August 26, 2024 • 56 mins
Navigating the complex journey from startup to enterprise success requires more than just a great product—it demands strategic alignment with your customers' needs. 🎯
In our latest episode of The Hidden Chasm, Jenna Watson-Brawn breaks down why "Build it, and they will come" is one of the biggest myths in tech. 🚫
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Episode Transcript
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Bo Motlagh (00:11):
You're listening to The Hidden Chasm, a discussion
of how tech debt and legacysolutions become barriers to
growth and innovation forestablished SaaS companies. The
Hidden Chasm is sponsored byUnited Effects where our purpose
is to help companies break freefrom legacy tech, improve
retention, and empower M&Agrowth. Learn more at
unitedeffects.com. Welcome toanother episode of The Hidden
(00:32):
Chasm, which you have to saywith with that deep voice. You
know, we've been exploring thechasm, from a lot of different
angles.
We spoke spoken to M&Aadvisors. We've spoken to
product executives. We have sometechnology folks coming up soon
as well. We've had the peopleangle, which has been really
interesting. But I think one ofthe most important elements of
(00:53):
any business is revenue.
Otherwise, you don't really havea business. And to help explore
this this particular angle isour friend and actually board
advisor. Welcome Jenna. JennaWatson-Brown. Jenna is a 15-year
veteran of business development.
I'm reading this. I always haveto read. Jenna is a 15-year
veteran of business development,sales, and growth coaching with
(01:15):
proven successes leadingenterprise sales as a senior
executive. She now focuses herenergy and experience on helping
early stage companies findproduct-market fit, gain
traction, and build revenue.She's currently the founder of
Jenna Watson-Brown Consulting,affiliated with several
accelerators and board advisorto several companies including
United Effects.
Welcome, Jenna.
Jenna Watson-Brown (01:35):
Thank you very much. Excited to be here.
Bo Motlagh (01:38):
Well, we're excited to have you. Obviously, Jenna,
you've been working with us fora while now. And it's funny, you
know, for our listeners, it'salways funny when we have to do
some digging on people wealready know to figure out how
these conversations are gonnago. As I dug into your past a
little bit and saw yourexperiences in enterprise sales
with Eventbase and then Motiveand then moving into your
(02:01):
coaching career now, just areally fascinating, journey. I'm
sure a lot of people would, youknow, would be interested
hearing more about it.
And I thought, you know, whydon't you
Jenna Watson-Brown (02:10):
just kick
Bo Motlagh (02:11):
things off is tell us about yourself and how you
found yourself on this call withus.
Jenna Watson-Brown (02:16):
Yeah. And I I always say, like, I didn't
take the easy path. And I Ithink once you get a taste of
the startup world, it's reallyhard to let go. So I joined my
first startup when I was 19,employee, I think, 9 or 10, 1st
salesperson working alongsidethe CEO and was there for 10
(02:38):
years. And I joke that, yes, itwas one company.
It had a couple different namesover the years, but it was
actually five differentcompanies. Because in every
different phase that we were at,whether it was bootstrapping,
pivoting into enterprise,raising our first VC, raising
subsequent VC, it was anentirely different company with
entirely different challenges.And executives and board members
(03:01):
and all of that evolved greatly.So that was where I really cut
my teeth in sales, selling tothe likes of SAP, Microsoft,
Charles Schwab, really with notmuch experience and having to be
self taught in a lot of ways. Mybackground's actually in
accounting, which I don't thinkyou guys knew.
Bo Motlagh (03:22):
I think you guys
Jenna Watson-Brown (03:23):
Yeah. So I I I like numbers. So I've always
liked numbers. I like algebra. Idon't like bigger things than
algebra, but I like, you sellthis many of this and you get x.
That's my perfect kinda math. Sothat's where I started, and then
over time, ended up taking oversales, leading sales, leading
(03:44):
customer success. Sounderstanding both pieces of
that as well of not just gettingthat sale, but keeping that sale
and growing that customer, whichI think gives me a unique
perspective on the importance ofgood fit customers, the
importance of true productmarket fit. I've heard I can't
don't know who to credit, but Ibelieve product market fit
(04:07):
actually comes in the renewal,not in the sale. Because a good
salesperson can get just aboutanything sold, whether or not
you need it or want it, andproduct market fit is actually
the renewal.
Did you find enough value inthat 1st or second or third year
of the product to renew? Sothat's that's my background.
That was the beginning of myenterprise and sales career. And
(04:30):
then after that, moved on to, acouple other startups, Motive
being one of them in acompletely different space back
to, you know, small scale,scrappy team, taking out the
garbage, trying to, you know, dobig deals with the likes of, you
know, fortune 10 companies andand made some excellent progress
there. But it it's, you know, Ithink building something from
(04:55):
nothing and finding people withthe problem that you can solve
for them that they want solvedis is, like, the thing I the
thing I look for in all my work.
And so now I help start ups helpand I'm starting to work more
with little bit further oldcompanies a little bit further
along, like, you know, 5,10,000,000 in revenue, but it's
(05:16):
how do we build a sales motion,scalable or not, that is going
to build the company in a waythat is not cutting off your
nose despite your face.
Bo Motlagh (05:31):
Interesting. Well, first of all, backing up a
little bit. So you you startedyou started at 19? Yeah. I was
definitely not thinking aboutbusiness or anything really at
19.
Jenna Watson-Brown (05:39):
Yeah. I and it was it was a total fluke,
like a kinda friend of a friend.Oh, do you wanna work here? And
I had another job, and thehusband of the owner of the
company said, oh, I I reallylike you. Like, would you be
open to trying sales?
I think you'd be really good
Bo Motlagh (05:53):
at it.
Jenna Watson-Brown (05:53):
And that's literally how it happened. And
then, like, I worked alongsidethe CEO. I was like, k. Let's
let's build this. I I would sayI've always like, I I came out
this way.
So it sales was a naturaltendency for me, and I'd always
been entrepreneurial, like, evenwhen I was 18 when social media
(06:13):
first came out, even youngerthan that. And, like, businesses
were trying to figure out how doyou monetize. Like, I did my own
little consulting on the side.It was helping companies set up
Twitter accounts. And so I'vealways had that in me.
But, yeah, like, I I officiallyembarked on. And the first, I
think, 5 years of my startupworld was bootstrapped, until we
(06:34):
were profitable, and we wereselling to the likes of SAP, and
really, really big companieswith no marketing, no sales, no
VC. So I know it's possible. Iknow it's possible, and I think
that's where I can rub somepeople the wrong way because I I
don't believe that you need allthe flashy stuff to to get Yeah.
(06:57):
Get off the ground.
Bo Motlagh (06:59):
Well, I think that's been what something, you know,
as Josh and I have worked withyou that resonated with me is is
is the let's just try this andmake and see if that works. It's
pragmatic and practical, which Ilove over, you know, theory and
and process, which is finebecause I'm a fan of process.
But I think as opposed tosomething that's dogmatic and
(07:21):
thinking through, you know,actual steps that work. As
you've sort of moved throughyour career, so you started with
startups, you then ended up inenterprise, and then you bet
you're back to startups. Wouldwould you say how did the the
enterprise world influence howyou coach start ups now?
Jenna Watson-Brown (07:39):
Yeah. I I think with the enterprise world,
what you learn is that you haveto play by their rules. Like,
you have to play by the endcustomer's rules. And when
you're selling to Microsoft andyou're selling 2, $3,000,000 of
of business a year, doesn'treally matter what you think or
(08:01):
what you want or how you wantthe sales process to go. It just
it doesn't matter in the sameway that I think some startups
think it does.
Like, oh, I'm gonna build thissales motion, and I'm just gonna
do it. And that's the way it'sgonna go. It's like, yeah, but
this is how Microsoft buys. So Ithink it gave me a very deep and
thorough understanding of,meeting customers where they
(08:26):
are. And if you're selling tothe enterprise and you're trying
to do a lightweight PLG motion,but you're selling to a SVP at
Microsoft, those two thingsdon't work together.
I I don't believe in a salesmotion for a sales motion. I
believe in matching salesmotions to the buyer. Sales
motions to the buyer, the waythey typically buy, their
(08:49):
expectations. So I think it'sgiven me a really big, a fee for
the buyer and, and I think it'sdispelled some of the myths of
build it and they will come.Because I think a lot of
startups, we had thisconversation just earlier today,
think that building the productis the hardest part of building
a startup.
(09:10):
And I can, without a shadow of adoubt, say that that is not
true.
Josh Smith (09:13):
You mean you mentioned PLG, you know
Jenna Watson-Brown (09:15):
Yes.
Josh Smith (09:16):
Doing product led growth. Right? Yes.
Jenna Watson-Brown (09:17):
Yes.
Josh Smith (09:18):
And that that is a continuing trend even now. And I
guess you would say that, thatas much as folks certainly love
to jump on the bandwagon and sayit could be a panacea for for
getting your startup off theground, you would say, hold on.
Wait one second. Let's take alook at exactly who those buyers
are first and whether or not PLGis even a fit.
Jenna Watson-Brown (09:38):
Yes. I think they say with PLG, and I I don't
this is a stat that kind ofpeople have different versions
of. Like, if your productdoesn't give them an moment
within the first five minutes ofusing it, you shouldn't have to
PLG. And if your product like,think of Calendly. Great
example.
Put your credit card in, signup, premium, whatever, you know,
(10:01):
however you've come to Calendly,free trial. You try it. You send
out your first meeting. You'relike, oh my gosh. Someone booked
a meeting.
I didn't have to go back andforth. That's incredible. There
wasn't a stakeholder group todecide whether is the right fit.
It didn't integrate with yourarchitecture. It didn't
integrate with it didn't need asecurity review, like but then
(10:22):
when people say, oh, I'm gonnatake this, like, highly
specialized enterprise securityproduct and put it with PLG.
It's like, well, that's not howthe CISO buys. The CISO doesn't
A (10:33):
there's no AHA moment in 5 minutes. B
such that they're not enteringin a credit card inform their
credit card information. And, C: that's not how this purchase (10:40):
undefined
gets made. It's not anindividual user using an
individual tool.
So, of course, there'sexceptions to everything, but I
so often, I see founders say,oh, I like the sales process or
I like this market. I'm gonna goafter it. But completely
(11:01):
ignoring who actually wants theproduct, who has the demand to
solve the problem, and how dothey typically buy, how do they
typically interact with vendors,and the realities of the product
you're selling.
Bo Motlagh (11:13):
It's funny because we I mean, Josh and I had have
gone back and forth on productled growth a lot as well. And
you're right. It all it soundsso amazing.
Jenna Watson-Brown (11:22):
Mhmm.
Bo Motlagh (11:23):
It's like this yeah. Let's do that. And then you get
into it and you're like, oh,that that didn't work. That
seems like one commonmisconception. Are there other
common misconceptions andchallenges you see early stage
companies face, pretty often?
Jenna Watson-Brown (11:37):
One of the big misconceptions is around,
like, I just need to show youthe product. And if I show you
the product, you'll be ready tolike, that's all I need to do.
And, like, I'm gonna do a demoand I'm just gonna show you the
product and then that willhappen. And it it depends on the
vertical and the industry andthe segment, all of those things
(11:58):
of what you're selling intobecause there are some products
that the sales cycle is onecall, 2 calls, 3 days. But in
most cases, the discovery demoportion is really about solving
problems.
And you go back to the, youknow, old adage of bad
(12:19):
salespeople just showing youevery feature when you care
about one feature. And if youdon't know what that one feature
is because you didn't ask theright questions, well, you've
just wasted 45 minutes forsomeone because, you know, they
saw 90% of the things theydidn't need to see, and then
they, you know, somewhere inthere, you kind of skimmed over
the one thing they really careabout. So I think that's one of
them is that, oh, I'm just gonnashow you the product, and that's
(12:42):
it. And it's like, no. Youactually need to understand this
individual buyer, thisindividual organization, their
specific needs.
