September 2, 2025 • 45 mins
Andrea Kayal, a seasoned go-to-market leader with experience as both a CMO and CRO, shares her unique perspective on bridging the gap between marketing and sales functions while making the transition to C-Suite leadership. Having worked across some of the fastest-growing B2B SaaS companies, Andrea reveals the critical mindset shifts that separate functional VPs from true C-level executives.
• Appreciating the art of sales requires hiring professionals who truly understand deal management and negotiation
• Using passion, curiosity, and grit as key indicators when identifying top talent during the hiring process
• Shifting focus from team metrics (pipeline) to business metrics (EBITDA, cash burn, rule of 40)
• Developing foresight to plan 3-5 years ahead rather than focusing only on quarterly results
• Making capital allocation decisions based on unit economics rather than traditional growth playbooks
• Expanding peripheral vision by studying competitors' strategies and identifying new revenue opportunities
• Aligning compensation structure with long-term business health metrics, not just functional KPIs
To learn more about developing executive leadership skills, check out Pavilion's CMO school where Andrea teaches sessions on the differences between functional VP roles and C-suite positions.
Music by Ben Cina & Ayler Young
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 2 (00:05):
Hello everyone and attempt to create clarity in
(00:27):
terms of what good looks likefor current and aspiring sales
leaders.
Today, I am fortunate to bejoined by Andrea Kael, a
seasoned go-to-market leader whohas held both CMO roles and CRO
roles across some of thefastest growing B2B SaaS
companies.
Andrea has led DemandGen, builtmarketing engines from the
(00:50):
ground up, later transitionedinto owning both sales and
marketing as a revenue leader.
Now I know Andrea for hercandor, her directness and
ability to cut through the noise, which is great.
Andrea is now the CRO of HelpScout, a CS platform, and she
shares her experience teachingPavilion's CMO school, where one
(01:12):
of her most impactful sessionscovers the real differences
between being a functional VPand stepping into the seat of
the C-suite leadership position.
So, andrea, welcome to PillarTalk.
Speaker 3 (01:25):
Thank you, Rick.
Appreciate you having me.
Speaker 2 (01:28):
So, andrea, sales and marketing are often at odds.
There's some finger pointingthat tends to happen, some memes
and jokes that can come up fromthat type of thing.
From your vantage point, how doyou go about blaming yourself
when things aren't going great?
Speaker 3 (01:43):
Well, I never blame myself, of course.
I find that the leaders whoI've worked best to like kind of
combat that like fingerpointing where we've agreed on a
shared language about when thehandoff, when it's appropriate
to make the handoff betweensales and marketing, they're
like very specific.
We call them like you know, anSLA around what quality means
(02:08):
and we're like very specificabout that.
So up until opportunity, salesreally doesn't care because
that's all marketing's domainand we're really working to kind
of like nurture that until itmeets the qualifications, that
we believe is like ready forsales.
And then at that point salesagrees because it met the
criteria and that's when thehandshake happens, that's when
an opportunity is created and wereally find that like the
(02:30):
finger pointing kind of likedissipates because we've all
agreed beforehand.
This is what makes somethinggreat.
Speaker 2 (02:35):
I've always collaborated really well with
marketing.
My primary background has beenin the sales side of things, and
it has always been fun, though,and playful, to sort of have
that tension that exists wheremarketing is known for, you know
, success being measured in thegenerating of leads and then, of
course, sales being measured insuccess with the closing of
deals, and of course it's likethere's the, you know, the SLA
(02:57):
type of environment that youdescribed, which needs to exist
so that we can celebrate thesame thing.
But it is fun.
I can recall certain times whenI've been on an all hands and
like things are not goingparticularly well in the
business and marketing iscelebrating because they're at
like 117.
So it's just very funny.
And now you're in a positionwhere you own both.
And so you know, hopefully thathelps provide a lot more, a lot
(03:18):
less friction in creating thecohesion.
Speaker 3 (03:20):
It certainly does, and for all those years I've
been beating up my salescounterparts.
I'm regretting that a littlebit.
Yeah, well, I would have gotteninto that a little bit.
Speaker 2 (03:30):
You've been in both seats, which I find to still be
pretty rare and giving you aunique perspective.
Is there something you know?
Your background originally wason the marketing side, when you
started to own sales.
In addition, was there onething that stood out and
surprised you that you hadn'tanticipated?
Speaker 3 (03:47):
Well, the one thing I don't know that it surprised me
, but got validated was you know, I've always, like, had a lot
of respect for my salescounterparts, but truly, there
is a very obvious art to salesthat you really can't teach.
I mean, you can teach it,obviously, because you know
people come up through the game,but I, I I always knew that if
(04:10):
I was ever going to take thisrole, I was going to need to
hire a professional who knowshow to sell.
I learned from him every day.
That includes, like salesprocesses, deal management,
pipeline management, the art ofthe deal, how to negotiate for
certain things.
You know that those are all, Ithink, skills that I still I'm
learning and so really justappreciate more and more being
(04:33):
in the CRO role, what it takesto be a sales leader who really
excels.
It's, it's, it's difficult, andso, yeah, I have a lot of
appreciation for that now.
Speaker 2 (04:41):
I bet you're learning faster than you give yourself
credit for.
Speaker 3 (04:44):
I don't know, you know, sometimes I, you know, I
like to think, oh, I could haveclosed that deal, you know.
But I think back to how thedeal was then constructed and
I'm like, wow, this is smart,you know.
And so I think it just takesyears of learning how to be
really good at sales and cannottake it for granted anymore.
Speaker 2 (05:07):
Well, to your point, when you see something that's
put together whether it's a dealor a project, and you see like,
wow, that was really thoughtful.
I wouldn't necessarily havethought of that, those are like
some of the best moments as aleader, right.
Speaker 3 (05:16):
A hundred percent, yeah, and but you know I've
never, I was never the bestmarketer either, rick, like I, I
, I think my, my talent isprobably more on like knowing
how to hire people who are justbetter than me at all these
things.
Cause you know there is, yeah,there, a lot of these roles and
go to market are, you know, sortof like undervalued, I think to
(05:38):
some extent, because you'relike, oh, you're just like an
account executive, or you knowjust how hard does it hit to hit
the quota.
You know it's like they're allreally challenging, like content
marketing, product marketing.
These are all reallychallenging roles.
So to find people who are likereally good at them, I think, is
just my job.
Speaker 2 (05:54):
Now is that ability to identify talent?
Do you feel that is a result ofan increased time investment in
terms of doing the work?
Is it a you know?
You feel like you have astrength in identifying it a
little faster than others.
Like what do you attribute yoursuccess in getting those people
that can do the thing reallywell to?
Speaker 3 (06:16):
I think it's two things.
I have a profile I like to hirefor.
This may not be like a surpriseor novel, necessarily, but the
three characteristics that Ithink like show up in an
interview when they're able toarticulate passion, curiosity
and grit, which I thinkcuriosity, in particular, is
going to become the mostimportant skill as AI continues
(06:37):
to be like on the rise how toask good questions and get good
answers.
That is like that's what I digfor when I'm in.
Are they asking me goodquestions?
Do they like dig below thesurface layer of this job to
really understand, like, what itis they're going to do and how
they're going to make an impactis one so like passion,
curiosity and grit.
The second is demonstrating atrack record of success and
(06:59):
having done the role, I giveeverybody a project.
Show me how you did this inyour last company.
So, for the sales hire I madebecause that is not my strength,
as I mentioned, I think I had30 interviews.
I went through like I don'tknow 15 projects.
Out of those 30 interviews,really, only two of them could
articulate their track record ofsuccess in a way that made me
(07:22):
feel like wow, this person getsit and they're going to cross
here because they just showed methey can do it.
So this is a message to salesleaders listening like get good
at storytelling like your, youknow your success record Cause I
think that ends up putting youabove the noise.
Speaker 2 (07:35):
I have to concede that, like, while I feel you
like, sometimes it takes 30interviews or 30, you know first
interviews in order to get thelike caliber of talent that you
want.
Yeah, finding the time to putthat in can be extremely
difficult.
It's so easy and tempting tolike shortcut it over, rely on
referrals and somebody that'slike you've heard from somebody
(07:56):
else is already good.
It's tough.
Speaker 3 (07:58):
It's really hard.
I want to shortcut it everytime, but it's my, it's my job
and I think if you're beinghired at C-level um, if you do
not have a good track recordbringing in high quality, high
bar setters to the company, youend up losing trust of, like
everyone else in theorganization.
So I think putting in the timeis is so important because if
(08:20):
you're managing those people aremanaging people getting that
wrong, very costly, like veryproblematic.
So do the work.
Speaker 2 (08:29):
Curiosity.
I understand how you test forany like fun little tips around
passion and grit.
Speaker 3 (08:34):
You know, I think passion like kind of shows up in
their curiosity, because youcan and maybe this is just like
a feeling, I don't know, but theway that somebody is like
talking about how they likesolve problems, you kind of feel
like is this person just likechecking boxes, or are they like
you know, just you know BSing,or if they're like you know what
(09:07):
this is going to be, somebodywho's going to be a good culture
fit, because they're reallygoing to dig in here.
Speaker 2 (09:12):
Yeah, I have.
I have trouble testing forpassion because I'm, I'm, I'm
explicitly passionate, likeeveryone who speaks to me can
quickly see that I'm high energyand.
I'm excited and so I candemonstrate passion more easily,
but that doesn't mean that thepassion that I have is better
than the quiet intensity.
(09:34):
I agree, yeah, situation whereI was reluctant to hire somebody
that was known to be the best,and everyone you talk to view
this individual as the best, andin my interaction with this
individual, they were verycareful, very careful, wouldn't
say one more word than wasnecessary.
And so if you're like lookingfor people like yourself, that
(09:57):
all of a sudden, all the redflags are going off, alarms are
going off and you're like gosh,I'm not sure this person has the
passion.
Now I was fortunate to make thedecision that I don't want
people that are exactly like me.
And I'm going to take all of thevariables into play and we
brought this person on and whatI learned was there are many
(10:17):
forms of passion.
Passion yeah, this is the mostintense, competitive individual
held themselves to a standardthat I could only aspire to one
day and is an absolute winner.
And so I was like, wow, lookingback, was there a way that I
could have tested for thatintensity beyond the hands?
You know, moving the decibel,volume of the voice.
Speaker 3 (10:40):
Yeah Well, rick, I actually think you kind of like
mentioned it in that.
