November 18, 2025 • 47 mins
We explore how a solo Camino de Santiago pilgrimage reset attention, then translate those lessons into a pragmatic playbook for fixing stalled revenue. We walk through segmentation, ICP, LTV:CAC, methodology, enablement, culture, and the myth that “it’s all talent.”
• solo travel as a reset for presence and purpose
• inch pebbles as a tactic for motivation and change
• myth-busting the talent-first diagnosis for missed targets
• clean-slate org design with segmentation by motion and support
• ICP as an executive alignment tool across GTM, product, and finance
• first-team mindset and Team of Teams principles
• aligning compensation with retention to stop silo optimization
• culture mechanics: recognition, repetition, and making progress fun
Find Bridget on LinkedIn. “My DMs are open. Feel free.”
Music by Ben Cina & Ayler Young
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_02 (00:15):
Hello, everyone, and welcome to another episode of
Pillar Talk.
This is where we build thefoundations of sales leadership
success and try to createclarity in terms of what good
looks like for current andaspiring sales leaders.
Today on Pillar Talk, I amjoined by Bridget Winston.
(00:36):
Thank you for being here,Bridget.
She brings, before I let herspeak, she brings over 20 years
of experience in scalinggo-to-market organizations
across marketing, sales,customer success, the entire
customer lifecycle.
She was most recently the ChiefRevenue Officer at Chief.
This is where she helped growmembership in that community
(00:57):
from 1,500 to over 20,000.
Previously, beyond that, she wasin many roles, including
Shutterstock, where she ledglobal sales through a pivotal
transformation period.
Bridget also advises CEOs,boards, investors on all things
go-to-market strategy, growth,and customer experience.
(01:18):
She's someone who blendsambition with reflection because
between roles, she recentlywalked 75 miles of the Camino de
Santiago, a sort of pilgrimagethat offered lessons, and this
is based on what I read, onslowing down presence, and
rediscovering purpose.
(01:39):
Bridget, welcome to Pillar Talk.
SPEAKER_00 (01:42):
Oh, I'm so glad to be here with you, Rick.
That is that's a lovelyintroduction.
And what I will say to you isyes, it was meant to be a
pilgrimage.
A lot of people use it for avery religious pilgrimage.
I was going to very much, youknow, kind of accomplish a goal
that I had.
And it was it was really goodthough, because it ended up
(02:03):
being much more of a reflectivemeditative jaunt for myself.
So that was lovely.
SPEAKER_02 (02:10):
So I get excited when I see something interesting
and different.
And, you know, you just had alot of responsibility in your
last role, probably runningaround, handling huge amounts of
initiatives, pressure, largescopes of organizational
development, uh, strategy.
And then you go from that to I'mgonna do something totally
different, and I'm gonna go, youknow, accomplish this, you know,
(02:32):
personal goal.
So I love to learn more aboutthat.
Can you share a little bit aboutwhat inspired that trip and what
did you take away from it?
SPEAKER_00 (02:41):
Yeah, absolutely.
So uh, well, it was kind of atwo-week adventure for me.
So the first week I actuallywent to Tuscany and did an
immersive cooking course.
Um, but it was pretty difficult.
It was not actually asmeditative and as relaxing as I
thought because we were cookingfor five hours a day with an
(03:03):
Italian chef who was verydemanding.
So it was me and a bunch of 60and 70-year-old retirees going
to this uh villa in Tuscany todo a cooking course.
So that was fun.
But I the good news is I wasfueled up, I was carved up so
that I could go on the next weekto uh the Commune de Santiago.
(03:24):
And both of these I chose to dodo solo.
Uh I have a great, amazinghusband, but I really kind of
wanted to do something formyself.
I have, I'm 45 years old, so Ifelt like this was like that
moment of, you know, prove me tome a little bit, go and do
something uh that was a little,a little scary, a little, can I
(03:44):
do it?
These were things I'd alwayswanted to do.
And so it was a little bit ofprove me to me, particularly the
Camino, because you know, you'restrapping yourself into some day
pack.
I had to have, you know, waterfor the whole day.
You're walking four to six hoursa day.
Um, and you know, going, I chosenot to do the hostile route.
(04:05):
I did stay in hotels, so I hadit a little bit more uh of the
high end.
I wasn't doing the fullpilgrimage, but it was a four,
five-day jaunt that um was fourto six hours a day.
Uh, I think I walked at minimum12 miles a day to 18 miles a
day.
(04:26):
Um, and I I'm pleased to saythat it rained every single day,
poured raining every single day,completely different than what I
was expecting October in Spainto be like.
I was expecting it to be thislike beautifully, you know,
wonderful moment.
And it was, I mean, it was itwas torrential downpours the
entire time.
(04:47):
Uh, you're walking with otherpilgrims who are doing this.
I did the Camino coastal routeof Portugal.
Um, and so you are walking thisroute with other people,
sometimes seeing a lot ofpeople, sometimes seeing few.
Uh, and you're walking throughlittle small towns in Portugal
and Spain.
And there were certain townsthat I went to that didn't have
(05:10):
any people and just cats.
You're walking by chapels, youhave to get your Camino passport
stamped.
Uh, so you have to stop everynow and again to get your Camino
passport stamped to prove thatyou did the walk.
You walk next to certain people.
Some people really want to talkto you, some people are, you
know, kind of just walking insilence.
I watched one lady doing therosary the whole way, which was
(05:33):
really sweet to see.
But like the first couple ofdays, I will say, I was walking
and I was on a mission.
I was like, get this thing donebecause the rain, I was wringing
out my socks three times, youknow, I didn't stop for coffee,
I didn't stop for lunch.
I was just trying to get thisdone.
And that is probably prettystandard about the kind of
person I am.
I'm I was a Division I collegeathlete.
(05:53):
I was always like a person wholikes to achieve a goal,
relentless kind of pursuit ofthings.
And but I will say by day three,I uh day three was the day that
I was like, I don't feel likedoing this.
I am like annoyed that I have toget up and go walk this thing.
Um, and so while it wasenlightening and empowering, it
(06:15):
was also really hard, bothmentally and it grew to be hard
physically, but like physicallywas less hard.
It was mentally getting yourselfto like do the thing.
And so I had to honestly do thething that was opposite my
normal tendency.
I had to actually give myselflike little goals.
And I had to like, you know,tease that hey, you can stop
(06:37):
within two hours and rest yourfeet and take a coffee break.
Um, you can talk to the peoplenext to you.
I wouldn't kill you.
You know, this is not about thislike relentless pursuit of like
getting this thing done.
It is meant to be reallymeditative.
And I will say it culminated insome really like interesting
(06:58):
discussions and and talks.
And frankly, my blisters werebetter for it to stop a bit, but
it culminated in the last daywhen I had two miles left to go.
And I am almost to Santiago,which is this beautiful church
in in Spain.
Uh, and they say it's where St.
James is buried.
Who knows if this is true?
(07:19):
But um, but I was two miles awayfrom being done, and I come, I'm
on it in a forest, and I comeupon a man playing the piano in
the forest.
I mean, the most random thing.
And I think what was mostmeaningful about this is my
father, uh, who's passed away 17years ago, was a big musician,
(07:45):
and our home was always filledwith music and the piano in
particular.
And so he used to play thepiano, he used to play the piano
at mass and all of these things.
And I know that he would havebeen very proud of me for doing
this.
And I came upon this man in theforest playing the piano, and I
(08:05):
stopped for 20 minutes and justcried because it was first off,
he caught me at quite the time,two miles left to go.
But also, it was just this likemeaningful thing of being
present and remembering why youdo things and remembering the
people who are really importantin your lives, and um just
taking that moment to pause.
(08:26):
Um, and so it was just like oneof the most meaningful things.
I'll remember it for the rest ofmy life.
Um, and it, you know, I passedcountless cemeteries, right?
And so I was already in thissomewhat reflective mood of
like, gosh, all of these peoplewho came before us and who have
lived here, but like to be thereand to see in the middle of a
forest a man playing the piano,um, it really made me feel like
(08:48):
my dad was there and presentwith me in some ways.
I don't know if I believe in allof that, but like it was it was
just it was so poignant and andfrankly just breathtaking to me,
um, otherworldly in some ways.
SPEAKER_02 (09:02):
Yeah, you had written about that in your post
on LinkedIn, and that wascertainly uh a moving and
emotive uh aspect of that post.
You could feel as the reader umyou know a bit of what you were
feeling there.
So very powerful stuff.
What what was you know whenyou're between roles and you
have the opportunity to go dosomething different, there are
(09:23):
many options, and there's no oneright answer.
What was the rationale behindthese two journeys for you in
immersive cooking in Italy andyou know, the hiking um you know
across the Camino de Santiago?
SPEAKER_00 (09:40):
Yeah, I mean I think what was drawing me to do both
of these is something a littlebit more either in nature or
with my hands, right?
We sell SaaS and cloud, and Ialways think about I've got all
of these relatives who live inIreland, and whenever I go
there, I'm always explainingwhat my job is to them.
(10:02):
And the a good portion of thesepeople are teachers, they are
builders, they are people who umor chefs, and whenever I tell
them what I do, I mean I feellike I'm in some way selling
vaporware, right?
That we are just selling thisthing that is, you know,
fulfilling a um certainly autility, and it it's important,
(10:26):
and there are things that we aredoing, but I feel like you lose
a little bit of the one-on-oneconnection with others, um, and
the the meaning in life and likethe visibility of seeing what
you create.
Um, and so there was somethingin this around the cooking,
(10:49):
although I think I I I may havecome back a worse chef after
that.
unknown (10:53):
I've got to be honest.
SPEAKER_00 (10:55):
Like I'm even thinking of like, what is my
LinkedIn post?
And I really think like thelesson I learned was this did
not teach me anything.
It taught me just to like justenjoy it.
Like someone's gonna makesomething good and just eat it,
you know, like even if you're aterrible chef.
Um, so but it was it was one ofthose things.
And then the Camino wasseriously like the feet on the
(11:18):
ground of just meditativelywalking through towns that
honestly I just watched oldpeople, you know, harvesting
pumpkins and picking apples andyou know uh walking amongst
their cats.
It was, it was just, and I I sitthere and think, do these people
(11:40):
understand what I, you know,like are they gonna understand
the SaaS software solution I'mselling?