Again, that varies segment tosegment because you may have a
very homogeneous customer base,in which case there's more
things you can you can rely uponbetween conversations. The other
(13:03):
that I would say is that thefounder can pass it off. I see
it all the time. Oh, I'm gonnahire I'm gonna hire sales help.
And I'm gonna hire sales helpthat is going to be a
salesperson for me.
And I've never seen it succeed,both in startups I've worked
(13:25):
with and in startups that I've,seen from afar. Hiring a
salesperson too early usuallydoes far more harm than good.
And until you know what works,you cannot hire someone to do it
for you. You if you have afounder, like a cofounder that
is a sales expert, that'sdifferent. But if that person is
(13:49):
not part of your founding team,I see it all the time, you hire
an SDR or you hire an accountexecutive, but you don't know
what works.
So you're kind of trying tocoach this person to figure out
what could work in a salesmotion, and I've just seen it
fail 10 times out of 10 times.Like, I'm I'm yet to see that
succeed before you probably, Iwould say, like, till you have,
(14:12):
like, 10 happy customers, maybe5 to 10 happy customers.
Bo Motlagh (14:17):
Speaking of challenges, you know, for our
listeners, as we've been digginginto this hidden chasm concept,
Jen has actually been a keycomponent of that. She's been
behind the scenes helping us medmake heads or tails of what
we've been learning and thinkingthrough some of these concepts
as well. So, so you're not newto this, Jenna. It would be
(14:39):
interesting to maybe in your ownwords, if you if you could sort
of maybe take a second and and aswing at what is the hidden
chasm?
Jenna Watson-Brown (14:49):
Yeah. And I'm gonna take a sales lens on
it because I've I've been inthese rooms, more times than I'd
like to say. To me, the hiddenchasm is the brick wall that an
organization, usually anexecutive team, hits, once
they've kind of not like,they're in the middle of the
chasm. They hit this brick wall.And a lot of the times, the
(15:12):
brick wall comes in the form ofdisappointing customers.
And that could be disappointingcustomers who asked for a
feature, and another year hasrolled around, and you made a
commitment, and the feature isnot yet built. And what you're
hearing from the architecture orthe technical team is, it's
like, we we can't do this. It'sgonna incur so much cost. Or
(15:38):
it's the case that you have beenbuilding and building and
building, and the things thatthe customers are experiencing
are breaking. When it's beentaken seriously and when I've
really felt in the chasm as apart of an executive team is
when you're disappointingcustomers.
And disappointing customers withyour product, not with customer
(16:00):
service or pricing, but theproduct either not doing
something they need it to do, ornot following through on
commitments that you've made. Orin the case of, we have this
innovative new idea, your topcustomer, it's a great idea,
everyone agrees, you go back tothe development team and they
say, oh, yeah. That's gonna take2 years. And I've been there.
(16:23):
The tension between the growthand especially if you've taken
on significant venture capital,the growth, the commitments to
the board for growth, and the,technical realities of what you
can do for your customers.
So I I think that's the firstbecause never ever has that
happened, and this has been asurprise to the technical team.
(16:46):
Like, they've seen this comingfor 16, 18, 20 months of we're
gonna hit this wall. We're gonnahit this wall. We have to fix
it. But usually, and I've been aa culprit, growth, growth,
growth, growth.
I'm reporting into a board tohit my numbers for my team, and
I am gonna just keep pushing.And in a lot of the cases, the
(17:10):
CEO is also just gonna keeppushing the technical team to
build and build and build. Andthen you end up with a house of
cards that, that small breezecomes in, and you're you're left
in a dark, hidden chasm.
Josh Smith (17:26):
So much to say there. So I know, Bo, you have
more to say. But when you get tothat point where you suddenly
realize, oh, too many brokenpromises here happening, or what
are you saying it's gonna take 2years, tech developers? Has
there ever been a translationlayer around you at that time?
Because whenever I I mean, me,I'm not Yeah.
(17:48):
I I'm technical, but I'm notthat technical. I've been in
many rooms where I've asked I'vebeen with business folk asking
why is it gonna take this long?And the answer I get, I cannot
decipher. You know, I don't evenknow what they're saying.
Jenna Watson-Brown (18:01):
But Yeah.
Josh Smith (18:02):
Like, if you don't have that translation layer
who's saying, hey. Okay. If wedefer now because the incentive
structure is towards growth andwe're deferring the problem, I
just want you all to know thatwhen we hit it and we're gonna
hit it and this is what it'sgonna look like, you're gonna
have the moment that, oh, okay.We realize how we got here. That
(18:23):
does that happen, or is it morelike, wait.
Why is this happening? What'sgoing on now? Like, does that
make sense?
Jenna Watson-Brown (18:31):
It does. I would say a good analogy is
someone who, like, eatsMcDonald's for lunch 3 times a
week, and it's like their doctorsaying I had a I had a feeling
Yeah. You just look like aMcDonald's junkie. So it's like
it's like your doctor saying toyou, like, you're gonna get a
have a heart attack. Like,you're going to have a heart
attack.
If you eat McDonald's every 3days a week, you're going to
(18:55):
have a heart attack. I would sayin some organizations and in
times of others, there has beenthat translation layer. There's
been that incredibly businesscentric VP of engineering or
CTO, and they have been able tosay, hey. This is gonna be the
repercussion of the decisionsthat you're making. We're
prioritizing x instead of y,and, you know, this is gonna
(19:19):
come.
But just like we've seen withpeople, until you actually have
the heart attack, it is veryhard to change behavior based on
like, we we devalue that futureso much that that current, in
the case of McDonald's, like,oh, I really want a big mac,
(19:39):
overrides any value of thefuture. The other thing that I
think comes into play, which ishard, and and I've seen this
many times, is there's also aresentment that builds between
the business side and thetechnical side of the
organizations. So when you dohit that brick wall, I also
(19:59):
think that is a hard part.Because you have the technical
team be like, told you so. Like,what did you guys think was
gonna happen?
And, again, then even if youhave this incredibly business
centric CTO, they're thendealing with a very unhappy team
because this thing that theysaid was gonna happen happened.
(20:21):
Nobody's winning. And now, youknow, it it just changes the
mood, I would say. And and I Ido think that kind of thing
matters because then you have 2teams against each other instead
of 1 team collectively workingtogether. But I've I've had
those excellent CTOs, and I westill ran fast toward that brick
(20:43):
wall.
I think wherever possible, I'veseen, you know, the the the
really smart technical peoplepicking off little pieces here
and there to kind of prevent thebrick wall from being quite as
hard and quite as severe. Butalmost always, it takes that
heart attack for people toactually clue in.
Bo Motlagh (21:04):
It's it's interesting. So I think, maybe
stepping back a little bitbecause I think hindsight is
2020. Right? And you can lookback at this and analyze it. And
you're describing something thatare very similar to, what others
on the on the show havedescribed, in terms of that
journey to the wall, basically,or 2,000 in this case.
(21:25):
We could call it the hiddenwall. But in that moment, I
guess I'm curious about one ofthe things I think that would be
helpful is to to to thelisteners and in general is, you
know, how in in emotionalintelligence books, they they
talked about actively beingaware of of what's happening
Yes. And and helping and maybesomebody who was in or is in the
(21:46):
position you were in, helpingthem think through the immediate
reaction. So in that moment, asyou said, you weren't thinking
about, oh, this is gonna be aproblem. You were reacting in
the moment to however thesituation was unfolding.
So thinking back to that, I'mcurious, like, what was your
first instinct? So when somebodysaid and you heard them say,
(22:10):
we're going to have a problemand, you know, and obviously in
hindsight, it was 1. But Yes. Inthat moment, knowing that you
had your you had the the numbersthat you were trying to hit that
month, knowing and and maybemaybe there was some and there
were other KPIs maybe that werehappening. I don't know if there
(22:30):
was any blame on sales as well.
What was going through your mindin that moment as opposed to you
sort of reflecting on it now?
Jenna Watson-Brown (22:36):
Yeah. I think if I'm being completely
honest, in that moment, whenthough because that this is not
an isolated incident, but whenthat has happened to me and who
else can I talk to?
Bo Motlagh (22:48):
Okay.
Jenna Watson-Brown (22:48):
And I think we get into that pattern of when
we don't like the answer, thisis me being completely honest.
Yeah. We replace the technicalpeople because we think this is
a people problem. We don't thinkit's a technical prob like, we
don't truly understand themagnitude. And so I think that
(23:09):
that was always my firstinstinct of, well, like, who who
else could give me a differentanswer in that that might which
tells you exactly why we endedup in this position, the the
problem kind of perpetuating.
Right? Because there's alwayssomeone within an organization
that will give you the answerthat they want. They will that
you wanna hear. So, I think,like, in my most reactive state,
(23:31):
that would have been what Iwould say. I think in, like,
taking a deep breath andcounting to 10, I would have
seen well, I going back intothat situation, I think the the
key piece is that I wish I haddone is expanding the time
horizon.
(23:52):
And I think that's the culpritfor a lot of these problems is
when the time horizon is tooshort and when the KPIs are
quarter to quarter, month tomonth, when the board is, you
know, looking at metrics on avery short time horizon, you end
up doing things that are reallygonna hurt you down the road.
(24:14):
And from a financialperspective, that does matter
because your your lifetime valueof a customer decreases
dramatically. If you have acustomer for 3 years instead of
7 years, that's pretty big deal.So I think I wish I had expanded
the time horizon. And I think asa leadership team, that's a
really good way to think aboutthings.
(24:38):
And I think in startup world,that's hard because you're
usually working on a short timehorizon. But just zooming out a
little bit, I would have beenable to see, okay, this is worth
fixing now because, yes, it willmake the customer unhappy for,
you know, this quarter, thisyear, maybe we'll even lose
them. But that means I'm notgonna lose the other 10
(25:01):
customers that we're acquiringright now because we're gonna
solve this problem today. And ina year, the problem will be
solved. So I think that was a abig piece was just how small the
time horizons and the result.
Bo Motlagh (25:14):
And a lot of that comes back to just, you know,
what is your 3 to 5 yearstrategy. Right?
Jenna Watson-Brown (25:20):
And in a startup, I don't know and I I
think it it happens at differentphases, but when you've been
bootstrapped and you've been,can we make payroll? Can we
grow? Can we hire for 5 years?You raise VC. Like, there there
does have to be a veryintentional shift in the time
(25:40):
horizons that you look at.
And I think that continues tohappen as the organization grows
from, you know, 10 to a100,000,000, a 100 to
200,000,000, maybe the timehorizon isn't the it's not the
only thing, but I I know that wecan get trapped in thinking what
got me here is going to get meout of this. And that's I think
(26:02):
that the big trap that I've seensales teams fall into, I've seen
executive leadership teams fallinto is we just need to do more
faster instead of saying we needto do this differently.
Josh Smith (26:13):
One incentive that you mentioned, and I like the
that you you looked at it from atop down is, like, what
influences the incentivestructures of the other
departments is that short timehorizon. Are there any other
incentives that you see, inmidsized enterprise
(26:34):
organizations having to scaleand grow rapidly? Are there any
other incentives that you seethat is influencing the outcome
towards towards this brick wall,this cabin?
Jenna Watson-Brown (26:47):
Hiring, I think, is an incentive. Growing
teams, growing teams quickly.I've never met a manager that
doesn't want a bigger team, orI've met very few managers that
don't want a bigger team. And,you know, for every 8 people,
you should have another manager.Like, it's and I think then you
need to give everyone work, andthen you need to give everyone
(27:08):
revenue.
And I think that is besides justrevenue targets, commission
structures, compensationpackages for executives, I think
that is kind of an underlyingpiece is, like, people's
individual career progression.And I wanna become a manager.