But even just asking thequestion, like you know how
right, maybe I'm just testingfor like their external, like
(11:08):
mannerisms in terms of how theylike exhibit passion.
But I think people were askingquestions who are like involved,
who seem to just like want toknow about the role that they're
going to be involved in.
And, yeah, maybe I'm conflatingpassion and curiosity.
But where the dialogue feelslike the person is interested
beyond just the surface levelquestions I'm asking makes me
(11:29):
feel like OK, they're going tobe, they're going to fit in here
.
Speaker 2 (11:33):
Yeah, and then a grid , of course, if you're actually
successful in giving a projectand allowing people in to
provide coaching and you cansort of see whether they get
resigned.
It doesn't go well, or want todouble down and do all of that
and maybe passion.
Speaker 3 (11:45):
Yeah, and to what degree did they put into the
project right, Like that's great, Cause they're like I'm going
to, I'm going to get this thing,I'm going to set the bar for
this.
It means like they just workedharder than the next person to
kind of, and the person we justhired for like paid media, was
just that.
Speaker 2 (11:59):
I'm like wow this person went way above the other
presentations that came in interms of the quality of
information that they were ableto share.
Is it translating?
Are the folks?
Speaker 3 (12:14):
that you've brought on to be, you know, meeting an
exceeding expectation,surprisingly.
Yes, you know also surprisingly, but that's the answer is yes.
Yes, it's yes.
But also you know I, I alsodedicate a lot of time to make.
I would drag these people overthe line too if they weren't
getting there.
You know I am committed oncethey I do hire them to making
sure you know they're successful.
I'm a very like involved.
(12:36):
You know, leader, I don't justlike leave them to their own
devices.
You know I do provide a lot ofsupport to help that.
Speaker 2 (12:42):
I mean to me it's like kind of the most important
thing, right, like we can't.
We enjoy our work.
I this is like a theory weenjoy our work mostly based on
who we work with.
Speaker 3 (12:52):
Yeah, a hundred percent.
Speaker 2 (12:53):
Yeah, the mission is super important.
Speaker 3 (12:55):
Like.
Speaker 2 (12:55):
Hey, are we doing something we believe in?
Sure, the being on a winningteam matters a lot.
When you're succeeding, itfeels really good, but it's like
the grind day to day is thefolks that you're working with
and you are working with peoplethat inspire you, that you learn
from that hold themselves tothe same standard as you do.
Speaker 3 (13:15):
It's hard not to like work A hundred percent.
And you know what I will say.
I leave this one off because Idon't know how people will take
it, mostly because I don't wantto think people.
I'm not hiring people becausethey're not funny, but when
they're funny that makes all thedifference in the world.
Because if you can laugh aboutall the, if you're working in a
startup, you have a fire to putout every single day.
You need to be able to likelaugh about it.
(13:37):
You know you're taking a lot ofhits from all directions and
you know you need people who cankind of like shake it off and,
you know, laugh through it.
So I also think that helps alot.
Speaker 2 (13:45):
Yes, sense of humor is Sense of humor.
You know, you teach thedifferences about being a VP or
even SVP.
You know level and thenstepping into a true C-level
role and I want to dig into thisa bit.
Like what do?
Speaker 3 (14:08):
people miss about that shift until they're in it.
I think there are five thingsthat I wish I knew sooner or
coming up in my career, that nowthat I'm whatever going to be
45, I feel, like you know, Ihave this, like this wise old
sage you know because I've beenin startups for 20 years which
feels like I don't know, like Indog years that's 140.
(14:29):
A hundred percent, that's howmany years it feels like I've
been working.
But there's like five coreprinciples that like
differentiate a VP from a C.
And by the way, I'm using thetitles sort of like as examples
C-level means somethingdifferent in every company, but
(14:50):
I just mean like when you becomesomeone who is at sort of like
this executive level, where youbecome the peer to the CEO and
you're like running the businessalongside of him or her in
whatever capacity.
In whatever capacity, there area few principles that I think
are the difference between thefunctional role you have which
could be revenue, marketing,customer success or chief
(15:10):
operating and the actual acronymbefore those functional letters
, which is the VP is themanagement layer, the C is the
management layer.
And in that management layer,the first thing that I think is
like really important are justlike that you're operating
against business metrics, notteam metrics.
Your team metrics, for example,your chief marketing officer
(15:33):
you care a lot about pipeline.
You're going to be asked aboutpipeline and how much revenue
you've contributed from amarketing perspective.
But business metrics is likeEBITDA, cash burn, rule of 40,
gross margin, like those areactually what I'm gold against
now.
So very important that we getto pipeline, because marketing
reports into me very important,that we hit our sales numbers,
because sales reports into me,partners, that we hit our
(15:54):
partner number.
But, like the end of the day,if we are burning more cash than
we can consume over a longperiod of time, the business is
going to be in big.
We're going to have a problem.
So, as the C, I care aboutthose metrics as, like the
functional leader, I care aboutsome of the others.
So that's one way of thinkingabout my role like business
metrics, not team metrics.
(16:14):
The second is foresight.
I don't think that functionalleaders, like at the VP level,
necessarily have the like,sometimes the goal, or like even
the skill set yet to thinkabout where does the company
need to be in three to fiveyears.
I use a framework which isbasically called the iconic
(16:37):
enterprise five to help me thinkforward about where the
business is going and that helpsme set the revenue strategy.
But you should be thinkingabout this at the VP level.
I just don't think it's a skillpeople like think to do.
But you should be saying infive years and I can share this,
maybe you can include it in anyof the file material, rick, but
(16:59):
it's a really cool way of likeestablishing, like, the
valuation of the business in afew years, because everyone's
job at a tech company is toincrease enterprise value for
the organization.
That's the job, and you do thatby making sure that, like in X
years time, you've hit certainmetrics that make the company
valuable and Iconic uses, fivemetrics that signify value, and
(17:21):
that includes things like youryear growth rate, ndr, rule of
40, magic number, arop, fte.
So there's like five metrics.
They're saying like if you hitthese numbers when you're in
this revenue band, this is whatour top decile and median decile
of companies that are highestvalued, look like and they have
some of the best companies inthe world in their portfolio.
(17:42):
They have like Canva andSnowflake and Datadog.
I mean so, but they're like,look, if these are like the best
businesses in the world andyou're mapping up to this like
you're creating a lot ofenterprise value there.
So so that's the second one,which is like foresight.
I'll stop there, like, becauseI could go on and on and on for
like hours and hours, but likethose are two that I think are
(18:04):
you know.
Speaker 2 (18:05):
Well.
I think there are two greatones.
I think what I would do is thensay how does this manifest
itself in your day-to-daydecision-making?
So let's take the managementlayer, and I like the idea of
you know you focusing a bit moreon business metrics.
Take EBITDA as an example whichyou wouldn't think of the CRO
as mostly being EBITDA focused.
But hey, if you're a C-levelexecutive, like profitability of
(18:26):
the business like reallymatters.
It's not just growth at allcosts anymore, all business like
really matters.
It's not just growth at allcosts anymore.
All of that.
I get the fluency and awarenessaround that.
How might that change yourbehavior as the C-level versus
the VP of sales, as an example?
Who's got a quota to hit?
Speaker 3 (18:41):
Okay, well, let's say you're the VP of sales and you
don't care about cash burn orEBITDA.
You're adding as many reps asyou can possibly add and you're
asking marketing to spend asmuch money as they can in order
for you to get the quotacoverage you need in order to
hit the goals.
If you don't have the check andbalance on the money, okay, add
more people.
Well, you know you could addmore people, but every time you
(19:01):
add an AE, you're contributingto burn because they don't ramp
for five to six months.
So, should you add AEs, maybeyou add an AI, something that
you know helps.
Maybe the current AEs you havebe more productive.
So it does change your decisionmaking if you have the control
on the other side that you knowthat keeps you focused on cash
(19:22):
burn Marketing.
If I could get Help Scout to ahundred million, like I don't
know, in like two years, if Iwas, like you know, like
shooting the money gun around.
But we aren't running thebusiness that way.
We care about cash burn becausewe want to get to profitability
first.
Then we want to like, figureout how we like scale versus
(19:42):
just, you know, the other growthat all costs number.
So it does matter a lot.
Before I add a single person toheadcount, I'm figuring out how
do we get this job done withless people.
I add a single person toheadcount.
Speaker 2 (19:53):
I'm figuring out how do we get this job done with
less people.
So if cash for I still perceive.
Speaker 3 (20:02):
the C-level execs are often gold, similarly than the
VP.
I am not.
Yeah, I am not.
My compensation is comprised ofnew revenue at like 30%, which
is typically where a VP of salesis at a hundred percent of
their OT.
On new revenue, um, I am goldon NDR because that's, you know,
has to do with the expansionand churn in our base, and I'm
gold on cash burn 30.
(20:24):
So it's 30, 20.
No, what is it?
I don't know, I can't do math.
It's like 30, 20, 40.
Speaker 2 (20:33):
Wow, okay, so, yeah, so you 30, 20, 50.
So you're caring just as muchabout cash burn yeah, more than
you are about sort of newbusiness.
Yeah, so I think that is oneaspect where C-level needs to
think that way, but it helpswhen their goals are aligned
with thinking that way.
Speaker 3 (20:51):
Exactly, yeah, I mean true CRO, probably I'm really,
I think, not imbalanced, but I'mjust as incentivized to make
sure we are running a healthybusiness than, as we are, a
fast-growing one.
Speaker 2 (21:06):
And then on the foresight example, I love, love
this kind of framework of youknow, growth metrics, NDR, rule
of 40.
You're talking like netretention, right?
Speaker 3 (21:20):
Net dollar retention, yeah, and they're saying, like
you know, look, if net dollarretention is 105 percent when
you are a 25 to 50 millionmillion business, you are in the
median decile of their entireportfolio company in terms of
values that they've driven fromhaving 105% NDR.
You know, like you, if you godown and you check the boxes on
(21:42):
all the numbers that they havethere, well, you're just as
valuable as, like a snowflakeNow snowflakes in the top decile
.
So, okay, you're not going tomaybe compete with that
(22:04):
no-transcript, and that's thedifference.
Speaker 2 (22:14):
You need to make a valuable business, not just a
valuable moneymaker.
And so today, is there a way inwhich you're like making
decisions differently, or isthere a way like you're like how
is this manifesting in a changein your decision-making that
maybe you wouldn't have madeprior?