You know, it's probably neverentered their mind.
But God, there were laughter.
There was people who were, youknow, you could hear kids, you
could hear um, you know, youwatch generations of people be
all together.
And so there was just somethingvery moving about like what
(12:02):
really makes a difference in theworld, you know, and it is
sometimes it's just the food andthe connections that we have.
SPEAKER_02 (12:08):
In your post, you mentioned you you use this
phrase, a superpower overusedbecomes a weakness.
SPEAKER_00 (12:15):
Yes.
SPEAKER_02 (12:16):
Um tell me a little bit about that.
That's an interesting quote.
SPEAKER_00 (12:20):
Well, it was born out of one of my favorite things
is strengthfinders.
Have you ever read uh or haveyou ever done Strength Finders
as a um as one of thosepersonality tests or anything?
I believe I did that once, yes.
Yeah, and so um, and it's alsoborn out of, you know, whenever
anyone's like, what's yourbiggest weakness?
You know, what you usually whatI always do is I always throw in
(12:43):
a superpower for use becomes areason.
Yeah, yeah, yeah, exactly.
Well, yeah, exactly.
Like, I'm just such a hardworker, it's a workaholic.
Um, and so um, but I do thinkthat generally speaking, um it
is the things we are best atthat sometimes we over-rely upon
or over-index on that become thething that probably is our
(13:06):
shadow side, if you will.
Um and so, and that's what I'veseen.
Like my relentless pursuit, mydriven, my ambitious, my, you
know, probably, you know,sometimes command and control is
the thing that prohibits me frombeing the leader I should be,
and to get even better at beinga leader.
(13:28):
And so sometimes us doing theopposite, or at least being open
to doing the opposite.
Now, there's the other side ofme that's also like embrace your
strengths because like one ounceof energy tied towards something
you're already naturally good atis probably gonna deliver more
for you.
But wouldn't we all be better,more reflective people if at
some point we also said, andwhat's my opposite?
(13:50):
Or how do I supplement myselfwith either people on my team
who think differently than I do,or um, or inviting debate, and
you know, like argue this fromthe other side.
I do that sometimes with my teamwhen we're all in agreement, you
know?
SPEAKER_02 (14:06):
Yeah, yeah.
Well, I I certainly think umthis idea of doing something
completely different than yournorm, when your norm is a lot of
Zoom calls and zeros and ones,which is the world we live in,
and we're very lucky to be here,you know, trudging through the
mud in sort of like spiritual,truly powerful, you know,
historic areas, um, you know,definitely scratches that itch,
(14:29):
doesn't it?
SPEAKER_00 (14:30):
Yeah, absolutely.
I mean, and there was just funnythings.
I mean, the things that you justsee on the way.
I mean, the there was a chapel Ipassed that had like Mary
Magdalene laid out like she wasa French, you know, you know,
French painting.
It was so funny.
I mean, there were just thingsthat I would just snicker to
myself and just laugh.
(14:51):
And I didn't use headphones theentire time, which I was like,
all right, you are gonna bepresent, girl.
You are going to get throughthis, you're gonna talk to
people, you're gonna experiencethis, you're gonna hear the
roosters crowing.
And they they woke up late.
They woke up late at least 9a.m.
I was like, there's no moreSpanish rooster thing than
(15:11):
waking up at 9 a.m., you know?
SPEAKER_02 (15:15):
Well, Bridget, welcome back, and I know you're
gonna be getting back intoengaging all types of companies.
We're in a time of you know,uncertainty within the business
landscape, especially in SaaSand tech.
Um, you're gonna walk intosituations whether you're in
advisory capacity or full-timecapacity or anything in between,
(15:36):
and you're gonna see situationswhere organizations are
struggling with growth.
You're gonna see organizationsstruggling with the uncertainty
of where to go.
And one of the things you'regonna hear a lot about is we
have the wrong talent in theorganization.
So when you approach a situationwhere an organization is
struggling or not performing togoals, true or false, it's a
(15:58):
talent issue.
Just replace the people andyou're good.
SPEAKER_00 (16:01):
Oh, I can't tell you how many times I've heard that.
So when interviewing for ChiefRevenue Officer Jobs coming in,
uh, and I always hear,especially if they're struggling
with growth goals or uh they'vedone a lot of acquisitions and
the culture and the team moraleisn't there, um, you always hear
when you ask, you know, any ofthe folks that you're
(16:24):
interviewing with, well, what'swhat's the what's the main
challenge?
And the number one thing youhear is talent.
And what I would say is I'mgoing to dispel that myth right
now, Rick.
Not fully, but at least startwith first look inward, first
look inward organization, uh,and investigate have you
(16:44):
actually set the team up forsuccess.
It's not that it's never thetalent.
Um, so there's always talentimprovements.
And uh in certain organizationsthat I've been in, there was
definitely a time for us toaddress the talent.
But um in some of theorganizations that I've seen,
the first thing that I saw wasthat there was no plan for the
(17:05):
plan.
Uh, and there were there were nooperating rhythms that were
actually ensuring that the teamwas going to be successful.
So I always look atorganizations and say, first
look inward.
How are you ensuring that thistalent that you have is
successful?
SPEAKER_02 (17:21):
So let's talk about that.
What does it mean to lookinward?
Yeah.
SPEAKER_00 (17:25):
Well, um, I'll even use an example.
Um, personal level lookinginward, but that's the one.
Yeah, yeah, yeah.
Yeah, first look inward.
And then you're gonna go on aCamino de Santiago.
I hate to say it, Rick.
Then you'll go and maybe you'llgo to this uh go to this villa
in Tuscany.
Uh so yeah, so when you firstlook inward, uh, the biggest
(17:45):
thing I always like to see is isthere an operating rhythm?
Is there a plan for the plan?
Um, so for example, um, I wentinto an organization,
Shutterstock, as an example, andwhat we found was that no one
was hitting their goals.
Um the employee NPS score was atwo out of 10.
(18:06):
Uh, you know, the attrition ratewas 35% uh when I was joining.
And so obviously something wasgoing on.
And despite all of theseacquisitions that Shutterstock
had made, um, no one was sellingany of the new products uh that
they had.
And so it was reallyinteresting.
So therefore they weren'thitting their goals and growth
had really stalled uh andslowed.
(18:27):
And so what became reallyinteresting to me was, and of
course, as I was interviewing,it was the talent's terrible.
It's the talent, it's thetalent.
And it wasn't that the talentwas terrible.
I mean, a good portion of themhad been there for eight years.
They may needed to be retrainedand retooled a little bit, of
course.
Um, but the first thing that Isaw was there was no plan for
(18:49):
the plan.
There was no rhyme or reason towhy there were the number of
sales reps that they had, salesand customer success reps that
they had.
Anyone that they had within theorganization did not have any
kind of segmentation.
So, like you could have oneperson who was managing an SMB
account, but they also in theirlist had a$1.1 million
organization.
(19:09):
Um, they were in completelydifferent industries, completely
different verticals.
Uh, the person who and so, andthere was just a mishmash of
accounts.
So, one of the first things thatI looked at was all right, if we
were no names and boxes, nopeople, uh, you know, at all,
what do we look at?
Like, what should thisorganization look like?
How would we organize thisorganization if we were thinking
(19:31):
about vertical expertise, if wewere thinking about segmentation
and the way that an SMB accountneeds to be serviced versus a
large enterprise customer?
Um, you know, certain what wasthe sales cycle and velocity of
a sale for an SMB customerversus someone who needed a lot
more high attention and probablyconcierge-like support.
(19:53):
And so we began to design theorganizational structure to
support the multifaceted way wewere going about doing business.
Then we started looking at,okay, we'd have these different
eight different product types.
Um, how and which accounts areour biggest high potential
accounts versus also highperforming.
So, you know how there's thenine box that you do for talent
(20:14):
assessment, you know, is thishigh potential and high
performing?
You can do the same thing withaccounts.
Um, and that's in fact how wehow we looked at our customer
success modeling was highperformance and high high
potential.
Um, and started to assess, okay,what is the sales motion and the
support motion for those?
And then also what is thepotential for those?
(20:35):
So uh where can we actually, youknow, expect to see all eight
all eight of our product linesbeing sold versus someone who's
literally just doing somethingvery high velocity and a little
bit more transactional.
And so then we started to lookat our talent.
That's when we started lookingat our talent and started to
assess where do we have somebright spots?
Where do we have folks who arereally killing it and can teach
(20:58):
others?
So I didn't start by letting goof the team.
I started by looking at the teamand saying, okay, where do we
have really good performers?
Where can they teach others?
And so we brought in challengersales methodology into the
organization because a lot ofthem, even themselves, needed to
be challenged to thinkdifferently a little bit.
(21:20):
So we brought in challengersales methodology to the
organization.
And then there were certainfolks that honestly we uh after
doing different role plays andand um and listening to calls
and doing coaching, where we didhave to part ways with them or
reallocate them to other partsof the business.
We had an entire supportorganization that was that was a
really good um fit for some ofthe people.
(21:41):
And then some of the people justdidn't like the new approach and
so decided to self-select out.
Um, but it was reallyinteresting because it was um
such a great way for us to, youknow, kind of leverage the
existing talent to help us hirethe new talent.
And they became people who weadded on the panels.
They became the people that wedid recognition for.
(22:01):
And so every month we did funvideos and kept the change alive
by showcasing, look, see,there's success.
We have people who are havingsuccess doing this.
And so we would give out awardsevery month.
There were global awards, wewould do fun videos where we
would show all of the differentoffices.
We had offices in Brazil,Mexico, you know, Germany, uh,
(22:22):
Italy, all over the world, um,Singapore.
And everyone would send invideos once a month of, you
know, kind of their spotlightedcustomer and also like just fun
things that they'd been doing,whether it was like a plank
contest or something.
So there were just ways that wewere trying to keep the culture.
So in the end, we ended up withat least an employee MPS score
(22:42):
of like seven out of 10.
The attrition had switched froma high 35% down to a 2%
attrition rate.
And we had 67% of the team startto pay quota, so a little bit
more of that best practice.
So um, because we'd organizedappropriately and reassessed the
talent, but it was secondary,not the primary thing that we
(23:05):
did was just come in and fireeverybody.
SPEAKER_02 (23:07):
So let me play back to you the sequence of the
things that I heard and see howmuch of that can be a template
for you and others when theysort of enter an organization
and things aren't going the wayyou know we'd hoped uh they'd
be.