You've had someone in the samerole for 3 years. You want them
to become a manager. You wanttheir team to grow.
(27:29):
So I think that especially inthe startup world where people
go into it to learn and growquickly, I think that's an
underlying current that pushesus faster towards the hidden
chasm.
Bo Motlagh (27:41):
That's really interesting. I mean yeah. So
scaling up your your team tooquickly. I'm curious, when you
one of the things we we we sortof thought might be happening,
and you'd be in a good positionto tell us, is is there any
blowback on the salesorganization before or after
these things begin to happen aswell?
Jenna Watson-Brown (28:02):
1000000%. Yeah. I mean, like, lively like,
you you think you have a salesrep that's used to making 250 to
$500,000 a year, and you'retelling them, hey. I'm gonna say
no to this $1,000,000 contractbecause we can't fulfill, you
know, whatever productobligations or this customer's
gonna churn. Like, you verymeaningfully are impacting their
(28:25):
quality of life.
And maybe it's not even thatdramatic. Like, maybe they're
not a sales rep making a$1,000,000. Maybe they're a
sales rep making, you know, a$150,000 as the sole breadwinner
for their family, and you'retelling them, hey. We're gonna
say no to this deal because ourwe can't fulfill on the the
(28:46):
product promise that we made 6months ago that we're gonna
fulfill. Like, it there is avery, real impact on
compensation that I think isalso very different to the
engineering organization becausethe developer gets paid the same
kind of whether or not they dothe thing or don't do the thing
(29:08):
or do it well or don't do itwell.
Yes. There's other pieces andthings, but a sales rep, not to
say it's better, but they havemore to lose. So I think that's
also why you get the sales teamsare much louder and are willing
to fight much harder. And Ithink that also perpetuates the
(29:29):
cycle because you have a veryloud sales team because their
money is literally on the line.And you're overpowering an
engineering team that, you know,is kinda saying, like, hey.
We're gonna break hit a brickwall. We're gonna hit a brick
wall. Especially for a companythat's not public. Like,
liquidity, like, that stuff isstill so far out, that unless
(29:52):
you're immediately, you know,close to a raising a secondary
round or people can get out oran IPO. But in most cases, what
people take home today is thething that matters to them, and
you have a very, very loud salesorganization.
Bo Motlagh (30:07):
I mean, it it comes back to what you're saying. It's
the it's a misalignment. Well,maybe that's a strong term, but
it it's certainly, a competingYes. Yeah. It's a competing,
incentive structure, which, youknow, maybe there's something
there to look at because if Idon't know.
The developers and and the r andd organization should be
(30:29):
incentivized the same way assales, but, they're skin in the
game.
Jenna Watson-Brown (30:34):
They're in conflict.
Bo Motlagh (30:35):
Yeah. Yeah. Exactly. And and there's a much higher
risk reward scenario in terms ofcompensation for sales than
there is, with r and d. It'sreally interesting.
Jenna Watson-Brown (30:45):
And that's where, like, sales leadership
and that longer time horizon,that 3 to 5 year or 1 to 3 year
time horizon matters. Because ifyour sales leader understands
that and can, you know, set theright expectations with the team
and kind of keep them off thathamster wheel altogether, and
work very closely with productand engineering to be in
(31:06):
lockstep, the likelihood of thathappening is is so much lower.
But I would say in a lot ofcases, you have these sales
organizations that are veryfinancially driven that can
drive the company in a directionthat doesn't serve it over the
long term.
Bo Motlagh (31:26):
Have you ever been involved with a company like
this where you made strides outof the chasm, or or have you
found it to be more of a, ifyou're in it, this is gonna be a
long haul scenario?
Jenna Watson-Brown (31:41):
I think I've I've definitely worked with
companies making strides out. Ithink that that means that, you
know, the problem with the chasmis you get out ish, but there's
always like, the next chasm iskind of always coming. Right? So
I think I've yes. I've seenpartially the other side, but I
(32:01):
won't say I've seen anorganization, like, completely.
Bo Motlagh (32:05):
Bridge the divide.
Jenna Watson-Brown (32:06):
Yeah. Bridge the divide. Once you've
replatformed, there's the nextthing or there's m and a or,
like, it's it's just a cycle.
Bo Motlagh (32:15):
Going back to one of the points you were making was
the, the distrust, mistrust thatthat can form between sales,
product dev, and really I wouldimagine the executive, committee
and the board. And I guess it'sit's such a prevalent thing
(32:36):
because, like you said, there'sall of these misalignments.
There's confusion about what theproblem actually is. There's
disbelief. How could we possiblybe in this situation?
Let me speak to your manager.And, and so what would you say?
Because I think that's probablythe biggest killer. Right? The
moment that happens, the problemis 10 times harder than it was
(33:00):
the day before, because nowyou've got to work together and
now you're thinking throughhindsight or maybe having seen
it be addressed.
What are some recommendationsyou might make, especially
between sales and theengineering organization?
Because I think that to me hasalways felt so out of sync in a
lot of these companies. And Iknow that me and Josh, I would
(33:22):
not speak for you, but I suspectyou would agree. I've been in
the role where it's like, I justwant to talk to the salesperson,
You know? Like, can we figurethis out?
And Yeah. That for some reason,it's always very difficult.
Jenna Watson-Brown (33:34):
I think a key is actually start to the
CEO. I think the CEO or thepresident of the company needs
to reset the tone and reset someof the incentives and a lot and
whether they're, you know,specific incentives like
compensation or they're justexpectation setting. Because
(33:57):
what I've seen is the CEOs wantit all. They want to fulfill the
customer need in the short term,and they want to have the long
term technical plan. And so Ithink what if the CEO can come
into reality, address reality,and say, these are the short
term pains we're all gonna feelto get us to this new, better,
(34:20):
wonderful, brighter future, andlay that out.
I think that gives a morefertile ground for, you know,
the head of the technical side,whether it's the CTO and the
head of sales or revenue tocollaborate, because that is the
piece. Like, you have to bewilling to make short term
sacrifices, and both sides needto make short term sacrifices
(34:43):
for the long term better future.So it's it's 1 +1 equals 3. In
that, the engineering and thesales team both need to be
grounded in the same version ofreality, and they need to have
confidence that they are bothnot gonna be asked to fulfill
(35:03):
every short term commitment andevery long term commitment that
the CEO has or the board has setforth, because that is where you
the gate is impossible to to dothat without, you know, a
massive injection of capital orresources or, you know, other
external factors changing. So Ithink everyone needs to be on
board.
We're gonna take our medicinenow. This is what the medicine's
(35:25):
gonna look like. It's not justthe sales team taking their
medicine. It's not justengineering taking their
medicine. We are all gonna takeour medicine.
This is what it looks like, andthis is why. This is the 1, 2, 3
year plan. But when I've seenthe onus fall entirely on one
team to sacrifice in the shortterm, I think it does a lot of
(35:48):
damage. When it comes to morale,it does a lot of damage.
Josh Smith (35:52):
And as part of that that medicine taking, have you
seen something I I don't knowhow to to describe as the per
customer feature demands versusthe more broad what is the
benefit of implementing this, inthe entire product in a way that
(36:16):
benefits the business in thelong term? That that tension
where the short term thinkingwas paying off, you were
converting leads faster, but youwere incurring more debt because
you were building so many oneoffs for specific customers.
Jenna Watson-Brown (36:35):
Yeah. And that's that's I mean, that's the
crux of it. Right? And I've beenthere with anybody. It's a habit
to break.
And I think in my experience,like, whether you have a key of
a group of customer advisers,you need to be transparent and
get them on board with the plan.Because if they can also see
(36:56):
thinking of your your biggestkey customers, why you're gonna
be saying no in the short termto some of the things that you
used to not say no to, and whatthat long term payoff is for
them. And if that long termpayoff and that 1, 2, 3 year
plan addresses their needs. I'veseen that work, and I've
(37:17):
personally had thoseconversations with executives
and with board members of k.We're gonna say no now, and I'm
sorry.
It's gonna be reallyuncomfortable. I know it's gonna
put you in a hard spot, but thisis why. And, I mean, obviously,
working with the team to see ifthere's anything that you can do
that kind of gives them a littlebit of a cookie, like, you know,
(37:38):
k. Whether that's pricing,whether that's something else
that they want, but thenenrolling them and and this is
making sure that what you'rebuilding is going to address
them in the long term. I wouldalso say, in some cases, you may
just have a bad fit customer,and you've been bringing them
along and they've been costingway more than their work, it is
(38:00):
never worth keeping a bad fitcustomer.
And so that would be, hey,customer. Like, this isn't this
isn't working. Whether that'sbecause of the customer's
demand, whether that's becauseof the customer's use cases,
maybe they're using the productin a very different way. But
(38:21):
having that very open andtransparent conversation and
trying to, like, kill that deadweight, those are 2 things that
I've seen help, to to then giveyou the breathing room that you
need on the engineering side tonot be constantly putting out
fires and to instead bebuilding.
Josh Smith (38:38):
I don't even know if this exists, but to be able to
have some sort of KPI ormeasurement of the deadweight
per customer.
Bo Motlagh (38:50):
I was gonna say, how often I don't know that that
happens as often as it should isprobably the right way to put
that. But that's interesting.It's tricky because I think as
you're working with thesestartups from on their journey
from 0 to, like, let's say,5,000,000, So much of that is
opportunistic sales. Right? Andand it's, you know yeah.
You have a vision. That visionmight need to change. And so you
(39:13):
are you're doing the thing outof necessity that you hope you
don't keep doing after somepoint. And there's this
transition moment, which isprobably very difficult to say.
Well, when you get here, stopdoing that.
Where the things that got betterhave helped you be successful
all of a sudden start to lead tosome toxicity. It's gotta be
fascinating from yourperspective because in your work
(39:34):
with these these early stagecompanies, and I would imagine
you you probably see this mostlyin that 5,000,000 category.
Like, are you seeing thingswhere you're just like, okay.
This is good for an app, but,man, that's probably gonna be a
problem later.
Jenna Watson-Brown (39:48):
Absolutely. I mean, I think the biggest one
is, relying on personalnetworks. I think that's the the
biggest one. Like like, you hirea sales rep or you hire 2 sales
reps, and they have reallyextensive personal networks, and
they've built your first few$1,000,000 of sales through
(40:11):
their personal networks. But,you know, there are some
exceptions, but in most cases,you've actually not proven that
you have a sales motion thatworks.
You've proven that if people getto know about your product, they
wanna buy your product. So Ithink that's one for sure in
that, like, I'd say, like, 2 to$5,000,000 range. Of course, you
(40:33):
can look at the renewal numberson that, and that will give you
a better indication of, like, isthere a true product market fit
there? But I've seen that a lotof just relying on personal
networks. And anytime you have asingle point of of failure,
especially when that personisn't a founder.
I would say it's different ifit's a founder because that
network couldn't go anywhere.That's a big one. I would say
(40:55):
more often, though, I see peopletrying to scale sooner than they
should.
Bo Motlagh (41:01):
Mhmm.
Jenna Watson-Brown (41:01):
That's actually the way bigger problem
is people with 1 or 2 customerstrying to then build this super
scalable sales process orplanning documents or
opportunity criteria, or even ata few $1,000,000, they're like,
oh, we need to hire this bigsales team, and it's a crawl,
(41:25):
walk, run. It is not a crawl,run. And it so I think that is
more often people skipping stepsof, okay, we did a whole bunch
of things that aren't scalable.Now let's peel some of those
off. Let's keep doing some ofthe ones that are most critical,
but what do we think we could dothat is scalable?
And then adjusting that insteadof taking a band aid and ripping
(41:45):
it all off at once because youcan't troubleshoot and you can't
tweak. And then you're just leftwith this, well, we had all
these sales and now we have nosales, or we have less than we
thought. What do we do? And it'slike, well, you've changed 65
variables at one time. So Ithink that is more often the
issue that I see.
