May 3, 2024 • 46 mins
We're joined by Kary Jablonski, the CEO of Trucker Tools, Kary Jablonski. We discuss going beyond the mechanics of closing a deal. Kerry emphasizes the crucial role of specificity in showcasing value to clients. Through her lens, we gain a clearer understanding of how to pinpoint a client's needs and articulate the direct benefits of our solutions. She also stresses the significance of building trust, which often hinges on our ability to present ourselves with honesty and effectiveness.
Thanks again to your our sponsor, GoPayhawk. Stop overpaying and start thriving with GoPayhawk's payment process solutions. Visit GoPayhawk.com today and use code TLS24 to learn more about receiving a $250 credit on your payment processing solutions.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to episode seven of the Last Sell, where we
dive into the sales game withstories from industry leaders.
I'm your co-host, Kevin Hill,here with Richie Daigle, as
always.
How are you doing today, Richie?
Speaker 2 (00:15):
Yeah, doing great, doing great.
This was episode seven.
Yeah, we're moving along KerryJablonski, ceo of Trucker Tools,
along Carrie Jablonski, ceo ofTrucker Tools, really fantastic,
individual, super smart.
Yeah, I'm always impressed whenI'm hearing Carrie talk and
(00:35):
just having conversations withher Super approachable, you know
, just great person to chat with.
Was excited to have her on theshow and she had great stories.
She delivered.
She came through with somereally good stuff.
Yeah, what were your bigtakeaways from this one?
Speaker 1 (00:51):
The importance of channel sales right and learning
that early, Learning thedifference between retail or
knocking on each door and thenhaving sellers in line with
different channels and differentmarkets to push the product.
So I think that was a reallybig lesson that she learned very
early and it's probably one ofthe keys to her success, as well
(01:16):
as working on selling yourselfand what to do and what not to
do.
Speaker 2 (01:21):
Yep and listening to her talk about the difference
between working smarter and notharder.
You know, I think everybody inthe sales a lot of people in
sales are real quick to beattheir chest about how hard they
grind.
You know how hard I work.
Oh, I put in 100 hours thisweek and I made 10,000 cold
calls.
And I'm a grinder.
(01:41):
I'm just a worker when it comesdown to it, and part of me when
I hear that is like how much ofthat is necessary, you know, is
that the best way?
Are you maximizing your impactthat way, or is there a better
way to where you can grow yourimpact by leveraging other
sources or channels?
(02:02):
You know, and Kerry figuredthat out quite early, earlier
than most people probably couldguess- you better believe it,
she really has.
Speaker 1 (02:13):
And also, another key point that is really
interesting is the discussionaround questioning your
assumptions.
Right, once you get to astalled deal, deal to be able to
go back to the drawing board.
Take all your assumptions andquestion them all and try a
different tact, because everycompany is different.
(02:35):
Every bureaucracy is different.
She goes into detail about thatand I think that's a very
important uh lesson.
You know, put your pride aside,question what you've been doing
on this deal and change it ifnecessary.
Speaker 2 (02:48):
And learn and analyze things after the fact.
I mean, you are going to seewhether you win or lose a deal.
You're going to learn and seeway more information and details
about that deal after it's doneor not done or like closed in
some fashion.
Then you are in the middle ofit period, like you're never
(03:09):
going to be able to identify allthe levers and variables when
you're in the midst of it, andeven after the fact you'll see
more of them, but probably stillnot all of them, and so you
have to have that humility inplace to where you know you
never turn off the curiosityfaucet, so to speak.
Speaker 1 (03:27):
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But without any further adoagain, let's get straight to the
podcast.
Speaker 2 (04:09):
Let's get into it.
So, carrie, I'm embarrassed toask, but I have to ask what is
the right way to pronounce yourlast name, because people
butcher my last name frequentlyand I want to make sure I hear
from you like the correctpronunciation I appreciate you
asking that it is pronouncedexactly as it's spelt jabonski
(04:34):
jabonski got it because I thinkI butchered your name on a.
Speaker 1 (04:38):
Put that coffee down at a freight race event, even
after I asked you.
I think I got on camera andstill, but burst for whatever.
Speaker 3 (04:46):
I forgive you.
We're all good.
Speaker 2 (04:52):
And we're yeah, and so where?
Where are you sitting today,carrie, like where?
Remind me where you're basedout of.
Speaker 3 (04:59):
I'm based out of Chicago, so I I'm at my office
here in a bit of a odd phonebooth, which is why, if you're
watching us, the video mightlook a little strange, but I'm
I'm just in the heart of Chicagoright now nice, nice are you
always from Chicago?
or have you moved to differentplaces, or yeah, I have, um,
I've been in Chicago for somehowthis is, I think, coming up on
(05:23):
five years, which is wild thatI've been through five Chicago
winters and they really have notbeen as bad as they say they
are.
And I know everyone said thiswinter in particular has been
really warm.
But even the last four were nothorrible.
But that's probably because I'mfrom Boston originally, so I'm
very used to it and I would takecold temperatures over several
(05:44):
feet of snow and fortunately geta lot less snow out here than
we do in New England, so it'sbeen easy.
But yeah, I've lived.
I've actually lived all over.
I grew up in New Jersey andthen mostly Massachusetts, right
outside Boston, and then wentto college down in DC, spent
some time in DC and then livedabroad, briefly in Jakarta,
(06:05):
indonesia, and then for a whilein Mexico City before I came to
the Midwest.
So I've been in Central Timenow for seven or eight years and
Chicago is currently home.
Speaker 2 (06:17):
All those places sound cold until you got to
Indonesia and Mexico City.
So how did you deal with that?
That had to have been a bit ofa shock dealing with that sort
of heat in the summertime.
Speaker 3 (06:27):
Yes, indonesia was very, very hot.
There is no sugarcoating that.
Mexico City is actually atelevation in quite a bit.
It's 50% higher than Denver is.
It's about a mile and a half ofelevation, around 75,000, 8,000
feet.
So it can get warm but it's nothot Like.
(06:48):
Dc is probably the hottestplace I've lived for a long
period of time.
You know it just gets gross andsticky in the middle of the
summer.
There Mexico City was pretty,you know, get up to 75-ish, but
never significantly higher thanthat?
Speaker 1 (07:06):
Where were you doing in Mexico City?
Speaker 3 (07:08):
I was working for Uber, so I worked on ride
sharing and Uber Eats in LatinAmerica and Mexico City was the
home office, so I spent about ayear and a half there, working
all across the region, but basedin Mexico.
Speaker 1 (07:24):
What's different about living abroad?
Speaker 3 (07:27):
Oh, I mean it's such an awesome experience for anyone
who has the good fortune to beable to do it.
It sounds so obvious and cliche, but it does Just.
It expands the way you thinkabout the world and it's like as
someone who just lived inamerica my whole life and had
(07:49):
not traveled abroad extensivelyI it just opens up your eyes to
like there are these othermassive regions of the world
where everything is donedifferently and handled
differently.
And, yeah, I just felt like itwas like a little piece of my
brain was unlocked to realize,oh my God, there is a massive,
(08:10):
massive world out there, farbeyond just what's going on in
America day to day.
So kind of that still impactsme today when I think about it
From a day to day perspective,though, it is really humbling to
feel like you never quite areon the inside.
There's always going to be somesort of cultural difference.
I had wonderful, wonderful,wonderful colleagues in Mexico
(08:32):
who were so welcoming.
It was a really global crew.
It was not just Mexicans, itwas all over Latin America and
all over the world.
So it was really fortunate tohave a really diverse group of
friends there.
But yeah, just, you're justkind of constantly aware that
this is not my, my home, and, uh, that can be exhausting after a
(08:52):
while do you still travel afair amount?
Speaker 2 (08:55):
do you still try to travel internationally to kind
of scratch that itch, or, yeah,the country yeah, the last time
I left the country was in thefall.
Speaker 3 (09:05):
I was down in Chile and in Argentina.
Actually, my boyfriend is doinga graduate degree and he was
able to spend some time abroadas part of that, so he was in
Santiago for an extended periodof time.
So I went down to visit him andthen we went to Argentina over
Thanksgiving, which was reallyawesome.
Highly recommend to anyonewho's never been.
(09:26):
It's beautiful.
We're actually there for thepresidential election, which is
really interesting.
Don't have any biginternational trips on the books
this year.
Lots of domestic travel.
Now.
I've been home for the last twoweeks, but starting next week
I'll be hitting the road everysingle week of April.
(09:47):
So getting ready for that.