So one of the first things youmentioned was just like, well,
take a step back and put a cleanslate against the business and
(23:29):
say, hey, if I was going tobuild a go-to-market motion for
this business as it is today,what would that look like rather
than how do I make the best useof whatever's going on here
today?
And the example that you gavewithin that was segmentation.
So if I look at the types ofdeals that are being done by
this business, what is the whereis their variety?
So in a classic segmentationmodel, you have SMB, min-market,
(23:51):
and enterprise, if I see thatthere's a very different sales
motion that's happening, and yetI'm asking the team to do one
minute sell to the Fortune 100and the next minute sell to a
mom and pop, that there might bechallenges associated with
scaling.
And so segmentation might be thefirst thing.
And then if we know we're goingto segment, the second thing is
then around okay, what is theprofile of talent that I would
(24:12):
need for those types of roles,depending on how many of each
that I require?
Another thing that you mentionedwas around looking at, if you
have a multi-product portfolio,looking at the product types
individually and saying, okay,which of these is both
performing really well rightnow, and which of these has the
potential to perform with someadded investment, and then be
(24:32):
making decisions around, again,with the clean slate, how do you
bring additional productsoutside of maybe the core to
market?
And then maybe two other thingsthat you mentioned within there.
One, I heard a lot oncommunication of change.
So communication of what's goingon as you try to move an org,
and then communication in itsforms, whether they're videos
(24:55):
and highlighting folks andmaking people feel a part of
that change, that alone,communication is probably a big
driver of MPS.
Like feeling like you're on theteam and not just like people
making decisions in the ivorytower alone is probably pretty
possible.
SPEAKER_01 (25:10):
Yeah.
SPEAKER_02 (25:11):
And then to the extent you get that all going,
okay, how do I institute amethodology to get consistent
execution?
You selected the challengersale.
And it's like, man, if you canjust do these things that you're
gonna help.
I mean, anybody would want toachieve the results of going
from zero quota performance totwo-thirds or from um 35%
(25:32):
attrition to two.
So uh that's just like what I'mhearing.
I'm wondering how much of thatis the sort of playbook, if you
will, of entering otherdifficult situations.
SPEAKER_00 (25:43):
Well, I love that.
Gosh, that was so well said.
The um the other thing I thinkthat we did that I think is
really relevant too was weoutfitted the team with tools as
well so that they could sell amulti-product solution.
Part of what happened wasobviously like the uh the same,
or I'm sorry, the challengersales methodology was really
helpful for sure.
(26:04):
But also it was the mechanismfor them to be able to sell new
products to their solution totheir to their customers was one
of those things that they didn'tknow necessarily how to bring it
up always.
And so we had outfitted themwith sales loft at the time.
Um, but now I think of all ofthe different AI tools that you
could be leveraging to either umuncover who has the most
(26:28):
potential.
Uh you know, not obviouslyyou've got your performance
already with the revenue, uh,revenue that folks are doing,
but you can look with any ofthese AI tools to start to go,
okay, who might be have thepropensity to be able to use it?
And then obviously, then how doI do any outreach with marketing
tools and all that?
(26:49):
And so we had used sales off atthe time, but now I think that
there's all sorts of other waysto uncover intent uh and
propensity to buy too.
The other thing I would say isin that performance and
potential uh on the performanceside, one of the other elements
that was really interesting andrequired partnership with our
finance team in particular wasevaluating the LTV to CAC for
(27:12):
each of these.
And so there were also segmentsthat we decided to exit and say,
this is actually not aprofitable segment for us to for
us to sell to anymore becausethey don't stay with us, or
because the CAC is not worth it.
Um so you could evaluate all ofthose elements.
And so when we started to lookat, you know, all of the
different segmentation, youstarted to almost see, okay,
(27:34):
here's where we're going toorganize, here's how we're going
to organize, here's how we'regoing to support it, and then
here are ones that we're justgoing to exit.
Um so it was a reallyinteresting kind of RevOps
finance product and salesmarketing and customer success,
um, you know, kind ofcross-functional initiative that
made us stronger and got usgrowing again.
SPEAKER_02 (27:55):
Why do you think, in the example that you use, which
is an excellent one withShutterstock, why wasn't that
happening already?
SPEAKER_00 (28:01):
I think they had just had so much chaos.
There had been so much chaos inadding all of these companies.
And they had been on a growingspree, you know, they had been
on an acquisition spree,frankly.
And so they were bringing all ofthese people together.
And so if you had been there foreight years, which as I
mentioned was the averagetenure, you could just kind of
(28:22):
keep doing your thing and notadd all of these.
And then it it only, you know,it only became apparent once you
weren't hitting your number.
Why you weren't hitting yournumber was because you were
selling the thing you had eightyears ago, as opposed to all of
the new stuff that you had tosell.
SPEAKER_02 (28:38):
Did you come in after all those acquisitions?
SPEAKER_00 (28:40):
Yeah.
So I came in after all theacquisitions.
SPEAKER_02 (28:43):
What an interesting dimension.
And I think we're starting tosee consolidation and
acquisitions happening.
Acquisitions are um so difficultto execute because of all the
examples that you just gave.
It's like fun to get the dealdone, but then making it work
afterwards is like way harder.
Oh, and so I mean, I had tomultiple times over, it does
(29:04):
just naturally create a highstate of unsettledness, and
that's being you knowoptimistic.
SPEAKER_00 (29:11):
Absolutely.
Well, and I've had to do thatshort held before that.
We were a premises-based unifiedcommunication solution, and we
bought a cloud company.
Everything about us wasdifferent, right?
Uh, it was monthly recurringrevenue versus upfront CapEx
investment, making all of yourmoney through partners uh and
through that upfront investment,in fact, selling against each
(29:33):
other a lot of the times.
Um, and so it was reallyinteresting to watch that
happen.
And that was the first placethat I became, frankly, uh it
was a VP of sales and customersuccess where I saw the impact
across marketing, sales,onboarding, customer success,
support.
I saw the impact of selling tothe wrong type of customer.
Um, we had an example of we usedto sell to law firms as an
(29:56):
example in our cloud solution.
And you You would do so muchwork to market to them, to then
go through the months of redlines with this law firm, right?
Then it would take months andmonths to onboard them.
Um, and then the second that yougot them live and there was any
disruption in service at all,they churned.
(30:17):
And so it turned into, it wasactually very fascinating.
This was my entire career, hadjust been in sales.
And so here I am thinking, well,we did our thing right.
We got that, we got that dealclosed, right?
Um, we got our commission.
And it turned into this was thefirst time where I really went,
oh my gosh, it's not about doingyour thing right, it's about
doing the right thing.
(30:38):
And so we evolved and changedour entire 150-person team to
where no longer was anyone ableto sell to law firms or market
to law firms or keep a law firmbecause we now went, who is the
longest, who's the LTV, who hasthe longest tenure, retention,
et cetera, with us?
Who is the right ICP for us tobe selling to?
(30:59):
And so not only did we changewho our ICP was and like all get
aligned to it, but then I alsochanged the compensation model
for everyone.
So everyone had the compensationthat they were entitled, you
know, that they were responsiblefor.
So sellers, it was new ARR forthe support team, it was their,
you know, uh their uh first callresolution, uh, was their
(31:21):
primary way of getting paid,right?
Either for their bonus or theircommission.
But 25% of everyone's variablecompensation had a retention
element to it.
So that you were not just doingyour thing right, but you were
doing the right thingholistically for the
organization to succeed, whichwas all about retention and
long-term value of thecustomers.
SPEAKER_02 (31:42):
Bridget, you know, just in this conversation, it's
clear you've walked into sometumultuous situations.
Walk into acquisition-basedtumult.
That's probably like on thedegree of difficulty scale as
high as it gets.
And if you can successfullynavigate the change management
or transformation in thatcontext, imagine what you can do
(32:04):
when you don't have the onehand, the one arm tied behind
your back in terms of doingthat.
I wouldn't underestimate the umthe skills that one acquires to
be able to effectively um managegrowth.
Um, but if you think aboutcoming into a situation in a you
(32:25):
know more favorable startingpoint, so to speak, um, you
know, that the idea ofaccelerating growth might be
really compelling and excitingbased on what because you've
already seen the harder uh youknow, sort of picture.
Another thing that kind of comesto mind for me is in order to
effectively transform anorganization in any way, I
(32:45):
imagine you you talked aboutthis cross-functional dynamic
working with finance and workingwith RevOps and looking at LTB
and cat to cat and making thetough decisions that you can't
make on your own about what arewe not going to do anymore?
Law firms, in your example,being the perfect thing.
We're able to close deals there,but it's not good business.
It takes a village, so to speak,to come to agreement that we
(33:09):
can't do this anymore.
Can you talk a little bit aboutum you know how you pursue now
cross-functional relationshipsat the executive level and maybe
the learnings that have gottenyou to your worldview today?
SPEAKER_00 (33:21):
Yeah, I mean, I'm a big, let's say, management book
reader.
I love books on leadership.
So one of my favorite ones is uhshockingly, Stanley McChrystal,
General Stanley McChrystal'sbook called Team of Teams, where
he talks about how they wereable to defeat Al-Qaeda in Iraq.
(33:43):
And he uh he managed the jointoperations special forces, and
it was all of these individualbranches of the government,
right?
And so they were all in Iraqtrying to, you know, kind of
defeat this very nimble enemy.
And he found that this, youknow, we're the US had the
strongest military in the world,and we're getting beat every day
(34:05):
by a more nimble, flexible, youknow, adversary.
And it was because of the thingsthey were doing internally to
make things harder.
So one branch of the militaryhad like an informant and
someone who was, you know, kindof their their go-to guy.
Another branch of the militarywas like targeting that person.
(34:26):
So, you know, they it everythingwas misaligned.
And so I think of that book alot, and that's where I got that
whole, you know, do the rightthing versus doing your thing
right, um, because he basicallychanged it to where he said, now
we are a team of teams, we aredoing missions together, we are
aligned on what our missionsare, and the ultimate goal is
(34:47):
the, is like, is the is todefeat al-Qaeda and Iraq.
Uh, in the same sense, I thinkof, you know, the ultimate goal
is the organization's goal, notjust your sales goal or not just
your product team's goal.