Josh Smith (42:06):
Yes. Like, you wanna stand behind the wave so you can
see it and and adjust because ifyou say, okay. I'm gonna just
stand in front of it and buildthis this huge, invest all of
this money because I'm justlooking at I'm connecting 2 dots
and creating a straight linesomewhere. Well, you can't see
the wave anymore. And ifsomething changes, well, you've
you've just you've
Jenna Watson-Brown (42:27):
Yeah.
Josh Smith (42:27):
Expanded based on a perception of, like, a
trajectory that is not always ina flat line up in up into the
right. So
Bo Motlagh (42:38):
You talked a little bit about, that that change
starts with the CEO, and yougave some some examples of
things that they should be doingto help when these things happen
or when they find themselves inthe chasm. Do you have any
thoughts in terms of practicaladvice for a CRO, or or even a
CTO or CPO who may findthemselves in this situation?
Jenna Watson-Brown (43:00):
I would, so I think there's 22 tendencies.
There's one to stop the bleedingand then get to the root cause.
And I think most people stop itstop the bleeding. And they say,
okay. We stopped the bleeding.
I'm gonna kind of continueforth. I think stopping the
bleeding and then getting to theroot cause. I think looking at
(43:22):
your people, like, a lot of thetimes, the people that got you
into a situation aren't thepeople that will get you out of
it. Like, it's it's a sad truth.There are some people that are
really good at startups, and Iwould say myself included, like,
I'm not a $2,000,000,000salesperson.
Like, that that is not mywheelhouse. And there are people
(43:43):
that are really good at gettingyou to a $100,000,000 or
$50,000,000 that are not goingto be able to get you where you
need to go next. So I think thatis that is hard. It doesn't mean
that they are to be redundant,like, to be taken out, but how
do you bolster them with peoplethat have been on this path
forward? So I think it's it'sadding executives, adding
(44:05):
advisors of people that havedone this portion of the journey
that you're about to do next,and also looking at vendors that
have done this portion of thejourney that you're doing next.
Because, again, you don't wannabe at 50,000,000 and look to a
$1,000,000,000 CEO and say,okay. You're gonna be my mentor.
How do I get to a 1,000,000,000?It's finding the right people
(44:26):
that have done that 50 to$250,000,000 journey, because
that's the journey you're on.Who can help with that?
Whether it's adding to yourexecutive team, adding to your
board, adding to your advisors,working with vendors that have
done that portion of thejourney. I think that's often
overlooked because if everyonearound you has only ever gotten
(44:49):
to 50,000,000 Yeah. The chancesthat you're going like, who can
help who can you learn from? Ofcourse, adding your own flavor,
adding your own spin. You Youknow, you're not looking for a
playbook per se, but a guide orpeople that can help you avoid
some of the common pitfalls.
Bo Motlagh (45:07):
What about in in a scenario where maybe there maybe
there is attention being finallygiven to the platform, the
product. I'm sure from a salesperspective, if you're somebody
who's tasked with bringing inrevenue and all of a sudden
you're being told that yourproduct is going under, you
(45:27):
know, major refactoring orthings like that. That can feel
scary. Right? Did you have anythoughts in terms of maintaining
the sales momentum in anenvironment where everything is
in flux like this?
Jenna Watson-Brown (45:41):
So I would say 2 things. 1, find more like,
you you always have a pocket ofhappy customers. And maybe the
customers are using only 75% ofthe product, or they're really
focused on a specific use caseor feature, or they moved from a
certain competitor and theymoved to your product and
they're just thrilled, and maybethey're 20% of your customers.
(46:04):
Find more like them andincentivize the sales team to
find more like them. So whileyour product is going under
major overhaul, don't try andfind more customers that are
disgruntled or upset or wantingit to be different waiting for
those new features.
Find more customers that arehappy with it as it is today,
and that the new features willhelp in the future. So kind of
(46:27):
gearing the sales efforts, themarketing efforts, the events,
the everything, all theactivations you're doing to give
them the best shot of success atcustomers that will be happy
with the product while it goesthrough this transition. I think
that's number 1. Number 2 isthis is where the engineering
team, technical team, productteam needs to put on their sales
(46:49):
hats. Yeah.
Sell this vision to the salesteam. Like, it is your job to
get the sales team on board withwhere you're going. And if it
was a good plan and if it waswell thought through, you've
taken customer feedback, you'velistened to customers. So there
is something for them to getexcited about, but it is your
(47:10):
job to enroll the sales team, inwhat you're doing so that they
can say, okay. Littleuncomfortable right now, but in
a year, I'm gonna be able tosell 2 x my average contract
value because we're integratinga new product or because we're
rolling out this new feature.
Help them understand how it'sgonna help them make more money.
Bo Motlagh (47:30):
That's so interesting because a big part
of, you know, when I speak totechnologists, architects,
developers, a big conversationwe eventually end up having is
how to talk businesseffectively. Right? I think it's
a really important piece ofproduct development leadership
to teach your technicalresources how to speak to the
(47:53):
business in and of itself inorder to have that conversation.
Exactly what you're saying. Andknow that, well, I think it
would be really cool isn't agood reason.
And, oh, you're going to lose alot of money if you don't. Maybe
it's a better one.
Jenna Watson-Brown (48:05):
And we need to do it. That's a terrible
reason as well. But if you canexplain the potential revenue
benefits, the potential newfeatures and products, and this
is gonna take your annualcontract value from, you know,
$75,000 to a $115,000 becausewe're adding these widgets. We
heard from 80% of customers thatthey want it. That's a totally
(48:25):
different conversation.
Josh Smith (48:26):
Yeah. Yeah. That makes sense. The context that
you like what you're doing now,sales, but here, let me tell you
what the possibilities are wherewhere you could be and what you
could be achieving with withthis this time, which may not be
pleasant this time, but thistime that we need to invest.
Jenna Watson-Brown (48:46):
Yes. And then the other piece is, like,
how is the executive teamengaging with customers? Because
that goes a long way. And whenyou're gonna be pissing off a
customer, like, I'm thinking,let's say, you're doing a m and
a. You're acquiring another keyproduct in this space, and
you're gonna integrate thatproduct into your product.
(49:07):
But it means it's gonna beclunky for a little bit, and,
you know, they're gonna beupset. Well, call from your CEO
or a call from someoneexplaining the vision,
explaining the the value, andexplaining what they're gonna
get out of it at the end goes areally long way.
Bo Motlagh (49:25):
So that's an important piece because it's a
question for me, actually. SoI'll ask you is is, I've seen
this happen, which is thecompany is in the midst of, you
know, they know what whatthey've been doing isn't working
all of a sudden. And so areaction to that is is what, you
know, I guess you could calllike visionary syndrome.
Somebody sits down and comes upwith this brand new concept of
(49:49):
how everything is gonna bedifferent and looks completely
different. They might eveninvest in, you know, somebody to
come in and drop what this wholenew vision of is gonna look
like.
And most of the time I mean,it's great. It's an amazing idea
and maybe and and and in manyways, it may address the the
business and market issues,although it certainly wouldn't
(50:09):
immediately address thetechnical issues that have led
them there. But it is alsosomewhat divorced from the
reality of their currentscenario and it's like, while
you're trading the hardships ofof your existing reality with
the hardships of a reality thatdoesn't even exist yet. And then
they go out and start trying tosell that, which from a startup
perspective is is like, well,that that makes sense. You're
(50:30):
you're selling something beforeyou build it so that you can get
paid to build it.
From an enterprise perspective,I don't know if you're it feels
very risky, but maybe maybe thatI don't know. I'm curious what
your thoughts are.
Jenna Watson-Brown (50:41):
Yeah. Risky is a really, really good term to
use. I think there's a balance.There is getting a little ahead
of your skis, selling somethingthat's coming. But the
enterprise needs to be excitedabout what they have today.
So it will not exempt you fromusers reporting bugs on your
platform. That doesn't helpnecessarily. It can buy you more
(51:04):
credibility and more time, butit is absolutely a balance. And
I think too often people unveilthis entire new version of their
product all at once. And I I forthe enterprise specifically,
like, I was speaking with acustomer the other day, and they
(51:25):
have a a SaaS tool, and theychanged the color of something.
Mhmm. And someone complained.They changed the color from blue
to white. And someone complainedbecause they were used to it
being blue, and it is now white.It is still incredibly legible.
It was like a decoration. It wasnot actually a key piece of the
UI. So I think these visionarymoments, people think, oh, I'm
(51:50):
gonna unveil this entirely newthing, and, you know, we can
think of some SaaS tools thatthe 3 of us use where they
unveiled a new menu and all atonce. And while it's maybe
better for us in the long term,like, that was a hard adjustment
to make. So, of course, there'llbe some things that you need to
do all at once, but I would saytoo often, it's like, oh, 3
(52:14):
point o.
We're gonna take everything andblow it up and make it different
and better, is often not thesolution, and the solution is
more iterative.
Josh Smith (52:24):
The delta between what is now and all the muscle
memory that people have to knowwhat is now, all the comfort
they have, even if it'sterrible, they've gotten it to
work. They figured it out. Andthe dealt between that and the
new thing, that's change thatneeds to be designed, and it's
often not applied. The newthing's designed, but the the
(52:47):
path and the journey to handholdsomeone to the new thing, that's
often missed.
Jenna Watson-Brown (52:53):
Yeah. And the same with entering a new
market. Like, we're gonna go upmarket. We're gonna go down
market. Okay?
Great. And you have a sales teamthat is an expert in one market,
and now you think you're gonnaapply it to a new market. Or
we're gonna integrate we're aSaaS tool that is a $150,000 a
year or bought a competitorthat's $5,000 a year. And now
(53:14):
we're gonna try and integrate itall together. I think the vision
is important and the vision isthere, but the connection, like,
strategy in action, I think isthe critical, critical piece
that often gets missed, and thenyou end up with a bungled, half
(53:37):
baked, not on time, frustratedsituation.
And that's where you get thesecustomers that are sitting on
legacy tech for years yearsyears because they won't move to
the latest version, because itdoesn't meet their needs.
Bo Motlagh (53:55):
It's another version of the, build it and they will
come fallacy you were talkingabout. It it's just a much more
expensive version.
Jenna Watson-Brown (54:03):
Absolutely.
Bo Motlagh (54:04):
I think we covered a ton of ground. This was really
cool. Jenna, thank you so muchfor making this time. You know,
wanna open up the mic to youhere. Spotlight is on you.
Anything you want to plug ortalk about? Go ahead. Let
everybody know.
Jenna Watson-Brown (54:16):
I would say feel free to reach out if anyone
listening to this wants to talkmore about start up sales. But
my if I could put it on abillboard, and I'm gonna put it
on this billboard now, please,please, please don't hire sales
too early. You need to be ableto repeatably sell yourself as a
founder. If you cannotrepeatedly sell this yourself,
(54:38):
you will never have luck with asalesperson. You need to learn
to get good at sales.
So I think for founders, that'swhat I'm gonna leave we with.
And then for any execs that arelistening to this that are,
focused on kind of that 50 to250,000,000, I'm in this stack.
Like, find people like Bo, likeJosh. Find people that have done
(55:02):
this part of the journey before,because you will be far better
off. And I think thinking whatgot you here will get you out of
it is a hard path.
Bo Motlagh (55:12):
We really appreciate that plug. How would people
reach out to you?
Jenna Watson-Brown (55:16):
Great. Jenna Watson-Brown on LinkedIn, or
jenna@jennawb.com as my email.So feel free to reach out there,
but LinkedIn is also great.
Bo Motlagh (55:28):
Awesome. Well, this has been another episode of The
Hidden Chasm. Thank you, andstay tuned for more. You've been
listening to The Hidden Chasmbrought to you by
United Effects. If anything inour conversation resonated with
you today, please reach out.