Because I do think there'sstill some validity in that
people don't people don't haveblinders on like I think that
most people, especially goodbusiness folks, generally have
(22:35):
an aversion to like let's justspend money to hit the number.
Sure, think about theconsequences.
Like I think people generallywant to do the right thing, um,
but so I'm kind of trying to getinto that next click down of
like okay, how does thisactually, how's this changed
your behavior in the way you're,you know?
Speaker 3 (22:53):
I'll give you two examples.
Speaker 2 (22:55):
Yeah.
Speaker 3 (22:55):
I'll give you two examples.
Um, so we have an ACV of $1,200, which means we can't add a
whole bunch of accountexecutives to go at or SDRs to
go after, upmarket or otherwise.
So I added a partner channelbecause we only pay when those
deals close through reselling.
(23:16):
So I needed to hire a directorof partnerships so that she
could get reselling off theground, so that that's a whole
new channel to open up but thatwe don't pay for and there's
exponential growth.
Would I have added a partnerchannel if we could go directly
after the money and didn'tnecessarily not care but cared
less about the unit economicsfor like adding account
executives, like absolutelywould have added direct because
(23:38):
you control that you have likemuch more.
Speaker 2 (23:41):
You train them, you certify them.
Yeah, all the reasons.
Speaker 3 (23:46):
Exactly For all the reasons, you have an inside
sales team and it's very likeMachiavelli and like to say like
oh, say, oh, you want to ownyour army, but sort of because
of this reason, but once that'sopen now we could scale without
cost.
So that's one.
Speaker 2 (24:04):
That's a great example of going a partner route
due to the ACV rather than theinstinct of building direct.
Speaker 3 (24:10):
Exactly.
So that's a decision I madespecifically because of this.
The second is on marketing.
We have a when I was atElectric because the ACV was
$40,000, we could test and growusing a bunch, bunch of
(24:32):
different activities likeprimarily being like events,
which is like a higher costthing.
So we did I don't know maybelike 100 events at Electric, but
at Help Scout I'm just doinglike smaller, more highly
targeted events where we're likedoing we're doing like a lot of
(24:56):
like ruthless work around, likemaking sure exactly the ICP
gets there that we want to see,and they're like they're much
different, they're like muchsmaller, they're like more
intimate, and so we just like wehave to organize tactically
around, like some of themarketing efforts, because our
ACV is different and because weneed to like definitely get a
return out of every single thingwe're doing.
So, even tactically, my approachto like events or paid search,
(25:20):
or affiliate marketing,newsletters, direct mail,
sending like it all just changedin light of the ACV and like
the market we're going after.
So that's how it changed on themarketing side.
Speaker 2 (25:33):
It sounds like there's a lot more trade-offs to
make.
I mean, how are you makingthose Like?
What approach are you taking tomake those trade-offs between
investment ideas or peoplestrategy and so on?
Speaker 3 (25:44):
Yeah, I mean, you know we're just good about.
First, the marketing budget ingeneral is fixed against
generally like our paybackperiod, um.
So so our cac payback period isone of the like metrics we use
to say like what can the totalbudget be?
(26:04):
We, we don't want to kind oflike get outside of that um, and
then the marketing mix isreally optimized against which
one of these channels is likethe most productive.
So we don't have every channelon.
We have like very specificchannels on.
At Electric I could really haveevery channel on because you
know some of them just workbetter than they're working at
(26:25):
Help Scout because it's morecompetitive, and then some of
them are just too costprohibitive.
So it's all, yeah, it's alljust around the unit economics
of like what's working.
So that's kind of like howwe're limiting the scope of what
we do.
Speaker 2 (26:41):
When you teach folks about the difference between VP
and C-level.
I mean what you're describingis a lot of the logic You're
describing, like the metrics.
You look at these metrics, notthose metrics.
For these reasons, all prettyobjective, all reasonable, all
sort of logic-driven.
I think there's also perhaps anaspect of I don't know, it's
like the mental sort of sidearound the thinking that way or
(27:05):
graduating from a more tacticallevel of thinking day-to-day to
trying to put into practice,like what are the things I do to
focus on these bigger levelmetrics that aren't maybe
directly within the control of afunctional area but it's across
the harmony across multiplefunctional areas, like was there
a pivot point or a switch thatflipped for you that helped make
(27:25):
it easier for you to sort oflive in that, in the logical
environment you just described?
Speaker 3 (27:35):
to sort of live in that, in the logical environment
you just described, I meanmaybe just 20 years of like
mistakes or like living with it.
You know, I did notice, though,in my role as CMO, I do think
like a lot of tech companieslike to fill like a lot of the
functional roles at the C-leveland again, I'm talking mostly
about companies that are underlike $100 million or $50 million
or below.
So this obviously changes whenyou get massive.
(27:58):
But if you're in that range, Ithink the flip was switched when
I'm like wow, I have a bunch ofthese very senior counterpart
and we're all having to makestrategic decisions that could
be in conflict with each other.
And so I just thought to myself,what if there was one arbiter
(28:21):
of like the revenue strategy andthen you just like hired a
bunch of like great lieutenantsbelow that to really just like
nail the function, below that,to really just like nail the
function.
So I because I saw like, ifit's, if it, there's too many
senior people just like the CCO,the VP of marketing, cmo of
marketing, the head of saleswe're all like trying to like
(28:44):
create revenue strategiestogether with our own like
separate goals, and that endedup becoming like a lot of bloat
and and like very disjointedstrategy, I would say, for lack
of a better term Despite thefact that all my partners were
like amazing and smart.
I think the flip switch for mewhen I like was thinking about
(29:05):
this from the view of the CEOand I'm like, holy shit, he has
to like really figure out who tolisten to here, and this like
mix of people.
Speaker 2 (29:13):
So translate connection points between all
the good ideas.
Speaker 3 (29:16):
Exactly and I'm like there's no one like helping to
do that translation and thenjust go to the CEO and say, look
, here are like the things Iheard from my lieutenants, who
are all very smart people butlike very functionally focused.
Here's how I'm translating thatfor you into something that's
cohesive and this is why I go tothe foresight.
(29:37):
Or like the revenue strategy,where I'm saying like this is
when I started at Help Scout, Icreated the revenue strategy,
which was just like one personwho was saying to Nick look, I
think we need to add moreconsumption-based pricing.
We don't have that today, Ithink and you know, rick, I mean
you're in this role at yourcompany but you're saying here
are all the ways in which wegrow this business.
Let's pick together versus thatcoming from four different
(30:01):
people.
And then he or she is like waita minute, how do I then become
the CRO, for lack of a betterterm?
You put that work actually onthe CEO and it's a hard job
because that's not really wherethe CEO should be focusing their
time necessarily.
Speaker 2 (30:19):
Right, this is not about.
You know, it's funny,individual contributors often
sort of shovel their problemsonto their manager and then the
manager has to run around andsort of fix it.
What you're describing is wherefunctional leaders are
shoveling their strategies ontothe CEO, left in a world where
they have to sort of, and thengreat leadership is more about
not enabling that dynamic andturning into a flywheel of
running around and fightingfires and being reactive to it,
(30:39):
but a sort of forcing mechanismin which to create an
environment where folks are ableto not be reliant upon you, the
leader, and able to do that,and so that's a great example of
it happening at a more elevatedlevel versus down.
You know, on the day-to-day.
How do I differentiate this?
Speaker 3 (30:55):
or, you know, run this campaign or whatever it is
Exactly, and I'm happy to be thefunnel this way.
You just can't be the funnelthat way.
You know like you need to, youknow everything needs to come
into you and you need to.
Just well, I don't know if it'seven a funnel the other way,
but like it's just a conduit ofthat funnel, just saying like
now I've distilled everythingand, like I said, this is why
(31:16):
hiring is so important.
You're taking all thatinformation from the ground
level and then you just becomethe arbiter of, you know,
information about what thatstrategy should be to the CEO
and they can decide, but they'renot having to decide and then
go through that with fourdifferent people.
Speaker 2 (31:31):
So I still believe the easier people take generally
the easier path and the easierpath Generally it's not like a
bad thing, it's just the waythings are.
The easier path is to sort offocus on the narrow metrics
within the things that you cancontrol and to demonstrate the
behaviors of what we'll callfunctional execution.
Speaker 3 (31:46):
Right.
Speaker 2 (31:46):
That's just the general like inertia of how
things are going to go and so wecan talk a lot about.
Well, you need to thinkdifferently and you need to look
at different metrics and youneed to have an action plan that
connects to other functions andlike that, all sounds really
good.
People want to get there.
They go to CMO school and theygo to other schools growth and
they listen to this podcast as away to aspire to be more senior
(32:08):
.
I guess, what advice do you endup giving to someone that's
looking to make that transitionand to try to up-level their
thinking?
You know, in the way youdescribed.
Speaker 3 (32:18):
So, outside of just like making sure that, like from
day one, you know that your jobis to think about the business
metrics and then think about howyou're looking at longer term
so that you can plan headcountand you can figure out how
you're looking at longer term,so that you can plan headcount
and you can figure out howyou're going to get there.
Whether that's adding a BDstrategy today so that it
produces in two years.
Whether that's adding PLGmotions so that you don't need a
whole bunch of AEs to sell thething and you can move down
(32:40):
market a little bit.
Whether that's adding a partnerchannel, going indirect, going
up market, like whatever.
There's a list of probably like15 things a CRO should have in
their toolkit and that's on dayone.
You're like well, if we want tobe here in three years between
25 to 50 million, because we'reonly a five to $10 million
business now, here are the sixthings I would consider doing
(33:00):
and that's the foresight.
The other things that I I wouldconsider outside of hiring.
Speaker 2 (33:05):
Is that just a like, trying to narrow focus and
trying to think like like?
So is that the first thing youdo differently is to not worry
as much about the quarter thatyou're in, which is?
Speaker 3 (33:13):
what a lot of people are worried about.
Speaker 2 (33:14):
And it's actually trying to like.
Take a step back and go throughan exercise of like what does
success look like at the end ofnext year If you don't have to
go out five years?
Go out to the end of next yearand say, all right, what are the
things that need to be true inorder for us to be at whatever
level is defined as success?
Speaker 3 (33:31):
Exactly.
Yeah, because and let's justsay you you, you theoretically
went out three years becauseyou're using your FB&A team or
some help you're getting fromfinance to say, like, can we
build a fake model with justlike fake numbers in it that
show us what this business wouldlook like between, let's just
call it $50 million and nails,these metrics?
