GTM 163: From $2M to $50M ARR to Unicorn: How Owner Scaled with AI & Talent Density | CRO Kyle Norton

Kyle Norton is the Chief Revenue Officer at Owner, the fast-scaling restaurant SaaS platform valued at over $1B. Since joining from Shopify, Kyle has helped grow the company from $2M to $50M+ in ARR by instilling a high bar for sales talent, building RevOps early, and driving a disciplined go-to-market strategy. A podcast host himself, Kyle shares deep expertise on sales hiring, leadership, and GTM AI, while keeping his focus on building a generational company.

Discussed in This Episode

• Why Kyle let go of half the sales team just 45 days in
• The importance of setting a high bar for sales talent and cultural fit
• Investing in RevOps and data foundations far earlier than conventional wisdom
• How to reduce churn by narrowing ICP and saying no to misfit customers
• Lessons from running hiring retros to assess interview process effectiveness
• The balance between remote vs. in-office roles for scaling GTM teams
• How Owner approaches AI in go-to-market, starting with data over “shiny tools”
• Kyle’s leadership philosophy: servant leadership and building for growth

Episode Highlights

00:44 — Owner’s journey from $2M ARR to unicorn

02:01 — Kyle explains why he fired half the sales team just weeks into the role

04:56 — Why Owner set a sky-high bar for early sales hiring

08:13 — Kyle’s case for bringing in RevOps “too early” and why it paid off

12:39 — Reducing churn by saying no to 30% of potential customers

15:57 — Why hiring fit matters more than a candidate’s “pedigree”

21:49 — What Kyle learned from running hiring retros on interview data

30:25 — Owner’s AI GTM transformation: starting with third-party data

48:34 — Kyle’s take on the remote vs. in-office debate for sales teams

54:53 — His leadership philosophy: servant leadership + relentless coaching

59:19 — Kyle’s essential reading list for sales leaders

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Guest Links

• LinkedIn:https://www.linkedin.com/in/kylecnorton/
• Podcast: https://therevenueleadershippodcast.com/

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.

Episode Transcript

Speaker 1 (00:00):
Anytime you're trying to build a company that you
want to take somewhere big, youhave to make difficult decisions
up front and lay the rightfoundations.
It was always my intention totry to build a generational
company, to build something huge.
We're all playing this powerlaw game where a modest outcome
doesn't do anything.
You have to be honest withyourself and decide what game

(00:21):
you're playing.

Speaker 2 (00:43):
Owner is one of the fastest scaling SMB SaaS
companies right now, going from2 million to over 50 million in
annual recurring revenue, over10,000 customers, restaurants
specifically and now over abillion dollar valuation.
Congratulations, thank you.
But that wasn't always the case.
When you joined, churn wasrampant, sales wasn't really

(01:05):
moving the way it should.
The engine wasn't spinning.
So what we're going to do rightnow is really break down the
systems, the frameworks, some ofthe mindsets that you use to
really take a company from 2million to a unicorn status.
Kyle, welcome to the podcast.

Speaker 1 (01:21):
Thanks for having me.

Speaker 2 (01:22):
Absolutely.
Thanks for being here.
Great to get together and chatin person.
I always find episodes areextremely special when you're
talking to somebody that alsohosts a podcast.

Speaker 1 (01:30):
Yeah, it's a very different perspective.
Yeah, it's fun.
I've loved doing mine, so it'salways fun to be on the other
side of it.

Speaker 2 (01:37):
Yeah, definitely, definitely.
I want to start at a veryinteresting decision that you
made, at a very interestingdecision that you made 45 days
into the role, you let go ofhalf of the sales team Pretty
bold decision and it essentiallydictated the rest of the
outcome for owner, which isclearly a very, very positive

(01:57):
growth trajectory.
Why did you make that bolddecision?

Speaker 1 (02:01):
Anytime you're trying to build a company that you
want to take somewhere big, youhave to make difficult decisions
upfront and lay the rightfoundations.
And the first 10 people in yoursales team that becomes a lot
of the fingerprint of what youbuild on in terms of their

(02:23):
dedication, their drive, theirintensity, the craft, the acumen
.
If your first 10 sales hiresaren't at that upper tier and
bringing a level of intensityand drive, then it's really hard
to build an organization thathas that into the future.

(02:45):
And so it was pretty apparentthat there was some good sales
talent on the team.
The three, the manager and thetwo reps that remained after
that are still in the businesstoday and thriving and doing
awesome.
But you know, we needed toraise the talent bar and I got
to work on bringing in folks whoI thought were the right

(03:07):
foundation to build somethingspecial.
It was always my intention Iwould have never left Shopify
had I not believed this but itwas always my intention to try
to build a generational company,to build something huge.
That's what I saw in Adam andDean.
At the time, gtm Fund Invested,which is how I got introduced,
and so from the very beginningwhether it was investing in

(03:30):
systems, building up leadershipteams maybe earlier than you
otherwise would have or makingcalls like that.
It's always been about playingfor a really big outcome and
trying to make early decisionsthat gave us the best chance to
do it, and that was one of themthat certainly played an
impactful role.

Speaker 2 (03:49):
Definitely.
And what were the other coredecisions that you felt like
were those pivotal ones?
Yeah, inside that one.

Speaker 1 (03:56):
So having a really high talent bar.
Everybody that we hired inthose first few quarters and
this is still the case today,but much more difficult back
then they were all president'sclub performers, the number one
or number two rep in the companythat they came from.
They were all, uh, one degreeof separation away from me.

(04:18):
They were people that I couldlike very easily back channel
and personally validate, likevery easily back channel and
personally validate, and wedidn't accept anything but the
best and so we've had anextremely high hit rate with
sales hiring, especially on theaccount executive side.
Very, very few people have notworked out Now like less than

(04:41):
10%.
In the sort of three-yearhistory of hiring account
executives, our hit rate's beenreally good.
Of three-year history of hiringaccount executives, our hit
rate's been really good.
So high bar for talent andbringing in people that I could
really easily validate.

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Speaker 1 (05:39):
So, like our first BDR was the cousin of a BDR that
worked for me like threecompanies before that.

Speaker 2 (05:45):
Okay.

Speaker 1 (05:46):
And then there was like multiple people that came
from the same company becausethey were all referred in and I
obviously had a strong backchannel, or it was leaders that
worked for CRO friends of minein the past, worked for CRO
friends of mine in the past.
So talent density, really highbar and people that could really

(06:10):
go validate, were excellent andlived our values.
Was number one An earlyinvestment in systems and
infrastructure.
We spent a lot of money on techand infrastructure much earlier
than you would at like a $5million ARR stage or a $10
million ARR stage Again, becausewe were playing for this really
big outcome and I was trying toavoid the situation that many

(06:32):
companies get themselves intowhere it's like man, our
Salesforce is a mess and we wantto do this.
But we have to like completelychange how we use the tooling or
re-implement Salesforce.
You see people go through.
So we invested in tech veryearly and I invested in people
that were non quota carryingindividuals to support quota

(06:55):
carrying individuals also veryearly.
So I brought in my formerRevOps leader on a contract
basis in my like fourth month orsomething.
We were like three or fourmillion in ARR at the time and I
was like, hey, can you startdoing some consulting for us?
We want to build the rightthings.
And I hired Steve full time.