We'd love to hear from you.Email us at
podcast@unitedeffects.com, orsimply visit us at
(55:49):
Thanks for listening.
You're listening to The Hidden Chasm, a discussion
of how tech debt and legacysolutions become barriers to
growth and innovation forestablished SaaS companies. The
Hidden Chasm is sponsored byUnited Effects where our purpose
is to help companies break freefrom legacy tech, improve
retention, and empower M&Agrowth. Learn more at
unitedeffects.com. Welcome toanother episode of The Hidden
(00:32):
Chasm, which you have to saywith with that deep voice. You
know, we've been exploring thechasm, from a lot of different
angles.
We spoke spoken to M&Aadvisors. We've spoken to
product executives. We have sometechnology folks coming up soon
as well. We've had the peopleangle, which has been really
interesting. But I think one ofthe most important elements of
(00:53):
any business is revenue.
Otherwise, you don't really havea business. And to help explore
this this particular angle isour friend and actually board
advisor. Welcome Jenna. JennaWatson-Brown. Jenna is a 15-year
veteran of business development.
I'm reading this. I always haveto read. Jenna is a 15-year
veteran of business development,sales, and growth coaching with
(01:15):
proven successes leadingenterprise sales as a senior
executive. She now focuses herenergy and experience on helping
early stage companies findproduct-market fit, gain
traction, and build revenue.She's currently the founder of
Jenna Watson-Brown Consulting,affiliated with several
accelerators and board advisorto several companies including
United Effects.
Welcome, Jenna.
Jenna Watson-Brown (01:35):
Thank you very much. Excited to be here.
Bo Motlagh (01:38):
Well, we're excited to have you. Obviously, Jenna,
you've been working with us fora while now. And it's funny, you
know, for our listeners, it'salways funny when we have to do
some digging on people wealready know to figure out how
these conversations are gonnago. As I dug into your past a
little bit and saw yourexperiences in enterprise sales
with Eventbase and then Motiveand then moving into your
(02:01):
coaching career now, just areally fascinating, journey. I'm
sure a lot of people would, youknow, would be interested
hearing more about it.
And I thought, you know, whydon't you
Jenna Watson-Brown (02:10):
just kick
Bo Motlagh (02:11):
things off is tell us about yourself and how you
found yourself on this call withus.
Jenna Watson-Brown (02:16):
Yeah. And I I always say, like, I didn't
take the easy path. And I Ithink once you get a taste of
the startup world, it's reallyhard to let go. So I joined my
first startup when I was 19,employee, I think, 9 or 10, 1st
salesperson working alongsidethe CEO and was there for 10
(02:38):
years. And I joke that, yes, itwas one company.
It had a couple different namesover the years, but it was
actually five differentcompanies. Because in every
different phase that we were at,whether it was bootstrapping,
pivoting into enterprise,raising our first VC, raising
subsequent VC, it was anentirely different company with
entirely different challenges.And executives and board members
(03:01):
and all of that evolved greatly.So that was where I really cut
my teeth in sales, selling tothe likes of SAP, Microsoft,
Charles Schwab, really with notmuch experience and having to be
self taught in a lot of ways. Mybackground's actually in
accounting, which I don't thinkyou guys knew.
Bo Motlagh (03:22):
I think you guys
Jenna Watson-Brown (03:23):
Yeah. So I I I like numbers. So I've always
liked numbers. I like algebra. Idon't like bigger things than
algebra, but I like, you sellthis many of this and you get x.
That's my perfect kinda math. Sothat's where I started, and then
over time, ended up taking oversales, leading sales, leading
(03:44):
customer success. Sounderstanding both pieces of
that as well of not just gettingthat sale, but keeping that sale
and growing that customer, whichI think gives me a unique
perspective on the importance ofgood fit customers, the
importance of true productmarket fit. I've heard I can't
don't know who to credit, but Ibelieve product market fit
(04:07):
actually comes in the renewal,not in the sale. Because a good
salesperson can get just aboutanything sold, whether or not
you need it or want it, andproduct market fit is actually
the renewal.
Did you find enough value inthat 1st or second or third year
of the product to renew? Sothat's that's my background.
That was the beginning of myenterprise and sales career. And
(04:30):
then after that, moved on to, acouple other startups, Motive
being one of them in acompletely different space back
to, you know, small scale,scrappy team, taking out the
garbage, trying to, you know, dobig deals with the likes of, you
know, fortune 10 companies andand made some excellent progress
there. But it it's, you know, Ithink building something from
(04:55):
nothing and finding people withthe problem that you can solve
for them that they want solvedis is, like, the thing I the
thing I look for in all my work.
And so now I help start ups helpand I'm starting to work more
with little bit further oldcompanies a little bit further
along, like, you know, 5,10,000,000 in revenue, but it's
(05:16):
how do we build a sales motion,scalable or not, that is going
to build the company in a waythat is not cutting off your
nose despite your face.
Bo Motlagh (05:31):
Interesting. Well, first of all, backing up a
little bit. So you you startedyou started at 19? Yeah. I was
definitely not thinking aboutbusiness or anything really at
19.
Jenna Watson-Brown (05:39):
Yeah. I and it was it was a total fluke,
like a kinda friend of a friend.Oh, do you wanna work here? And
I had another job, and thehusband of the owner of the
company said, oh, I I reallylike you. Like, would you be
open to trying sales?
I think you'd be really good
Bo Motlagh (05:53):
at it.
Jenna Watson-Brown (05:53):
And that's literally how it happened. And
then, like, I worked alongsidethe CEO. I was like, k. Let's
let's build this. I I would sayI've always like, I I came out
this way.
So it sales was a naturaltendency for me, and I'd always
been entrepreneurial, like, evenwhen I was 18 when social media
(06:13):
first came out, even youngerthan that. And, like, businesses
were trying to figure out how doyou monetize. Like, I did my own
little consulting on the side.It was helping companies set up
Twitter accounts. And so I'vealways had that in me.
But, yeah, like, I I officiallyembarked on. And the first, I
think, 5 years of my startupworld was bootstrapped, until we
(06:34):
were profitable, and we wereselling to the likes of SAP, and
really, really big companieswith no marketing, no sales, no
VC. So I know it's possible. Iknow it's possible, and I think
that's where I can rub somepeople the wrong way because I I
don't believe that you need allthe flashy stuff to to get Yeah.
(06:57):
Get off the ground.
Bo Motlagh (06:59):
Well, I think that's been what something, you know,
as Josh and I have worked withyou that resonated with me is is
is the let's just try this andmake and see if that works. It's
pragmatic and practical, which Ilove over, you know, theory and
and process, which is finebecause I'm a fan of process.
But I think as opposed tosomething that's dogmatic and
(07:21):
thinking through, you know,actual steps that work. As
you've sort of moved throughyour career, so you started with
startups, you then ended up inenterprise, and then you bet
you're back to startups. Wouldwould you say how did the the
enterprise world influence howyou coach start ups now?
Jenna Watson-Brown (07:39):
Yeah. I I think with the enterprise world,
what you learn is that you haveto play by their rules. Like,
you have to play by the endcustomer's rules. And when
you're selling to Microsoft andyou're selling 2, $3,000,000 of
of business a year, doesn'treally matter what you think or
(08:01):
what you want or how you wantthe sales process to go. It just
it doesn't matter in the sameway that I think some startups
think it does.
Like, oh, I'm gonna build thissales motion, and I'm just gonna
do it. And that's the way it'sgonna go. It's like, yeah, but
this is how Microsoft buys. So Ithink it gave me a very deep and
thorough understanding of,meeting customers where they
(08:26):
are. And if you're selling tothe enterprise and you're trying
to do a lightweight PLG motion,but you're selling to a SVP at
Microsoft, those two thingsdon't work together.
I I don't believe in a salesmotion for a sales motion. I
believe in matching salesmotions to the buyer. Sales
motions to the buyer, the waythey typically buy, their
(08:49):
expectations. So I think it'sgiven me a really big, a fee for
the buyer and, and I think it'sdispelled some of the myths of
build it and they will come.Because I think a lot of
startups, we had thisconversation just earlier today,
think that building the productis the hardest part of building
a startup.
(09:10):
And I can, without a shadow of adoubt, say that that is not
true.
Josh Smith (09:13):
You mean you mentioned PLG, you know
Jenna Watson-Brown (09:15):
Yes.
Josh Smith (09:16):
Doing product led growth. Right? Yes.
Jenna Watson-Brown (09:17):
Yes.
Josh Smith (09:18):
And that that is a continuing trend even now. And I
guess you would say that, thatas much as folks certainly love
to jump on the bandwagon and sayit could be a panacea for for
getting your startup off theground, you would say, hold on.
Wait one second. Let's take alook at exactly who those buyers
are first and whether or not PLGis even a fit.
Jenna Watson-Brown (09:38):
Yes. I think they say with PLG, and I I don't
this is a stat that kind ofpeople have different versions
of. Like, if your productdoesn't give them an moment
within the first five minutes ofusing it, you shouldn't have to
PLG. And if your product like,think of Calendly. Great
example.
Put your credit card in, signup, premium, whatever, you know,
(10:01):
however you've come to Calendly,free trial. You try it. You send
out your first meeting. You'relike, oh my gosh. Someone booked
a meeting.
I didn't have to go back andforth. That's incredible. There
wasn't a stakeholder group todecide whether is the right fit.
It didn't integrate with yourarchitecture. It didn't
integrate with it didn't need asecurity review, like but then
(10:22):
when people say, oh, I'm gonnatake this, like, highly
specialized enterprise securityproduct and put it with PLG.
It's like, well, that's not howthe CISO buys. The CISO doesn't
A (10:33):
there's no AHA moment in 5 minutes. B
such that they're not enteringin a credit card inform their
credit card information. And, C: that's not how this purchase (10:40):
undefined
gets made. It's not anindividual user using an
individual tool.
So, of course, there'sexceptions to everything, but I
so often, I see founders say,oh, I like the sales process or
I like this market. I'm gonna goafter it. But completely
(11:01):
ignoring who actually wants theproduct, who has the demand to
solve the problem, and how dothey typically buy, how do they
typically interact with vendors,and the realities of the product
you're selling.
Bo Motlagh (11:13):
It's funny because we I mean, Josh and I had have
gone back and forth on productled growth a lot as well. And
you're right. It all it soundsso amazing.
Jenna Watson-Brown (11:22):
Mhmm.
Bo Motlagh (11:23):
It's like this yeah. Let's do that. And then you get
into it and you're like, oh,that that didn't work. That
seems like one commonmisconception. Are there other
common misconceptions andchallenges you see early stage
companies face, pretty often?
Jenna Watson-Brown (11:37):
One of the big misconceptions is around,
like, I just need to show youthe product. And if I show you
the product, you'll be ready tolike, that's all I need to do.
And, like, I'm gonna do a demoand I'm just gonna show you the
product and then that willhappen. And it it depends on the
vertical and the industry andthe segment, all of those things
(11:58):
of what you're selling intobecause there are some products
that the sales cycle is onecall, 2 calls, 3 days. But in
most cases, the discovery demoportion is really about solving
problems.
And you go back to the, youknow, old adage of bad
(12:19):
salespeople just showing youevery feature when you care
about one feature. And if youdon't know what that one feature
is because you didn't ask theright questions, well, you've
just wasted 45 minutes forsomeone because, you know, they
saw 90% of the things theydidn't need to see, and then
they, you know, somewhere inthere, you kind of skimmed over
the one thing they really careabout. So I think that's one of
them is that, oh, I'm just gonnashow you the product, and that's
(12:42):
it. And it's like, no. Youactually need to understand this
individual buyer, thisindividual organization, their
specific needs.