What would need to be trueabout the business today in
order to do that?
(33:51):
Because you could have highchurn, you could have an NDR
that sucks.
But you're saying, but in orderto get here, this is what the
NDR.
So, visually, people can startto paint the picture in their
head like, oh, wow, here's wherethe focus needs to happen all
around the org.
And that helps you put peopleinto seats, helps you think more
, like it helps you think, yeah,a little bit more broadly than
(34:12):
just the quarter here, becausethis quarter actually doesn't
matter at all.
It's like the quarter's over.
Also, if you're a marketer, thequarter this quarter is for
based on your sales cycle, likefor the next six months or
whatever.
You need to be thinking way farahead if you're a marketer, but
um, but so so the foreforesight helps.
So the three things are businessmetrics, not team metrics.
Make sure you like hire reallywell as like a.
(34:34):
That's a difference between VPand C Understanding the
importance of hiring.
The third is the foresight.
The fourth is capitalallocation.
Like that's the.
You know, the flow of money islike the LP to the VC, to the
CEO, to you.
That's the flow of money Everystep of the way.
(34:54):
Every single person on thatchain expects you then to have
made more money than they gaveyou.
So if you can't articulate tothe CEO or the CFO a plan that
makes them more money and whenthey're excited to invest in
like quit the job because that'sthe job.
It's like you are just a valuecreator.
You're like a hedge fund.
Like you wouldn't give yourmoney to a financial planner.
(35:16):
My financial planner was losingme money every time I gave them
another dollar.
Like we have to move the money.
So you have to think ofyourself in that way, because
that's how you're beingevaluated.
They give you one dollar, theywant three back.
That's it, period.
I mean that's on the PE side.
On the VC side they want 10back.
Speaker 2 (35:32):
You know, and that certainly happens over time and
you think that's an adjustmentfor folks is to be thinking that
way, do you?
I think so.
I don't think people.
As I listen, I'm trying to putmyself in the shoes of someone
in functional leadership andit's true, we do get caught up
in the minutiae ofinefficiencies that happen in
(35:53):
our business and things we wantto improve.
We want to improve the salesprocess, we want to improve our
search results, as an example.
There's plenty of things thatare inefficient about how we
work together or how thingshappen in the company, and it is
easy to have your compass benavigated by where you're sort
(36:15):
of feeling personal pain orwhere you see the greatest
inefficiency.
But that inefficiency isn'tnecessarily tied to what you're
talking about, which would bereturn on investment yes, beyond
impact, to profitability onrevenue, and I do sort of see
how even our instinct to fixthings as leaders right.
Speaker 3 (36:37):
We want to improve everything.
Speaker 2 (36:39):
It is often challenging to connect the
things we want to fix to whatwould move the needle for the
business the most, and I don'tknow that there's a science to
solve that.
But what I guess you'readvocating for is don't do it
independent of that.
Actually, try to determinewhat's going to move and ask
(37:00):
people like hey, I understandyou want to do these three
things, which one you know?
And people will beuncomfortable, they will not
want to answer which 100, 100.
But so how do you force them todo it like, how do you help
them with that exact?
That's a perfect example.
I have three things we have todo.
Great, we can only do one.
Which one exactly?
You will not get a directanswer to that.
They will hem and haw and tryto find a way to make it all
(37:21):
three.
What do you do?
Speaker 3 (37:23):
what do you do, and even an exercise I'm doing now
with the marketing team is I'mactually going to be the one
that sits at the top of theprioritization for the input
queue of things people areasking of the design team,
Because I'm like what if I wasprioritizing this with that lens
, Would we be doing bespokeblogger?
I'm like hell, no, we are goingto.
(37:43):
I'm going to have my head ofdesign now that I'm going to sit
at the top of theprioritization, figure out how
he makes the team of three sixby using bespoke AI generators.
Now you know.
And so, anyway, like I'm justI'm trying to go through, like
that's a practical example youcan do today is like figure out
what's coming in and are peopleusing that lens to like kick
(38:04):
things out and like make themnumber one or whatever.
The thing I'd say rick.
The fifth thing for the umthinking about vp to see is, um,
just peripheral vision, like inthe same way that I don't
necessarily think and, by theway, I I didn't know this, I
wasn't doing this either like inmy even up till 40.
These are things that, like,again, I feel like I'm old and
(38:26):
now 100 years in tech, butcompiled along the way.
So I'm not like I always knewthis and I was always doing it,
it's just like.
These are things I've feltalong the way.
But the last one is just aperipheral vision.
Are people reading S1s?
Do you know how yourcompetition has thought about
going to market?
Or are you thinking about howyou could just acquire that
(38:49):
business over there for amillion bucks and get their
whatever I don't know, like gettheir book of business If you
bought it for 4 million?
Cause it's like kind ofstruggling?
Like are you thinking aboutindirect or inorganic
acquisition Because, like that'sgoing to help you, like with
product, You're going to fill aproduct gap and actually, as a
revenue leader, you just added,like you know, a million bucks
(39:09):
to your book.
Read an S1, like figure outwhat people are acquiring and
like what people are doing andhow they're how they're growing.
And the S1 is the documentationthat gets filed before a
company goes public.
I think that's part of the jobtoo is just being like the SME
on your market, and maybe that'sobvious as an individual
contributor in marketing, but um, it always it wasn't natural
(39:31):
for me to like think that thatwas my job.
Speaker 2 (39:34):
And it is.
I can see again, like justspeaking of the I I, I overused
the term inertia, but it's likewhenever we get into roles
within companies, there is ageneral like trajectory
activities that we end up doingfrom the things that are closest
to us, which are inside thebubble of the company.
Your advocacy here is to likeas the more senior you get in an
(39:54):
organization, the more you'vegot to actually get out of the
weeds and look across thelandscape and say, hey, there
might be interesting things thatyour competitors are doing from
a go-to-market standpoint thatyou might learn from.
There might be dynamics withinthe industry that are happening
that you might need to be moreaware of, because your
individual contributors aren'tgoing to like be able to do that
.
They're on deal calls, tryingto close, and if you're not
(40:17):
doing it, no one is.
Speaker 3 (40:19):
Exactly.
And, rick, the specific exampleI can give here and I know
we're probably just at time, soI'll make this one quick but
when I was at UpServe, my mentorsaid to me did you read Squares
S1?
Because their fastest growingrevenue stream is instant
deposit.
It was basically a product thatthey spun up which made fees
off of restaurant owners wantingtheir money same day, like
(40:39):
Venmo does.
So they became a bank and I waslike holy crap, I'm like wow, I
thought we were competingagainst POS and they became a
bank.
And while we weren't going tobecome a bank, that was a big
unlock for me as a revenueleader, because I'm like you
want to talk about pipeline.
I'm like they became a bank.
You know, like that was likethe most obvious.
Like pick your head up, willyou?
(41:02):
We could have monetized allthese transactions in a
different way.
Wasn't even thinking about thatat all.
Speaker 2 (41:09):
So that's just one of the so that reset your thinking
, just in terms of like there'snot one way to skin a cat here.
Speaker 3 (41:14):
Like there's a lot of approaches we can take.
Speaker 2 (41:16):
We can learn from everything in the market's doing
and, yeah, the journey fromsort of different companies,
from marketing, to owning bothsales, to being a functional
leader, to a strategic leaderwe've covered a lot of ground
here.
So, andrea, I want to thank youfor joining us today.
I think we could talk for hours.
Speaker 3 (41:33):
Same.
Speaker 2 (41:34):
This has been great.
We'll continue the conversationand thanks.
Absolutely, Ray.
Thanks for having me.
Reflecting on the conversationthat we had with Andrea Kael her
journey from being a marketingleader to a revenue leader and
(41:54):
having responsibility over salesthat stood out to me.
She takes a fresh look at sales, having not been experienced in
that area before, so she makessure that she's hiring the right
leadership and ownership aroundit and she can spot what good
looks like.
She talked about having a lotof respect for a deal that got
structured and being veryimpressed by that and it made me
(42:15):
think that, like sometimes wehave the benefit of being able
to see what good looks like whenwe aren't super experienced in
an area and we should lean intothat.
I reflect back as a seller andwe should lean into that.
(42:36):
I reflect back as a seller.
We teach sort of when you'renew into an organization.
Generally a rookie within asales org asks a lot of
questions because they're notburdened by a lot of knowledge,
so they have to ask customersquestions and then, as they get
more experienced and become aveteran, they stop asking
questions and start telling howit is and can have actual
setback in their performance,because they're not.
They've stopped, they've lostthe curiosity and it's all about
telling people what they shoulddo and people might resist that
and I just kind of like how youknow, when you don't have
expertise in an area and you canbring curiosity to it, you can
(42:58):
really start to see what goodlooks like in a way where you
know from sales execution.
I have the bias of my ownpreferred style of doing it and
there might be a better styleout there and it might be hard
for me to see that and I likehow Andrea is able to see that
with a clear lens, especially asit relates to sales.
She also talked about thejourney of a functional leader
to a business leader.
(43:19):
This is a really important area.
We spend a lot of time talkingabout it.
To me, this all matches upreally well with the pillar of
ownership.
Can you be more about thebusiness and not just about the
team?
And there's a continuum of that.
And as you move up as a leaderbeing more about the business
and less just about the team isa growth curve associated with
(43:40):
it, and I think a key thing thatstood out in our discussion was
the incentive structure.
Andrea explained her incentivestructure in a way that matched
the business metrics and notjust delivering a number of
leads or not just hitting thenumber in revenue for the
quarter.
So I think that's a reallyimportant area.
That is, as we become seniorleaders, we have to have our
(44:01):
incentive plan match the metricsthat we're trying to have Seems
pretty intuitive, but I don'tthink it always matches up that
way in reality.
Have seems pretty intuitive,but I don't think it always
matches up that way in reality.
And then I think just you knowthe roadmap of thinking bigger.
She explained a bunch of areasin which to do that and so just
you know, in each of us thinkingabout how this applies to our
business, business metrics likewhich are the ones that are
(44:23):
going to move the needle.
She talked about the concept offoresight and planning ahead for
the future, peripheral visionand like stepping out of the
trenches as a senior leader andlooking around the landscape
what are competitors doing, whatare other potential revenue
streams?
She had a great example aboutpayments associated with that
Capital allocation.
Like we now are in a role wherewe have to think about maybe
(44:45):
potentially inorganic strategiesand not just hitting the number
around it.
And then, of course, it is allabout the people.