Speaker 2 (09:49):
So, speaking of travel, if there's one place
that you can go for vacation,like one last vacation, like
where are you going?
Your favorite destination,either someplace that you've
been before, that you want to goback to, or if you just have
one more vacation left, where inthe world are you going to go?
Speaker 3 (10:10):
That is such a hard question.
My mind initially went to Maine.
Actually, I grew up in NewEngland.
I grew up going to Maine a lotand in the summertime it's so,
so beautiful.
Uh, I think Maine slogan ontheir license plates is the way
life should be.
So probably go up to LakeSebago and Maine and spend some
(10:31):
time on the lake Just enjoyingthe summertime there.
Speaker 2 (10:34):
And follow up question what is your favorite
beverage?
Could be alcoholic,non-alcoholic.
What?
Speaker 3 (10:40):
what does it?
Speaker 2 (10:42):
like to sip on.
Speaker 3 (10:43):
Oh man, okay, I'll do .
I love chocolate milk.
What is it?
Fair Life chocolate milk.
It's so delicious I often cravethat.
My go-to drink is a hazy IPA,though A good hazy is tough to
beat for me.
Speaker 2 (10:59):
Okay, so imagine fast forward into the future.
You're done working.
You know work is way behind youand you are.
What was this lake in Maine?
You said Lake Sebago.
Speaker 3 (11:12):
Lake Sebago yeah.
Speaker 2 (11:13):
You were at Lake Sebago.
You still have the chocolatemustache, you know, from the
chocolate milk that you justfinished.
You just, you know, forgot towipe it.
But it's been long enough sothat the hazy IPA that you have
in your hand doesn't feel likeit's going to be some weird mix
of chocolate milk and hazy IPA.
But you're sitting here on theside of the lake and work is
done.
You're retired, you're livinglife the way it should be in
(11:37):
Maine and you're thinking back.
You're just having a moment oflooking back over the course of
your career.
What was the last sale, whatwas the last thing that you ever
sold, or what was the lastproject that you worked on in
your professional career beforeretiring?
Speaker 3 (11:54):
I sold my own company .
That's got to be it.
I built something and I took itall the way through to a sale.
So TBD is exactly what that isgoing to be.
But I would love to be afounder someday, start something
and fully see it off on my own.
Speaker 1 (12:14):
I take it as a next chapter in your life.
Right, that's down the road andsomething that you're thinking
about eventually.
Speaker 3 (12:23):
Exactly exactly.
I'm a long ways away from thatright now.
I've got my hands full andreally loving what we're
building with trucker tools.
But it's always been a dream ofmine to start my own business
and sell it.
And it could be.
It could be big, it could besmall, it could be, I think you
know, owning a bookstore orsomething like that.
It would be an absolute blastand dream.
(12:43):
So TBD exactly what it is, butit's something that I have built
with a team of people I reallycare about.
Speaker 2 (12:50):
Do you always have?
I find myself with variousideas that are bouncing around
in my brain.
From time to time I share someof these ideas with Kevin or
with other friends.
I'll say do you think thiscould work?
Or like, what are your thoughtson this?
And other friends I'll say doyou think this could work?
Or like what are your thoughtson this?
And do you feel the same way.
Do you constantly have likelittle micro ideas that are
always like I wonder if thiscould be something, or I wonder
(13:12):
if it's this, and do youcriticize?
Like what do you do with thoseideas?
Like what, what do you have to?
What does an idea have to do tobe something that you would act
upon?
Speaker 3 (13:21):
yeah all the time.
And then sometimes I realizeI've just invented something
that already exists.
Like I think I inventedrailroads.
The other day when I was likewhat if, instead of having to
drive, you could just putsomething on a box and it would
move on a preset rail, I waslike, oh, that is a train, so we
already have that.
Good thing, we already havethat going.
(13:42):
So, yes, I do, I do think aboutthat all the time and talk
about all the time.
Um and uh.
The nice thing about at work atleast you know, we have the
resources to be able to buildand move fast at trucker tools,
that when it's kind of withinthe context of freight tech, I'm
able to execute really quicklyon those things, um, which is
really really fulfilling.
(14:02):
But I I have them all the time,just kind of walking down the
street and talking to friends.
Speaker 1 (14:07):
Do you have an angle or something that would really
create excitement?
Because we all talk toentrepreneurs every single day
in what we do and I find somereally great ideas, right,
people have some really greatideas.
They're executing those, butit's just not in my wheelhouse,
right.
Nothing that I would want todrop everything and go spend 60
(14:31):
80 hours a week, but you know Ihave a lot of respect for them,
but I have my own littlewheelhouse that I'm always
looking for something that youknow it's like a bug you get
bitten by the bug and go all in.
Do you have any kind of lanesor things that always pique your
interest?
Speaker 3 (14:50):
Yeah, so I mean, obviously, anything in brokerage
tech right now is reallyinteresting to me and I'm really
interested in particular aroundhow we're evolving.
I think there's a lot of SaaSproducts obviously developed in
the brokerage space over thelast let's call it five to seven
years, but we're really movinginto the era of DAS and data
products and how data productscan be augmented on top of those
SaaS products.
(15:10):
So that's something I'mthinking a lot about right now
at at work itself.
Outside of, I mean, I have tonsof other interests beyond what.
What we're doing at Trevortools and in freight tech.
I would love, I love the idea ofbuilding something around
community for women andempowerment for women.
So I think a lot about what arethings I could be doing there
(15:32):
and how could I support um womenwith them developing their own
careers.
Um, I, I really like I wouldlove to start at like a.
I live in a neighborhoodwithout a great bagel shop.
I would love to start a bagelshop.
You know there's there's a lotof like very kind of brass tacks
businesses too that I, I, Ithink I would love to execute
(15:53):
out on beyond the realm of likejust software right now.
Speaker 2 (15:57):
Yeah, I love that there's certain, like small
businesses that are morecommunity oriented, like a
breakfast restaurant or a coffeeshop or a bookstore or, you
know, a bed and breakfast or insome beautiful location or
something like that.
That are kind of lifestylebusinesses, that are kind of
attractive as well.
Speaker 3 (16:17):
Exactly, exactly, so, if you think back in time.
Speaker 2 (16:20):
What was the first sale in time?
What was the first sale?
And this could be you sellingan idea or a concept, or it
could be selling something aspart of a fundraiser when you're
in high school or middle schoolor something.
But what is the first idea oritem that you ever remember
selling?
Speaker 3 (16:42):
Yeah, the actual item that I first ever remember
selling is I think it was, itmust have been elementary school
, not even quite middle schoolfor me, but we would have a
wrapping paper fundraiser everyyear where basically the idea
was to raise money for school byselling wrapping paper to your
parents and their friends andother people about town.
And that is what I remember asmy first introduction to like
(17:06):
here's how you be commercial andum, um.
And the point I really rememberis that I think that's how I
discovered channel sales,because I remember a bunch of
friends would be going door todoor trying to say hey you want
some wrapping paper, mrsSo-and-so, and I had two parents
who worked.
My mom and dad both worked andwent into offices by having them
(17:36):
sell on my behalf, by bringingin the sheet of paper that we
had to take orders on andplacing it with some cookies on
a conference table in thelunchroom and having them do
some of that sales developmenton my behalf.
So I remember being very, verysuccessful with that, and
everyone else around town wastrying to tap into the same
people locally in theneighborhood and I was able to.
They worked downtown in thecity, so I was able to tap into
those networks with people whodid not live in the town I grew
(17:57):
up in, who were not beinginundated by, you know, tens and
dozens of middle schoolers tobuy wrapping paper, which was an
exciting realization for me andstill informs how I think about
how do you scale and get intonew markets.
Speaker 1 (18:11):
It's a very important lesson, isn't it?
You know they're going to knockon every door or you're going
to get a channel partnershipsand channel sales and kind of
retail versus wholesale sort ofquandary.
It's very important, isn't it?
Speaker 3 (18:26):
For sure, for sure.
Yeah, it's always nice tounlock something and you're like
, oh wow, this is actually a loteasier than I thought it would
be, as opposed to me having toput in the sweat equity of going
door to door.
If I can just put that onsomeone else who's willing to
work on my behalf, hey, I'lltake that.
Work smart, not hard.
Speaker 2 (18:45):
I love that you figured all this out in
elementary school.
Speaker 3 (18:48):
I mean that's, I think I only put it like all
together as a framework later inlife.
Put it like all together as aframework later in life.