(07:16):
I don't know, maybe I was likesix months into the company and
he's like a senior, like worldclass RevOps practitioner, and
that would have been way earlierthan you would otherwise think
prudent.
And he's like a senior, likeworld-class RevOps practitioner,
and that would have been wayearlier than you would otherwise
think prudent.
You're like, oh, it's expensiveand that's a really senior
person.
Same thing with enablement.
Same thing with building theenablement team and the RevOps

(07:37):
team.
The data team was another bigarea of investment and in most
companies you'd look at that andgo like there's so much CAC
going into non-quota-carryingpeople, but that's what gave us
the ability to scale at the pacethat we scaled at and it's a
big reason why we're soefficient as a go-to-market org.

(08:00):
So I'd say those are the threethings.

Speaker 2 (08:02):
One of the big lessons that we hear
consistently I wish I had donethis earlier is RevOps and
investing in RevOps earlier andearlier.
We're starting to see startupsdo that earlier and earlier,
which is great.

Speaker 1 (08:13):
It's advice I give to CROs and founders all the time
If you have legit product markettraction, product market fit
and traction and think that youhave like sort of figured out
gtm, bring in rev ops, like it,the way the world is going and
the power of the tooling outthere today, it it makes so much

(08:36):
sense to bring those hires inearly.
But people are really I don'tknow gun shy about doing it.
They don't.
It's a big cost.
We had like six reps and like aVP caliber rev ops leader.
In many traditional views thatis way too early but man, it's
paid off crazy dividends for us.

(08:57):
But you have to be confidentand you have to be pretty honest
with yourself.
That's like okay, our PMF isreally good, we're really
figuring out gtm.
Like I think there's a path toa lot of repeatability and I can
scale.
If you're growing 60 year overyear and you've got like four or
five reps, it's not the samedecision making.

(09:19):
But if you think you've got theopportunity to go for it, then
bring those people in earlier.
Because we are all playing thepower law game, like as venture
investors, as founders or earlyexecutives of these companies.
We're all playing this powerlaw game where you know, like a
modest PE outcome doesn't doanything for me as a CRO really,

(09:43):
because you're going to get youto get squashed under a prep
stack and the liquidity is goingto go to everybody but the
employees.
That's just the nature of thegame, and so you should be
trying to go for the big win.

Speaker 2 (09:57):
What's so interesting about what you just said, too,
is the mindset you always hadabout trying to build a
multigenerational company,because essentially, every
startup wants to build anenduring company.

Speaker 1 (10:08):
Yeah.

Speaker 2 (10:08):
So every startup should really implement the
principles that you just sharedto build an enduring company and
approach it with that lens.

Speaker 1 (10:14):
Yeah.

Speaker 2 (10:15):
Which is really really interesting.

Speaker 1 (10:16):
Not every company has the market size or the traction
or the team to try to play forthat type of outcome and they
really shouldn't beventure-backed.
I think there's a lot of themarkets starting to come to
terms with that.
You're seeing now people gothis like seed scaling or seed

(10:36):
strapping route, where theyraise a seed round and then
don't raise again and you keep abunch of liquidity, you keep a
lot of optionality as founders.
But yeah, venture capital isinvesting for those types of
outcomes and so if you have it,and you have the seeds there of
being able to do it, then youhave to place really

(10:57):
aggressively.
In my mind, the downside is ifyou spend aggressively and you
didn't have the PMF, you don'thave the market size, then you
sort of spend yourself into thewall and you end up laying a
whole bunch of people off and itis really painful.
So you have to be honest withyourself and know what game

(11:17):
you're playing and decide whatgame you're playing and have a
congruent strategy, from yourfundraising strategy to your
product strategy, to yourgo-to-market strategy.
I think like CROs oftentimesdon't understand those dynamics
well enough and they're notconversant enough in
understanding the pressures ofventure capital and how it works

(11:39):
.
And so you see, like earlystage revenue leaders
complaining on LinkedIn, likeyou know, early stage revenue
leaders complaining on linkedin,they're like, oh, like the.
The complaints, like oh, I wasforced to do this thing and it
wasn't the right approach, andthe founders are dumb and the
vcs are meanies yeah, it's likeno fingers pointing it's like
that's the game we're playing.
If you don't want to play thatgame, go do something else.

(12:01):
Venture capital is investing inthese businesses so that a very
small percentage of them becomeextraordinarily valuable and
you need to understand thatthat's what you're signing up
for.
Or just go do something else,like work for a bootstrap
founder or play a different game.
But I think strategiccongruence is something that is

(12:22):
sometimes missing.

Speaker 2 (12:24):
Super, super interesting, and so you talked
about sales and the reps youhired and how you hired them
based on proximity.
Churn was another area that youtackled earlier.
How did that play out in termsof your go-to-market strategy?

Speaker 1 (12:39):
So Adam and I started spending a bunch of time
together after GTM Fund invested.
Owner is Shopify forrestaurants.
Basically, I was at Shopify.
I had some early stageexperience and so, as part of
being an LP like I, was going tospend time with Adam to help
figure things out and veryquickly he understood it.

(12:59):
I understood the challenge isthat a bunch of inefficiency and
go to market was because theywere closing like questionably
fit customers and the handoffwasn't good.
So the early churn was was muchhigher than the company wanted
and it didn't make sense to uhpour a bunch of money into GTM
into a bit of a leaky bucket.

(13:20):
And so one of the first thingsthat I tried to tackle was
getting early churn into abetter spot, and that meant
narrowing the aperture of thecustomers that we chose to work
with, which actually meant monthover month.
We sold fewer deals in my firstmonth, fewer deals in my second

(13:40):
month than my first month, butthe metrics would show you that
the quality was much higher.
If you looked at high qualityrevenue that we were closing was
actually growing month overmonth.
But we were getting rid of abunch of fluff and luckily I had
Adam's support.
I have the sort of backgroundand stature to do that and

(14:01):
maintain confidence, becausethat would probably be harder if
you were first time VP of sales.
That doesn't have thebackground.
But those were the right stepsto take and we got way more
clear about expectation setting,which means some deals chose
not to work with us and we saidno to a lot of customers like
30% of the customers that wecould have closed previously we

(14:24):
were saying no to now.
And it just cleaned everythingup and now we could go out and
add marketing dollars and addsales headcount and add
onboarding capacity into asystem that had a lot less sand
in the gears, Because you know,many sales leaders don't like to
admit it, but a lot of churn'sour fault.
At Shopify I owned onboardingand CS at the end of my time

(14:47):
there.
I picked up the onboardingfunction in my first year at
Owner and so I've had to managethat side of the business, which
I think is a very productivething for revenue leaders to do.
It's a good empathy buildingexercise and I think it's good
from a decision-makingstandpoint, and we were able to

(15:11):
get to a place where thesales-driven churn dropped
dramatically, and then we couldgo tackle everything else
Incredible, incredible.

Speaker 2 (15:16):
Now that makes sense and I mean that's fantastic that
you and Adam had that alignmentand that trust built up.
You're actually a perfectexample of one of the points
that you made around.
It's the people.
It really matters who you'rehiring.
You were using the context ofthe sales rep, but it applies to
everyone.
It applies to you, it appliesto all of your leadership hires.
How do you think about hiring?
Because I've heard you say thatyou don't really buy into the

(15:37):
traditional method and I saw youcomment on the Shopify's chief
data officer's post that you doa don't hire with us video and
things like that.
So I'm really curious aboutyour methods of hiring, because
every startup is trying to hirethe best talent and you were
able to do that early beforeOwner obviously grew to be the
company and brand it is now.