We spent some time talkingabout hiring, um, and you get
the right people on the on theteam and that they're perfectly
suited for role.
And the magic happens.
And when you don't, you knowthis.
We all know and have been intothe challenges associated with
that.
So lots to take away from thisepisode.
(45:07):
I I want to thank Andrea againfor joining.
Speaker 1 (45:22):
I want to thank Ari Smolin for producing Sons of
Summer and Isla Young for thetunes, and I want to thank you
for listening to this episode ofPillar Talk.
We will how you really feel,just be honest, like a joke.
I can't shake, I can't quit.
Hello everyone and attempt to create clarity in
(00:27):
terms of what good looks likefor current and aspiring sales
leaders.
Today, I am fortunate to bejoined by Andrea Kael, a
seasoned go-to-market leader whohas held both CMO roles and CRO
roles across some of thefastest growing B2B SaaS
companies.
Andrea has led DemandGen, builtmarketing engines from the
(00:50):
ground up, later transitionedinto owning both sales and
marketing as a revenue leader.
Now I know Andrea for hercandor, her directness and
ability to cut through the noise, which is great.
Andrea is now the CRO of HelpScout, a CS platform, and she
shares her experience teachingPavilion's CMO school, where one
(01:12):
of her most impactful sessionscovers the real differences
between being a functional VPand stepping into the seat of
the C-suite leadership position.
So, andrea, welcome to PillarTalk.
Speaker 3 (01:25):
Thank you, Rick.
Appreciate you having me.
Speaker 2 (01:28):
So, andrea, sales and marketing are often at odds.
There's some finger pointingthat tends to happen, some memes
and jokes that can come up fromthat type of thing.
From your vantage point, how doyou go about blaming yourself
when things aren't going great?
Speaker 3 (01:43):
Well, I never blame myself, of course.
I find that the leaders whoI've worked best to like kind of
combat that like fingerpointing where we've agreed on a
shared language about when thehandoff, when it's appropriate
to make the handoff betweensales and marketing, they're
like very specific.
We call them like you know, anSLA around what quality means
(02:08):
and we're like very specificabout that.
So up until opportunity, salesreally doesn't care because
that's all marketing's domainand we're really working to kind
of like nurture that until itmeets the qualifications, that
we believe is like ready forsales.
And then at that point salesagrees because it met the
criteria and that's when thehandshake happens, that's when
an opportunity is created and wereally find that like the
(02:30):
finger pointing kind of likedissipates because we've all
agreed beforehand.
This is what makes somethinggreat.
Speaker 2 (02:35):
I've always collaborated really well with
marketing.
My primary background has beenin the sales side of things, and
it has always been fun, though,and playful, to sort of have
that tension that exists wheremarketing is known for, you know
, success being measured in thegenerating of leads and then, of
course, sales being measured insuccess with the closing of
deals, and of course it's likethere's the, you know, the SLA
(02:57):
type of environment that youdescribed, which needs to exist
so that we can celebrate thesame thing.
But it is fun.
I can recall certain times whenI've been on an all hands and
like things are not goingparticularly well in the
business and marketing iscelebrating because they're at
like 117.
So it's just very funny.
And now you're in a positionwhere you own both.
And so you know, hopefully thathelps provide a lot more, a lot
(03:18):
less friction in creating thecohesion.
Speaker 3 (03:20):
It certainly does, and for all those years I've
been beating up my salescounterparts.
I'm regretting that a littlebit.
Yeah, well, I would have gotteninto that a little bit.
Speaker 2 (03:30):
You've been in both seats, which I find to still be
pretty rare and giving you aunique perspective.
Is there something you know?
Your background originally wason the marketing side, when you
started to own sales.
In addition, was there onething that stood out and
surprised you that you hadn'tanticipated?
Speaker 3 (03:47):
Well, the one thing I don't know that it surprised me
, but got validated was you know, I've always, like, had a lot
of respect for my salescounterparts, but truly, there
is a very obvious art to salesthat you really can't teach.
I mean, you can teach it,obviously, because you know
people come up through the game,but I, I I always knew that if
(04:10):
I was ever going to take thisrole, I was going to need to
hire a professional who knowshow to sell.
I learned from him every day.
That includes, like salesprocesses, deal management,
pipeline management, the art ofthe deal, how to negotiate for
certain things.
You know that those are all, Ithink, skills that I still I'm
learning and so really justappreciate more and more being
(04:33):
in the CRO role, what it takesto be a sales leader who really
excels.
It's, it's, it's difficult, andso, yeah, I have a lot of
appreciation for that now.
Speaker 2 (04:41):
I bet you're learning faster than you give yourself
credit for.
Speaker 3 (04:44):
I don't know, you know, sometimes I, you know, I
like to think, oh, I could haveclosed that deal, you know.
But I think back to how thedeal was then constructed and
I'm like, wow, this is smart,you know.
And so I think it just takesyears of learning how to be
really good at sales and cannottake it for granted anymore.
Speaker 2 (05:07):
Well, to your point, when you see something that's
put together whether it's a dealor a project, and you see like,
wow, that was really thoughtful.
I wouldn't necessarily havethought of that, those are like
some of the best moments as aleader, right.
Speaker 3 (05:16):
A hundred percent, yeah, and but you know I've
never, I was never the bestmarketer either, rick, like I, I
, I think my, my talent isprobably more on like knowing
how to hire people who are justbetter than me at all these
things.
Cause you know there is, yeah,there, a lot of these roles and
go to market are, you know, sortof like undervalued, I think to
(05:38):
some extent, because you'relike, oh, you're just like an
account executive, or you knowjust how hard does it hit to hit
the quota.
You know it's like they're allreally challenging, like content
marketing, product marketing.
These are all reallychallenging roles.
So to find people who are likereally good at them, I think, is
just my job.
Speaker 2 (05:54):
Now is that ability to identify talent?
Do you feel that is a result ofan increased time investment in
terms of doing the work?
Is it a you know?
You feel like you have astrength in identifying it a
little faster than others.
Like what do you attribute yoursuccess in getting those people
that can do the thing reallywell to?
Speaker 3 (06:16):
I think it's two things.
I have a profile I like to hirefor.
This may not be like a surpriseor novel, necessarily, but the
three characteristics that Ithink like show up in an
interview when they're able toarticulate passion, curiosity
and grit, which I thinkcuriosity, in particular, is
going to become the mostimportant skill as AI continues
(06:37):
to be like on the rise how toask good questions and get good
answers.
That is like that's what I digfor when I'm in.
Are they asking me goodquestions?
Do they like dig below thesurface layer of this job to
really understand, like, what itis they're going to do and how
they're going to make an impactis one so like passion,
curiosity and grit.
The second is demonstrating atrack record of success and
(06:59):
having done the role, I giveeverybody a project.
Show me how you did this inyour last company.
So, for the sales hire I madebecause that is not my strength,
as I mentioned, I think I had30 interviews.
I went through like I don'tknow 15 projects.
Out of those 30 interviews,really, only two of them could
articulate their track record ofsuccess in a way that made me
(07:22):
feel like wow, this person getsit and they're going to cross
here because they just showed methey can do it.
So this is a message to salesleaders listening like get good
at storytelling like your, youknow your success record Cause I
think that ends up putting youabove the noise.
Speaker 2 (07:35):
I have to concede that, like, while I feel you
like, sometimes it takes 30interviews or 30, you know first
interviews in order to get thelike caliber of talent that you
want.
Yeah, finding the time to putthat in can be extremely
difficult.
It's so easy and tempting tolike shortcut it over, rely on
referrals and somebody that'slike you've heard from somebody
(07:56):
else is already good.
It's tough.
Speaker 3 (07:58):
It's really hard.
I want to shortcut it everytime, but it's my, it's my job
and I think if you're beinghired at C-level um, if you do
not have a good track recordbringing in high quality, high
bar setters to the company, youend up losing trust of, like
everyone else in theorganization.
So I think putting in the timeis is so important because if
(08:20):
you're managing those people aremanaging people getting that
wrong, very costly, like veryproblematic.
So do the work.
Speaker 2 (08:29):
Curiosity.
I understand how you test forany like fun little tips around
passion and grit.
Speaker 3 (08:34):
You know, I think passion like kind of shows up in
their curiosity, because youcan and maybe this is just like
a feeling, I don't know, but theway that somebody is like
talking about how they likesolve problems, you kind of feel
like is this person just likechecking boxes, or are they like
you know, just you know BSing,or if they're like you know what
(09:07):
this is going to be, somebodywho's going to be a good culture
fit, because they're reallygoing to dig in here.
Speaker 2 (09:12):
Yeah, I have.
I have trouble testing forpassion because I'm, I'm, I'm
explicitly passionate, likeeveryone who speaks to me can
quickly see that I'm high energyand.
I'm excited and so I candemonstrate passion more easily,
but that doesn't mean that thepassion that I have is better
than the quiet intensity.
(09:34):
I agree, yeah, situation whereI was reluctant to hire somebody
that was known to be the best,and everyone you talk to view
this individual as the best, andin my interaction with this
individual, they were verycareful, very careful, wouldn't
say one more word than wasnecessary.
And so if you're like lookingfor people like yourself, that
(09:57):
all of a sudden, all the redflags are going off, alarms are
going off and you're like gosh,I'm not sure this person has the
passion.
Now I was fortunate to make thedecision that I don't want
people that are exactly like me.
And I'm going to take all of thevariables into play and we
brought this person on and whatI learned was there are many
(10:17):
forms of passion.
Passion yeah, this is the mostintense, competitive individual
held themselves to a standardthat I could only aspire to one
day and is an absolute winner.
And so I was like, wow, lookingback, was there a way that I
could have tested for thatintensity beyond the hands?
You know, moving the decibel,volume of the voice.
Speaker 3 (10:40):
Yeah Well, rick, I actually think you kind of like
mentioned it in that.
But even just asking thequestion, like you know how
right, maybe I'm just testingfor like their external, like
(11:08):
mannerisms in terms of how theylike exhibit passion.
But I think people were askingquestions who are like involved,
who seem to just like want toknow about the role that they're
going to be involved in.
And, yeah, maybe I'm conflatingpassion and curiosity.
But where the dialogue feelslike the person is interested
beyond just the surface levelquestions I'm asking makes me
(11:29):
feel like OK, they're going tobe, they're going to fit in here
.
Speaker 2 (11:33):
Yeah, and then a grid , of course, if you're actually
successful in giving a projectand allowing people in to
provide coaching and you cansort of see whether they get
resigned.