But uh, I do remember realizingthat, oh, I can move really
fast if I just get us to someoneelse, to go to a different
place and talk to new people didyou?
Speaker 2 (19:04):
did you like file like a report?
Afterwards you have to do aproject of like here's why,
here's how channel sales willhelp you with wrapping paper
sales, and what I learned anddid you.
I could just just see designingsome project in fourth grade of
the successfulness of channelsales.
Speaker 3 (19:20):
I was such a nerd growing up and absolutely loved
schoolwork and doing well andprojects.
I don't think I actually had tosubmit anything, but I can rest
assured that I had plenty ofother like nice posters uh, that
I that I put together forschool.
I really must put together agood poster after a project,
(19:41):
it's so satisfying.
Speaker 2 (19:43):
Did you do the, the, the like, the folding?
Speaker 3 (19:48):
you know what I'm talking about like, the big
trifolds, yeah, yeah yeah I mean, I was so into like projects
and I remember making a trifoldposter in my free time for fun
about weather.
I must have been like in fourthor fifth grade and, as opposed
to doing what normal kids woulddo on the weekend, I decided to
pull together.
I don't know, I must have beenreading some book about weather.
(20:08):
I was like, oh, I'm going toput this into a poster format
and I think that is it's reallysad to say aloud, but um,
unfortunately how I was as a kidand I do think it does
translate into how I operate asan adult now and that I I think
about a very structured thinkerand I like taking big, nebulous
ideas and making them very, verypalatable and digestible, and
(20:30):
that's what those trifle postersdid for me excel is probably a
really good tool that that youlike to use quite a bit, because
you can put the numbers down ina structured format.
Speaker 1 (20:42):
You can run any scenario you kind of want to and
play around with it.
Speaker 3 (20:48):
You can have my team.
Google Sheets is my lovelanguage.
I love it.
I use it constantly.
I run the business off of it.
It's pretty sad.
Speaker 1 (20:58):
Doesn't everybody?
Speaker 3 (20:59):
Yeah, that's true.
Yeah, definitely.
When I was at Uber, we werelike I don't know $40 million
excuse me, $40 billion business.
That company was running off ofGoogle Sheets.
Still, it's crazy, it is theultimate tool for business.
Speaker 1 (21:14):
It really is.
It really is, um.
Going back to sales, uh, so, sothere's your first sell, what
was kind of your easiest sellthat you ever wandered into and
thought it was going to be muchmore complicated than it was
maybe not yeah and it just, it'severything just clicked.
Speaker 3 (21:34):
Yeah, I think sometimes, when it comes to
selling myself, I've had a bunchof sales where it's been easier
than I expected and I don'tmean that to come off not
without humility.
But I think when I think aboutsome job interviews over the
(21:56):
years and the amount of thestakes that I felt going into
them and then realizing if I'mgoing to show up really well, if
I really truly do just show upas myself and tell stories like
from the heart, without tryingto make myself seem like I am
something I'm not, there havebeen some that have clicked and
(22:20):
gone a lot better than I think Iexpected them to.
So, yeah, when it really comesto selling myself, I think
that's because it's a skill I'vebeen working on now for 20, 30
years.
I've really been able to justhone that and be able to show up
and show up authentically.
Speaker 1 (22:39):
It's essential, isn't it?
Yeah, you have to sell yourselfbefore you can sell anything
else.
Speaker 3 (22:43):
It's everything, whether it's a client, employer,
to anybody right?
Speaker 1 (22:47):
Absolutely, Absolutely.
It's one of the hardest thingsto do, too.
It's one of the hardest thingsto grasp, right how?
Do you go about it.
I'm not really sure myself.
Yeah, kind of fall into it I'vespent so much.
Speaker 3 (23:01):
I think it's such an iterative process.
I mean, I've been, I've beenworking on it and in a
self-aware kind of like, oh, I'mtrying to think about how do I
sell myself, what is the value Ican bring to a group?
Since I was 18 and getting ajob in college I've been I've
been going through just thisconstant process of thinking
okay, what is my story?
How have I gotten to where I am?
What were the major inflectionpoints?
(23:22):
And now, how do I use that totalk about what value I can
bring moving forward?
It's something I've beenworking on for well over 20
years now.
Speaker 1 (23:30):
Yeah, because you do.
You have to leave out all theboring parts or the
non-essentials, right the leastdramatic points, and really hone
in on those inflection points.
Speaker 3 (23:41):
Exactly.
Speaker 1 (23:41):
To bite sides.
Sound bites almost Exactlyexactly.
Speaker 2 (23:46):
Just like a weird contradiction that's with
selling yourself, right, becauseif I walk into a meeting and
I'm like Kevin Carrie, let metell you about how amazing
Richie is and this is likeRichie is just incredible you
won't even believe it.
You, I feel like you're bothlike all right, how quickly can
I leave?
Like how long do I have to stay?
(24:07):
This guy is making my skincrawl.
I want to run away.
So, like this, this whole ideaof selling yourself, the more
you do it straightforward,forward, the worse it is.
But then you have to be likeindirect, you have to be more
kind of I don't know objectivein how you talk about different
milestones and then also morevalue and other people focused.
(24:29):
I feel like as authentic and youhave to be, authentic about
those things as well, in orderto come off as authentic.
You know, and it's about thosethings as well, in order to come
off as authentic.
Speaker 1 (24:38):
And it's kind of like when you're selling a product
and you come in and you justvomit features and benefits.
It covers everything.
It's the same thing, right?
People just tune out becauseit's too much, they're not
interested in it.
I think you have to sharethings that people are
interested in and have kind ofgiven you a clue that they're
(24:59):
interested in this, or they havea past experience in X and you
share your experience with thatand make it sound impressive, I
suppose.
But keep it short and sweet ina lot of respects.
Speaker 3 (25:11):
Yeah, and I think you have to do discovery as well.
When you're thinking about howdo I sell myself much like when
you're selling a softwareproduct, for example figuring
out, ok, what actually mattersto this other person and this
all sounds so nefarious when I'msaying it, but it really does
just come down to being curiousabout other people and
understanding what theirmotivations are, why they care,
why they're there, and then themore you can figure that out,
(25:36):
the more you can tailor your ownstory to really hit the high
points that are there, similarhigh points, and I think that's
also a really effective.
Speaker 1 (25:41):
if you go back to yourself right if you have 10
features right, and we've allbeen buyers of, of technology or
anything right?
Maybe I just only care aboutone thing and I go into
something.
I don't care what else it does,does it do this and that's
where you start, and then youcan kind of add on things after
that, but that's where andthat's discovery right yep,
(26:03):
totally, totally it's a.
Speaker 2 (26:05):
There's a little bit of a nuance there, right, if I
walk in trying to provesomething, it's I'm gonna the
conversation that everything'sgoing to go one direction.
If I walk in with a curiositymindset, then the conversation
that everything's going to goone direction.
If I walk in with a curiositymindset, then the conversation
everything's going to go it'sgoing to have a completely
different trajectory.
I feel like that's kind of what.
What we're getting at and whatyou might be alluding to a
(26:26):
little bit, carrie, is like howdo you?
You don't necessarily want toprove something, but sometimes,
being curious, you're going toprove things naturally along the
way, when you're not eventrying to just from asking good
questions.
Speaker 3 (26:40):
Yeah, and everyone wants to be asked questions
about themselves and theirexperiences.
The more you can make someonefeel like you care and you're
interested, you'll be so muchmore effective at what you're,
whatever you're trying toaccomplish so what would kind of
go in a different direction?
Speaker 2 (26:54):
The hardest, most difficult, you know, pull your
hair out frustrating,emotionally draining sale what
was that?
What sale kind of was mostdifficult in all of those ways.
Speaker 3 (27:23):
Yeah, so many come to mind that it's hard to narrow
it down to a single one.
I think we've had a couple inmy time at trucker tools that
have been well over a year and ahalf in the making and I think
those, those are the hardestones because they require so
(27:45):
much patience and realize, likeyou can, you can want to be
doing everything in your powerto bring something to life and I
myself can see, okay, if wejust do these five things, get
these people on board, likelet's just do it, we could do
that all, we'd have it all doneby friday this week.
Why would there not be a reasonto sell and realizing, or
(28:05):
reason to sign, realizing that,uh, they're very, very real
internal politics, that a lot ofthe customers that we sell to
which are freight brokerages,and that those need to be
respected and given time todevelop, and that the process of
getting buy-in is not somethingthat a third party can come in
and do, because it's going todestroy trust between the people
(28:26):
at the organization.