The other thing I've read wasFive Dysfunctions of a Team.
That's one of my favorite booksever, too.
And they always highlight thatthe team that you are on is your
(35:08):
most senior team that you are oncross-functionally, not the team
you lead.
And so, again, my team is not mysales or my customer success or
my marketing team.
My team is me and my chiefproduct officer, my chief
financial officer.
We are solving the CEO'sproblems, uh, not necessarily
(35:28):
just the problems of our team,um, or only answering that.
And so, and I think there's nobetter, you know, kind of
definition of that than aligningon, let's say, an ideal customer
profile.
That I would be, you know, thatis like one of the perfect
examples of you think that maybethat's just a go-to-market
challenge.
Absolutely not.
(35:48):
Your CFO, your chief productofficer, your CEO, um, everyone
within your organization needsto be aligned on who your ICP is
and what that means if you areonly selling to that or if you
are choosing to go beyond it.
Um, so even something like theICP work that I think is
probably the most importantthing, allows you to know where
(36:10):
are we, where are we targetingand and what are we willing to
spend to get that customer andwhat are we doing, you know, to
service and support and keepthat customer.
Uh, and I think there there'sthere's no more kind of example
of something where it aligns theentire executive team more than
something like ICP.
SPEAKER_02 (36:31):
Yeah, I mean, that's a great example.
Um, you know, Lencioni's fivedysfunctions of a team.
Um, I've heard a lot about this,that the idea that your team is
your peers and not the folksthat roll up to you.
And I think everybody nods andyou know vigorously agrees,
yeah, sure.
But the actual like applicationof that in the real world is
much tougher than it sounds.
(36:53):
It's very easy to live withinyour um your silo of
responsibility.
Uh, first of all, those folksreport up to you, and so if you
call, they answer, and youunderstand the deep context of
the things that A, that theyshould be doing, B, the things
they are doing, and C thestruggles or challenges or
objectives or obstacles thatthey might be facing.
(37:15):
And so the inertia is pushingyou at all times to work within
that silo.
Yeah.
Like, for example, you might notbe the head of engineering, you
might not have any idea how towrite code.
So, like, what are you gonnatalk to the head of engineering
about?
It's like you don't want to tellhim about or her about the
quality of the engineers becausethat's not your role.
(37:35):
So you don't want to be comingacross like you're infringing,
or the head of product, orfinance, or whatever the area of
specialization is.
So I think the idea that, like,hey, your first team is your
peers and not just like thefolks that report up into your
org is much harder to actuallyapply because all the inertia is
(37:56):
also pushing them to focus onthe things they need to do day
to day and so on and so forth.
So I think a challenge forleaders is a the recognition of
what you described, but then B,how do I put that into practice?
How have you done so?
SPEAKER_00 (38:11):
Oh, yeah.
Well, it's aligned compensation,number one.
So, you know, the salesperson inme dies hard because I think
aligned compensation always is away to reinforce the the goals
that you have.
So, um, and I mean that companywide.
Um, I think there's also um Ithink what is it, people have to
(38:31):
hear something nine times beforeit actually sticks.
Um so I think it's also everysingle I think yeah, exactly.
Yeah, yeah.
It was nine.
I think it's nine.
I don't know.
It's either seven or nine, and Ican never remember.
Yeah.
And I'm like, I clearly I needto hear it more often.
So the um, but I think at everyuh, you know, all team meeting
(38:52):
that you hold, everyorganizational meeting that you
have, every time you kick off ameeting, as a reminder, our goal
is that we are getting to thisrevenue target or retention rate
should be this, or ICP is this,and we are looking at our ICP
penetration rate.
Like whatever that one thing is,and I always usually, if it can
be one thing, it's ideal.
(39:13):
Uh, if it is one thing that youcan find is the ruthless
priority of the organizationthat you are galvanizing the
team around, then it is it's theone thing that you are always
talking about.
It's the one thing you arepaying them on, whether it's
their bonuses for uh usually thenon-commission carrying folks or
the uh or the commissioncarrying folks having a
(39:33):
component of it to be uh to beum uh you know something that
they are incentivized to.
And then the third element Iwould say, so it's you know,
aligned compensation, number twowould be the you know,
relentless discussion about it.
The third would be find some wayto make it fun.
Find some way to make it fun.
Um, and that they care about itbecause I have done, I can't
(39:56):
even tell you the amount ofembarrassing things that I've
done where like if we hit acertain goal, there's pie in the
face.
If we hit a certain goal, I'mdoing chapel roan karaoke, which
you don't have to ask me toomuch.
I will, I will raise my hand todo.
But the there's so many thingsthat are, you know, ways to like
make that fun, or you know, thewhole company gets um, you know,
(40:19):
I don't know, a what have wedone?
We've done like yoga classtogether.
Um, uh the entire company getsto have a half day off or
something.
You know, like there were therewere things like that that we
would do, and there were alwayslittle small milestones.
And I've also heard this is whatthey do.
Um, that, you know, as you werein pursuit of a goal, you don't
(40:40):
do milestones, you do inchpebbles.
Love that term.
Um, I stole that from myfavorite book, Switch, How to
Change When Change is Hard.
That's another one of my booksthat I love.
Um, and they basically are like,this is the this the way that
you create success is to showthat success can be uh can can
(41:01):
happen.
And so, for example, if you'reshowing a timeline, you never
show yourself at the beginningof this.
You show yourself, see, we'vealready started.
We're about 25% of the waythere.
So you already show, look,success is is already begetting
success.
People would rather be in partway through a longer journey
than at the beginning of ashorter one.
(41:22):
That is one of the invaluablelessons uh that Switch teaches
you.
And so that's where these littleinch pebbles of shrinking the
change that you were trying toget to work.
And I will tell you, on thatthird day, on that Camino de
Santiago, when I did not want todo this, I was using inch
pebbles to motivate myself onthis journey.
(41:42):
I was doing, I was like, justget to that place so that you
can have a coffee.
Just get to that place so youcan wring out your socks.
It was small little change, orand I was like, you know, giving
myself, uh giving myself littletreats.
Oh, then you can get yourprotein bar.
You know, I was doing littlethings to like motivate myself
because I couldn't talk to her,you know, I wasn't really
(42:03):
talking to anybody.
Um, and so all of those thingsare, you know, all of these
change management tactics thatyou use are things that you can
use on yourself too.
SPEAKER_02 (42:13):
Totally.
Bridget, you're back here in NewYork.
What's next for you?
SPEAKER_00 (42:17):
Um I'll be uh the chief revenue officer at a
company called Patient Now.
Uh it is the back-end practicemanagement uh for med spas and
aesthetic practices, uh, anamazing vertical SaaS company
that is in the hyper-growth$20billion uh market and growing at
(42:39):
15% every year.
So extremely great space and uhallows for Patient Now to be the
market leader in that.
So I'm excited for that.
SPEAKER_02 (42:50):
Fantastic, Bridget.
I feel like we just got startedhere talking, but we have run
out of time.
Best wishes, and I'm sure you'regonna do an amazing job in the
new role.
It was fun talking about yourpersonal experience and your
personal reasons, about yourexperience with revamping
process and incorporating talentinto the bigger picture and how
you sort of cross-functionallybring the org along with you.
(43:12):
Um, it's been awesome.
So, Bridget, thank you very muchfor joining.
Where should people find you?
LinkedIn the place to go?
SPEAKER_00 (43:18):
Yes, LinkedIn is the place.
My DMs are open.
Feel free.
Awesome.
Thank you very much.
Thank you so much, Rick.
This was so fun.
SPEAKER_02 (43:33):
Reflecting on the conversation we just had with
Bridget Winston, so many littletidbits of wisdom that were
shared, it's hard to sort ofcompile it down to three big
themes, but I'm gonna attempt todo that.
And the first thing that standsout to me, so much of this show,
is about tactics to help us bebetter sales leaders, better
(43:54):
leaders, better professionals.
And there's a whole nother sideto us beyond our professional
selves that in our personaljourneys outside of just work,
and Bridget's sharing her storyand her personal journey between
roles, taking a trip on theother side of the world, stories
of adversity, stories of loss,stories of meaning, stories of
(44:15):
spirituality, it gives us anopportunity to reflect and think
about what is our own journey?
What is the meaning we arefinding beyond the work that we
do?
And when you hear anotherleader, a successful leader,
share a story with somevulnerability in it, with some,
you know, unconventional or not,you know, not your typical trip
(44:35):
that folks would take, it helpsform thoughts about our own
search for meaning in ourhumanity beyond our ambition and
our professional careers.
So thank you, Bridget, for thatuh storytelling.
The second thing, the difficultyin when you have a company that
grows through acquisition.
And I'm not saying just oneacquisition, I'm talking
(44:56):
multiple acquisitions.
And Bridget told stories thatreflect the challenges
associated with digesting andconsuming and moving forward
successfully when you've been inan acquisition-heavy
environment.
She told stories of having tolike take a step back and get to
the fundamentals of how would werun this business if we were to
start it today and having to dobasic things that weren't being
(45:19):
done in an environment that youknow might be described as
chaotic.
Um, and so that you know, I wantto tip my hat to all of the
sales leaders out there that areleading businesses that have
been acquisition heavy, and Iwant to acknowledge the
difficulty it is.
And now I kind of understand ata greater level why such a large
percentage of deals that getdone don't translate into the
(45:43):
value creation that was sold aspart of that acquisition effort.
Now, if you have a leader likeBridget, you have a better
chance of being able to take astep back and then execute
accordingly.
But boy, her stories uh showedthe difficulty in doing that.
And so it's like almostoperating with one arm tied
behind your back.
And so um, for me, it's like,okay, uh acquisitions sound fun,
(46:04):
and when you see them happen onLinkedIn, people are celebrating
them, but the there is hard workthat has to happen on the other
side of that.
Um, the last reflection I havefrom the episode is when Bridget
was talking aboutcross-functional leadership.
And she made the point of makingit fun.
And I think it's a superimportant point.
We all are trying to make thebiggest impact we can on our
(46:26):
organizations and develop theright relationships.
And it's difficult when we arein a large group of humans
working together towards acommon goal.
And it is important that thejourney doesn't just have to be
hard.
It can be hard and fun.
And it can be fun to be in achallenging environment.
And I loved Bridget uhemphasizing the importance of
that.