It doesn't go well, or want todouble down and do all of that
and maybe passion.
Speaker 3 (11:45):
Yeah, and to what degree did they put into the
project right, Like that's great, Cause they're like I'm going
to, I'm going to get this thing,I'm going to set the bar for
this.
It means like they just workedharder than the next person to
kind of, and the person we justhired for like paid media, was
just that.
Speaker 2 (11:59):
I'm like wow this person went way above the other
presentations that came in interms of the quality of
information that they were ableto share.
Is it translating?
Are the folks?
Speaker 3 (12:14):
that you've brought on to be, you know, meeting an
exceeding expectation,surprisingly.
Yes, you know also surprisingly, but that's the answer is yes.
Yes, it's yes.
But also you know I, I alsodedicate a lot of time to make.
I would drag these people overthe line too if they weren't
getting there.
You know I am committed oncethey I do hire them to making
sure you know they're successful.
I'm a very like involved.
(12:36):
You know, leader, I don't justlike leave them to their own
devices.
You know I do provide a lot ofsupport to help that.
Speaker 2 (12:42):
I mean to me it's like kind of the most important
thing, right, like we can't.
We enjoy our work.
I this is like a theory weenjoy our work mostly based on
who we work with.
Speaker 3 (12:52):
Yeah, a hundred percent.
Speaker 2 (12:53):
Yeah, the mission is super important.
Speaker 3 (12:55):
Like.
Speaker 2 (12:55):
Hey, are we doing something we believe in?
Sure, the being on a winningteam matters a lot.
When you're succeeding, itfeels really good, but it's like
the grind day to day is thefolks that you're working with
and you are working with peoplethat inspire you, that you learn
from that hold themselves tothe same standard as you do.
Speaker 3 (13:15):
It's hard not to like work A hundred percent.
And you know what I will say.
I leave this one off because Idon't know how people will take
it, mostly because I don't wantto think people.
I'm not hiring people becausethey're not funny, but when
they're funny that makes all thedifference in the world.
Because if you can laugh aboutall the, if you're working in a
startup, you have a fire to putout every single day.
You need to be able to likelaugh about it.
(13:37):
You know you're taking a lot ofhits from all directions and
you know you need people who cankind of like shake it off and,
you know, laugh through it.
So I also think that helps alot.
Speaker 2 (13:45):
Yes, sense of humor is Sense of humor.
You know, you teach thedifferences about being a VP or
even SVP.
You know level and thenstepping into a true C-level
role and I want to dig into thisa bit.
Like what do?
Speaker 3 (14:08):
people miss about that shift until they're in it.
I think there are five thingsthat I wish I knew sooner or
coming up in my career, that nowthat I'm whatever going to be
45, I feel, like you know, Ihave this, like this wise old
sage you know because I've beenin startups for 20 years which
feels like I don't know, like Indog years that's 140.
(14:29):
A hundred percent, that's howmany years it feels like I've
been working.
But there's like five coreprinciples that like
differentiate a VP from a C.
And by the way, I'm using thetitles sort of like as examples
C-level means somethingdifferent in every company, but
(14:50):
I just mean like when you becomesomeone who is at sort of like
this executive level, where youbecome the peer to the CEO and
you're like running the businessalongside of him or her in
whatever capacity.
In whatever capacity, there area few principles that I think
are the difference between thefunctional role you have which
could be revenue, marketing,customer success or chief
(15:10):
operating and the actual acronymbefore those functional letters
, which is the VP is themanagement layer, the C is the
management layer.
And in that management layer,the first thing that I think is
like really important are justlike that you're operating
against business metrics, notteam metrics.
Your team metrics, for example,your chief marketing officer
(15:33):
you care a lot about pipeline.
You're going to be asked aboutpipeline and how much revenue
you've contributed from amarketing perspective.
But business metrics is likeEBITDA, cash burn, rule of 40,
gross margin, like those areactually what I'm gold against
now.
So very important that we getto pipeline, because marketing
reports into me very important,that we hit our sales numbers,
because sales reports into me,partners, that we hit our
(15:54):
partner number.
But, like the end of the day,if we are burning more cash than
we can consume over a longperiod of time, the business is
going to be in big.
We're going to have a problem.
So, as the C, I care aboutthose metrics as, like the
functional leader, I care aboutsome of the others.
So that's one way of thinkingabout my role like business
metrics, not team metrics.
(16:14):
The second is foresight.
I don't think that functionalleaders, like at the VP level,
necessarily have the like,sometimes the goal, or like even
the skill set yet to thinkabout where does the company
need to be in three to fiveyears.
I use a framework which isbasically called the iconic
(16:37):
enterprise five to help me thinkforward about where the
business is going and that helpsme set the revenue strategy.
But you should be thinkingabout this at the VP level.
I just don't think it's a skillpeople like think to do.
But you should be saying infive years and I can share this,
maybe you can include it in anyof the file material, rick, but
(16:59):
it's a really cool way of likeestablishing, like, the
valuation of the business in afew years, because everyone's
job at a tech company is toincrease enterprise value for
the organization.
That's the job, and you do thatby making sure that, like in X
years time, you've hit certainmetrics that make the company
valuable and Iconic uses, fivemetrics that signify value, and
(17:21):
that includes things like youryear growth rate, ndr, rule of
40, magic number, arop, fte.
So there's like five metrics.
They're saying like if you hitthese numbers when you're in
this revenue band, this is whatour top decile and median decile
of companies that are highestvalued, look like and they have
some of the best companies inthe world in their portfolio.
(17:42):
They have like Canva andSnowflake and Datadog.
I mean so, but they're like,look, if these are like the best
businesses in the world andyou're mapping up to this like
you're creating a lot ofenterprise value there.
So so that's the second one,which is like foresight.
I'll stop there, like, becauseI could go on and on and on for
like hours and hours, but likethose are two that I think are
(18:04):
you know.
Speaker 2 (18:05):
Well.
I think there are two greatones.
I think what I would do is thensay how does this manifest
itself in your day-to-daydecision-making?
So let's take the managementlayer, and I like the idea of
you know you focusing a bit moreon business metrics.
Take EBITDA as an example whichyou wouldn't think of the CRO
as mostly being EBITDA focused.
But hey, if you're a C-levelexecutive, like profitability of
(18:26):
the business like reallymatters.
It's not just growth at allcosts anymore, all business like
really matters.
It's not just growth at allcosts anymore.
All of that.
I get the fluency and awarenessaround that.
How might that change yourbehavior as the C-level versus
the VP of sales, as an example?
Who's got a quota to hit?
Speaker 3 (18:41):
Okay, well, let's say you're the VP of sales and you
don't care about cash burn orEBITDA.
You're adding as many reps asyou can possibly add and you're
asking marketing to spend asmuch money as they can in order
for you to get the quotacoverage you need in order to
hit the goals.
If you don't have the check andbalance on the money, okay, add
more people.
Well, you know you could addmore people, but every time you
(19:01):
add an AE, you're contributingto burn because they don't ramp
for five to six months.
So, should you add AEs, maybeyou add an AI, something that
you know helps.
Maybe the current AEs you havebe more productive.
So it does change your decisionmaking if you have the control
on the other side that you knowthat keeps you focused on cash
(19:22):
burn Marketing.
If I could get Help Scout to ahundred million, like I don't
know, in like two years, if Iwas, like you know, like
shooting the money gun around.
But we aren't running thebusiness that way.
We care about cash burn becausewe want to get to profitability
first.
Then we want to like, figureout how we like scale versus
(19:42):
just, you know, the other growthat all costs number.
So it does matter a lot.
Before I add a single person toheadcount, I'm figuring out how
do we get this job done withless people.
I add a single person toheadcount.
Speaker 2 (19:53):
I'm figuring out how do we get this job done with
less people.
So if cash for I still perceive.
Speaker 3 (20:02):
the C-level execs are often gold, similarly than the
VP.
I am not.
Yeah, I am not.
My compensation is comprised ofnew revenue at like 30%, which
is typically where a VP of salesis at a hundred percent of
their OT.
On new revenue, um, I am goldon NDR because that's, you know,
has to do with the expansionand churn in our base, and I'm
gold on cash burn 30.
(20:24):
So it's 30, 20.
No, what is it?
I don't know, I can't do math.
It's like 30, 20, 40.
Speaker 2 (20:33):
Wow, okay, so, yeah, so you 30, 20, 50.
So you're caring just as muchabout cash burn yeah, more than
you are about sort of newbusiness.
Yeah, so I think that is oneaspect where C-level needs to
think that way, but it helpswhen their goals are aligned
with thinking that way.
Speaker 3 (20:51):
Exactly, yeah, I mean true CRO, probably I'm really,
I think, not imbalanced, but I'mjust as incentivized to make
sure we are running a healthybusiness than, as we are, a
fast-growing one.
Speaker 2 (21:06):
And then on the foresight example, I love, love
this kind of framework of youknow, growth metrics, NDR, rule
of 40.
You're talking like netretention, right?
Speaker 3 (21:20):
Net dollar retention, yeah, and they're saying, like
you know, look, if net dollarretention is 105 percent when
you are a 25 to 50 millionmillion business, you are in the
median decile of their entireportfolio company in terms of
values that they've driven fromhaving 105% NDR.
You know, like you, if you godown and you check the boxes on
(21:42):
all the numbers that they havethere, well, you're just as
valuable as, like a snowflakeNow snowflakes in the top decile
.
So, okay, you're not going tomaybe compete with that
(22:04):
no-transcript, and that's thedifference.
Speaker 2 (22:14):
You need to make a valuable business, not just a
valuable moneymaker.
And so today, is there a way inwhich you're like making
decisions differently, or isthere a way like you're like how
is this manifesting in a changein your decision-making that
maybe you wouldn't have madeprior?
Because I do think there'sstill some validity in that
people don't people don't haveblinders on like I think that
most people, especially goodbusiness folks, generally have
(22:35):
an aversion to like let's justspend money to hit the number.
Sure, think about theconsequences.
Like I think people generallywant to do the right thing, um,
but so I'm kind of trying to getinto that next click down of
like okay, how does thisactually, how's this changed
your behavior in the way you're,you know?
Speaker 3 (22:53):
I'll give you two examples.
Speaker 2 (22:55):
Yeah.
Speaker 3 (22:55):
I'll give you two examples.