So I can think of one inparticular that we sold just a
couple of months ago.
That was well over an 18-monthsale and we just kind of kept
running into the same wall ofnot being able to get our
solution, our low-trackingsolution, prioritized by the
(28:49):
decision maker.
So what we ended up having to dois find a couple of different
champions within theorganization who were willing to
go to the mat for us and reallyexert their own power of
influence.
Even though we had a directline with the decision maker,
nothing we said was everactually going to make a
difference.
We really had to equip thesepeople who are at slightly lower
levels within the organizationto influence up and really use
(29:12):
data more than anything to makethe business case for what we
were trying to do.
So I think any sale like that,where it just feels like this is
it logically does not makesense to not do this.
We're going to save you money,we're going to give you higher
levels of service, but you don'twant to hear it from me, you've
got to hear it from someoneelse are the most frustrating
because, yeah, sometimes youknow corporate politics are
(29:38):
annoying and silly, but theyreally do matter in the power,
dynamic and culture oforganizations and they have to
be respected.
Speaker 1 (29:46):
They exist at all places, at all times, with
within any corporate orbureaucracy you do, you have to,
you have to deal with it andyou have to be proactive and
creative about it.
Speaker 3 (30:00):
Totally, Totally, and figuring out who can kind of
operate on your behalf.
I think is is key.
Speaker 1 (30:07):
And it's someone different each each organization
.
You have to go in and someonedifferent each organization.
Yeah, you have to go in andfind that.
Speaker 3 (30:13):
Exactly, exactly.
Speaker 2 (30:15):
It's a humbling thing , right to come face-to-face
with the reality that you don'tknow everything about this other
company that you've been inconversation with for 18 months.
You know, as in sales, we wantto control everything and we
want to find out our champion,figure out our work back plan,
figure out our timelines, figureout the need, quantify the ROI,
(30:37):
put everything on paper and saythis is a watertight deal.
We know all the variables andwe have a handle on things.
But I think I would argue thatwe never that's's never a 100%.
You know math problem, likethere's always going to be an
element of unknown, there'salways going to be a dimension
and it might even that dimensionof unknown may even be unknown
(31:00):
within that organization.
They also may not really know,and that's kind of the
unsettling piece for salespeopleespecially when they come face
with that.
Why?
Why is this happening?
Why is this dragging what'sgoing on?
I think we've got to lean intothose issues in that
(31:21):
uncomfortable position.
There's a lot that can belearned there and that can make
or break a deal.
Speaker 3 (31:27):
Definitely, definitely.
Speaker 1 (31:29):
It is.
You always have to go back tothe drawing board, no matter
what project it is, whether it'snumbers based or people's based
, you know, sales basedengineering doesn't really
matter.
You have to.
Always, at some point in theprocess, when things aren't
working or you need to get overa plateau, you need to be very
willing to go back to thedrawing board and rethink every
(31:49):
assumption that you have andplay that exercise, because
that's the only way throughthose, those barriers.
Speaker 2 (31:59):
So what's the sale that you are most proud of?
May not be the biggest or thesmallest or the quickest or the
longest or the most arduous, butis there a sale that you're a
part of, that you're like, Ifeel so good about this, whether
it was the creativity to getthe deal done, or who you were
(32:20):
doing business with, or whatcame after the fact, but
whatever, or maybe somethingdifferent, but what are you most
proud of in terms of sales or aspecific sale?
Speaker 3 (32:31):
Yeah, I'll go all the way back to college for this
one.
So I worked at a student runbusiness in college.
We were a catering company oncampus and we worked with
largely academic departments,student groups, professors, you
know, symposiums that wouldhappen on campus, selling bagels
, coffee, sandwiches, reallyjust anything to make the event,
(32:54):
to bring catering to the event.
So we had a couple of reallybig contracts with some
university events and my junioryear, heading into my senior
year, when I was in theleadership position, we were
going after our biggest saleever.
It was for new studentorientation.
It was going to require us toput together something like
4,000 boxed lunches in a very,very short period of time and we
(33:18):
were a small team, we weremaybe 20 people and again we
were like this was all collegekids, the inmates ran the asylum
, there were no adults in theroom here.
So convincing academicadministrators to trust us with
such a big event Orientation isreally, when you're making the
(33:39):
sale as a university, to say,hey, you made the right choice,
you're coming to the right placefor the next four years, great
job, Welcome aboard.
You want to make the rightimpression.
And I think there are parentsat this event too, which only
raised the stakes even higher.
It wasn't just students.
So I was really really proud ofthat sale.
We made that sale in the springsemester heading out to
orientation, which happenedsometime in August later that
(34:01):
year, because it was by far themost operationally complex deal
we'd ever done in catering.
Again, this was a smallcatering operation.
So putting together somethingas complicated as 4000 box
breakfasts, we didn't have thespace for it, we didn't have the
cooler space for it, we didn'thave the hands.
We had to figure out kind ofall of these things on the fly.
(34:22):
We had to really sell the dreamof what we could do and how, by
supporting us and kind of ourstudent run mission.
By supporting us and kind ofour student run mission, the
university was going to beacting in really good faith and
kind of living out, practicingwhat they preach in terms of
supporting students and thenachieving their dreams.
And we're up against realprofessionals and you know that
(34:45):
as a, as a, it feels reallyreally good to be trusted with
something that could easily goto someone with so much more
legitimacy and credibility totheir name.
Speaker 1 (35:01):
So I was really proud of that kind of impassioned
sale that we made and theability that we were able to
pull it off.
That's always good, right.
The ones where you sell thedream and vision.
You don't have it figured outyet.
Speaker 3 (35:09):
Exactly.
Speaker 1 (35:10):
But it pushes you to figure it out.
Speaker 3 (35:12):
Exactly, exactly.
Speaker 1 (35:14):
Where did you go to college at?
Speaker 3 (35:18):
I went to Georgetown University in Washington DC.
Yeah, very cool yeah, the cityschool, so there's not a ton of
room on campus, so it's hard tofind all that space to put
together the box breakfast it isVery limited on space there.
Speaker 1 (35:30):
Yeah, Within DC.
What's the funniest sale youever have?
You ever had that.
You just keep sitting back andlaughing whenever you think
about it.
Speaker 3 (35:39):
Oh man, I don't know if I have a funniest sale itself
More than we have really funnycustomers and crazy things
happen and the characters arepretty hilarious.
Man, I don't know if I have agreat answer off the top of my
(36:01):
head for that.
Speaker 1 (36:02):
I actually care Let me ask you this You've been in
different industries, right?
We all three have.
You've been in differentindustries, right?
We all three have.
Do you find that freightbrokerage and transportation
have per capita, maybedensity-wise, the most
characters of any industry thatyou've been in?
Speaker 3 (36:23):
It is not even close, without a doubt, and I think
that's in part because you knowwe all talk about selling
service and technology and allthese things that brokerages.
But brand is such a massivepart of it when you're in a
pretty commoditized industrylike truck brokerage, you have
to it's, you know it's.
It's much like any brokeragefunction.
(36:45):
You really have to figure outhow you stand out.
So being a character andbuilding that personal brand for
yourself is, of course, youhave to back it up, like there's
no excuse for actual deliveryand service timeliness, having a
easier work with tech stack.
But I really do think that'swhy we see a higher percentage
of characters in this space,because it's just good business
(37:06):
and if you're not doing it, Ithink you're doing something
wrong.
Speaker 2 (37:10):
You're more memorable character.
Speaker 3 (37:13):
Yeah, exactly Exactly , and that's really all that
matters.
Do you come top of mind, ifyou're memorable and you give
off confidence Like there's?
There's truly nothing that youcan do to better set yourself up
from a personal brandingperspective.
Speaker 1 (37:27):
Yeah, yeah, and I agree with that by far.
The most characters naturalborn characters, you know.
Speaker 3 (37:34):
Why do you think that is?
Speaker 1 (37:36):
I think it's for many of the same reasons that you
just laid out.
You know, you have to be alittle bit different.
A lot of these characters areentrepreneurs anyway, which is a
little bit of a crazy mentality.
And yeah, you just have to be alittle bit wild and bold to to,
to make it as a freight broker.
Yeah, yeah, it seems like a lotof people say that freight
(38:01):
brokerage found them.
Speaker 2 (38:03):
You know, like I I don't know too many people that
when I asked them they're like,yeah, ever since I was in
kindergarten I've wanted to be afreight broker.
You know, like it's not the thechildhood dream of I mean I'm
sure there's that person outthere and apologies for that
person.