Speaker 1 (15:56):
Yeah, brand matters a lot, like if being able to hire
the right people means that youneed a really compelling story,
and I've had the advantage ofbuilding an audience on LinkedIn
over a bunch of years, whichcertainly helps, and I had a
track record.
So I encourage people to dothat and like really be sharp

(16:17):
about the narrative they'retelling and how to get people
excited.
But the thing I think that's alittle bit less consensus in our
approach is two major thingsLike one and this is a big
credit to Farhan Thawar fromShopify.
So he was the engineeringleader that I worked with in the
point of sale team, who's nowthe head of engineering at

(16:39):
Shopify, and he shared a bunchof data and like really
interesting insight about howlittle a hiring process actually
allows you to predict in-roleperformance, like behavioral
interviews and case studies andall of this stuff.
A little bit of it is liketheater.
It makes us feel a lot betterabout the hiring decisions we're

(17:01):
making, but when you actuallylook at the data it doesn't
actually doesn't actuallyimprove outcomes all that much.
But you have to be really dataoriented with with hiring or
else you never learn that.
Lesson One is is appreciating,like what does interviewing
actually tell you and whatdoesn't it tell you?
And the other big principle thatthat I lean into a lot is

(17:24):
hiring is about fit.
There's no like best rep.
There's no rep that will besuccessful in every single
scenario.
You need to find reps who wantto work the way that you want to
work and reps that want to dothe type of work you do we sell
to restaurant owners.
They're like gritty blue-collarfolks who want to shoot

(17:44):
straight and can be like prettygruff at times and won't just
like hop on to a Google Meet,like you have to call them and
help them get on to it.
And some people get reallyfrustrated by that experience.
They're like why can't peoplejust like show up for the Google
meet?
If you've sold the white collaryour whole life, then that
might just be like a frustrationfor you.
But the reps who are successfuland something that I really

(18:08):
enjoy is like selling to salt ofthe earth people and just being
able to shoot straight and notlike dress up our language in a
bunch of tech jargon.
And so for us it's aboutfinding people who can fit that
environment and fit my style ofleadership, because we are quite
opinionated about how we wantto go to market and the style of

(18:30):
sales that we teach is veryspecific and the style of
organization we run is like notfor everybody, but some people
it's like the best thing thatwill ever happen to them in
their careers because they'regoing to learn awesome skills
that they can be successful withlater.
But it is not for everybody, andso the video that you're
referring to is something that Ido for especially leadership

(18:52):
hires.
There's like an explainer videowhere I talk about the
situation of the company andwhat the role is meant to do and
the state of the team.
And then there's like probablyfive minutes at the end of the
video where I'm like okay, owneris an exciting place and on the
outside everybody, most peoplewould be thrilled to work at a

(19:17):
company that's winning in themarket and has all these
accolades.
But I was like but owner's notfor everybody, and here's why
and I explain it's reallyintense.
We're performance-based.
It's not a great work-lifebalance culture, like that's not
what we're optimizing for, andI explain the reason somebody
might not be a good fit.
And I do that before theirfirst meeting with me, because

(19:38):
the video is helpful too,because now in an interview I
don't have to waste a bunch oftime like explaining the basics.
They come in knowing that andthey can just get into much more
interesting questions.
But in the video I explain whyowner's like not a fit for
people and I have folks drop outof the interview process
semi-regular basis and I'veactually had examples of people
responding to that, respondingto the video, saying hey, like I

(19:59):
really appreciate that you wereso honest and transparent.
It doesn't feel like theenvironment that's right for me,
but like it's great that wecould just figure that out now.
And and everybody time everybodytime, it's a good candidate,
experience and and um, it is.
What you don't want is to hiresomebody who doesn't know any of

(20:20):
the bad thing, the trade-offsbecause it's not necessarily bad
but somebody who comes in notunderstanding any of the
trade-offs and then they're atthe company for three or four
months.
They're not working at theirbest because they're like man,
like everybody works here solate and like I don't.
That's not really what I wantto do.
And they're stressed becausethey feel like they have to

(20:45):
answer slacks after five o'clock, which is like not their shtick
.
And then they end up resigning,like four or six months in and
you just wasted a colossalamount of time and energy and
you haven't progressed the youknow those strategic priorities
that person would have owned andyou're just back at square one
hiring that role again.
And it happens all the time.
We try to do that at the verytop of the funnel and then also

(21:05):
like, if we hire somebody and wecan tell that they're
struggling or it's like not afit, we'll often have a
conversation, like an open,transparent conversation, with
them pretty early on and be likelook like Sophie, if this, like
I get the sense that this is,you're not having a great time,
and if that's the case, that'stotally fine and we should just
be like let's have an honestconversation and solve it or

(21:28):
figure out if this is just likenot a right match.
And so when we have lost salesreps most of the time it's very
early it's at the the.
We had one that was like lessthan 30 days.
Somebody had 75 days becausethey've just realized it's not
what they want to do and that'sa way better scenario than it
dragging on and on and ondefinitely definitely better to
find out earlier yeah, um, theother thing we can talk about is

(21:51):
going back to the first pointabout interviews being a poor
predictor is let's unpack.
Yeah, the exercise we just ranwhere we did a big hiring retro
this is another area that isoftentimes missed in hiring is
we hire and we hire and we hire,and we never go back to that
hiring process and analyzewhether or not it's good or bad

(22:15):
and what we could possibly dobetter.
And in product management youdo retros.
In sales you do MBRs or QBRs,but the most important thing in
your business is being great athiring and we never go back with
a critical eye to understand it.
And so what we did a couplemonths ago was go back to every

(22:40):
single person we've hired in2024 and 2025.
And we pulled in all of theirinterview scores by the hiring
manager, and so we looked at afew different and compared it to
enroll performance, and sothere's a few things that we
learn.
So we use a one to four scoringframework and there's four

(23:02):
people that score that candidateacross the interview process,
so they get a score at 16, andwhat we noticed is there was not
a lot of correlation betweenin-role performance and whether
or not they were a 13, 14 or 16.
Not a lot of.
There were a couple 13s and anduh, so there wasn't a lot of
correlation, like okay, so likesomething.

(23:24):
It means like we're not scoringvery well.
And then you could go managerby manager and and unpack it's
like well, I was a four and thedirector was a four, but this
person was a two and this person, this person ended up being
awesome, like what happenedthere.
And so you have to go givefeedback to that hiring manager

(23:50):
because clearly they're seeingsomething different, to coach
them up.
But the most interesting insight, going back to this concept
that hiring can be a little bitof like a performative theater,
is the case study scores hadlike no correlation actually
were inversely correlated withsuccess in role.
So the people who crush theircase studies didn't really do
any better, uh, in the roleversus the people who we hired

(24:13):
that didn't do well in the casestudies.
And if you think about it likeif somebody did poorly in the
case study but we hired thatdidn't do well in the case
studies, and if you think aboutit like if somebody did poorly
in the case study but we hiredthem anyways, there must've been
a bunch of other stuff wereally liked to get over it,
which in our case, was theirlike raw DNA and we're looking
for super competitive drivenpeople.
You have to be really organizedto do what we do, cause there's

(24:35):
a lot of you're managing a lotof deals, the velocity is very
high and so if you'redisorganized it's hard to be
successful at owner, which islike not a common thing to
screen for in sales hiring.
And so we started to like tweakhow we thought about the case
study and we've like really nowweighted DNA and mindset more

(24:56):
highly, even in like our SDRcohorts, especially in our SDR
cohorts, because you know noneof them are going to come in
with that much skill or craft.
It's really just all about DNA.
So we haven't done it yet, wehaven't been brave enough.
But there's part of me thatmakes me want to like scrap the
case study altogether becauseit's so unpredictable.