I think we all need to be havingfun along the way while we do
(46:49):
the hard work of being greatleaders, of learning how to be
positive impacts across theareas of responsibility that we
are working through.
So thank you, Bridget, for agreat discussion.
Really appreciate it.
Thank you to Ari Smolin forproducing.
Thank you to Sons of Summer forthe tunes.
Thank you, listener, for beinghere today.
We will see you next time onPillow Talks.
Hello, everyone, and welcome to another episode of
Pillar Talk.
This is where we build thefoundations of sales leadership
success and try to createclarity in terms of what good
looks like for current andaspiring sales leaders.
Today on Pillar Talk, I amjoined by Bridget Winston.
(00:36):
Thank you for being here,Bridget.
She brings, before I let herspeak, she brings over 20 years
of experience in scalinggo-to-market organizations
across marketing, sales,customer success, the entire
customer lifecycle.
She was most recently the ChiefRevenue Officer at Chief.
This is where she helped growmembership in that community
(00:57):
from 1,500 to over 20,000.
Previously, beyond that, she wasin many roles, including
Shutterstock, where she ledglobal sales through a pivotal
transformation period.
Bridget also advises CEOs,boards, investors on all things
go-to-market strategy, growth,and customer experience.
(01:18):
She's someone who blendsambition with reflection because
between roles, she recentlywalked 75 miles of the Camino de
Santiago, a sort of pilgrimagethat offered lessons, and this
is based on what I read, onslowing down presence, and
rediscovering purpose.
(01:39):
Bridget, welcome to Pillar Talk.
SPEAKER_00 (01:42):
Oh, I'm so glad to be here with you, Rick.
That is that's a lovelyintroduction.
And what I will say to you isyes, it was meant to be a
pilgrimage.
A lot of people use it for avery religious pilgrimage.
I was going to very much, youknow, kind of accomplish a goal
that I had.
And it was it was really goodthough, because it ended up
(02:03):
being much more of a reflectivemeditative jaunt for myself.
So that was lovely.
SPEAKER_02 (02:10):
So I get excited when I see something interesting
and different.
And, you know, you just had alot of responsibility in your
last role, probably runningaround, handling huge amounts of
initiatives, pressure, largescopes of organizational
development, uh, strategy.
And then you go from that to I'mgonna do something totally
different, and I'm gonna go, youknow, accomplish this, you know,
(02:32):
personal goal.
So I love to learn more aboutthat.
Can you share a little bit aboutwhat inspired that trip and what
did you take away from it?
SPEAKER_00 (02:41):
Yeah, absolutely.
So uh, well, it was kind of atwo-week adventure for me.
So the first week I actuallywent to Tuscany and did an
immersive cooking course.
Um, but it was pretty difficult.
It was not actually asmeditative and as relaxing as I
thought because we were cookingfor five hours a day with an
(03:03):
Italian chef who was verydemanding.
So it was me and a bunch of 60and 70-year-old retirees going
to this uh villa in Tuscany todo a cooking course.
So that was fun.
But I the good news is I wasfueled up, I was carved up so
that I could go on the next weekto uh the Commune de Santiago.
(03:24):
And both of these I chose to dodo solo.
Uh I have a great, amazinghusband, but I really kind of
wanted to do something formyself.
I have, I'm 45 years old, so Ifelt like this was like that
moment of, you know, prove me tome a little bit, go and do
something uh that was a little,a little scary, a little, can I
(03:44):
do it?
These were things I'd alwayswanted to do.
And so it was a little bit ofprove me to me, particularly the
Camino, because you know, you'restrapping yourself into some day
pack.
I had to have, you know, waterfor the whole day.
You're walking four to six hoursa day.
Um, and you know, going, I chosenot to do the hostile route.
(04:05):
I did stay in hotels, so I hadit a little bit more uh of the
high end.
I wasn't doing the fullpilgrimage, but it was a four,
five-day jaunt that um was fourto six hours a day.
Uh, I think I walked at minimum12 miles a day to 18 miles a
day.
(04:26):
Um, and I I'm pleased to saythat it rained every single day,
poured raining every single day,completely different than what I
was expecting October in Spainto be like.
I was expecting it to be thislike beautifully, you know,
wonderful moment.
And it was, I mean, it was itwas torrential downpours the
entire time.
(04:47):
Uh, you're walking with otherpilgrims who are doing this.
I did the Camino coastal routeof Portugal.
Um, and so you are walking thisroute with other people,
sometimes seeing a lot ofpeople, sometimes seeing few.
Uh, and you're walking throughlittle small towns in Portugal
and Spain.
And there were certain townsthat I went to that didn't have
(05:10):
any people and just cats.
You're walking by chapels, youhave to get your Camino passport
stamped.
Uh, so you have to stop everynow and again to get your Camino
passport stamped to prove thatyou did the walk.
You walk next to certain people.
Some people really want to talkto you, some people are, you
know, kind of just walking insilence.
I watched one lady doing therosary the whole way, which was
(05:33):
really sweet to see.
But like the first couple ofdays, I will say, I was walking
and I was on a mission.
I was like, get this thing donebecause the rain, I was wringing
out my socks three times, youknow, I didn't stop for coffee,
I didn't stop for lunch.
I was just trying to get thisdone.
And that is probably prettystandard about the kind of
person I am.
I'm I was a Division I collegeathlete.
(05:53):
I was always like a person wholikes to achieve a goal,
relentless kind of pursuit ofthings.
And but I will say by day three,I uh day three was the day that
I was like, I don't feel likedoing this.
I am like annoyed that I have toget up and go walk this thing.
Um, and so while it wasenlightening and empowering, it
(06:15):
was also really hard, bothmentally and it grew to be hard
physically, but like physicallywas less hard.
It was mentally getting yourselfto like do the thing.
And so I had to honestly do thething that was opposite my
normal tendency.
I had to actually give myselflike little goals.
And I had to like, you know,tease that hey, you can stop
(06:37):
within two hours and rest yourfeet and take a coffee break.
Um, you can talk to the peoplenext to you.
I wouldn't kill you.
You know, this is not about thislike relentless pursuit of like
getting this thing done.
It is meant to be reallymeditative.
And I will say it culminated insome really like interesting
(06:58):
discussions and and talks.
And frankly, my blisters werebetter for it to stop a bit, but
it culminated in the last daywhen I had two miles left to go.
And I am almost to Santiago,which is this beautiful church
in in Spain.
Uh, and they say it's where St.
James is buried.
Who knows if this is true?
(07:19):
But um, but I was two miles awayfrom being done, and I come, I'm
on it in a forest, and I comeupon a man playing the piano in
the forest.
I mean, the most random thing.
And I think what was mostmeaningful about this is my
father, uh, who's passed away 17years ago, was a big musician,
(07:45):
and our home was always filledwith music and the piano in
particular.
And so he used to play thepiano, he used to play the piano
at mass and all of these things.
And I know that he would havebeen very proud of me for doing
this.
And I came upon this man in theforest playing the piano, and I
(08:05):
stopped for 20 minutes and justcried because it was first off,
he caught me at quite the time,two miles left to go.
But also, it was just this likemeaningful thing of being
present and remembering why youdo things and remembering the
people who are really importantin your lives, and um just
taking that moment to pause.
(08:26):
Um, and so it was just like oneof the most meaningful things.
I'll remember it for the rest ofmy life.
Um, and it, you know, I passedcountless cemeteries, right?
And so I was already in thissomewhat reflective mood of
like, gosh, all of these peoplewho came before us and who have
lived here, but like to be thereand to see in the middle of a
forest a man playing the piano,um, it really made me feel like
(08:48):
my dad was there and presentwith me in some ways.
I don't know if I believe in allof that, but like it was it was
just it was so poignant and andfrankly just breathtaking to me,
um, otherworldly in some ways.
SPEAKER_02 (09:02):
Yeah, you had written about that in your post
on LinkedIn, and that wascertainly uh a moving and
emotive uh aspect of that post.
You could feel as the reader umyou know a bit of what you were
feeling there.
So very powerful stuff.
What what was you know whenyou're between roles and you
have the opportunity to go dosomething different, there are
(09:23):
many options, and there's no oneright answer.
What was the rationale behindthese two journeys for you in
immersive cooking in Italy andyou know, the hiking um you know
across the Camino de Santiago?
SPEAKER_00 (09:40):
Yeah, I mean I think what was drawing me to do both
of these is something a littlebit more either in nature or
with my hands, right?
We sell SaaS and cloud, and Ialways think about I've got all
of these relatives who live inIreland, and whenever I go
there, I'm always explainingwhat my job is to them.
(10:02):
And the a good portion of thesepeople are teachers, they are
builders, they are people who umor chefs, and whenever I tell
them what I do, I mean I feellike I'm in some way selling
vaporware, right?
That we are just selling thisthing that is, you know,
fulfilling a um certainly autility, and it it's important,
(10:26):
and there are things that we aredoing, but I feel like you lose
a little bit of the one-on-oneconnection with others, um, and
the the meaning in life and likethe visibility of seeing what
you create.
Um, and so there was somethingin this around the cooking,
(10:49):
although I think I I I may havecome back a worse chef after
that.
unknown (10:53):
I've got to be honest.
SPEAKER_00 (10:55):
Like I'm even thinking of like, what is my
LinkedIn post?
And I really think like thelesson I learned was this did
not teach me anything.
It taught me just to like justenjoy it.
Like someone's gonna makesomething good and just eat it,
you know, like even if you're aterrible chef.
Um, so but it was it was one ofthose things.
And then the Camino wasseriously like the feet on the
(11:18):
ground of just meditativelywalking through towns that
honestly I just watched oldpeople, you know, harvesting
pumpkins and picking apples andyou know uh walking amongst
their cats.
It was, it was just, and I I sitthere and think, do these people
(11:40):
understand what I, you know,like are they gonna understand
the SaaS software solution I'mselling?
You know, it's probably neverentered their mind.
But God, there were laughter.
There was people who were, youknow, you could hear kids, you
could hear um, you know, youwatch generations of people be
all together.
And so there was just somethingvery moving about like what
(12:02):
really makes a difference in theworld, you know, and it is
sometimes it's just the food andthe connections that we have.
SPEAKER_02 (12:08):
In your post, you mentioned you you use this
phrase, a superpower overusedbecomes a weakness.