Um, so we have an ACV of $1,200, which means we can't add a
whole bunch of accountexecutives to go at or SDRs to
go after, upmarket or otherwise.
So I added a partner channelbecause we only pay when those
deals close through reselling.
(23:16):
So I needed to hire a directorof partnerships so that she
could get reselling off theground, so that that's a whole
new channel to open up but thatwe don't pay for and there's
exponential growth.
Would I have added a partnerchannel if we could go directly
after the money and didn'tnecessarily not care but cared
less about the unit economicsfor like adding account
executives, like absolutelywould have added direct because
(23:38):
you control that you have likemuch more.
Speaker 2 (23:41):
You train them, you certify them.
Yeah, all the reasons.
Speaker 3 (23:46):
Exactly For all the reasons, you have an inside
sales team and it's very likeMachiavelli and like to say like
oh, say, oh, you want to ownyour army, but sort of because
of this reason, but once that'sopen now we could scale without
cost.
So that's one.
Speaker 2 (24:04):
That's a great example of going a partner route
due to the ACV rather than theinstinct of building direct.
Speaker 3 (24:10):
Exactly.
So that's a decision I madespecifically because of this.
The second is on marketing.
We have a when I was atElectric because the ACV was
$40,000, we could test and growusing a bunch, bunch of
(24:32):
different activities likeprimarily being like events,
which is like a higher costthing.
So we did I don't know maybelike 100 events at Electric, but
at Help Scout I'm just doinglike smaller, more highly
targeted events where we're likedoing we're doing like a lot of
(24:56):
like ruthless work around, likemaking sure exactly the ICP
gets there that we want to see,and they're like they're much
different, they're like muchsmaller, they're like more
intimate, and so we just like wehave to organize tactically
around, like some of themarketing efforts, because our
ACV is different and because weneed to like definitely get a
return out of every single thingwe're doing.
So, even tactically, my approachto like events or paid search,
(25:20):
or affiliate marketing,newsletters, direct mail,
sending like it all just changedin light of the ACV and like
the market we're going after.
So that's how it changed on themarketing side.
Speaker 2 (25:33):
It sounds like there's a lot more trade-offs to
make.
I mean, how are you makingthose Like?
What approach are you taking tomake those trade-offs between
investment ideas or peoplestrategy and so on?
Speaker 3 (25:44):
Yeah, I mean, you know we're just good about.
First, the marketing budget ingeneral is fixed against
generally like our paybackperiod, um.
So so our cac payback period isone of the like metrics we use
to say like what can the totalbudget be?
(26:04):
We, we don't want to kind oflike get outside of that um, and
then the marketing mix isreally optimized against which
one of these channels is likethe most productive.
So we don't have every channelon.
We have like very specificchannels on.
At Electric I could really haveevery channel on because you
know some of them just workbetter than they're working at
(26:25):
Help Scout because it's morecompetitive, and then some of
them are just too costprohibitive.
So it's all, yeah, it's alljust around the unit economics
of like what's working.
So that's kind of like howwe're limiting the scope of what
we do.
Speaker 2 (26:41):
When you teach folks about the difference between VP
and C-level.
I mean what you're describingis a lot of the logic You're
describing, like the metrics.
You look at these metrics, notthose metrics.
For these reasons, all prettyobjective, all reasonable, all
sort of logic-driven.
I think there's also perhaps anaspect of I don't know, it's
like the mental sort of sidearound the thinking that way or
(27:05):
graduating from a more tacticallevel of thinking day-to-day to
trying to put into practice,like what are the things I do to
focus on these bigger levelmetrics that aren't maybe
directly within the control of afunctional area but it's across
the harmony across multiplefunctional areas, like was there
a pivot point or a switch thatflipped for you that helped make
(27:25):
it easier for you to sort oflive in that, in the logical
environment you just described?
Speaker 3 (27:35):
to sort of live in that, in the logical environment
you just described, I meanmaybe just 20 years of like
mistakes or like living with it.
You know, I did notice, though,in my role as CMO, I do think
like a lot of tech companieslike to fill like a lot of the
functional roles at the C-leveland again, I'm talking mostly
about companies that are underlike $100 million or $50 million
or below.
So this obviously changes whenyou get massive.
(27:58):
But if you're in that range, Ithink the flip was switched when
I'm like wow, I have a bunch ofthese very senior counterpart
and we're all having to makestrategic decisions that could
be in conflict with each other.
And so I just thought to myself,what if there was one arbiter
(28:21):
of like the revenue strategy andthen you just like hired a
bunch of like great lieutenantsbelow that to really just like
nail the function, below that,to really just like nail the
function.
So I because I saw like, ifit's, if it, there's too many
senior people just like the CCO,the VP of marketing, cmo of
marketing, the head of saleswe're all like trying to like
(28:44):
create revenue strategiestogether with our own like
separate goals, and that endedup becoming like a lot of bloat
and and like very disjointedstrategy, I would say, for lack
of a better term Despite thefact that all my partners were
like amazing and smart.
I think the flip switch for mewhen I like was thinking about
(29:05):
this from the view of the CEOand I'm like, holy shit, he has
to like really figure out who tolisten to here, and this like
mix of people.
Speaker 2 (29:13):
So translate connection points between all
the good ideas.
Speaker 3 (29:16):
Exactly and I'm like there's no one like helping to
do that translation and thenjust go to the CEO and say, look
, here are like the things Iheard from my lieutenants, who
are all very smart people butlike very functionally focused.
Here's how I'm translating thatfor you into something that's
cohesive and this is why I go tothe foresight.
(29:37):
Or like the revenue strategy,where I'm saying like this is
when I started at Help Scout, Icreated the revenue strategy,
which was just like one personwho was saying to Nick look, I
think we need to add moreconsumption-based pricing.
We don't have that today, Ithink and you know, rick, I mean
you're in this role at yourcompany but you're saying here
are all the ways in which wegrow this business.
Let's pick together versus thatcoming from four different
(30:01):
people.
And then he or she is like waita minute, how do I then become
the CRO, for lack of a betterterm?
You put that work actually onthe CEO and it's a hard job
because that's not really wherethe CEO should be focusing their
time necessarily.
Speaker 2 (30:19):
Right, this is not about.
You know, it's funny,individual contributors often
sort of shovel their problemsonto their manager and then the
manager has to run around andsort of fix it.
What you're describing is wherefunctional leaders are
shoveling their strategies ontothe CEO, left in a world where
they have to sort of, and thengreat leadership is more about
not enabling that dynamic andturning into a flywheel of
running around and fightingfires and being reactive to it,
(30:39):
but a sort of forcing mechanismin which to create an
environment where folks are ableto not be reliant upon you, the
leader, and able to do that,and so that's a great example of
it happening at a more elevatedlevel versus down.
You know, on the day-to-day.
How do I differentiate this?
Speaker 3 (30:55):
or, you know, run this campaign or whatever it is
Exactly, and I'm happy to be thefunnel this way.
You just can't be the funnelthat way.
You know like you need to, youknow everything needs to come
into you and you need to.
Just well, I don't know if it'seven a funnel the other way,
but like it's just a conduit ofthat funnel, just saying like
now I've distilled everythingand, like I said, this is why
(31:16):
hiring is so important.
You're taking all thatinformation from the ground
level and then you just becomethe arbiter of, you know,
information about what thatstrategy should be to the CEO
and they can decide, but they'renot having to decide and then
go through that with fourdifferent people.
Speaker 2 (31:31):
So I still believe the easier people take generally
the easier path and the easierpath Generally it's not like a
bad thing, it's just the waythings are.
The easier path is to sort offocus on the narrow metrics
within the things that you cancontrol and to demonstrate the
behaviors of what we'll callfunctional execution.
Speaker 3 (31:46):
Right.
Speaker 2 (31:46):
That's just the general like inertia of how
things are going to go and so wecan talk a lot about.
Well, you need to thinkdifferently and you need to look
at different metrics and youneed to have an action plan that
connects to other functions andlike that, all sounds really
good.
People want to get there.
They go to CMO school and theygo to other schools growth and
they listen to this podcast as away to aspire to be more senior
(32:08):
.
I guess, what advice do you endup giving to someone that's
looking to make that transitionand to try to up-level their
thinking?
You know, in the way youdescribed.
Speaker 3 (32:18):
So, outside of just like making sure that, like from
day one, you know that your jobis to think about the business
metrics and then think about howyou're looking at longer term
so that you can plan headcountand you can figure out how
you're looking at longer term,so that you can plan headcount
and you can figure out howyou're going to get there.
Whether that's adding a BDstrategy today so that it
produces in two years.
Whether that's adding PLGmotions so that you don't need a
whole bunch of AEs to sell thething and you can move down
(32:40):
market a little bit.
Whether that's adding a partnerchannel, going indirect, going
up market, like whatever.
There's a list of probably like15 things a CRO should have in
their toolkit and that's on dayone.
You're like well, if we want tobe here in three years between
25 to 50 million, because we'reonly a five to $10 million
business now, here are the sixthings I would consider doing
(33:00):
and that's the foresight.
The other things that I I wouldconsider outside of hiring.
Speaker 2 (33:05):
Is that just a like, trying to narrow focus and
trying to think like like?
So is that the first thing youdo differently is to not worry
as much about the quarter thatyou're in, which is?
Speaker 3 (33:13):
what a lot of people are worried about.
Speaker 2 (33:14):
And it's actually trying to like.
Take a step back and go throughan exercise of like what does
success look like at the end ofnext year If you don't have to
go out five years?
Go out to the end of next yearand say, all right, what are the
things that need to be true inorder for us to be at whatever
level is defined as success?
Speaker 3 (33:31):
Exactly.
Yeah, because and let's justsay you you, you theoretically
went out three years becauseyou're using your FB&A team or
some help you're getting fromfinance to say, like, can we
build a fake model with justlike fake numbers in it that
show us what this business wouldlook like between, let's just
call it $50 million and nails,these metrics?
What would need to be trueabout the business today in
order to do that?
(33:51):
Because you could have highchurn, you could have an NDR
that sucks.
But you're saying, but in orderto get here, this is what the
NDR.
So, visually, people can startto paint the picture in their
head like, oh, wow, here's wherethe focus needs to happen all
around the org.
And that helps you put peopleinto seats, helps you think more
, like it helps you think, yeah,a little bit more broadly than
(34:12):
just the quarter here, becausethis quarter actually doesn't
matter at all.
It's like the quarter's over.
Also, if you're a marketer, thequarter this quarter is for
based on your sales cycle, likefor the next six months or
whatever.