(25:16):
But unless you're doing thework to analyze your results and
to take a critical eye and dothat retro, it's hard to
calibrate on hiring.

Speaker 2 (25:29):
I can imagine, especially at the velocity that
you guys are hiring.

Speaker 1 (25:32):
Yeah, yeah, yeah.
It's helpful that we hire likewe'll hire a hundred people and
go to market this year ish, andso we have.
We have a cohort to analyze.
But you could probably still doit with less.

Speaker 2 (25:47):
Yeah, yeah, definitely.
And what about leadership?
Does it differ?
Or are you still thinking aboutit from a very DNA perspective?

Speaker 1 (26:02):
DNA perspective Slightly different, but DNA
still matters a lot.
I think the biggest lesson thatwe've learned on the leadership
hiring front is the importanceof like philosophical alignment
and congruence, and so there areso many different ways to lead
people.
You know, like we have a veryservant leadership oriented
approach.
We are very systems engineeringcentric.
We're trying to build like highrepeat ability, and if somebody

(26:27):
comes into the business thathas like a slightly different
perspective on your core tenants, then it can be very, very
difficult for the organization,especially if you're bringing in
somebody senior.
And so what we've seen with themost successful leadership
hires is that they're peoplethat have a very like similar

(26:53):
mentality and set of principles,and also people that are very
adaptive.
I think this is the other thingthat I like underweighted
historically in leadershiphiring is and this might be
because, like again, I am veryopinionated about many things go
to market and so, but whichmeans I require people who want

(27:14):
to learn my system, and so theleaders on my team are so
productive because they use thesame language, they refer to the
same books, they talk with thiscommon vernacular.
So when I'm talking to the repsabout something in a recorded
training or a town hall, it'sthe same language they're
hearing from their director,from their frontline manager,

(27:36):
from their peers, and it seemslike semantic and a little bit
silly.
But just getting to commonlanguage is so critical, and so
you need leaders that arewilling to adapt and to operate
within your system.
I find Maybe that's like alittle unique to me because I'm
so particular or so opinionatedabout it, but like so particular

(27:57):
or so opinionated about it.
But that's something I need tounderstand about myself and the
system, the organization we'rebuilding, and know I need to go
higher for that.

Speaker 2 (28:07):
It makes me think organization, organism.

Speaker 1 (28:09):
You think about different blood types, like
you're hiring all type A bloodsor type B plus, or what have you
right, somebody that's got thatcongruency baked in, yeah and
it's a careful balance, becauseyou don't want to just try to
replicate yourself.
You need some diversity ofthought and background and you
don't want too much of amonoculture, and we try to

(28:31):
operate by the principle ofopinionated but open.
So I want people to beopinionated and like think
critically from first principlesand not to just accept things
because that's the way we'vealways done them.
I want people to disagree withme, but I want people that are
also open-minded, and I try tobe open-minded about new ways of
doing it, and so you have tofind the balance here between

(28:56):
that congruence.
And a good example is, you know, with my vp of rev ups, and I
like he's the guy that willdisagree with me the most
directly and be the most braveabout it.
We've worked together foralmost a decade now across three
companies and it works so wellbecause we can just like have
the argument.
We can try to like look at thedata together, disagree and

(29:18):
sometimes we like can't get tothe same answer, like we just
have slightly different opinions, and ultimately I'll be like
you know what this is your call,it's in your wheelhouse.
I trust you like let's go forit.
He'll do the same, uh with me.
There's a lot of nuance thereand and you have to find the
balance between, like avoidingavoiding an echo chamber, but
also having like havingcongruence on the really

(29:41):
important things.
Like servant leadership is anon, it's a non-negotiable.
Like you have to operate withthe mentality that you work for
the people that work for you themanagers work for the reps, I
work for the reps and I work formy leaders and the reps work
for the customer that's anon-negotiable for you.
The managers work for the reps,I work for the reps and I work
for my leaders and the reps workfor the customer that's a

(30:01):
non-negotiable for me.
But there's other things we canbe like more fungible about.

Speaker 2 (30:10):
So you're hiring a hundred go-to-market reps this
year alone.
So you're growing a ton andyou've been really successful
with your ai transformation.

Speaker 1 (30:19):
Love to hear a little bit more about your playbook
for implementing thattransformation and what you're
doing yeah, and so we werereally early, uh to try to steer
into this in in a big way.
So some of it was like justgetting lucky and, uh, following
our intuition, because therewasn't a lot of places to go

(30:40):
learn from.
And luckily, like I have thispodcast.
I talk a lot about GTMAI and Iget to talk to a bunch of smart
people who are doing things.
So having a network and usingyour network is definitely
important.
But we've like meandered ourway into, or intuited our way
into, a bunch of good decisionsand now that I've had some

(31:01):
distance from it, I've startedto like put some principles
behind it that I'm that I thinkare are fairly reasonable.
But again, this is so new that,like, uh, I reserve the right
to change my opinion over time.
But one of the things that Ithink the most important thing
that we did right, and aprinciple that now I push people

(31:21):
on, is we spent most of our GTMAI energy on data.
So the very first thing that wedid and this was led by our
head of BizOps he gets all thecredit was figure out prospect
data, and so we used AI toscrape and crawl websites and
pull information into Snowflakeand transform it and score it

(31:44):
and figure out who the very bestpeople are that we should be
approaching.
So getting really greatthird-party data was step one,
and so now when I give thisadvice to other founders and
revenue leaders, I'm reallypushing them before anything
else.
Get really great third-partydata, and this could be like

(32:05):
clay plus a clay agency to helpyou like answer a bunch of these
questions or an internal datascience resource.
But like spend the money, get agood data on the market your
accounts, people, and thenenrich with like information
that can help you with the rightplay for that account or

(32:26):
prospect.
And so like now we use Datalanefor a whole bunch of this stuff
because it's restaurantspecific and they've built
better things that we builtinternally.
But the first investment we madehere was getting good
third-party data, and I in thatwe were not.
I didn't at the time go like Iwant to be on this

(32:47):
transformation journey with AI,but like I think the third-party
data is the first thing, wesort of intuited our way there,
but now I feel good about likethat as a principle.
The other thing is greatfirst-party data, um, and so
this is where momentum comes in.
This was like our second reallybig ai application where you

(33:08):
know there's all of thisinformation in call transcripts
and in emails and like allacross the the customer journey
that, yeah, you can go access,you can pull open gong and like
read a transcript or search atranscript, but like it's not
all that helpfulprogrammatically unless that
data is structured.
And so for Momentum, it used tobe on top of Gong and then we

(33:30):
replaced Gong and now we useMomentum as the call recorder,
which has been great.
That will take all of thisinformation and put it into a
structured format so that we canactually now power a bunch of
analysis off of it so it cananswer specific questions Did
the rep say this or that, likeyes or no box?

(33:51):
Is the customer using this listof 10 competitors or something
else?
Open text fields?
Um, what were the challengesthe customers like most
interested in in solving, likeranked one to three?
So you start to bring structureto all this unstructured
information and now that I havegood first party and third party

(34:11):
data, I really have a verydifferent understanding of of
business and you can make such,you can make much, much better
decisions and how we do it inSMB is a little bit different
than how you might do it in in aenterprise.
Ours is like a data science ledmotion, because the TAM is
massive and and there's so manyuh data inputs.