But a lot of people will saythat you know, oh, freight
brokerage found me and now I'mnever leaving.
(38:23):
You know, it's like a lot ofpeople just fall into this
industry one way or another andthey get stuck and I don't know
if that's because theircharacters or because it's like
which came first, the chicken orthe egg, I guess?
Speaker 3 (38:39):
Yeah, I, I, I definitely think so.
I certainly never thought Iwould be going into freight.
And here I am, three years in,and I can absolutely see why
that's the case, that once youget in you really don't get out.
Because there's I think it'sbecause there's it's such a
fragmented industry riddled withso many problems that everyone
can see potential to make adifference, to build something
(39:01):
themselves, to kind of solve aproblem that hasn't been solved
yet.
So there's just that sort offragmentation breeds opportunity
, from my perspective.
Speaker 1 (39:10):
Yep, it's full of opportunity.
There's no reason to leave.
It's a very small industry,smaller than you think and once
you start meeting everybody, theopportunities just become more
available.
Speaker 2 (39:27):
Yeah, yeah, carrie what was the sale that you
learned the most from.
If you went back and said thissale was such a meaningful and
educational experience, what wasthat sale that was most
educational?
Speaker 3 (39:45):
Yeah, I think I almost feel like you learn more
from the deals you lose than thedeals you win honestly.
Yeah, I think I almost feellike you learn more from the
deals you lose than the dealsyou win honestly.
So I think, yeah, I could talkabout a deal we won, but I
really do think the deals thatyou don't win are the ones where
you learn.
Ok, here's the gap and here'swhat we need to do to close a
(40:07):
future sale.
So I think I've learned a ton.
Really, back in the early firstcouple of weeks actually, I had
at Trucker Tools this isn't evena sale, but it was that we lost
(40:28):
a customer, a really largecustomer, top 20 brokerage, very
tech forward.
It was a huge deal, one of ourbiggest load tracking deals, and
I just started at the company.
So I had really getting up tospeed and I'm like, oh well,
this is too bad, I've got tofigure out what's going on.
So I hopped on a call with oneof their senior decision makers
and turned out that it was funto understand.
Hey, what happened here?
How did you decide to leave us?
Why don't we win this renewal?
And it was really all about ELTtracking and I'll be completely
(40:53):
honest, that was not somethingthat we had really prioritized
Back when.
When I was starting a business,you know we were always mobile
first tracking solution.
And I am so grateful that thathappened so early on in my
tenure because it was definitelylike the kick in the rear end
that I needed to say OK, we'vegot to make moves fast because
if we don't, we're not going toexist as a load tracking
(41:15):
business in a year or two If wedon't solve this massive product
gap we have now.
So we started really doublingdown on our ELD team and
standing up an entireorganization to support
onboarding and figure out how dowe do this better and different
than some of our competitorsare doing.
Organization to supportonboarding and figure out how do
we do this better and differentthan some of our competitors
are doing.
And you know, three years later, I think we're getting noticed
all the time now for what we'vebuilt from the ELD world.
(41:36):
So I think losing those sort ofsales or losing a customer is
an absolute punch to the gutbecause you know how hard you
work to bring them on board.
But in this case I think it wasactually it ended up being good
for us because it it led tothis whole new development of a
whole new part of our productand has totally changed our
product strategy.
So that's, that's the deal I'dsay I learned the most from.
Speaker 1 (42:00):
Going off on that a little bit.
You know what's the mostimportant sales lesson or
lessons that you learned sincebecoming CEO.
You know things that you didn'trealize about sales before that
, that you now grasp or that younow hold dear.
Speaker 3 (42:19):
Yeah, I think that sales is.
Yes, you know we talked aboutselling ourselves and showing up
well, and the interpersonalnature of it.
That is absolutely important.
But sales is a really reallytechnical science as well, and
appreciating what goes intoorchestrating a large deal where
(42:39):
you've got five, six, sevenstakeholders involved on the
customer side, maybe two tothree on your own internal side,
how important it is to bewriting a really really tight
process there, and how that canmake or break you as an
organization, how, when it comesto sales, it's not just about
kind of showing up and takingsomeone out to lunch and really
getting their buy-in as, oh,we're buds.
(43:00):
That's not what sales is about.
Sales is about building anironclad business case for
someone to help them solve avery, very specific problem, and
kind of that problemorientation, as opposed to I'm
selling this whole feature andthis whole product set.
Now we are selling a couple ofsolutions to specific pain
(43:21):
points has been a big shift forme when I think about how I sell
as a CEO.
Speaker 2 (43:27):
Yeah, that's fantastic.
I couldn't agree more.
I mean, it's the big sales comefrom specificity.
Did I say that?
Right, it's got lots ofsyllables in it, but it's being
able to pinpoint an exact ROIand make it real.
And that comes out of the exactuse case.
And it's this another kind ofcontradictory sort of stance
(43:50):
where you have, on one hand,it's not personal right, it's
not you and your thoughts andopinions, or your customers
thoughts and opinions, it's no,there's a problem and this
problem needs to be fixed, andeither your technology does that
or it doesn't like it's one orthe other.
So there's an impersonable,impersonal aspect to it all.
(44:11):
But there's also a personalaspect in that the other side
has to have trust that they canbelieve that what you're saying
is true and honest and gearedtowards solving that problem.
So there's this weird kind ofdialectical thing happening
where it's about you and thetrust and them having trust in
you, but it's also not about youor them.
(44:33):
It's mostly about solving aproblem.
Speaker 3 (44:36):
Yeah, and that's what's going to win you.
A deal is solving that problemand doing it in a very specific,
pointed way.
They're only going to beinterested in doing that if they
trust you.
So that's kind of the dooropener, but it's not going to
close the deal.
Speaker 1 (44:52):
Yeah, I think a lot of people gauge salespeople on
their likability in a lot ofways or how good they are at
getting in front of people.
But there's that back half ofit that you actually have to fix
the problem right, yep.
So you have to actually have agood solution.
People can go have lunch withyou all the time and enjoy
themselves, but if you don'thave the capabilities to fix
(45:13):
that problem, that you don'thave the solution.
That's where it ends and it'sgoing to end there every single
time.
Speaker 3 (45:19):
Exactly, exactly.
Speaker 2 (45:21):
Yeah.
So, carrie, where can ourlisteners find you?
How can they get in touch withyou?
How can they learn more aboutTrucker Tools?
Yeah, what's the best way forpeople to reach you?
How can they get in touch withyou?
How can they learn more aboutTrucker?
Speaker 3 (45:32):
Tools.
Yeah, what's the best way forpeople to reach you?
Yeah, find me on LinkedIn KariJablonski spelled like it sounds
and on Twitter as well.
Same, my handle is just my name.
Or feel free to shoot me anemail at kjablonski, at
truckertoolscom.
Love hearing from folks.
Thank you, I had a great time.
Speaker 2 (45:46):
Yeah, thanks for joining, gary.
Always a pleasure speaking withyou.
Every time I'm going to variousconferences, you're always one
of the people I'm hoping to runinto to say hi and catch up if
we have time.
So pleasure having you on thison the show and thanks again,
really enjoy the conversation.
We'll have to have you back.
I feel like there's morestories that we can dive into.
(46:07):
So, yeah, thanks for your timetoday.
Speaker 3 (46:12):
Thank you both, I really appreciate it.
Welcome to episode seven of the Last Sell, where we
dive into the sales game withstories from industry leaders.
I'm your co-host, Kevin Hill,here with Richie Daigle, as
always.
How are you doing today, Richie?
Speaker 2 (00:15):
Yeah, doing great, doing great.
This was episode seven.
Yeah, we're moving along KerryJablonski, ceo of Trucker Tools,
along Carrie Jablonski, ceo ofTrucker Tools, really fantastic,
individual, super smart.
Yeah, I'm always impressed whenI'm hearing Carrie talk and
(00:35):
just having conversations withher Super approachable, you know
, just great person to chat with.
Was excited to have her on theshow and she had great stories.
She delivered.
She came through with somereally good stuff.
Yeah, what were your bigtakeaways from this one?
Speaker 1 (00:51):
The importance of channel sales right and learning
that early, Learning thedifference between retail or
knocking on each door and thenhaving sellers in line with
different channels and differentmarkets to push the product.
So I think that was a reallybig lesson that she learned very
early and it's probably one ofthe keys to her success, as well
(01:16):
as working on selling yourselfand what to do and what not to
do.