SPEAKER_00 (12:15):
Yes.
SPEAKER_02 (12:16):
Um tell me a little bit about that.
That's an interesting quote.
SPEAKER_00 (12:20):
Well, it was born out of one of my favorite things
is strengthfinders.
Have you ever read uh or haveyou ever done Strength Finders
as a um as one of thosepersonality tests or anything?
I believe I did that once, yes.
Yeah, and so um, and it's alsoborn out of, you know, whenever
anyone's like, what's yourbiggest weakness?
You know, what you usually whatI always do is I always throw in
(12:43):
a superpower for use becomes areason.
Yeah, yeah, yeah, exactly.
Well, yeah, exactly.
Like, I'm just such a hardworker, it's a workaholic.
Um, and so um, but I do thinkthat generally speaking, um it
is the things we are best atthat sometimes we over-rely upon
or over-index on that become thething that probably is our
(13:06):
shadow side, if you will.
Um and so, and that's what I'veseen.
Like my relentless pursuit, mydriven, my ambitious, my, you
know, probably, you know,sometimes command and control is
the thing that prohibits me frombeing the leader I should be,
and to get even better at beinga leader.
(13:28):
And so sometimes us doing theopposite, or at least being open
to doing the opposite.
Now, there's the other side ofme that's also like embrace your
strengths because like one ounceof energy tied towards something
you're already naturally good atis probably gonna deliver more
for you.
But wouldn't we all be better,more reflective people if at
some point we also said, andwhat's my opposite?
(13:50):
Or how do I supplement myselfwith either people on my team
who think differently than I do,or um, or inviting debate, and
you know, like argue this fromthe other side.
I do that sometimes with my teamwhen we're all in agreement, you
know?
SPEAKER_02 (14:06):
Yeah, yeah.
Well, I I certainly think umthis idea of doing something
completely different than yournorm, when your norm is a lot of
Zoom calls and zeros and ones,which is the world we live in,
and we're very lucky to be here,you know, trudging through the
mud in sort of like spiritual,truly powerful, you know,
historic areas, um, you know,definitely scratches that itch,
(14:29):
doesn't it?
SPEAKER_00 (14:30):
Yeah, absolutely.
I mean, and there was just funnythings.
I mean, the things that you justsee on the way.
I mean, the there was a chapel Ipassed that had like Mary
Magdalene laid out like she wasa French, you know, you know,
French painting.
It was so funny.
I mean, there were just thingsthat I would just snicker to
myself and just laugh.
(14:51):
And I didn't use headphones theentire time, which I was like,
all right, you are gonna bepresent, girl.
You are going to get throughthis, you're gonna talk to
people, you're gonna experiencethis, you're gonna hear the
roosters crowing.
And they they woke up late.
They woke up late at least 9a.m.
I was like, there's no moreSpanish rooster thing than
(15:11):
waking up at 9 a.m., you know?
SPEAKER_02 (15:15):
Well, Bridget, welcome back, and I know you're
gonna be getting back intoengaging all types of companies.
We're in a time of you know,uncertainty within the business
landscape, especially in SaaSand tech.
Um, you're gonna walk intosituations whether you're in
advisory capacity or full-timecapacity or anything in between,
(15:36):
and you're gonna see situationswhere organizations are
struggling with growth.
You're gonna see organizationsstruggling with the uncertainty
of where to go.
And one of the things you'regonna hear a lot about is we
have the wrong talent in theorganization.
So when you approach a situationwhere an organization is
struggling or not performing togoals, true or false, it's a
(15:58):
talent issue.
Just replace the people andyou're good.
SPEAKER_00 (16:01):
Oh, I can't tell you how many times I've heard that.
So when interviewing for ChiefRevenue Officer Jobs coming in,
uh, and I always hear,especially if they're struggling
with growth goals or uh they'vedone a lot of acquisitions and
the culture and the team moraleisn't there, um, you always hear
when you ask, you know, any ofthe folks that you're
(16:24):
interviewing with, well, what'swhat's the what's the main
challenge?
And the number one thing youhear is talent.
And what I would say is I'mgoing to dispel that myth right
now, Rick.
Not fully, but at least startwith first look inward, first
look inward organization, uh,and investigate have you
(16:44):
actually set the team up forsuccess.
It's not that it's never thetalent.
Um, so there's always talentimprovements.
And uh in certain organizationsthat I've been in, there was
definitely a time for us toaddress the talent.
But um in some of theorganizations that I've seen,
the first thing that I saw wasthat there was no plan for the
(17:05):
plan.
Uh, and there were there were nooperating rhythms that were
actually ensuring that the teamwas going to be successful.
So I always look atorganizations and say, first
look inward.
How are you ensuring that thistalent that you have is
successful?
SPEAKER_02 (17:21):
So let's talk about that.
What does it mean to lookinward?
Yeah.
SPEAKER_00 (17:25):
Well, um, I'll even use an example.
Um, personal level lookinginward, but that's the one.
Yeah, yeah, yeah.
Yeah, first look inward.
And then you're gonna go on aCamino de Santiago.
I hate to say it, Rick.
Then you'll go and maybe you'llgo to this uh go to this villa
in Tuscany.
Uh so yeah, so when you firstlook inward, uh, the biggest
(17:45):
thing I always like to see is isthere an operating rhythm?
Is there a plan for the plan?
Um, so for example, um, I wentinto an organization,
Shutterstock, as an example, andwhat we found was that no one
was hitting their goals.
Um the employee NPS score was atwo out of 10.
(18:06):
Uh, you know, the attrition ratewas 35% uh when I was joining.
And so obviously something wasgoing on.
And despite all of theseacquisitions that Shutterstock
had made, um, no one was sellingany of the new products uh that
they had.
And so it was reallyinteresting.
So therefore they weren'thitting their goals and growth
had really stalled uh andslowed.
(18:27):
And so what became reallyinteresting to me was, and of
course, as I was interviewing,it was the talent's terrible.
It's the talent, it's thetalent.
And it wasn't that the talentwas terrible.
I mean, a good portion of themhad been there for eight years.
They may needed to be retrainedand retooled a little bit, of
course.
Um, but the first thing that Isaw was there was no plan for
(18:49):
the plan.
There was no rhyme or reason towhy there were the number of
sales reps that they had, salesand customer success reps that
they had.
Anyone that they had within theorganization did not have any
kind of segmentation.
So, like you could have oneperson who was managing an SMB
account, but they also in theirlist had a$1.1 million
organization.
(19:09):
Um, they were in completelydifferent industries, completely
different verticals.
Uh, the person who and so, andthere was just a mishmash of
accounts.
So, one of the first things thatI looked at was all right, if we
were no names and boxes, nopeople, uh, you know, at all,
what do we look at?
Like, what should thisorganization look like?
How would we organize thisorganization if we were thinking
(19:31):
about vertical expertise, if wewere thinking about segmentation
and the way that an SMB accountneeds to be serviced versus a
large enterprise customer?
Um, you know, certain what wasthe sales cycle and velocity of
a sale for an SMB customerversus someone who needed a lot
more high attention and probablyconcierge-like support.
(19:53):
And so we began to design theorganizational structure to
support the multifaceted way wewere going about doing business.
Then we started looking at,okay, we'd have these different
eight different product types.
Um, how and which accounts areour biggest high potential
accounts versus also highperforming.
So, you know how there's thenine box that you do for talent
(20:14):
assessment, you know, is thishigh potential and high
performing?
You can do the same thing withaccounts.
Um, and that's in fact how wehow we looked at our customer
success modeling was highperformance and high high
potential.
Um, and started to assess, okay,what is the sales motion and the
support motion for those?
And then also what is thepotential for those?
(20:35):
So uh where can we actually, youknow, expect to see all eight
all eight of our product linesbeing sold versus someone who's
literally just doing somethingvery high velocity and a little
bit more transactional.
And so then we started to lookat our talent.
That's when we started lookingat our talent and started to
assess where do we have somebright spots?
Where do we have folks who arereally killing it and can teach
(20:58):
others?
So I didn't start by letting goof the team.
I started by looking at the teamand saying, okay, where do we
have really good performers?
Where can they teach others?
And so we brought in challengersales methodology into the
organization because a lot ofthem, even themselves, needed to
be challenged to thinkdifferently a little bit.
(21:20):
So we brought in challengersales methodology to the
organization.
And then there were certainfolks that honestly we uh after
doing different role plays andand um and listening to calls
and doing coaching, where we didhave to part ways with them or
reallocate them to other partsof the business.
We had an entire supportorganization that was that was a
really good um fit for some ofthe people.
(21:41):
And then some of the people justdidn't like the new approach and
so decided to self-select out.
Um, but it was reallyinteresting because it was um
such a great way for us to, youknow, kind of leverage the
existing talent to help us hirethe new talent.
And they became people who weadded on the panels.
They became the people that wedid recognition for.
(22:01):
And so every month we did funvideos and kept the change alive
by showcasing, look, see,there's success.
We have people who are havingsuccess doing this.
And so we would give out awardsevery month.
There were global awards, wewould do fun videos where we
would show all of the differentoffices.
We had offices in Brazil,Mexico, you know, Germany, uh,
(22:22):
Italy, all over the world, um,Singapore.
And everyone would send invideos once a month of, you
know, kind of their spotlightedcustomer and also like just fun
things that they'd been doing,whether it was like a plank
contest or something.
So there were just ways that wewere trying to keep the culture.
So in the end, we ended up withat least an employee MPS score
(22:42):
of like seven out of 10.
The attrition had switched froma high 35% down to a 2%
attrition rate.
And we had 67% of the team startto pay quota, so a little bit
more of that best practice.
So um, because we'd organizedappropriately and reassessed the
talent, but it was secondary,not the primary thing that we
(23:05):
did was just come in and fireeverybody.
SPEAKER_02 (23:07):
So let me play back to you the sequence of the
things that I heard and see howmuch of that can be a template
for you and others when theysort of enter an organization
and things aren't going the wayyou know we'd hoped uh they'd
be.
So one of the first things youmentioned was just like, well,
take a step back and put a cleanslate against the business and
(23:29):
say, hey, if I was going tobuild a go-to-market motion for
this business as it is today,what would that look like rather
than how do I make the best useof whatever's going on here
today?
And the example that you gavewithin that was segmentation.