You need to be thinking way farahead if you're a marketer, but
um, but so so the foreforesight helps.
So the three things are businessmetrics, not team metrics.
Make sure you like hire reallywell as like a.
(34:34):
That's a difference between VPand C Understanding the
importance of hiring.
The third is the foresight.
The fourth is capitalallocation.
Like that's the.
You know, the flow of money islike the LP to the VC, to the
CEO, to you.
That's the flow of money Everystep of the way.
(34:54):
Every single person on thatchain expects you then to have
made more money than they gaveyou.
So if you can't articulate tothe CEO or the CFO a plan that
makes them more money and whenthey're excited to invest in
like quit the job because that'sthe job.
It's like you are just a valuecreator.
You're like a hedge fund.
Like you wouldn't give yourmoney to a financial planner.
(35:16):
My financial planner was losingme money every time I gave them
another dollar.
Like we have to move the money.
So you have to think ofyourself in that way, because
that's how you're beingevaluated.
They give you one dollar, theywant three back.
That's it, period.
I mean that's on the PE side.
On the VC side they want 10back.
Speaker 2 (35:32):
You know, and that certainly happens over time and
you think that's an adjustmentfor folks is to be thinking that
way, do you?
I think so.
I don't think people.
As I listen, I'm trying to putmyself in the shoes of someone
in functional leadership andit's true, we do get caught up
in the minutiae ofinefficiencies that happen in
(35:53):
our business and things we wantto improve.
We want to improve the salesprocess, we want to improve our
search results, as an example.
There's plenty of things thatare inefficient about how we
work together or how thingshappen in the company, and it is
easy to have your compass benavigated by where you're sort
(36:15):
of feeling personal pain orwhere you see the greatest
inefficiency.
But that inefficiency isn'tnecessarily tied to what you're
talking about, which would bereturn on investment yes, beyond
impact, to profitability onrevenue, and I do sort of see
how even our instinct to fixthings as leaders right.
Speaker 3 (36:37):
We want to improve everything.
Speaker 2 (36:39):
It is often challenging to connect the
things we want to fix to whatwould move the needle for the
business the most, and I don'tknow that there's a science to
solve that.
But what I guess you'readvocating for is don't do it
independent of that.
Actually, try to determinewhat's going to move and ask
(37:00):
people like hey, I understandyou want to do these three
things, which one you know?
And people will beuncomfortable, they will not
want to answer which 100, 100.
But so how do you force them todo it like, how do you help
them with that exact?
That's a perfect example.
I have three things we have todo.
Great, we can only do one.
Which one exactly?
You will not get a directanswer to that.
They will hem and haw and tryto find a way to make it all
(37:21):
three.
What do you do?
Speaker 3 (37:23):
what do you do, and even an exercise I'm doing now
with the marketing team is I'mactually going to be the one
that sits at the top of theprioritization for the input
queue of things people areasking of the design team,
Because I'm like what if I wasprioritizing this with that lens
, Would we be doing bespokeblogger?
I'm like hell, no, we are goingto.
(37:43):
I'm going to have my head ofdesign now that I'm going to sit
at the top of theprioritization, figure out how
he makes the team of three sixby using bespoke AI generators.
Now you know.
And so, anyway, like I'm justI'm trying to go through, like
that's a practical example youcan do today is like figure out
what's coming in and are peopleusing that lens to like kick
(38:04):
things out and like make themnumber one or whatever.
The thing I'd say rick.
The fifth thing for the umthinking about vp to see is, um,
just peripheral vision, like inthe same way that I don't
necessarily think and, by theway, I I didn't know this, I
wasn't doing this either like inmy even up till 40.
These are things that, like,again, I feel like I'm old and
(38:26):
now 100 years in tech, butcompiled along the way.
So I'm not like I always knewthis and I was always doing it,
it's just like.
These are things I've feltalong the way.
But the last one is just aperipheral vision.
Are people reading S1s?
Do you know how yourcompetition has thought about
going to market?
Or are you thinking about howyou could just acquire that
(38:49):
business over there for amillion bucks and get their
whatever I don't know, like gettheir book of business If you
bought it for 4 million?
Cause it's like kind ofstruggling?
Like are you thinking aboutindirect or inorganic
acquisition Because, like that'sgoing to help you, like with
product, You're going to fill aproduct gap and actually, as a
revenue leader, you just added,like you know, a million bucks
(39:09):
to your book.
Read an S1, like figure outwhat people are acquiring and
like what people are doing andhow they're how they're growing.
And the S1 is the documentationthat gets filed before a
company goes public.
I think that's part of the jobtoo is just being like the SME
on your market, and maybe that'sobvious as an individual
contributor in marketing, but um, it always it wasn't natural
(39:31):
for me to like think that thatwas my job.
Speaker 2 (39:34):
And it is.
I can see again, like justspeaking of the I I, I overused
the term inertia, but it's likewhenever we get into roles
within companies, there is ageneral like trajectory
activities that we end up doingfrom the things that are closest
to us, which are inside thebubble of the company.
Your advocacy here is to likeas the more senior you get in an
(39:54):
organization, the more you'vegot to actually get out of the
weeds and look across thelandscape and say, hey, there
might be interesting things thatyour competitors are doing from
a go-to-market standpoint thatyou might learn from.
There might be dynamics withinthe industry that are happening
that you might need to be moreaware of, because your
individual contributors aren'tgoing to like be able to do that
.
They're on deal calls, tryingto close, and if you're not
(40:17):
doing it, no one is.
Speaker 3 (40:19):
Exactly.
And, rick, the specific exampleI can give here and I know
we're probably just at time, soI'll make this one quick but
when I was at UpServe, my mentorsaid to me did you read Squares
S1?
Because their fastest growingrevenue stream is instant
deposit.
It was basically a product thatthey spun up which made fees
off of restaurant owners wantingtheir money same day, like
(40:39):
Venmo does.
So they became a bank and I waslike holy crap, I'm like wow, I
thought we were competingagainst POS and they became a
bank.
And while we weren't going tobecome a bank, that was a big
unlock for me as a revenueleader, because I'm like you
want to talk about pipeline.
I'm like they became a bank.
You know, like that was likethe most obvious.
Like pick your head up, willyou?
(41:02):
We could have monetized allthese transactions in a
different way.
Wasn't even thinking about thatat all.
Speaker 2 (41:09):
So that's just one of the so that reset your thinking
, just in terms of like there'snot one way to skin a cat here.
Speaker 3 (41:14):
Like there's a lot of approaches we can take.
Speaker 2 (41:16):
We can learn from everything in the market's doing
and, yeah, the journey fromsort of different companies,
from marketing, to owning bothsales, to being a functional
leader, to a strategic leaderwe've covered a lot of ground
here.
So, andrea, I want to thank youfor joining us today.
I think we could talk for hours.
Speaker 3 (41:33):
Same.
Speaker 2 (41:34):
This has been great.
We'll continue the conversationand thanks.
Absolutely, Ray.
Thanks for having me.
Reflecting on the conversationthat we had with Andrea Kael her
journey from being a marketingleader to a revenue leader and
(41:54):
having responsibility over salesthat stood out to me.
She takes a fresh look at sales, having not been experienced in
that area before, so she makessure that she's hiring the right
leadership and ownership aroundit and she can spot what good
looks like.
She talked about having a lotof respect for a deal that got
structured and being veryimpressed by that and it made me
(42:15):
think that, like sometimes wehave the benefit of being able
to see what good looks like whenwe aren't super experienced in
an area and we should lean intothat.
I reflect back as a seller andwe should lean into that.
(42:36):
I reflect back as a seller.
We teach sort of when you'renew into an organization.
Generally a rookie within asales org asks a lot of
questions because they're notburdened by a lot of knowledge,
so they have to ask customersquestions and then, as they get
more experienced and become aveteran, they stop asking
questions and start telling howit is and can have actual
setback in their performance,because they're not.
They've stopped, they've lostthe curiosity and it's all about
telling people what they shoulddo and people might resist that
and I just kind of like how youknow, when you don't have
expertise in an area and you canbring curiosity to it, you can
(42:58):
really start to see what goodlooks like in a way where you
know from sales execution.
I have the bias of my ownpreferred style of doing it and
there might be a better styleout there and it might be hard
for me to see that and I likehow Andrea is able to see that
with a clear lens, especially asit relates to sales.
She also talked about thejourney of a functional leader
to a business leader.
(43:19):
This is a really important area.
We spend a lot of time talkingabout it.
To me, this all matches upreally well with the pillar of
ownership.
Can you be more about thebusiness and not just about the
team?
And there's a continuum of that.
And as you move up as a leaderbeing more about the business
and less just about the team isa growth curve associated with
(43:40):
it, and I think a key thing thatstood out in our discussion was
the incentive structure.
Andrea explained her incentivestructure in a way that matched
the business metrics and notjust delivering a number of
leads or not just hitting thenumber in revenue for the
quarter.
So I think that's a reallyimportant area.
That is, as we become seniorleaders, we have to have our
(44:01):
incentive plan match the metricsthat we're trying to have Seems
pretty intuitive, but I don'tthink it always matches up that
way in reality.
Have seems pretty intuitive,but I don't think it always
matches up that way in reality.
And then I think just you knowthe roadmap of thinking bigger.
She explained a bunch of areasin which to do that and so just
you know, in each of us thinkingabout how this applies to our
business, business metrics likewhich are the ones that are
(44:23):
going to move the needle.
She talked about the concept offoresight and planning ahead for
the future, peripheral visionand like stepping out of the
trenches as a senior leader andlooking around the landscape
what are competitors doing, whatare other potential revenue
streams?
She had a great example aboutpayments associated with that
Capital allocation.
Like we now are in a role wherewe have to think about maybe
(44:45):
potentially inorganic strategiesand not just hitting the number
around it.
And then, of course, it is allabout the people.
We spent some time talkingabout hiring, um, and you get
the right people on the on theteam and that they're perfectly
suited for role.
And the magic happens.
And when you don't, you knowthis.
We all know and have been intothe challenges associated with
that.
So lots to take away from thisepisode.
(45:07):
I I want to thank Andrea againfor joining.
Speaker 1 (45:22):
I want to thank Ari Smolin for producing Sons of
Summer and Isla Young for thetunes, and I want to thank you
for listening to this episode ofPillar Talk.
We will how you really feel,just be honest, like a joke.
I can't shake, I can't quit.
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