Again, that varies segment tosegment because you may have a
very homogeneous customer base,in which case there's more
things you can you can rely uponbetween conversations. The other
(13:03):
that I would say is that thefounder can pass it off. I see
it all the time. Oh, I'm gonnahire I'm gonna hire sales help.
And I'm gonna hire sales helpthat is going to be a
salesperson for me.
And I've never seen it succeed,both in startups I've worked
(13:25):
with and in startups that I've,seen from afar. Hiring a
salesperson too early usuallydoes far more harm than good.
And until you know what works,you cannot hire someone to do it
for you. You if you have afounder, like a cofounder that
is a sales expert, that'sdifferent. But if that person is
(13:49):
not part of your founding team,I see it all the time, you hire
an SDR or you hire an accountexecutive, but you don't know
what works.
So you're kind of trying tocoach this person to figure out
what could work in a salesmotion, and I've just seen it
fail 10 times out of 10 times.Like, I'm I'm yet to see that
succeed before you probably, Iwould say, like, till you have,
(14:12):
like, 10 happy customers, maybe5 to 10 happy customers.
Bo Motlagh (14:17):
Speaking of challenges, you know, for our
listeners, as we've been digginginto this hidden chasm concept,
Jen has actually been a keycomponent of that. She's been
behind the scenes helping us medmake heads or tails of what
we've been learning and thinkingthrough some of these concepts
as well. So, so you're not newto this, Jenna. It would be
(14:39):
interesting to maybe in your ownwords, if you if you could sort
of maybe take a second and and aswing at what is the hidden
chasm?
Jenna Watson-Brown (14:49):
Yeah. And I'm gonna take a sales lens on
it because I've I've been inthese rooms, more times than I'd
like to say. To me, the hiddenchasm is the brick wall that an
organization, usually anexecutive team, hits, once
they've kind of not like,they're in the middle of the
chasm. They hit this brick wall.And a lot of the times, the
(15:12):
brick wall comes in the form ofdisappointing customers.
And that could be disappointingcustomers who asked for a
feature, and another year hasrolled around, and you made a
commitment, and the feature isnot yet built. And what you're
hearing from the architecture orthe technical team is, it's
like, we we can't do this. It'sgonna incur so much cost. Or
(15:38):
it's the case that you have beenbuilding and building and
building, and the things thatthe customers are experiencing
are breaking. When it's beentaken seriously and when I've
really felt in the chasm as apart of an executive team is
when you're disappointingcustomers.
And disappointing customers withyour product, not with customer
(16:00):
service or pricing, but theproduct either not doing
something they need it to do, ornot following through on
commitments that you've made. Orin the case of, we have this
innovative new idea, your topcustomer, it's a great idea,
everyone agrees, you go back tothe development team and they
say, oh, yeah. That's gonna take2 years. And I've been there.
(16:23):
The tension between the growthand especially if you've taken
on significant venture capital,the growth, the commitments to
the board for growth, and the,technical realities of what you
can do for your customers.
So I I think that's the firstbecause never ever has that
happened, and this has been asurprise to the technical team.
(16:46):
Like, they've seen this comingfor 16, 18, 20 months of we're
gonna hit this wall. We're gonnahit this wall. We have to fix
it. But usually, and I've been aa culprit, growth, growth,
growth, growth.
I'm reporting into a board tohit my numbers for my team, and
I am gonna just keep pushing.And in a lot of the cases, the
(17:10):
CEO is also just gonna keeppushing the technical team to
build and build and build. Andthen you end up with a house of
cards that, that small breezecomes in, and you're you're left
in a dark, hidden chasm.
Josh Smith (17:26):
So much to say there. So I know, Bo, you have
more to say. But when you get tothat point where you suddenly
realize, oh, too many brokenpromises here happening, or what
are you saying it's gonna take 2years, tech developers? Has
there ever been a translationlayer around you at that time?
Because whenever I I mean, me,I'm not Yeah.
(17:48):
I I'm technical, but I'm notthat technical. I've been in
many rooms where I've asked I'vebeen with business folk asking
why is it gonna take this long?And the answer I get, I cannot
decipher. You know, I don't evenknow what they're saying.
Jenna Watson-Brown (18:01):
But Yeah.
Josh Smith (18:02):
Like, if you don't have that translation layer
who's saying, hey. Okay. If wedefer now because the incentive
structure is towards growth andwe're deferring the problem, I
just want you all to know thatwhen we hit it and we're gonna
hit it and this is what it'sgonna look like, you're gonna
have the moment that, oh, okay.We realize how we got here. That
(18:23):
does that happen, or is it morelike, wait.
Why is this happening? What'sgoing on now? Like, does that
make sense?
Jenna Watson-Brown (18:31):
It does. I would say a good analogy is
someone who, like, eatsMcDonald's for lunch 3 times a
week, and it's like their doctorsaying I had a I had a feeling
Yeah. You just look like aMcDonald's junkie. So it's like
it's like your doctor saying toyou, like, you're gonna get a
have a heart attack. Like,you're going to have a heart
attack.
If you eat McDonald's every 3days a week, you're going to
(18:55):
have a heart attack. I would sayin some organizations and in
times of others, there has beenthat translation layer. There's
been that incredibly businesscentric VP of engineering or
CTO, and they have been able tosay, hey. This is gonna be the
repercussion of the decisionsthat you're making. We're
prioritizing x instead of y,and, you know, this is gonna
(19:19):
come.
But just like we've seen withpeople, until you actually have
the heart attack, it is veryhard to change behavior based on
like, we we devalue that futureso much that that current, in
the case of McDonald's, like,oh, I really want a big mac,
(19:39):
overrides any value of thefuture. The other thing that I
think comes into play, which ishard, and and I've seen this
many times, is there's also aresentment that builds between
the business side and thetechnical side of the
organizations. So when you dohit that brick wall, I also
(19:59):
think that is a hard part.Because you have the technical
team be like, told you so. Like,what did you guys think was
gonna happen?
And, again, then even if youhave this incredibly business
centric CTO, they're thendealing with a very unhappy team
because this thing that theysaid was gonna happen happened.
(20:21):
Nobody's winning. And now, youknow, it it just changes the
mood, I would say. And and I Ido think that kind of thing
matters because then you have 2teams against each other instead
of 1 team collectively workingtogether. But I've I've had
those excellent CTOs, and I westill ran fast toward that brick
(20:43):
wall.
I think wherever possible, I'veseen, you know, the the the
really smart technical peoplepicking off little pieces here
and there to kind of prevent thebrick wall from being quite as
hard and quite as severe. Butalmost always, it takes that
heart attack for people toactually clue in.
Bo Motlagh (21:04):
It's it's interesting. So I think, maybe
stepping back a little bitbecause I think hindsight is
2020. Right? And you can lookback at this and analyze it. And
you're describing something thatare very similar to, what others
on the on the show havedescribed, in terms of that
journey to the wall, basically,or 2,000 in this case.
(21:25):
We could call it the hiddenwall. But in that moment, I
guess I'm curious about one ofthe things I think that would be
helpful is to to to thelisteners and in general is, you
know, how in in emotionalintelligence books, they they
talked about actively beingaware of of what's happening
Yes. And and helping and maybesomebody who was in or is in the
(21:46):
position you were in, helpingthem think through the immediate
reaction. So in that moment, asyou said, you weren't thinking
about, oh, this is gonna be aproblem. You were reacting in
the moment to however thesituation was unfolding.
So thinking back to that, I'mcurious, like, what was your
first instinct? So when somebodysaid and you heard them say,
(22:10):
we're going to have a problemand, you know, and obviously in
hindsight, it was 1. But Yes. Inthat moment, knowing that you
had your you had the the numbersthat you were trying to hit that
month, knowing and and maybemaybe there was some and there
were other KPIs maybe that werehappening. I don't know if there
(22:30):
was any blame on sales as well.
What was going through your mindin that moment as opposed to you
sort of reflecting on it now?
Jenna Watson-Brown (22:36):
Yeah. I think if I'm being completely
honest, in that moment, whenthough because that this is not
an isolated incident, but whenthat has happened to me and who
else can I talk to?
Bo Motlagh (22:48):
Okay.
Jenna Watson-Brown (22:48):
And I think we get into that pattern of when
we don't like the answer, thisis me being completely honest.
Yeah. We replace the technicalpeople because we think this is
a people problem. We don't thinkit's a technical prob like, we
don't truly understand themagnitude. And so I think that
(23:09):
that was always my firstinstinct of, well, like, who who
else could give me a differentanswer in that that might which
tells you exactly why we endedup in this position, the the
problem kind of perpetuating.
Right? Because there's alwayssomeone within an organization
that will give you the answerthat they want. They will that
you wanna hear. So, I think,like, in my most reactive state,
(23:31):
that would have been what Iwould say. I think in, like,
taking a deep breath andcounting to 10, I would have
seen well, I going back intothat situation, I think the the
key piece is that I wish I haddone is expanding the time
horizon.
(23:52):
And I think that's the culpritfor a lot of these problems is
when the time horizon is tooshort and when the KPIs are
quarter to quarter, month tomonth, when the board is, you
know, looking at metrics on avery short time horizon, you end
up doing things that are reallygonna hurt you down the road.
(24:14):
And from a financialperspective, that does matter
because your your lifetime valueof a customer decreases
dramatically. If you have acustomer for 3 years instead of
7 years, that's pretty big deal.So I think I wish I had expanded
the time horizon. And I think asa leadership team, that's a
really good way to think aboutthings.
(24:38):
And I think in startup world,that's hard because you're
usually working on a short timehorizon. But just zooming out a
little bit, I would have beenable to see, okay, this is worth
fixing now because, yes, it willmake the customer unhappy for,
you know, this quarter, thisyear, maybe we'll even lose
them. But that means I'm notgonna lose the other 10
(25:01):
customers that we're acquiringright now because we're gonna
solve this problem today. And ina year, the problem will be
solved. So I think that was a abig piece was just how small the
time horizons and the result.
Bo Motlagh (25:14):
And a lot of that comes back to just, you know,
what is your 3 to 5 yearstrategy. Right?
Jenna Watson-Brown (25:20):
And in a startup, I don't know and I I
think it it happens at differentphases, but when you've been
bootstrapped and you've been,can we make payroll? Can we
grow? Can we hire for 5 years?You raise VC. Like, there there
does have to be a veryintentional shift in the time
(25:40):
horizons that you look at.
And I think that continues tohappen as the organization grows
from, you know, 10 to a100,000,000, a 100 to
200,000,000, maybe the timehorizon isn't the it's not the
only thing, but I I know that wecan get trapped in thinking what
got me here is going to get meout of this. And that's I think
(26:02):
that the big trap that I've seensales teams fall into, I've seen
executive leadership teams fallinto is we just need to do more
faster instead of saying we needto do this differently.
Josh Smith (26:13):
One incentive that you mentioned, and I like the
that you you looked at it from atop down is, like, what
influences the incentivestructures of the other
departments is that short timehorizon. Are there any other
incentives that you see, inmidsized enterprise
(26:34):
organizations having to scaleand grow rapidly? Are there any
other incentives that you seethat is influencing the outcome
towards towards this brick wall,this cabin?
Jenna Watson-Brown (26:47):
Hiring, I think, is an incentive. Growing
teams, growing teams quickly.I've never met a manager that
doesn't want a bigger team, orI've met very few managers that
don't want a bigger team. And,you know, for every 8 people,
you should have another manager.Like, it's and I think then you
need to give everyone work, andthen you need to give everyone
(27:08):
revenue.
And I think that is besides justrevenue targets, commission
structures, compensationpackages for executives, I think
that is kind of an underlyingpiece is, like, people's
individual career progression.And I wanna become a manager.
You've had someone in the samerole for 3 years. You want them
to become a manager. You wanttheir team to grow.
(27:29):
So I think that especially inthe startup world where people
go into it to learn and growquickly, I think that's an
underlying current that pushesus faster towards the hidden
chasm.