Speaker 2 (01:21):
Yep and listening to her talk about the difference
between working smarter and notharder.
You know, I think everybody inthe sales a lot of people in
sales are real quick to beattheir chest about how hard they
grind.
You know how hard I work.
Oh, I put in 100 hours thisweek and I made 10,000 cold
calls.
And I'm a grinder.
(01:41):
I'm just a worker when it comesdown to it, and part of me when
I hear that is like how much ofthat is necessary, you know, is
that the best way?
Are you maximizing your impactthat way, or is there a better
way to where you can grow yourimpact by leveraging other
sources or channels?
(02:02):
You know, and Kerry figuredthat out quite early, earlier
than most people probably couldguess- you better believe it,
she really has.
Speaker 1 (02:13):
And also, another key point that is really
interesting is the discussionaround questioning your
assumptions.
Right, once you get to astalled deal, deal to be able to
go back to the drawing board.
Take all your assumptions andquestion them all and try a
different tact, because everycompany is different.
(02:35):
Every bureaucracy is different.
She goes into detail about thatand I think that's a very
important uh lesson.
You know, put your pride aside,question what you've been doing
on this deal and change it ifnecessary.
Speaker 2 (02:48):
And learn and analyze things after the fact.
I mean, you are going to seewhether you win or lose a deal.
You're going to learn and seeway more information and details
about that deal after it's doneor not done or like closed in
some fashion.
Then you are in the middle ofit period, like you're never
(03:09):
going to be able to identify allthe levers and variables when
you're in the midst of it, andeven after the fact you'll see
more of them, but probably stillnot all of them, and so you
have to have that humility inplace to where you know you
never turn off the curiosityfaucet, so to speak.
Speaker 1 (03:27):
You're exactly right, and with that said, gopayhawk.
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You need a credit cardprocessing and a payment
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(03:51):
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Tell them that you got it fromthe last sell and they will set
you up with that deal.
But without any further adoagain, let's get straight to the
podcast.
Speaker 2 (04:09):
Let's get into it.
So, carrie, I'm embarrassed toask, but I have to ask what is
the right way to pronounce yourlast name, because people
butcher my last name frequentlyand I want to make sure I hear
from you like the correctpronunciation I appreciate you
asking that it is pronouncedexactly as it's spelt jabonski
(04:34):
jabonski got it because I thinkI butchered your name on a.
Speaker 1 (04:38):
Put that coffee down at a freight race event, even
after I asked you.
I think I got on camera andstill, but burst for whatever.
Speaker 3 (04:46):
I forgive you.
We're all good.
Speaker 2 (04:52):
And we're yeah, and so where?
Where are you sitting today,carrie, like where?
Remind me where you're basedout of.
Speaker 3 (04:59):
I'm based out of Chicago, so I I'm at my office
here in a bit of a odd phonebooth, which is why, if you're
watching us, the video mightlook a little strange, but I'm
I'm just in the heart of Chicagoright now nice, nice are you
always from Chicago?
or have you moved to differentplaces, or yeah, I have, um,
I've been in Chicago for somehowthis is, I think, coming up on
(05:23):
five years, which is wild thatI've been through five Chicago
winters and they really have notbeen as bad as they say they
are.
And I know everyone said thiswinter in particular has been
really warm.
But even the last four were nothorrible.
But that's probably because I'mfrom Boston originally, so I'm
very used to it and I would takecold temperatures over several
(05:44):
feet of snow and fortunately geta lot less snow out here than
we do in New England, so it'sbeen easy.
But yeah, I've lived.
I've actually lived all over.
I grew up in New Jersey andthen mostly Massachusetts, right
outside Boston, and then wentto college down in DC, spent
some time in DC and then livedabroad, briefly in Jakarta,
(06:05):
indonesia, and then for a whilein Mexico City before I came to
the Midwest.
So I've been in Central Timenow for seven or eight years and
Chicago is currently home.
Speaker 2 (06:17):
All those places sound cold until you got to
Indonesia and Mexico City.
So how did you deal with that?
That had to have been a bit ofa shock dealing with that sort
of heat in the summertime.
Speaker 3 (06:27):
Yes, indonesia was very, very hot.
There is no sugarcoating that.
Mexico City is actually atelevation in quite a bit.
It's 50% higher than Denver is.
It's about a mile and a half ofelevation, around 75,000, 8,000
feet.
So it can get warm but it's nothot Like.
(06:48):
Dc is probably the hottestplace I've lived for a long
period of time.
You know it just gets gross andsticky in the middle of the
summer.
There Mexico City was pretty,you know, get up to 75-ish, but
never significantly higher thanthat?
Speaker 1 (07:06):
Where were you doing in Mexico City?
Speaker 3 (07:08):
I was working for Uber, so I worked on ride
sharing and Uber Eats in LatinAmerica and Mexico City was the
home office, so I spent about ayear and a half there, working
all across the region, but basedin Mexico.
Speaker 1 (07:24):
What's different about living abroad?
Speaker 3 (07:27):
Oh, I mean it's such an awesome experience for anyone
who has the good fortune to beable to do it.
It sounds so obvious and cliche, but it does Just.
It expands the way you thinkabout the world and it's like as
someone who just lived inamerica my whole life and had
(07:49):
not traveled abroad extensivelyI it just opens up your eyes to
like there are these othermassive regions of the world
where everything is donedifferently and handled
differently.
And, yeah, I just felt like itwas like a little piece of my
brain was unlocked to realize,oh my God, there is a massive,
(08:10):
massive world out there, farbeyond just what's going on in
America day to day.
So kind of that still impactsme today when I think about it
From a day to day perspective,though, it is really humbling to
feel like you never quite areon the inside.
There's always going to be somesort of cultural difference.
I had wonderful, wonderful,wonderful colleagues in Mexico
(08:32):
who were so welcoming.
It was a really global crew.
It was not just Mexicans, itwas all over Latin America and
all over the world.
So it was really fortunate tohave a really diverse group of
friends there.
But yeah, just, you're justkind of constantly aware that
this is not my, my home, and, uh, that can be exhausting after a
(08:52):
while do you still travel afair amount?
Speaker 2 (08:55):
do you still try to travel internationally to kind
of scratch that itch, or, yeah,the country yeah, the last time
I left the country was in thefall.
Speaker 3 (09:05):
I was down in Chile and in Argentina.
Actually, my boyfriend is doinga graduate degree and he was
able to spend some time abroadas part of that, so he was in
Santiago for an extended periodof time.
So I went down to visit him andthen we went to Argentina over
Thanksgiving, which was reallyawesome.
Highly recommend to anyonewho's never been.
(09:26):
It's beautiful.
We're actually there for thepresidential election, which is
really interesting.
Don't have any biginternational trips on the books
this year.
Lots of domestic travel.
Now.
I've been home for the last twoweeks, but starting next week
I'll be hitting the road everysingle week of April.
(09:47):
So getting ready for that.
Speaker 2 (09:49):
So, speaking of travel, if there's one place
that you can go for vacation,like one last vacation, like
where are you going?
Your favorite destination,either someplace that you've
been before, that you want to goback to, or if you just have
one more vacation left, where inthe world are you going to go?
Speaker 3 (10:10):
That is such a hard question.
My mind initially went to Maine.
Actually, I grew up in NewEngland.
I grew up going to Maine a lotand in the summertime it's so,
so beautiful.
Uh, I think Maine slogan ontheir license plates is the way
life should be.
So probably go up to LakeSebago and Maine and spend some
(10:31):
time on the lake Just enjoyingthe summertime there.
Speaker 2 (10:34):
And follow up question what is your favorite
beverage?
Could be alcoholic,non-alcoholic.
What?
Speaker 3 (10:40):
what does it?
Speaker 2 (10:42):
like to sip on.
Speaker 3 (10:43):
Oh man, okay, I'll do .
I love chocolate milk.
What is it?
Fair Life chocolate milk.
It's so delicious I often cravethat.
My go-to drink is a hazy IPA,though A good hazy is tough to
beat for me.
Speaker 2 (10:59):
Okay, so imagine fast forward into the future.
You're done working.
You know work is way behind youand you are.
What was this lake in Maine?
You said Lake Sebago.
Speaker 3 (11:12):
Lake Sebago yeah.
Speaker 2 (11:13):
You were at Lake Sebago.
You still have the chocolatemustache, you know, from the
chocolate milk that you justfinished.
You just, you know, forgot towipe it.
But it's been long enough sothat the hazy IPA that you have
in your hand doesn't feel likeit's going to be some weird mix
of chocolate milk and hazy IPA.
