer of Reggie's,
so title was built with Reggie

at the core as an agency.

That's how we were able to create content
for 47 clients at the same time, and.

. So the, you know, I'm one of those
stories that goes, I've been a part of

it before, so I get to work with agencies
now who don't know anything about it

and try and not talk about myself.

But tell them like, here's
what you don't know, right?

Is that there isn't a tool that's
specifically built for you to

design content for your, for your
customers today and have 47 different.

SDR is doing 47 different things and
enabling them in the right way until now.

And so when we're doing a demo, we ingest
our website in about two seconds and

spin out the first round of the cadence.

And they're like, how did you do that?

And then we say it's a framework
into your point, art and science.

Like there is a human
element of art, right?

So don't forget, we are
not, Reggie is a robot.

Reggie is ai.

And machine learning, you still
want to go in and personalize it.

Make it yours, so, mm-hmm.

, it's wild.

There's a lot of, lot of conversation.

Jasper came on the marketing
side of this space.

Their average customer
spends $330 a month.

They grew in 16 months from zero.

To 70 million in revenue.


Off of a $300 monthly R

Warren Zenna: That's amazing.


It's a big space.

Well, great.

And, uh, that's Reggie ai and, uh, I mean,
I'll, I'll, I'm gonna check that out.

I have actually a couple of, uh,
cadences that I need to start.

Drafting myself at this point.

So why not?

Well, look, I'm, as I, as I suspected,
this is a great conversation.

We could probably talk for another
three hours, but I wanna thank you.

I know we've had a couple rough
patches trying to get this together

cause of the holidays and stuff.

So thanks for your patience and really
appreciate your time being here.

Thank you Warren, and I look
forward to working with you.

I'm sure we will.

I'm sure we'll find
more, more opportunities.

But, um, Steve Schmidt, Reggie a
I, Steve, thank you so much for

Steven Schmidt: being here today.

Thank you for being a voice and
an advocate for the C R O space.

We need more people like you, Warren.

Thanks, man.