Bo Motlagh (27:41):
That's really interesting. I mean yeah. So
scaling up your your team tooquickly. I'm curious, when you
one of the things we we we sortof thought might be happening,
and you'd be in a good positionto tell us, is is there any
blowback on the salesorganization before or after
these things begin to happen aswell?
Jenna Watson-Brown (28:02):
1000000%. Yeah. I mean, like, lively like,
you you think you have a salesrep that's used to making 250 to
$500,000 a year, and you'retelling them, hey. I'm gonna say
no to this $1,000,000 contractbecause we can't fulfill, you
know, whatever productobligations or this customer's
gonna churn. Like, you verymeaningfully are impacting their
(28:25):
quality of life.
And maybe it's not even thatdramatic. Like, maybe they're
not a sales rep making a$1,000,000. Maybe they're a
sales rep making, you know, a$150,000 as the sole breadwinner
for their family, and you'retelling them, hey. We're gonna
say no to this deal because ourwe can't fulfill on the the
(28:46):
product promise that we made 6months ago that we're gonna
fulfill. Like, it there is avery, real impact on
compensation that I think isalso very different to the
engineering organization becausethe developer gets paid the same
kind of whether or not they dothe thing or don't do the thing
(29:08):
or do it well or don't do itwell.
Yes. There's other pieces andthings, but a sales rep, not to
say it's better, but they havemore to lose. So I think that's
also why you get the sales teamsare much louder and are willing
to fight much harder. And Ithink that also perpetuates the
(29:29):
cycle because you have a veryloud sales team because their
money is literally on the line.And you're overpowering an
engineering team that, you know,is kinda saying, like, hey.
We're gonna break hit a brickwall. We're gonna hit a brick
wall. Especially for a companythat's not public. Like,
liquidity, like, that stuff isstill so far out, that unless
(29:52):
you're immediately, you know,close to a raising a secondary
round or people can get out oran IPO. But in most cases, what
people take home today is thething that matters to them, and
you have a very, very loud salesorganization.
Bo Motlagh (30:07):
I mean, it it comes back to what you're saying. It's
the it's a misalignment. Well,maybe that's a strong term, but
it it's certainly, a competingYes. Yeah. It's a competing,
incentive structure, which, youknow, maybe there's something
there to look at because if Idon't know.
The developers and and the r andd organization should be
(30:29):
incentivized the same way assales, but, they're skin in the
game.
Jenna Watson-Brown (30:34):
They're in conflict.
Bo Motlagh (30:35):
Yeah. Yeah. Exactly. And and there's a much higher
risk reward scenario in terms ofcompensation for sales than
there is, with r and d. It'sreally interesting.
Jenna Watson-Brown (30:45):
And that's where, like, sales leadership
and that longer time horizon,that 3 to 5 year or 1 to 3 year
time horizon matters. Because ifyour sales leader understands
that and can, you know, set theright expectations with the team
and kind of keep them off thathamster wheel altogether, and
work very closely with productand engineering to be in
(31:06):
lockstep, the likelihood of thathappening is is so much lower.
But I would say in a lot ofcases, you have these sales
organizations that are veryfinancially driven that can
drive the company in a directionthat doesn't serve it over the
long term.
Bo Motlagh (31:26):
Have you ever been involved with a company like
this where you made strides outof the chasm, or or have you
found it to be more of a, ifyou're in it, this is gonna be a
long haul scenario?
Jenna Watson-Brown (31:41):
I think I've I've definitely worked with
companies making strides out. Ithink that that means that, you
know, the problem with the chasmis you get out ish, but there's
always like, the next chasm iskind of always coming. Right? So
I think I've yes. I've seenpartially the other side, but I
(32:01):
won't say I've seen anorganization, like, completely.
Bo Motlagh (32:05):
Bridge the divide.
Jenna Watson-Brown (32:06):
Yeah. Bridge the divide. Once you've
replatformed, there's the nextthing or there's m and a or,
like, it's it's just a cycle.
Bo Motlagh (32:15):
Going back to one of the points you were making was
the, the distrust, mistrust thatthat can form between sales,
product dev, and really I wouldimagine the executive, committee
and the board. And I guess it'sit's such a prevalent thing
(32:36):
because, like you said, there'sall of these misalignments.
There's confusion about what theproblem actually is. There's
disbelief. How could we possiblybe in this situation?
Let me speak to your manager.And, and so what would you say?
Because I think that's probablythe biggest killer. Right? The
moment that happens, the problemis 10 times harder than it was
(33:00):
the day before, because nowyou've got to work together and
now you're thinking throughhindsight or maybe having seen
it be addressed.
What are some recommendationsyou might make, especially
between sales and theengineering organization?
Because I think that to me hasalways felt so out of sync in a
lot of these companies. And Iknow that me and Josh, I would
(33:22):
not speak for you, but I suspectyou would agree. I've been in
the role where it's like, I justwant to talk to the salesperson,
You know? Like, can we figurethis out?
And Yeah. That for some reason,it's always very difficult.
Jenna Watson-Brown (33:34):
I think a key is actually start to the
CEO. I think the CEO or thepresident of the company needs
to reset the tone and reset someof the incentives and a lot and
whether they're, you know,specific incentives like
compensation or they're justexpectation setting. Because
(33:57):
what I've seen is the CEOs wantit all. They want to fulfill the
customer need in the short term,and they want to have the long
term technical plan. And so Ithink what if the CEO can come
into reality, address reality,and say, these are the short
term pains we're all gonna feelto get us to this new, better,
(34:20):
wonderful, brighter future, andlay that out.
I think that gives a morefertile ground for, you know,
the head of the technical side,whether it's the CTO and the
head of sales or revenue tocollaborate, because that is the
piece. Like, you have to bewilling to make short term
sacrifices, and both sides needto make short term sacrifices
(34:43):
for the long term better future.So it's it's 1 +1 equals 3. In
that, the engineering and thesales team both need to be
grounded in the same version ofreality, and they need to have
confidence that they are bothnot gonna be asked to fulfill
(35:03):
every short term commitment andevery long term commitment that
the CEO has or the board has setforth, because that is where you
the gate is impossible to to dothat without, you know, a
massive injection of capital orresources or, you know, other
external factors changing. So Ithink everyone needs to be on
board.
We're gonna take our medicinenow. This is what the medicine's
(35:25):
gonna look like. It's not justthe sales team taking their
medicine. It's not justengineering taking their
medicine. We are all gonna takeour medicine.
This is what it looks like, andthis is why. This is the 1, 2, 3
year plan. But when I've seenthe onus fall entirely on one
team to sacrifice in the shortterm, I think it does a lot of
(35:48):
damage. When it comes to morale,it does a lot of damage.
Josh Smith (35:52):
And as part of that that medicine taking, have you
seen something I I don't knowhow to to describe as the per
customer feature demands versusthe more broad what is the
benefit of implementing this, inthe entire product in a way that
(36:16):
benefits the business in thelong term? That that tension
where the short term thinkingwas paying off, you were
converting leads faster, but youwere incurring more debt because
you were building so many oneoffs for specific customers.
Jenna Watson-Brown (36:35):
Yeah. And that's that's I mean, that's the
crux of it. Right? And I've beenthere with anybody. It's a habit
to break.
And I think in my experience,like, whether you have a key of
a group of customer advisers,you need to be transparent and
get them on board with the plan.Because if they can also see
(36:56):
thinking of your your biggestkey customers, why you're gonna
be saying no in the short termto some of the things that you
used to not say no to, and whatthat long term payoff is for
them. And if that long termpayoff and that 1, 2, 3 year
plan addresses their needs. I'veseen that work, and I've
(37:17):
personally had thoseconversations with executives
and with board members of k.We're gonna say no now, and I'm
sorry.
It's gonna be reallyuncomfortable. I know it's gonna
put you in a hard spot, but thisis why. And, I mean, obviously,
working with the team to see ifthere's anything that you can do
that kind of gives them a littlebit of a cookie, like, you know,
(37:38):
k. Whether that's pricing,whether that's something else
that they want, but thenenrolling them and and this is
making sure that what you'rebuilding is going to address
them in the long term. I wouldalso say, in some cases, you may
just have a bad fit customer,and you've been bringing them
along and they've been costingway more than their work, it is
(38:00):
never worth keeping a bad fitcustomer.
And so that would be, hey,customer. Like, this isn't this
isn't working. Whether that'sbecause of the customer's
demand, whether that's becauseof the customer's use cases,
maybe they're using the productin a very different way. But
(38:21):
having that very open andtransparent conversation and
trying to, like, kill that deadweight, those are 2 things that
I've seen help, to to then giveyou the breathing room that you
need on the engineering side tonot be constantly putting out
fires and to instead bebuilding.
Josh Smith (38:38):
I don't even know if this exists, but to be able to
have some sort of KPI ormeasurement of the deadweight
per customer.
Bo Motlagh (38:50):
I was gonna say, how often I don't know that that
happens as often as it should isprobably the right way to put
that. But that's interesting.It's tricky because I think as
you're working with thesestartups from on their journey
from 0 to, like, let's say,5,000,000, So much of that is
opportunistic sales. Right? Andand it's, you know yeah.
You have a vision. That visionmight need to change. And so you
(39:13):
are you're doing the thing outof necessity that you hope you
don't keep doing after somepoint. And there's this
transition moment, which isprobably very difficult to say.
Well, when you get here, stopdoing that.
Where the things that got betterhave helped you be successful
all of a sudden start to lead tosome toxicity. It's gotta be
fascinating from yourperspective because in your work
(39:34):
with these these early stagecompanies, and I would imagine
you you probably see this mostlyin that 5,000,000 category.
Like, are you seeing thingswhere you're just like, okay.
This is good for an app, but,man, that's probably gonna be a
problem later.
Jenna Watson-Brown (39:48):
Absolutely. I mean, I think the biggest one
is, relying on personalnetworks. I think that's the the
biggest one. Like like, you hirea sales rep or you hire 2 sales
reps, and they have reallyextensive personal networks, and
they've built your first few$1,000,000 of sales through
(40:11):
their personal networks. But,you know, there are some
exceptions, but in most cases,you've actually not proven that
you have a sales motion thatworks.
You've proven that if people getto know about your product, they
wanna buy your product. So Ithink that's one for sure in
that, like, I'd say, like, 2 to$5,000,000 range. Of course, you
(40:33):
can look at the renewal numberson that, and that will give you
a better indication of, like, isthere a true product market fit
there? But I've seen that a lotof just relying on personal
networks. And anytime you have asingle point of of failure,
especially when that personisn't a founder.
I would say it's different ifit's a founder because that
network couldn't go anywhere.That's a big one. I would say
(40:55):
more often, though, I see peopletrying to scale sooner than they
should.
Bo Motlagh (41:01):
Mhmm.
Jenna Watson-Brown (41:01):
That's actually the way bigger problem
is people with 1 or 2 customerstrying to then build this super
scalable sales process orplanning documents or
opportunity criteria, or even ata few $1,000,000, they're like,
oh, we need to hire this bigsales team, and it's a crawl,
(41:25):
walk, run. It is not a crawl,run. And it so I think that is
more often people skipping stepsof, okay, we did a whole bunch
of things that aren't scalable.Now let's peel some of those
off. Let's keep doing some ofthe ones that are most critical,
but what do we think we could dothat is scalable?
And then adjusting that insteadof taking a band aid and ripping
(41:45):
it all off at once because youcan't troubleshoot and you can't
tweak. And then you're just leftwith this, well, we had all
these sales and now we have nosales, or we have less than we
thought. What do we do? And it'slike, well, you've changed 65
variables at one time. So Ithink that is more often the
issue that I see.