(34:33):
In an enterprise environmentI'm I'm using AI more to like
deeply enrich accounts withspecific information, but you're
like writing those promptsthoughtfully, um, and so I would
say like the biggest thing thatwe've done is start with the
data foundations and now, whenwe layer on a use case, it's so
much more effective because AIis just a pattern recognition

(34:56):
machine but if you have goodpatterns for it to learn from.
Now we've got we use OneMind asthis AI SDR education avatar, so
you can talk to an AI versionof our founder about anything
related to restaurant marketingand it can explain what you
should be doing better based onyour specific website, because
we've got this AI website grader, but that all works.

(35:17):
Because we've got this AIwebsite grader, but that all
works because we've got thiscorpus of information to work
from.
So I would say like that'sprobably the single most
important thing that we've doneStart with the data foundations.

Speaker 2 (35:29):
Before we dive in, a quick word on hiring.
It's a weird market out thereright now, but finding top
go-to-market talent is still oneof the biggest levers for
growth.
At GTM Fund, we've made over2,000 candidate intros and
placed hundreds of eight players.
One of our go-to recruitingpartners is Pursuit.
They specialize in sales andmarketing talent and they do it
without a retainer.
We work with them closelyacross many roles.
If you're hiring, go topursuitsalesolutionscom forward,

(35:52):
slash GTM That'll be in theshow notes or ping someone from
the GTM.
It kind of sounds like how youbuilt the go-to-market engine.
You started with RevOps, youstarted with the Data Foundation
and then you built on top of ittoo.
Same thing, coming back to thedata first.

Speaker 1 (36:10):
Yeah, and even if you go one level of abstraction out
, we just start with the boringstuff, and I think that's one of
the places that people go wrongwith AI is they want to chase
the shiny things first, and thisis a Jordan Crawford thing.
He's like people need to eattheir damn vegetables.
You have to do the hard work onthe data foundations.

(36:33):
You do have to do the hard workto really thoughtfully decide
who is your ICP, what are thekey segments, what is the
digital footprint of thosespecific high-fit segments, what
is our positioning like, whatare the specific things we want
to say so that you can feed thatinto these models.
That so that when you areproducing, either like cold

(36:55):
outbound messaging that it issharp and on point and not like
ai slop, or when you know yousee so many startups trying to
do this, like, oh, we're like asales co-pilot, we'll tell you
what, what play you should.
So many startups trying to dothis like, oh, we're like a
sales co-pilot, we'll tell youwhat play you should run, we'll
give you all this accountinformation.
But so many of these tools gowrong because it's just like
generative layer over generativelayer of probabilistic

(37:18):
reasoning, and you've neverinserted deterministic
constraints onto this model andso you're just stacking like in
AI, it's called lossiness.
So you're just stacking layerand layer of lossiness on top of
each other and so your tool islike oh, enter in your company
website URL or company URL andwe'll give you sales messaging.

(37:42):
You're like I wonder why thesales messaging sucks?
Because the model had to viewyour website and take a guess at
what your positioning is andtake a guess at what your ICP is
and then take a guess about thechallenges and who you want to
talk to and this and this andthis, and every one of those
guesses is probably going to bepretty good.
But if you stack on these 10guesses, it's like broken

(38:03):
telephone as a kid.
You just end up with somethingthat's like yeah, it sort of is
what we do, but it's not goodenough to send to a customer.
Really, people still send it tocustomers, but that's one of the
problems.
It's like people aren'tinserting enough constraints on.
It's like no, i't aren't, uh,inserting enough constraints on.

(38:25):
It's like no, like I will tellyou what our positioning is, I
will tell you what the icp isand and the digital footprint of
that icp, and then the ai canuse all of the wonderful
generative capabilities to gofind all of the people and all
of the evidence that supportsthe specific criteria of your

(38:49):
ICP, filling in a smaller set ofblanks we found to be very,
very helpful, rather than justletting AI answer every question
and make every determination ina system.

Speaker 2 (39:02):
It sounds like the lesson for founders and
operators would be don't replaceyour actual foundational work
around the company orpositioning messaging with AI at
all.
Do the work and then use AI toscale.

Speaker 1 (39:15):
Yeah, or use AI to help you get to that answer, but
there needs to be adeterministic layer because even
, um, you know, like even for mewriting, like I use AI a lot as
a writing co-pilot, but I'malways editing and changing and
tweaking and I'm like, no,that's like obvious or silly,
and and so there's always aprocess of me uh, being human in

(39:39):
the loop and and like makingthoughtful decisions rather than
, like, we really avoid, um, ai,making like many sets of
decisions on top of each otherand this is a reason I like
momentum as well, because, uh,we can write the prompts that
fill out the specific fields andso we get the power of AI, but

(40:04):
within this constraint.
So it's like tell me what thenext step was that was discussed
and then maybe suggest, basedon other interactions, what next
steps could be.
But then a rep has to go in andadjust that before it just goes
off and starts executingworkflows.

Speaker 2 (40:23):
Got it, so it's not autonomous.
Essentially it's doing the hardwork and then prompting the rep
to give it some instruction andthen go off.

Speaker 1 (40:31):
Yeah, that could be the architecture.
The important principle, Ithink for people is being
thoughtful about combiningdeterministic decision-making
and workflows with thegenerative side of things like
that.
That's where we've seen themost success, even like our ai
website grader.
Uh, you know, we are thoughtfulabout the things that we're

(40:54):
we're telling the grader to gothink about and analyze.
Um, it's not just like an aifree, free form, like tell me
whatever you want about thesewebsites and you make the
decision about what drives goodconversion rates versus bad.
Like there is a lot ofAI-driven decision making in it,

(41:15):
but there's also a constraint,which is why that output is so
powerful.
I just see this pattern all thetime, like you just need the
deterministic constraintsomewhere.
It could be a human in the loop, it could be you, like setting
the rules within the agenticworkflow.
You just can't let AI layerseven AI steps on top of itself,

(41:43):
or else you start to meanderand get to slop territory.

Speaker 2 (41:47):
That's great advice, because I think that's what a
lot of people are trying to dois trying to automate as much as
possible and create more of awaterfall effect from it.
But it sounds like you'resaying you know, be really
intentional with how you'reactually putting the inputs in
along the journey.

Speaker 1 (42:00):
If it feels way too easy, it's probably If it feels
way too easy.
it's probably If it feels toogood to be true it probably is
Like even you know, being reallymindful about the prompt
engineering and spending thetime to build the evals and run,
change the prompt and run theeval, run the eval, run the eval
Like going and doing the workto really like test and iterate

(42:21):
and tweak the contextengineering that is involved in
these workflows.
Like you can't the out of themagic box answers of like oh,
just enter in your website andwe'll tell you everything.
I have I've yet to seen thosetools work all that well versus
something that, like you know,why I chose Momentum over a

(42:43):
bunch of the other tools isbecause I could go write the
prompt and I could go set it upwith that specific field and
then we could run it.
We would run it.
I would look at the end of theday and look at the fields that
have filled out.
I'm like, okay, well, it'sactually it's like giving you
way too much and it's like oneof the things that I'm like we
use a call recording tool that'sfor interviews that I won't

(43:04):
name because I'm about to trashthem, but like the, the, the,
the transcript, like summary, islike the interviewer asked the
candidate about whatever.
The candidate responded yada,yada, yada.
I'm like this is a completelyunhelpful transcript because
it's so long and it like tellsme about like stuff.
That is obvious.