But you're sitting here on theside of the lake and work is
done.
You're retired, you're livinglife the way it should be in
(11:37):
Maine and you're thinking back.
You're just having a moment oflooking back over the course of
your career.
What was the last sale, whatwas the last thing that you ever
sold, or what was the lastproject that you worked on in
your professional career beforeretiring?
Speaker 3 (11:54):
I sold my own company .
That's got to be it.
I built something and I took itall the way through to a sale.
So TBD is exactly what that isgoing to be.
But I would love to be afounder someday, start something
and fully see it off on my own.
Speaker 1 (12:14):
I take it as a next chapter in your life.
Right, that's down the road andsomething that you're thinking
about eventually.
Speaker 3 (12:23):
Exactly exactly.
I'm a long ways away from thatright now.
I've got my hands full andreally loving what we're
building with trucker tools.
But it's always been a dream ofmine to start my own business
and sell it.
And it could be.
It could be big, it could besmall, it could be, I think you
know, owning a bookstore orsomething like that.
It would be an absolute blastand dream.
(12:43):
So TBD exactly what it is, butit's something that I have built
with a team of people I reallycare about.
Speaker 2 (12:50):
Do you always have?
I find myself with variousideas that are bouncing around
in my brain.
From time to time I share someof these ideas with Kevin or
with other friends.
I'll say do you think thiscould work?
Or like, what are your thoughtson this?
And other friends I'll say doyou think this could work?
Or like what are your thoughtson this?
And do you feel the same way.
Do you constantly have likelittle micro ideas that are
always like I wonder if thiscould be something, or I wonder
(13:12):
if it's this, and do youcriticize?
Like what do you do with thoseideas?
Like what, what do you have to?
What does an idea have to do tobe something that you would act
upon?
Speaker 3 (13:21):
yeah all the time.
And then sometimes I realizeI've just invented something
that already exists.
Like I think I inventedrailroads.
The other day when I was likewhat if, instead of having to
drive, you could just putsomething on a box and it would
move on a preset rail, I waslike, oh, that is a train, so we
already have that.
Good thing, we already havethat going.
(13:42):
So, yes, I do, I do think aboutthat all the time and talk
about all the time.
Um and uh.
The nice thing about at work atleast you know, we have the
resources to be able to buildand move fast at trucker tools,
that when it's kind of withinthe context of freight tech, I'm
able to execute really quicklyon those things, um, which is
really really fulfilling.
(14:02):
But I I have them all the time,just kind of walking down the
street and talking to friends.
Speaker 1 (14:07):
Do you have an angle or something that would really
create excitement?
Because we all talk toentrepreneurs every single day
in what we do and I find somereally great ideas, right,
people have some really greatideas.
They're executing those, butit's just not in my wheelhouse,
right.
Nothing that I would want todrop everything and go spend 60
(14:31):
80 hours a week, but you know Ihave a lot of respect for them,
but I have my own littlewheelhouse that I'm always
looking for something that youknow it's like a bug you get
bitten by the bug and go all in.
Do you have any kind of lanesor things that always pique your
interest?
Speaker 3 (14:50):
Yeah, so I mean, obviously, anything in brokerage
tech right now is reallyinteresting to me and I'm really
interested in particular aroundhow we're evolving.
I think there's a lot of SaaSproducts obviously developed in
the brokerage space over thelast let's call it five to seven
years, but we're really movinginto the era of DAS and data
products and how data productscan be augmented on top of those
SaaS products.
(15:10):
So that's something I'mthinking a lot about right now
at at work itself.
Outside of, I mean, I have tonsof other interests beyond what.
What we're doing at Trevortools and in freight tech.
I would love, I love the idea ofbuilding something around
community for women andempowerment for women.
So I think a lot about what arethings I could be doing there
(15:32):
and how could I support um womenwith them developing their own
careers.
Um, I, I really like I wouldlove to start at like a.
I live in a neighborhoodwithout a great bagel shop.
I would love to start a bagelshop.
You know there's there's a lotof like very kind of brass tacks
businesses too that I, I, Ithink I would love to execute
(15:53):
out on beyond the realm of likejust software right now.
Speaker 2 (15:57):
Yeah, I love that there's certain, like small
businesses that are morecommunity oriented, like a
breakfast restaurant or a coffeeshop or a bookstore or, you
know, a bed and breakfast or insome beautiful location or
something like that.
That are kind of lifestylebusinesses, that are kind of
attractive as well.
Speaker 3 (16:17):
Exactly, exactly, so, if you think back in time.
Speaker 2 (16:20):
What was the first sale in time?
What was the first sale?
And this could be you sellingan idea or a concept, or it
could be selling something aspart of a fundraiser when you're
in high school or middle schoolor something.
But what is the first idea oritem that you ever remember
selling?
Speaker 3 (16:42):
Yeah, the actual item that I first ever remember
selling is I think it was, itmust have been elementary school
, not even quite middle schoolfor me, but we would have a
wrapping paper fundraiser everyyear where basically the idea
was to raise money for school byselling wrapping paper to your
parents and their friends andother people about town.
And that is what I remember asmy first introduction to like
(17:06):
here's how you be commercial andum, um.
And the point I really rememberis that I think that's how I
discovered channel sales,because I remember a bunch of
friends would be going door todoor trying to say hey you want
some wrapping paper, mrsSo-and-so, and I had two parents
who worked.
My mom and dad both worked andwent into offices by having them
(17:36):
sell on my behalf, by bringingin the sheet of paper that we
had to take orders on andplacing it with some cookies on
a conference table in thelunchroom and having them do
some of that sales developmenton my behalf.
So I remember being very, verysuccessful with that, and
everyone else around town wastrying to tap into the same
people locally in theneighborhood and I was able to.
They worked downtown in thecity, so I was able to tap into
those networks with people whodid not live in the town I grew
(17:57):
up in, who were not beinginundated by, you know, tens and
dozens of middle schoolers tobuy wrapping paper, which was an
exciting realization for me andstill informs how I think about
how do you scale and get intonew markets.
Speaker 1 (18:11):
It's a very important lesson, isn't it?
You know they're going to knockon every door or you're going
to get a channel partnershipsand channel sales and kind of
retail versus wholesale sort ofquandary.
It's very important, isn't it?
Speaker 3 (18:26):
For sure, for sure.
Yeah, it's always nice tounlock something and you're like
, oh wow, this is actually a loteasier than I thought it would
be, as opposed to me having toput in the sweat equity of going
door to door.
If I can just put that onsomeone else who's willing to
work on my behalf, hey, I'lltake that.
Work smart, not hard.
Speaker 2 (18:45):
I love that you figured all this out in
elementary school.
Speaker 3 (18:48):
I mean that's, I think I only put it like all
together as a framework later inlife.
Put it like all together as aframework later in life.
But uh, I do remember realizingthat, oh, I can move really
fast if I just get us to someoneelse, to go to a different
place and talk to new people didyou?
Speaker 2 (19:04):
did you like file like a report?
Afterwards you have to do aproject of like here's why,
here's how channel sales willhelp you with wrapping paper
sales, and what I learned anddid you.
I could just just see designingsome project in fourth grade of
the successfulness of channelsales.
Speaker 3 (19:20):
I was such a nerd growing up and absolutely loved
schoolwork and doing well andprojects.
I don't think I actually had tosubmit anything, but I can rest
assured that I had plenty ofother like nice posters uh, that
I that I put together forschool.
I really must put together agood poster after a project,
(19:41):
it's so satisfying.
Speaker 2 (19:43):
Did you do the, the, the like, the folding?
Speaker 3 (19:48):
you know what I'm talking about like, the big
trifolds, yeah, yeah yeah I mean, I was so into like projects
and I remember making a trifoldposter in my free time for fun
about weather.
I must have been like in fourthor fifth grade and, as opposed
to doing what normal kids woulddo on the weekend, I decided to
pull together.
I don't know, I must have beenreading some book about weather.
(20:08):
I was like, oh, I'm going toput this into a poster format
and I think that is it's reallysad to say aloud, but um,
unfortunately how I was as a kidand I do think it does
translate into how I operate asan adult now and that I I think
about a very structured thinkerand I like taking big, nebulous
ideas and making them very, verypalatable and digestible, and
(20:30):
that's what those trifle postersdid for me excel is probably a
really good tool that that youlike to use quite a bit, because
you can put the numbers down ina structured format.