Josh Smith (42:06):
Yes. Like, you wanna stand behind the wave so you can
see it and and adjust because ifyou say, okay. I'm gonna just
stand in front of it and buildthis this huge, invest all of
this money because I'm justlooking at I'm connecting 2 dots
and creating a straight linesomewhere. Well, you can't see
the wave anymore. And ifsomething changes, well, you've
you've just you've
Jenna Watson-Brown (42:27):
Yeah.
Josh Smith (42:27):
Expanded based on a perception of, like, a
trajectory that is not always ina flat line up in up into the
right. So
Bo Motlagh (42:38):
You talked a little bit about, that that change
starts with the CEO, and yougave some some examples of
things that they should be doingto help when these things happen
or when they find themselves inthe chasm. Do you have any
thoughts in terms of practicaladvice for a CRO, or or even a
CTO or CPO who may findthemselves in this situation?
Jenna Watson-Brown (43:00):
I would, so I think there's 22 tendencies.
There's one to stop the bleedingand then get to the root cause.
And I think most people stop itstop the bleeding. And they say,
okay. We stopped the bleeding.
I'm gonna kind of continueforth. I think stopping the
bleeding and then getting to theroot cause. I think looking at
(43:22):
your people, like, a lot of thetimes, the people that got you
into a situation aren't thepeople that will get you out of
it. Like, it's it's a sad truth.There are some people that are
really good at startups, and Iwould say myself included, like,
I'm not a $2,000,000,000salesperson.
Like, that that is not mywheelhouse. And there are people
(43:43):
that are really good at gettingyou to a $100,000,000 or
$50,000,000 that are not goingto be able to get you where you
need to go next. So I think thatis that is hard. It doesn't mean
that they are to be redundant,like, to be taken out, but how
do you bolster them with peoplethat have been on this path
forward? So I think it's it'sadding executives, adding
(44:05):
advisors of people that havedone this portion of the journey
that you're about to do next,and also looking at vendors that
have done this portion of thejourney that you're doing next.
Because, again, you don't wannabe at 50,000,000 and look to a
$1,000,000,000 CEO and say,okay. You're gonna be my mentor.
How do I get to a 1,000,000,000?It's finding the right people
(44:26):
that have done that 50 to$250,000,000 journey, because
that's the journey you're on.Who can help with that?
Whether it's adding to yourexecutive team, adding to your
board, adding to your advisors,working with vendors that have
done that portion of thejourney. I think that's often
overlooked because if everyonearound you has only ever gotten
(44:49):
to 50,000,000 Yeah. The chancesthat you're going like, who can
help who can you learn from? Ofcourse, adding your own flavor,
adding your own spin. You Youknow, you're not looking for a
playbook per se, but a guide orpeople that can help you avoid
some of the common pitfalls.
Bo Motlagh (45:07):
What about in in a scenario where maybe there maybe
there is attention being finallygiven to the platform, the
product. I'm sure from a salesperspective, if you're somebody
who's tasked with bringing inrevenue and all of a sudden
you're being told that yourproduct is going under, you
(45:27):
know, major refactoring orthings like that. That can feel
scary. Right? Did you have anythoughts in terms of maintaining
the sales momentum in anenvironment where everything is
in flux like this?
Jenna Watson-Brown (45:41):
So I would say 2 things. 1, find more like,
you you always have a pocket ofhappy customers. And maybe the
customers are using only 75% ofthe product, or they're really
focused on a specific use caseor feature, or they moved from a
certain competitor and theymoved to your product and
they're just thrilled, and maybethey're 20% of your customers.
(46:04):
Find more like them andincentivize the sales team to
find more like them. So whileyour product is going under
major overhaul, don't try andfind more customers that are
disgruntled or upset or wantingit to be different waiting for
those new features.
Find more customers that arehappy with it as it is today,
and that the new features willhelp in the future. So kind of
(46:27):
gearing the sales efforts, themarketing efforts, the events,
the everything, all theactivations you're doing to give
them the best shot of success atcustomers that will be happy
with the product while it goesthrough this transition. I think
that's number 1. Number 2 isthis is where the engineering
team, technical team, productteam needs to put on their sales
(46:49):
hats. Yeah.
Sell this vision to the salesteam. Like, it is your job to
get the sales team on board withwhere you're going. And if it
was a good plan and if it waswell thought through, you've
taken customer feedback, you'velistened to customers. So there
is something for them to getexcited about, but it is your
(47:10):
job to enroll the sales team, inwhat you're doing so that they
can say, okay. Littleuncomfortable right now, but in
a year, I'm gonna be able tosell 2 x my average contract
value because we're integratinga new product or because we're
rolling out this new feature.
Help them understand how it'sgonna help them make more money.
Bo Motlagh (47:30):
That's so interesting because a big part
of, you know, when I speak totechnologists, architects,
developers, a big conversationwe eventually end up having is
how to talk businesseffectively. Right? I think it's
a really important piece ofproduct development leadership
to teach your technicalresources how to speak to the
(47:53):
business in and of itself inorder to have that conversation.
Exactly what you're saying. Andknow that, well, I think it
would be really cool isn't agood reason.
And, oh, you're going to lose alot of money if you don't. Maybe
it's a better one.
Jenna Watson-Brown (48:05):
And we need to do it. That's a terrible
reason as well. But if you canexplain the potential revenue
benefits, the potential newfeatures and products, and this
is gonna take your annualcontract value from, you know,
$75,000 to a $115,000 becausewe're adding these widgets. We
heard from 80% of customers thatthey want it. That's a totally
(48:25):
different conversation.
Josh Smith (48:26):
Yeah. Yeah. That makes sense. The context that
you like what you're doing now,sales, but here, let me tell you
what the possibilities are wherewhere you could be and what you
could be achieving with withthis this time, which may not be
pleasant this time, but thistime that we need to invest.
Jenna Watson-Brown (48:46):
Yes. And then the other piece is, like,
how is the executive teamengaging with customers? Because
that goes a long way. And whenyou're gonna be pissing off a
customer, like, I'm thinking,let's say, you're doing a m and
a. You're acquiring another keyproduct in this space, and
you're gonna integrate thatproduct into your product.
(49:07):
But it means it's gonna beclunky for a little bit, and,
you know, they're gonna beupset. Well, call from your CEO
or a call from someoneexplaining the vision,
explaining the the value, andexplaining what they're gonna
get out of it at the end goes areally long way.
Bo Motlagh (49:25):
So that's an important piece because it's a
question for me, actually. SoI'll ask you is is, I've seen
this happen, which is thecompany is in the midst of, you
know, they know what whatthey've been doing isn't working
all of a sudden. And so areaction to that is is what, you
know, I guess you could calllike visionary syndrome.
Somebody sits down and comes upwith this brand new concept of
(49:49):
how everything is gonna bedifferent and looks completely
different. They might eveninvest in, you know, somebody to
come in and drop what this wholenew vision of is gonna look
like.
And most of the time I mean,it's great. It's an amazing idea
and maybe and and and in manyways, it may address the the
business and market issues,although it certainly wouldn't
(50:09):
immediately address thetechnical issues that have led
them there. But it is alsosomewhat divorced from the
reality of their currentscenario and it's like, while
you're trading the hardships ofof your existing reality with
the hardships of a reality thatdoesn't even exist yet. And then
they go out and start trying tosell that, which from a startup
perspective is is like, well,that that makes sense. You're
(50:30):
you're selling something beforeyou build it so that you can get
paid to build it.
From an enterprise perspective,I don't know if you're it feels
very risky, but maybe maybe thatI don't know. I'm curious what
your thoughts are.
Jenna Watson-Brown (50:41):
Yeah. Risky is a really, really good term to
use. I think there's a balance.There is getting a little ahead
of your skis, selling somethingthat's coming. But the
enterprise needs to be excitedabout what they have today.
So it will not exempt you fromusers reporting bugs on your
platform. That doesn't helpnecessarily. It can buy you more
(51:04):
credibility and more time, butit is absolutely a balance. And
I think too often people unveilthis entire new version of their
product all at once. And I I forthe enterprise specifically,
like, I was speaking with acustomer the other day, and they
(51:25):
have a a SaaS tool, and theychanged the color of something.
Mhmm. And someone complained.They changed the color from blue
to white. And someone complainedbecause they were used to it
being blue, and it is now white.It is still incredibly legible.
It was like a decoration. It wasnot actually a key piece of the
UI. So I think these visionarymoments, people think, oh, I'm
(51:50):
gonna unveil this entirely newthing, and, you know, we can
think of some SaaS tools thatthe 3 of us use where they
unveiled a new menu and all atonce. And while it's maybe
better for us in the long term,like, that was a hard adjustment
to make. So, of course, there'llbe some things that you need to
do all at once, but I would saytoo often, it's like, oh, 3
(52:14):
point o.
We're gonna take everything andblow it up and make it different
and better, is often not thesolution, and the solution is
more iterative.
Josh Smith (52:24):
The delta between what is now and all the muscle
memory that people have to knowwhat is now, all the comfort
they have, even if it'sterrible, they've gotten it to
work. They figured it out. Andthe dealt between that and the
new thing, that's change thatneeds to be designed, and it's
often not applied. The newthing's designed, but the the
(52:47):
path and the journey to handholdsomeone to the new thing, that's
often missed.
Jenna Watson-Brown (52:53):
Yeah. And the same with entering a new
market. Like, we're gonna go upmarket. We're gonna go down
market. Okay?
Great. And you have a sales teamthat is an expert in one market,
and now you think you're gonnaapply it to a new market. Or
we're gonna integrate we're aSaaS tool that is a $150,000 a
year or bought a competitorthat's $5,000 a year. And now
(53:14):
we're gonna try and integrate itall together. I think the vision
is important and the vision isthere, but the connection, like,
strategy in action, I think isthe critical, critical piece
that often gets missed, and thenyou end up with a bungled, half
(53:37):
baked, not on time, frustratedsituation.
And that's where you get thesecustomers that are sitting on
legacy tech for years yearsyears because they won't move to
the latest version, because itdoesn't meet their needs.
Bo Motlagh (53:55):
It's another version of the, build it and they will
come fallacy you were talkingabout. It it's just a much more
expensive version.
Jenna Watson-Brown (54:03):
Absolutely.
Bo Motlagh (54:04):
I think we covered a ton of ground. This was really
cool. Jenna, thank you so muchfor making this time. You know,
wanna open up the mic to youhere. Spotlight is on you.
Anything you want to plug ortalk about? Go ahead. Let
everybody know.
Jenna Watson-Brown (54:16):
I would say feel free to reach out if anyone
listening to this wants to talkmore about start up sales. But
my if I could put it on abillboard, and I'm gonna put it
on this billboard now, please,please, please don't hire sales
too early. You need to be ableto repeatably sell yourself as a
founder. If you cannotrepeatedly sell this yourself,
(54:38):
you will never have luck with asalesperson. You need to learn
to get good at sales.
So I think for founders, that'swhat I'm gonna leave we with.
And then for any execs that arelistening to this that are,
focused on kind of that 50 to250,000,000, I'm in this stack.
Like, find people like Bo, likeJosh. Find people that have done
(55:02):
this part of the journey before,because you will be far better
off. And I think thinking whatgot you here will get you out of
it is a hard path.
Bo Motlagh (55:12):
We really appreciate that plug. How would people
reach out to you?
Jenna Watson-Brown (55:16):
Great. Jenna Watson-Brown on LinkedIn, or
jenna@jennawb.com as my email.So feel free to reach out there,
but LinkedIn is also great.
Bo Motlagh (55:28):
Awesome. Well, this has been another episode of The
Hidden Chasm. Thank you, andstay tuned for more. You've been
listening to The Hidden Chasmbrought to you by
United Effects. If anything inour conversation resonated with
you today, please reach out.
We'd love to hear from you.Email us at
podcast@unitedeffects.com, orsimply visit us at
(55:49):
Thanks for listening.
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