(43:25):
It's like no, just like give methe answers to their questions
based on the, the lever, um, ourats, the lever feedback form.
But because it's just there'sno constraints, we haven't like
we're not able to do the promptengineering in that tool, versus
like we can do the promptengineering in momentum.

(43:47):
So the results are way better,and so it's funny to see these
two things side by side One thatmy RevOps team spends a bunch
of time tweaking and testing,one which is just like hiring AI
black box that gives me likeunusable junk, basically.

Speaker 2 (44:03):
Super interesting and I mean we're seeing a lot more
founders, leaders, use AI towrite content and publish it
online, and I've heard you sayhow monumental or impactful it
was to actually build a brand Ifyou're recruiting early you
talked about that.
What are your thoughts onactual content creation for
founders and early stageoperators?

(44:24):
Should everyone be buildingtheir own personal brand?

Speaker 1 (44:29):
not everyone, because not everybody has like a ton to
say that's all that interestingand it probably won't.
You'll put a bunch of effortinto it and you won't get the
result you necessarily want.
Like I think people who aresuccessful creating content have
something unique to say andthey're able to bring new ideas
to the table.

(44:49):
Um, and you have to like it.
Like, you have to enjoy writingand enjoy like putting your
ideas together and spending timelooking at a page and be like,
oh, like the taxonomy of likehow these things fit together.
It's not right, I want to dothis, I want to do that and so,
cause it's a huge commitment,like it's it's taxonomy of like
how these things fit together.
It's not right, I want to dothis, I want to do that, and so,

(45:11):
because it's a huge commitment,like it's.
I generally like writing and Iwrite.
I wrote a lot internally and soI just started open sourcing
stuff that I was writing for myteams or training docs in little
like bite-sized components, andso it was enjoyable for me and
so it wasn't like a taxing job.
Some people don't want to do itand it's going to be a chore
and you'll never be thatsuccessful at it.

(45:32):
I don't think if, if it is achore, but I think today, like
you know, it is, the market'svery competitive.
Especially competing for thetop talent is very, very
difficult and having a brand ismeaningful.
There's other ways to likesolve that problem.
On talent attraction, you couldjust be like a hardcore

(45:53):
outbound sourcer.
So, like earlier in my career,that's the game I had to play
and I, you know like sharpenedmy messaging and I did a bunch
of outreach and so I think, forthe right person, it makes a ton
of sense.
And you know, it was because ofNaval and Seth Godin that I
really started to be like I gotto build an audience.

(46:15):
I have to build a brand becauseit's a compounding asset, it's
something that I'll take with mefor the rest of my life, and
I'm like so bad at monetizing itLike I basically don't bother.
It's really just about hiringand I have friends who like make
a bunch of money doing contentstuff and influencer stuff and
I'm like it's just not.
It's like yeah, I should, but atsome point I will be able to

(46:38):
right, you're busy, you're busy,yeah, like the people owners
the only thing that matters,yeah, and all the other stuff
like podcasts and content andspeaking stuff, like that's all
to build my brand as a hiringleader and owner's brand as a
destination.

(46:58):
Like the number of eyeballsthat owner gets just because I'm
out there doing a bunch ofstuff is awesome and it's going
to help us in a bunch ofdifferent ways.
But you can build thiscompounding asset that you can
monetize in a whole bunch ofdifferent ways.
So if you like it and you wantto spend the time, I think it's

(47:19):
worth it.
But just know, like you'resigning up for like years of
nothing.
Basically Right, and maybe Icould have been more thoughtful
about it earlier and grownfaster.
But like there's just a coldstart problem where it takes a
while to get it going and youhave to be so consistent because
if you miss a week thenLinkedIn crushes you for it, and

(47:41):
so you're signing up for like along haul thing.
But it is a compounding asset.
So over time, like now, I justgain followers like by doing
nothing and it grows veryquickly.
But you know, I've been at itfor like six or whatever, six or
seven years, I don't know.

Speaker 2 (47:59):
Yeah, yeah, yeah.
Now you're on the hockey stickmomentum and trajectory, okay.
So you said you bring that withyou everywhere.
So do connections, theconnectivity between people.
You bring a lot of yourrelationships with you over time
and I know you implemented BDRsbeing in office five days a

(48:19):
week, which is a common point ofcontention, and I have a lot of
opinions too, because we'reactually in the office five days
a week which is a common pointof contention, and I have a lot
of opinions too, because we'reactually in the office five days
a week, but you've had a lot ofgrowth and success on the
revenue side.
So does that settle the debateon in-office versus remote?

Speaker 1 (48:34):
No, the debate will never be settled and it's very
nuanced.
And I had the Sierra of Oysteron the podcast, geraldine, and
they're obviously they'rethey're like a eor company,
they're very pro remote.
A bunch of the content theirfounder puts out is like super
remote's the only thing and it'sit lacks nuance.

(48:54):
But the conversation we had waswas like very nuanced and and
productive, because remote makessense for some companies, in
person makes sense for somecompanies in some roles.
But again, going back to thistheme of like, congruence, like
what is the thing that you'rebuilding and what serves you
best in terms of a strategy?

(49:15):
Because if you are remote butyou're like not great at
documentation and you are likenot taking advantage of hiring
internationally, like, thenyou're sort of just sacrificing
the connection, the speed, theengagement that by not having
people in person without gettingall of the outcomes.

(49:37):
And so, for example, you knowlike our most of our sales team
is still remote.
Our AE team is almost entirelyremote, other than the brand new
AEs we've hired very recently.
But the SGR team is five days aweek in office.
That's the requirement and,yeah, absolutely, the
performance between remote hiredSGRs and BDRs versus in person

(50:02):
has been drastic.
We pulled the numbers and itwas like grain of salt because
it was a small sample size butit was like the ramping
performance.
So in that first 90-day windowit was like 3X for in-person
than it was for remote.
And you know the system's moremature now.
We've revamped onboarding so youcan't chalk it all up to
onboarding, but those roles dobenefit so much from being

(50:25):
around their peers and beingaround their manager, like when
I'm in the office the managersare always sitting like hip to
hip with one rep going throughworkflows really inspecting
things.
You know, my vp of rev ops wasin the office, uh, two or four
weeks ago sitting there besidethe SDRs watching them dial, and
we realized a bunch of stuff.

(50:45):
We're like, oh my God, wethought they were doing this and
like the system has designedthis but we didn't enable them
properly.
And so there's like this bighole that we found and you can
just like there's some bigadvantages but the strategy
moving forward and we haven'tnailed all the pieces but
generally we're gonna have likebdrs and sdrs in the office five

(51:06):
days a week.
There's because you just it'sso input driven and it's so hard
to do that job if you'resitting at home in your tiny
little apartment with all thosedistractions.
So they'll be five days a week.
We'll graduate people intoassociate account executive.
Their first, you know three tosix months is probably also five
days a week in person.
Once they start hitting quota,then we'll graduate people to

(51:29):
four days and then, once theymove to an outbound AE now
they've been in AE with us for18 months, maybe 24.
We'll make it three days a weekand then, once people move to
our highest segments, we'll saylike look, come in as much as
you want.
We would love to have you moreas better Cause.
Then other people get to learnfrom them.
But we'll basically tell themthat they can be fully flex.