So if I look at the types ofdeals that are being done by
this business, what is the whereis their variety?
So in a classic segmentationmodel, you have SMB, min-market,
(23:51):
and enterprise, if I see thatthere's a very different sales
motion that's happening, and yetI'm asking the team to do one
minute sell to the Fortune 100and the next minute sell to a
mom and pop, that there might bechallenges associated with
scaling.
And so segmentation might be thefirst thing.
And then if we know we're goingto segment, the second thing is
then around okay, what is theprofile of talent that I would
(24:12):
need for those types of roles,depending on how many of each
that I require?
Another thing that you mentionedwas around looking at, if you
have a multi-product portfolio,looking at the product types
individually and saying, okay,which of these is both
performing really well rightnow, and which of these has the
potential to perform with someadded investment, and then be
(24:32):
making decisions around, again,with the clean slate, how do you
bring additional productsoutside of maybe the core to
market?
And then maybe two other thingsthat you mentioned within there.
One, I heard a lot oncommunication of change.
So communication of what's goingon as you try to move an org,
and then communication in itsforms, whether they're videos
(24:55):
and highlighting folks andmaking people feel a part of
that change, that alone,communication is probably a big
driver of MPS.
Like feeling like you're on theteam and not just like people
making decisions in the ivorytower alone is probably pretty
possible.
SPEAKER_01 (25:10):
Yeah.
SPEAKER_02 (25:11):
And then to the extent you get that all going,
okay, how do I institute amethodology to get consistent
execution?
You selected the challengersale.
And it's like, man, if you canjust do these things that you're
gonna help.
I mean, anybody would want toachieve the results of going
from zero quota performance totwo-thirds or from um 35%
(25:32):
attrition to two.
So uh that's just like what I'mhearing.
I'm wondering how much of thatis the sort of playbook, if you
will, of entering otherdifficult situations.
SPEAKER_00 (25:43):
Well, I love that.
Gosh, that was so well said.
The um the other thing I thinkthat we did that I think is
really relevant too was weoutfitted the team with tools as
well so that they could sell amulti-product solution.
Part of what happened wasobviously like the uh the same,
or I'm sorry, the challengersales methodology was really
helpful for sure.
(26:04):
But also it was the mechanismfor them to be able to sell new
products to their solution totheir to their customers was one
of those things that they didn'tknow necessarily how to bring it
up always.
And so we had outfitted themwith sales loft at the time.
Um, but now I think of all ofthe different AI tools that you
could be leveraging to either umuncover who has the most
(26:28):
potential.
Uh you know, not obviouslyyou've got your performance
already with the revenue, uh,revenue that folks are doing,
but you can look with any ofthese AI tools to start to go,
okay, who might be have thepropensity to be able to use it?
And then obviously, then how doI do any outreach with marketing
tools and all that?
(26:49):
And so we had used sales off atthe time, but now I think that
there's all sorts of other waysto uncover intent uh and
propensity to buy too.
The other thing I would say isin that performance and
potential uh on the performanceside, one of the other elements
that was really interesting andrequired partnership with our
finance team in particular wasevaluating the LTV to CAC for
(27:12):
each of these.
And so there were also segmentsthat we decided to exit and say,
this is actually not aprofitable segment for us to for
us to sell to anymore becausethey don't stay with us, or
because the CAC is not worth it.
Um so you could evaluate all ofthose elements.
And so when we started to lookat, you know, all of the
different segmentation, youstarted to almost see, okay,
(27:34):
here's where we're going toorganize, here's how we're going
to organize, here's how we'regoing to support it, and then
here are ones that we're justgoing to exit.
Um so it was a reallyinteresting kind of RevOps
finance product and salesmarketing and customer success,
um, you know, kind ofcross-functional initiative that
made us stronger and got usgrowing again.
SPEAKER_02 (27:55):
Why do you think, in the example that you use, which
is an excellent one withShutterstock, why wasn't that
happening already?
SPEAKER_00 (28:01):
I think they had just had so much chaos.
There had been so much chaos inadding all of these companies.
And they had been on a growingspree, you know, they had been
on an acquisition spree,frankly.
And so they were bringing all ofthese people together.
And so if you had been there foreight years, which as I
mentioned was the averagetenure, you could just kind of
(28:22):
keep doing your thing and notadd all of these.
And then it it only, you know,it only became apparent once you
weren't hitting your number.
Why you weren't hitting yournumber was because you were
selling the thing you had eightyears ago, as opposed to all of
the new stuff that you had tosell.
SPEAKER_02 (28:38):
Did you come in after all those acquisitions?
SPEAKER_00 (28:40):
Yeah.
So I came in after all theacquisitions.
SPEAKER_02 (28:43):
What an interesting dimension.
And I think we're starting tosee consolidation and
acquisitions happening.
Acquisitions are um so difficultto execute because of all the
examples that you just gave.
It's like fun to get the dealdone, but then making it work
afterwards is like way harder.
Oh, and so I mean, I had tomultiple times over, it does
(29:04):
just naturally create a highstate of unsettledness, and
that's being you knowoptimistic.
SPEAKER_00 (29:11):
Absolutely.
Well, and I've had to do thatshort held before that.
We were a premises-based unifiedcommunication solution, and we
bought a cloud company.
Everything about us wasdifferent, right?
Uh, it was monthly recurringrevenue versus upfront CapEx
investment, making all of yourmoney through partners uh and
through that upfront investment,in fact, selling against each
(29:33):
other a lot of the times.
Um, and so it was reallyinteresting to watch that
happen.
And that was the first placethat I became, frankly, uh it
was a VP of sales and customersuccess where I saw the impact
across marketing, sales,onboarding, customer success,
support.
I saw the impact of selling tothe wrong type of customer.
Um, we had an example of we usedto sell to law firms as an
(29:56):
example in our cloud solution.
And you You would do so muchwork to market to them, to then
go through the months of redlines with this law firm, right?
Then it would take months andmonths to onboard them.
Um, and then the second that yougot them live and there was any
disruption in service at all,they churned.
(30:17):
And so it turned into, it wasactually very fascinating.
This was my entire career, hadjust been in sales.
And so here I am thinking, well,we did our thing right.
We got that, we got that dealclosed, right?
Um, we got our commission.
And it turned into this was thefirst time where I really went,
oh my gosh, it's not about doingyour thing right, it's about
doing the right thing.
(30:38):
And so we evolved and changedour entire 150-person team to
where no longer was anyone ableto sell to law firms or market
to law firms or keep a law firmbecause we now went, who is the
longest, who's the LTV, who hasthe longest tenure, retention,
et cetera, with us?
Who is the right ICP for us tobe selling to?
(30:59):
And so not only did we changewho our ICP was and like all get
aligned to it, but then I alsochanged the compensation model
for everyone.
So everyone had the compensationthat they were entitled, you
know, that they were responsiblefor.
So sellers, it was new ARR forthe support team, it was their,
you know, uh their uh first callresolution, uh, was their
(31:21):
primary way of getting paid,right?
Either for their bonus or theircommission.
But 25% of everyone's variablecompensation had a retention
element to it.
So that you were not just doingyour thing right, but you were
doing the right thingholistically for the
organization to succeed, whichwas all about retention and
long-term value of thecustomers.
SPEAKER_02 (31:42):
Bridget, you know, just in this conversation, it's
clear you've walked into sometumultuous situations.
Walk into acquisition-basedtumult.
That's probably like on thedegree of difficulty scale as
high as it gets.
And if you can successfullynavigate the change management
or transformation in thatcontext, imagine what you can do
(32:04):
when you don't have the onehand, the one arm tied behind
your back in terms of doingthat.
I wouldn't underestimate the umthe skills that one acquires to
be able to effectively um managegrowth.
Um, but if you think aboutcoming into a situation in a you
(32:25):
know more favorable startingpoint, so to speak, um, you
know, that the idea ofaccelerating growth might be
really compelling and excitingbased on what because you've
already seen the harder uh youknow, sort of picture.
Another thing that kind of comesto mind for me is in order to
effectively transform anorganization in any way, I
(32:45):
imagine you you talked aboutthis cross-functional dynamic
working with finance and workingwith RevOps and looking at LTB
and cat to cat and making thetough decisions that you can't
make on your own about what arewe not going to do anymore?
Law firms, in your example,being the perfect thing.
We're able to close deals there,but it's not good business.
It takes a village, so to speak,to come to agreement that we
(33:09):
can't do this anymore.
Can you talk a little bit aboutum you know how you pursue now
cross-functional relationshipsat the executive level and maybe
the learnings that have gottenyou to your worldview today?
SPEAKER_00 (33:21):
Yeah, I mean, I'm a big, let's say, management book
reader.
I love books on leadership.
So one of my favorite ones is uhshockingly, Stanley McChrystal,
General Stanley McChrystal'sbook called Team of Teams, where
he talks about how they wereable to defeat Al-Qaeda in Iraq.
(33:43):
And he uh he managed the jointoperations special forces, and
it was all of these individualbranches of the government,
right?
And so they were all in Iraqtrying to, you know, kind of
defeat this very nimble enemy.
And he found that this, youknow, we're the US had the
strongest military in the world,and we're getting beat every day
(34:05):
by a more nimble, flexible, youknow, adversary.
And it was because of the thingsthey were doing internally to
make things harder.
So one branch of the militaryhad like an informant and
someone who was, you know, kindof their their go-to guy.
Another branch of the militarywas like targeting that person.
(34:26):
So, you know, they it everythingwas misaligned.
And so I think of that book alot, and that's where I got that
whole, you know, do the rightthing versus doing your thing
right, um, because he basicallychanged it to where he said, now
we are a team of teams, we aredoing missions together, we are
aligned on what our missionsare, and the ultimate goal is
(34:47):
the, is like, is the is todefeat al-Qaeda and Iraq.
Uh, in the same sense, I thinkof, you know, the ultimate goal
is the organization's goal, notjust your sales goal or not just
your product team's goal.
The other thing I've read wasFive Dysfunctions of a Team.
That's one of my favorite booksever, too.
And they always highlight thatthe team that you are on is your
(35:08):
most senior team that you are oncross-functionally, not the team
you lead.
And so, again, my team is not mysales or my customer success or
my marketing team.
My team is me and my chiefproduct officer, my chief
financial officer.
We are solving the CEO'sproblems, uh, not necessarily
(35:28):
just the problems of our team,um, or only answering that.