(51:52):
Come in when they want, don'tcome in when they want Cause.
I don't, I'm not worried aboutthem anymore.
I'm not worried about amulti-loke like in our are like
top segment reps like lackingmotivation or like not
understanding the process orneeding the like you know, deep
coaching, that that an earlierstage rep rep would yeah, and

(52:16):
they can operate great fullyremote and it's easier to.
It is still way easier to hirepeople remote.
People like reps want remotelike there's no doubt sometimes
they wanted.
It's actually not the rightthing for them, but it is an
expectation in the market and sowe're trying to find the middle
ground.
But, like engineering, stillall fully remote.
I'm in, I'm in person with thewhole exec team here in san

(52:38):
francisco now same with like abunch of product leadership.
So that makes a lot of sense.
But you know there's still tonsof people that are remote at
the company.
So we're not hybrid.
I don't know what you wouldcall owner.
Now, hybrid implies to me thateverybody is in the office.
Sometimes we have a bunch ofpeople that are never in the

(52:58):
office really other than foroff-sites.
We have some people that arefully five days a week in person
, and so some roles yes, someroles, no are fully five days a
week in person, and so someroles, yes, some roles, no, it
matters by like the role type,the seniority, and just trying
to find the right balance thereeven as just as you get older,
you have so many more lifedemands yeah

(53:19):
like I got two young kids.
Like I, I go in the office alot because it's like productive
and I like it, but but, yeah,some days I just I have to be
home because something is goingto go on.
And so try telling like a35-year-old enterprise rep that
it's five days a week.
You're not going to hireanybody good, so you just have
to.
You have to, like meet themarket where it is and try to

(53:40):
find the right things.
But you have to really thinkcritically and think from first
principles about the decisionsby role and not just be like
remote is or like in person isbad.
It's like this.
People make it this silly,moralistic decision and there's
a bunch of people on LinkedInthat are like, oh, it's like
it's unkind or it'sunconscionable that you to force

(54:02):
somebody to go in and grow upman.
And you just like.
If you believe that, then builda remote company.

Speaker 2 (54:10):
But like we, that company.
It's like what you said aboutventure Like there's other
places.
Find those places that youagree with and that resonates
with you.

Speaker 1 (54:17):
Find the place and be honest with people about it and
it's all good.
It doesn't need to be this likein-group versus out-group
argument.

Speaker 2 (54:28):
Yeah, and it might evolve.

Speaker 1 (54:29):
Like you might be in person as a startup when you
need all five people shoulder toshoulder and then when you need
to hire 50 engineers in a year,good luck doing that.
If you founded your company inDallas, like no, no, no, you're
remote now.

Speaker 2 (54:44):
Yeah, yeah, exactly so much context now.
Yeah, yeah, exactly so so muchcontext, okay.

Speaker 1 (54:47):
Yeah.

Speaker 2 (54:48):
And you've got I mean , a ton of leadership principles
through this even remotestructure.
But all the things that you'veshared around the good market
strategy, the hiring like what'sa core leadership principle
that you, just you takeeverywhere.

Speaker 1 (55:01):
So I have a bunch.

Speaker 2 (55:02):
Yeah, servant leadership is.

Speaker 1 (55:04):
Leadership is at the heart of it, which we've already
talked about this idea thatit's all of our jobs to figure
out how to enable the peopledoing the hard work, the people
on the front lines withcustomers, to do their best work
so that they can be in serviceof the customer.
It's always about the customer,so servant leadership is number

(55:26):
one be in service of thecustomer, like it's always about
the customer, so servantleadership is number one.
And I just actually recorded mypodcast with my VP of RevOps
because a bunch of people askedme to do it.

Speaker 2 (55:32):
Oh, I can't wait to listen to that one after this
conversation.

Speaker 1 (55:34):
One of the design principles we talked about
that's been so important for usis building RevOps
infrastructure and businessprocess in a way that helps do
the right thing as the easychoice, and so like removing
friction from the stuff we wantthem to do and just like being
extremely rep-centric in how wemake decisions and prioritize

(55:56):
projects, and really he callsthem quality of life
improvements.
We ship a lot of quality oflife improvements for our IC
team, so servant leadership isprobably number one.
The other one that's the mostimportant for me is like growth
is the thing that we should beoptimizing for Personal growth,
professional growth, companygrowth too, because if you are

(56:22):
growing as an individual,investing in yourself, trying to
learn and get a little bitbetter every single day this is
Darren Hardy compound effectLike you can compound those
little improvements over time tobe exponential.
And so the biggest investmentswe've made as leadership team,
as a GTM organization, as in ourenablement function, onboarding
and training and development,is in our enablement function,

(56:44):
onboarding and training anddevelopment.
Our managers are psycho coaches.
This is an open challenge foranybody listening to.
Bring me a frontline managementteam that spends more time
coaching than my team does.
We are so hardcore about itEvery single day, multiple hours
a day.

(57:04):
We do this thing called chopwood, carry water, which is
you're not allowed to havemeetings in the first three
hours of the day.
The managers all they'reallowed to do is be hip to hip
with their reps and be doingride-alongs or practice or
something to move, move the repforward.
The growth thing is the mostimportant thing.
It's it's what I'm reallypassionate about too.

(57:25):
Like you know, when I wasgrowing up in high school, I
taught preschool art and then Itaught martial arts for years
and years.
And when I got into sales, likeI wanted to teach people right
away and I became a manager veryearly, and it's the thing that
I get so much fulfillment out of.
And so I think a lot about andI study and I read a lot about

(57:49):
and I study and I read a lotabout how to, how to develop
skill and train people and and,uh, you know, I really want
people to come out of their timewith me feeling like they like
exploded in their career andthey learned all of this stuff,
and and like the, the, and likethe mantra that I have for
myself is I want to give peoplethe best years of their career

(58:13):
Like that's.
The expectation that I set formyself and for my leaders is
that the one, two, five, tenyears that any of these folks
spend with us, those should bethe best years of their career,
because they learned a lot, theyfelt like they made an impact
on the world, they won, theyfelt supported, they could trust

(58:34):
the organization, they mademoney, they got promoted.
That's really what we're tryingto do, because I think if you
can do that and people reallytruly feel it and believe it,
then you'll hold on to your toptalent, you'll attract great
people, you'll get the best outof them and and we want to help
people like find their likeinternal drive and purpose and

(58:56):
motivation, as opposed to likebeing this environment.
That's just like shoving peopleforward, because then they can
take that like internal locus ofcontrol, that intrinsic
motivation and drive, towhatever they do next.
That's one of the mostimportant things we try to
kindle.

Speaker 2 (59:12):
That is beautiful.
And what about books?
Any favorite books that havebeen really impactful for you in
your career?

Speaker 1 (59:18):
A ton so the book that I think everybody should
read is Thinking Fast and Slowby Daniel Kahneman.
Him and Amos Tversky are the uhcreators of the field of
behavioral economics.
It's like much more in ourzeitgeist today than it was when
I read it when it came out overa decade ago.
Um, but it's like how humansoperate and why do we I already

(59:42):
act?
Why do we act in these veryirrational ways, sometimes
Predictably Irrational isanother great book in that
category Nudge by Richard Thaler.
I think there's a bunch ofinteresting things in the
behavioral economics world thatonce you start to understand,
you're like, oh yeah, that's whymy reps do this, that's why

(01:00:04):
these people operate this way.
So those are all great books.
Uh, the book servant leadershipis is a really good one.
Messaging, I love made to stick.
That's one that I recommend alot.
And then, uh, atomic habits isanother one that I recommend to
every rep that works with us,every one of my leaders.

(01:00:25):
It's like something we steerinto.
The other one that's on myleadership mandatory list is the
Obstacles of the Way by RyanHoliday.
So those are some of thestarter.
That's like the starter Starterpack.
Kyle Norton leadership starterpack.

Speaker 2 (01:00:42):
Yeah.

Speaker 1 (01:00:44):
To get people going and I got to update my reading.
I published my longer readinglist a bunch of years ago.
I have to do a big update andput it on LinkedIn, but I'll
make that commitment.
I'll do that in the next coupleof weeks when this comes out.

Speaker 2 (01:00:57):
There we go, there we go.
We've got a commitment out ofit.

Speaker 1 (01:01:00):
Yeah.

Speaker 2 (01:01:00):
And Adam co-founded and is the CEO of Owner.
He's a Teal Fellow.
I'm curious what is it like towork for someone that is a Teal
Fellow?

Speaker 1 (01:01:13):
So I don't know if it's because he's a Teal Fellow
per se, but Adam has really setthe standard for what I think
the bar is to be a founder andbuild a generational company.
I've gotten the opportunity towork with really great founders.
The founder at League was likea third-time founder two super

(01:01:34):
successful experts.
Obviously Toby is like the goatI have like still any podcast.
He does anything.
He writes like I read and Ihave insane respect for him.
But I never got to work withsomebody in the early stages of
their journey.
Adam was like 23 when I startedan owner Crazy and so I got to

(01:01:57):
see like what the raw buildingblocks were of somebody that I
think has the opportunity tobuild like a truly great company
which has been reallyinformative, and so, like one,
he was just a force of nature,like just this insane drive and
presence and willpower and workethic Like I nobody it's funny

(01:02:18):
like nobody had ever made meself-conscious about the amount
I worked until Adam.

Speaker 2 (01:02:23):
Cause I was always like the hardworking guy.

Speaker 1 (01:02:25):
I was all I was always outworking everybody, and
so it was like a weird.
It was a weird thing to be likewhoa, like I'm not the
hardworking guy anymore, likethis guy is sort of running
circles around me because he'sjust like an absolute machine
and so like he's a force ofnature and very charismatic,
he's a great recruiter that Iput into this Since meeting Adam

(01:02:47):
.
This is like my new founderevaluation framework Are they a
force of nature?
Are they a supercomputer?
Do they just have like not justare they really smart, but are
they like freakishly smart anddo they learn at an obscene rate
?
And so the story I always tellabout Adam is like I mentioned
this book offhand Made to Stick,that book about messaging.
We were on a call and talkingabout messaging.

(01:03:08):
I'm like, oh, there's a bookmade to stick that I really like
.
And then he texted me 18 hourslater and was like hey, I read
that book and then had all ofthese questions.
So it was impressive.
He read a book in in likeliterally less than a day, but
then he was drilling me withthese questions.
I was like man, these arequestions that I should be
getting from somebody who's likea deep product marketing expert

(01:03:28):
who's got like years and yearsof building sales messaging.
He had like really cut to thecenter of the first principles
of that book and was asking mereally hard questions that I had
never gotten about the book andso that was like okay, like
supercomputer.
Then founder market fit was theother thing, like is there some

(01:03:49):
reason this founder should winin this market?
Yeah, adam built owner for hismom, like he's so deeply
passionate about about uhhelping small businesses and and
he like still so close to thecustomer and has such a crazy
customer intuition because hedoes care and I think it's
really hard to to break throughthe 20, 30 million ARR mark

(01:04:13):
unless you like have that uhtrue founder market fit in that
founder secret.
And the last thing is is enoughhumility not to blow it all up,
because I've seen a bunch offounders that have a lot of the
other stuff and the Venn diagramof force of nature,
supercomputer, founder marketfit and also humility that

(01:04:37):
sliver of the Venn diagram ofhumility overlapping is a very
rare one, but they need to haveenough intellectual curiosity
and humility to, when you hirelike senior leaders, to actually
like give them the rope to gothe amount of CROs that I talked
to that complain that their CEOis like way deep in the weeds

(01:04:59):
and making sort of weirddecisions on stuff that they
like don't have a ton of contexton is like crazy, because they
don't trust and they don't havethe humility to be like okay,
like I wanted this person tolike make these decisions and
adam has done like I'm verygrateful for the rope he's given
me to build, build this thingand and I and so you see it, the
like I don't know if it's anemployee count number, it's like

(01:05:20):
an ar number, but it's like the10 million ar number, like 100
employees, whatever the is.
Things just start to like frayand fall apart for those
founders who can't touchanything anymore, touch
everything all the time now, andso like that humility piece I
think is really important andAdam's done an admirable job

(01:05:47):
listening to feedback from thepeople in his network and and
being open-minded about thisdecisions we make internally and
he asks thoughtful questionsand he will go founder mode on
stuff he feels good about andwhen he does the founder mode
thing, I'm like all right, likehe, cause he doesn't do it all
the time and when he does ithe's like being right almost all

(01:06:07):
the time.

Speaker 2 (01:06:08):
Right.

Speaker 1 (01:06:09):
And so you just got to trust and be like, okay, he's
got some insight, someintuition.
I don't have the customerintuition of this specific thing
like he does.
That's why I chose to work forhim.
But there's enough of thehumility there that it all works
and it's something around.
I'm curious on people's opinionon this, so shoot me a note.

(01:06:31):
But like it's like 100employees or something around
there when you can't touchanything anymore, but the
founder still is trying to holdon to everything, like with an
iron fist, and it just allstarts to fall apart.
You can't keep great people.
You can't keep great people.
You can't attract good people.
Now you're like being pulled intoo many directions, but that's

(01:06:52):
a pattern that I've only pickedup on in the last like three to
five years, but now I see itall the time, all the time,
interesting, interesting.

Speaker 2 (01:07:01):
Yeah, that's incredible.
And where can people find youif they want to follow along?

Speaker 1 (01:07:07):
On LinkedIn is the best place, or follow the
podcast if you really want to godeep on revenue leadership
stuff.
It's me going usually superdeep on one topic that that
person is an expert in.
It's a lot of fun for me.
I would probably do it ifnobody listened, just cause I
learned so much every week.
Um, and it's, uh, the revenueleadership podcastcom.

(01:07:30):
That's the newsletter of thepodcast.
They're all there.

Speaker 2 (01:07:32):
So it'll be in the show notes for anyone who has
not read or listened to it.
Highly, highly recommend it isincredible.

Speaker 1 (01:07:38):
Thank you very much, appreciate that.

Speaker 2 (01:07:40):
And.

Speaker 1 (01:07:40):
LinkedIn and.
Yeah, I have now moved to SanFrancisco and dealt with a whole
bunch of stuff over the summer,so I will be back on the
content generation horse soon.
It's funny, I have a widget onmy phone like a Todoist button
so I can jot down ideas as theycome.

(01:08:02):
So I was running today and Iwas trail running, so I'm trying
to scrape my phone out of mypocket to put this idea in.
So I've got a backlog of thingsthat I want to talk about, uh,
that I'll start to start to jotdown.

Speaker 2 (01:08:14):
That's amazing.
We'll look out for them.
We'll know the the, the cure,the purest kind of ideas have
come from.

Speaker 1 (01:08:20):
If you can hear me panting through the newsletter
that was one of these.
Yeah, on a run or on a bike.

Speaker 2 (01:08:27):
I love it.
Well, thank you for joining us.

Speaker 1 (01:08:29):
This has been fantastic Thanks for having me.
This was fun.

Speaker 2 (01:08:30):
It was a pleasure.