And so, and I think there's nobetter, you know, kind of
definition of that than aligningon, let's say, an ideal customer
profile.
That I would be, you know, thatis like one of the perfect
examples of you think that maybethat's just a go-to-market
challenge.
Absolutely not.
(35:48):
Your CFO, your chief productofficer, your CEO, um, everyone
within your organization needsto be aligned on who your ICP is
and what that means if you areonly selling to that or if you
are choosing to go beyond it.
Um, so even something like theICP work that I think is
probably the most importantthing, allows you to know where
(36:10):
are we, where are we targetingand and what are we willing to
spend to get that customer andwhat are we doing, you know, to
service and support and keepthat customer.
Uh, and I think there there'sthere's no more kind of example
of something where it aligns theentire executive team more than
something like ICP.
SPEAKER_02 (36:31):
Yeah, I mean, that's a great example.
Um, you know, Lencioni's fivedysfunctions of a team.
Um, I've heard a lot about this,that the idea that your team is
your peers and not the folksthat roll up to you.
And I think everybody nods andyou know vigorously agrees,
yeah, sure.
But the actual like applicationof that in the real world is
much tougher than it sounds.
(36:53):
It's very easy to live withinyour um your silo of
responsibility.
Uh, first of all, those folksreport up to you, and so if you
call, they answer, and youunderstand the deep context of
the things that A, that theyshould be doing, B, the things
they are doing, and C thestruggles or challenges or
objectives or obstacles thatthey might be facing.
(37:15):
And so the inertia is pushingyou at all times to work within
that silo.
Yeah.
Like, for example, you might notbe the head of engineering, you
might not have any idea how towrite code.
So, like, what are you gonnatalk to the head of engineering
about?
It's like you don't want to tellhim about or her about the
quality of the engineers becausethat's not your role.
(37:35):
So you don't want to be comingacross like you're infringing,
or the head of product, orfinance, or whatever the area of
specialization is.
So I think the idea that, like,hey, your first team is your
peers and not just like thefolks that report up into your
org is much harder to actuallyapply because all the inertia is
(37:56):
also pushing them to focus onthe things they need to do day
to day and so on and so forth.
So I think a challenge forleaders is a the recognition of
what you described, but then B,how do I put that into practice?
How have you done so?
SPEAKER_00 (38:11):
Oh, yeah.
Well, it's aligned compensation,number one.
So, you know, the salesperson inme dies hard because I think
aligned compensation always is away to reinforce the the goals
that you have.
So, um, and I mean that companywide.
Um, I think there's also um Ithink what is it, people have to
(38:31):
hear something nine times beforeit actually sticks.
Um so I think it's also everysingle I think yeah, exactly.
Yeah, yeah.
It was nine.
I think it's nine.
I don't know.
It's either seven or nine, and Ican never remember.
Yeah.
And I'm like, I clearly I needto hear it more often.
So the um, but I think at everyuh, you know, all team meeting
(38:52):
that you hold, everyorganizational meeting that you
have, every time you kick off ameeting, as a reminder, our goal
is that we are getting to thisrevenue target or retention rate
should be this, or ICP is this,and we are looking at our ICP
penetration rate.
Like whatever that one thing is,and I always usually, if it can
be one thing, it's ideal.
(39:13):
Uh, if it is one thing that youcan find is the ruthless
priority of the organizationthat you are galvanizing the
team around, then it is it's theone thing that you are always
talking about.
It's the one thing you arepaying them on, whether it's
their bonuses for uh usually thenon-commission carrying folks or
the uh or the commissioncarrying folks having a
(39:33):
component of it to be uh to beum uh you know something that
they are incentivized to.
And then the third element Iwould say, so it's you know,
aligned compensation, number twowould be the you know,
relentless discussion about it.
The third would be find some wayto make it fun.
Find some way to make it fun.
Um, and that they care about itbecause I have done, I can't
(39:56):
even tell you the amount ofembarrassing things that I've
done where like if we hit acertain goal, there's pie in the
face.
If we hit a certain goal, I'mdoing chapel roan karaoke, which
you don't have to ask me toomuch.
I will, I will raise my hand todo.
But the there's so many thingsthat are, you know, ways to like
make that fun, or you know, thewhole company gets um, you know,
(40:19):
I don't know, a what have wedone?
We've done like yoga classtogether.
Um, uh the entire company getsto have a half day off or
something.
You know, like there were therewere things like that that we
would do, and there were alwayslittle small milestones.
And I've also heard this is whatthey do.
Um, that, you know, as you werein pursuit of a goal, you don't
(40:40):
do milestones, you do inchpebbles.
Love that term.
Um, I stole that from myfavorite book, Switch, How to
Change When Change is Hard.
That's another one of my booksthat I love.
Um, and they basically are like,this is the this the way that
you create success is to showthat success can be uh can can
(41:01):
happen.
And so, for example, if you'reshowing a timeline, you never
show yourself at the beginningof this.
You show yourself, see, we'vealready started.
We're about 25% of the waythere.
So you already show, look,success is is already begetting
success.
People would rather be in partway through a longer journey
than at the beginning of ashorter one.
(41:22):
That is one of the invaluablelessons uh that Switch teaches
you.
And so that's where these littleinch pebbles of shrinking the
change that you were trying toget to work.
And I will tell you, on thatthird day, on that Camino de
Santiago, when I did not want todo this, I was using inch
pebbles to motivate myself onthis journey.
(41:42):
I was doing, I was like, justget to that place so that you
can have a coffee.
Just get to that place so youcan wring out your socks.
It was small little change, orand I was like, you know, giving
myself, uh giving myself littletreats.
Oh, then you can get yourprotein bar.
You know, I was doing littlethings to like motivate myself
because I couldn't talk to her,you know, I wasn't really
(42:03):
talking to anybody.
Um, and so all of those thingsare, you know, all of these
change management tactics thatyou use are things that you can
use on yourself too.
SPEAKER_02 (42:13):
Totally.
Bridget, you're back here in NewYork.
What's next for you?
SPEAKER_00 (42:17):
Um I'll be uh the chief revenue officer at a
company called Patient Now.
Uh it is the back-end practicemanagement uh for med spas and
aesthetic practices, uh, anamazing vertical SaaS company
that is in the hyper-growth$20billion uh market and growing at
(42:39):
15% every year.
So extremely great space and uhallows for Patient Now to be the
market leader in that.
So I'm excited for that.
SPEAKER_02 (42:50):
Fantastic, Bridget.
I feel like we just got startedhere talking, but we have run
out of time.
Best wishes, and I'm sure you'regonna do an amazing job in the
new role.
It was fun talking about yourpersonal experience and your
personal reasons, about yourexperience with revamping
process and incorporating talentinto the bigger picture and how
you sort of cross-functionallybring the org along with you.
(43:12):
Um, it's been awesome.
So, Bridget, thank you very muchfor joining.
Where should people find you?
LinkedIn the place to go?
SPEAKER_00 (43:18):
Yes, LinkedIn is the place.
My DMs are open.
Feel free.
Awesome.
Thank you very much.
Thank you so much, Rick.
This was so fun.
SPEAKER_02 (43:33):
Reflecting on the conversation we just had with
Bridget Winston, so many littletidbits of wisdom that were
shared, it's hard to sort ofcompile it down to three big
themes, but I'm gonna attempt todo that.
And the first thing that standsout to me, so much of this show,
is about tactics to help us bebetter sales leaders, better
(43:54):
leaders, better professionals.
And there's a whole nother sideto us beyond our professional
selves that in our personaljourneys outside of just work,
and Bridget's sharing her storyand her personal journey between
roles, taking a trip on theother side of the world, stories
of adversity, stories of loss,stories of meaning, stories of
(44:15):
spirituality, it gives us anopportunity to reflect and think
about what is our own journey?
What is the meaning we arefinding beyond the work that we
do?
And when you hear anotherleader, a successful leader,
share a story with somevulnerability in it, with some,
you know, unconventional or not,you know, not your typical trip
(44:35):
that folks would take, it helpsform thoughts about our own
search for meaning in ourhumanity beyond our ambition and
our professional careers.
So thank you, Bridget, for thatuh storytelling.
The second thing, the difficultyin when you have a company that
grows through acquisition.
And I'm not saying just oneacquisition, I'm talking
(44:56):
multiple acquisitions.
And Bridget told stories thatreflect the challenges
associated with digesting andconsuming and moving forward
successfully when you've been inan acquisition-heavy
environment.
She told stories of having tolike take a step back and get to
the fundamentals of how would werun this business if we were to
start it today and having to dobasic things that weren't being
(45:19):
done in an environment that youknow might be described as
chaotic.
Um, and so that you know, I wantto tip my hat to all of the
sales leaders out there that areleading businesses that have
been acquisition heavy, and Iwant to acknowledge the
difficulty it is.
And now I kind of understand ata greater level why such a large
percentage of deals that getdone don't translate into the
(45:43):
value creation that was sold aspart of that acquisition effort.
Now, if you have a leader likeBridget, you have a better
chance of being able to take astep back and then execute
accordingly.
But boy, her stories uh showedthe difficulty in doing that.
And so it's like almostoperating with one arm tied
behind your back.
And so um, for me, it's like,okay, uh acquisitions sound fun,
(46:04):
and when you see them happen onLinkedIn, people are celebrating
them, but the there is hard workthat has to happen on the other
side of that.
Um, the last reflection I havefrom the episode is when Bridget
was talking aboutcross-functional leadership.
And she made the point of makingit fun.
And I think it's a superimportant point.
We all are trying to make thebiggest impact we can on our
(46:26):
organizations and develop theright relationships.
And it's difficult when we arein a large group of humans
working together towards acommon goal.
And it is important that thejourney doesn't just have to be
hard.
It can be hard and fun.
And it can be fun to be in achallenging environment.
And I loved Bridget uhemphasizing the importance of
that.
I think we all need to be havingfun along the way while we do
(46:49):
the hard work of being greatleaders, of learning how to be
positive impacts across theareas of responsibility that we
are working through.
So thank you, Bridget, for agreat discussion.
Really appreciate it.
Thank you to Ari Smolin forproducing.
Thank you to Sons of Summer forthe tunes.
Thank you, listener, for beinghere today.
We will see you next time onPillow Talks.
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.