Speaker 1 (20:42):
You can run any scenario you kind of want to and
play around with it.
Speaker 3 (20:48):
You can have my team.
Google Sheets is my lovelanguage.
I love it.
I use it constantly.
I run the business off of it.
It's pretty sad.
Speaker 1 (20:58):
Doesn't everybody?
Speaker 3 (20:59):
Yeah, that's true.
Yeah, definitely.
When I was at Uber, we werelike I don't know $40 million
excuse me, $40 billion business.
That company was running off ofGoogle Sheets.
Still, it's crazy, it is theultimate tool for business.
Speaker 1 (21:14):
It really is.
It really is, um.
Going back to sales, uh, so, sothere's your first sell, what
was kind of your easiest sellthat you ever wandered into and
thought it was going to be muchmore complicated than it was
maybe not yeah and it just, it'severything just clicked.
Speaker 3 (21:34):
Yeah, I think sometimes, when it comes to
selling myself, I've had a bunchof sales where it's been easier
than I expected and I don'tmean that to come off not
without humility.
But I think when I think aboutsome job interviews over the
(21:56):
years and the amount of thestakes that I felt going into
them and then realizing if I'mgoing to show up really well, if
I really truly do just show upas myself and tell stories like
from the heart, without tryingto make myself seem like I am
something I'm not, there havebeen some that have clicked and
(22:20):
gone a lot better than I think Iexpected them to.
So, yeah, when it really comesto selling myself, I think
that's because it's a skill I'vebeen working on now for 20, 30
years.
I've really been able to justhone that and be able to show up
and show up authentically.
Speaker 1 (22:39):
It's essential, isn't it?
Yeah, you have to sell yourselfbefore you can sell anything
else.
Speaker 3 (22:43):
It's everything, whether it's a client, employer,
to anybody right?
Speaker 1 (22:47):
Absolutely, Absolutely.
It's one of the hardest thingsto do, too.
It's one of the hardest thingsto grasp, right how?
Do you go about it.
I'm not really sure myself.
Yeah, kind of fall into it I'vespent so much.
Speaker 3 (23:01):
I think it's such an iterative process.
I mean, I've been, I've beenworking on it and in a
self-aware kind of like, oh, I'mtrying to think about how do I
sell myself, what is the value Ican bring to a group?
Since I was 18 and getting ajob in college I've been I've
been going through just thisconstant process of thinking
okay, what is my story?
How have I gotten to where I am?
What were the major inflectionpoints?
(23:22):
And now, how do I use that totalk about what value I can
bring moving forward?
It's something I've beenworking on for well over 20
years now.
Speaker 1 (23:30):
Yeah, because you do.
You have to leave out all theboring parts or the
non-essentials, right the leastdramatic points, and really hone
in on those inflection points.
Speaker 3 (23:41):
Exactly.
Speaker 1 (23:41):
To bite sides.
Sound bites almost Exactlyexactly.
Speaker 2 (23:46):
Just like a weird contradiction that's with
selling yourself, right, becauseif I walk into a meeting and
I'm like Kevin Carrie, let metell you about how amazing
Richie is and this is likeRichie is just incredible you
won't even believe it.
You, I feel like you're bothlike all right, how quickly can
I leave?
Like how long do I have to stay?
(24:07):
This guy is making my skincrawl.
I want to run away.
So, like this, this whole ideaof selling yourself, the more
you do it straightforward,forward, the worse it is.
But then you have to be likeindirect, you have to be more
kind of I don't know objectivein how you talk about different
milestones and then also morevalue and other people focused.
(24:29):
I feel like as authentic and youhave to be, authentic about
those things as well, in orderto come off as authentic.
You know, and it's about thosethings as well, in order to come
off as authentic.
Speaker 1 (24:38):
And it's kind of like when you're selling a product
and you come in and you justvomit features and benefits.
It covers everything.
It's the same thing, right?
People just tune out becauseit's too much, they're not
interested in it.
I think you have to sharethings that people are
interested in and have kind ofgiven you a clue that they're
(24:59):
interested in this, or they havea past experience in X and you
share your experience with thatand make it sound impressive, I
suppose.
But keep it short and sweet ina lot of respects.
Speaker 3 (25:11):
Yeah, and I think you have to do discovery as well.
When you're thinking about howdo I sell myself much like when
you're selling a softwareproduct, for example figuring
out, ok, what actually mattersto this other person and this
all sounds so nefarious when I'msaying it, but it really does
just come down to being curiousabout other people and
understanding what theirmotivations are, why they care,
why they're there, and then themore you can figure that out,
(25:36):
the more you can tailor your ownstory to really hit the high
points that are there, similarhigh points, and I think that's
also a really effective.
Speaker 1 (25:41):
if you go back to yourself right if you have 10
features right, and we've allbeen buyers of, of technology or
anything right?
Maybe I just only care aboutone thing and I go into
something.
I don't care what else it does,does it do this and that's
where you start, and then youcan kind of add on things after
that, but that's where andthat's discovery right yep,
(26:03):
totally, totally it's a.
Speaker 2 (26:05):
There's a little bit of a nuance there, right, if I
walk in trying to provesomething, it's I'm gonna the
conversation that everything'sgoing to go one direction.
If I walk in with a curiositymindset, then the conversation
that everything's going to goone direction.
If I walk in with a curiositymindset, then the conversation
everything's going to go it'sgoing to have a completely
different trajectory.
I feel like that's kind of what.
What we're getting at and whatyou might be alluding to a
(26:26):
little bit, carrie, is like howdo you?
You don't necessarily want toprove something, but sometimes,
being curious, you're going toprove things naturally along the
way, when you're not eventrying to just from asking good
questions.
Speaker 3 (26:40):
Yeah, and everyone wants to be asked questions
about themselves and theirexperiences.
The more you can make someonefeel like you care and you're
interested, you'll be so muchmore effective at what you're,
whatever you're trying toaccomplish so what would kind of
go in a different direction?
Speaker 2 (26:54):
The hardest, most difficult, you know, pull your
hair out frustrating,emotionally draining sale what
was that?
What sale kind of was mostdifficult in all of those ways.
Speaker 3 (27:23):
Yeah, so many come to mind that it's hard to narrow
it down to a single one.
I think we've had a couple inmy time at trucker tools that
have been well over a year and ahalf in the making and I think
those, those are the hardestones because they require so
(27:45):
much patience and realize, likeyou can, you can want to be
doing everything in your powerto bring something to life and I
myself can see, okay, if wejust do these five things, get
these people on board, likelet's just do it, we could do
that all, we'd have it all doneby friday this week.
Why would there not be a reasonto sell and realizing, or
(28:05):
reason to sign, realizing that,uh, they're very, very real
internal politics, that a lot ofthe customers that we sell to
which are freight brokerages,and that those need to be
respected and given time todevelop, and that the process of
getting buy-in is not somethingthat a third party can come in
and do, because it's going todestroy trust between the people
(28:26):
at the organization.
So I can think of one inparticular that we sold just a
couple of months ago.
That was well over an 18-monthsale and we just kind of kept
running into the same wall ofnot being able to get our
solution, our low-trackingsolution, prioritized by the
(28:49):
decision maker.
So what we ended up having to dois find a couple of different
champions within theorganization who were willing to
go to the mat for us and reallyexert their own power of
influence.
Even though we had a directline with the decision maker,
nothing we said was everactually going to make a
difference.
We really had to equip thesepeople who are at slightly lower
levels within the organizationto influence up and really use
(29:12):
data more than anything to makethe business case for what we
were trying to do.
So I think any sale like that,where it just feels like this is
it logically does not makesense to not do this.
We're going to save you money,we're going to give you higher
levels of service, but you don'twant to hear it from me, you've
got to hear it from someoneelse are the most frustrating
because, yeah, sometimes youknow corporate politics are
(29:38):
annoying and silly, but theyreally do matter in the power,
dynamic and culture oforganizations and they have to
be respected.
Speaker 1 (29:46):
They exist at all places, at all times, with
within any corporate orbureaucracy you do, you have to,
you have to deal with it andyou have to be proactive and
creative about it.
Speaker 3 (30:00):
Totally, Totally, and figuring out who can kind of
operate on your behalf.
I think is is key.
Speaker 1 (30:07):
And it's someone different each each organization
.
You have to go in and someonedifferent each organization.
Yeah, you have to go in andfind that.
Speaker 3 (30:13):
Exactly, exactly.
Speaker 2 (30:15):
It's a humbling thing , right to come face-to-face
with the reality that you don'tknow everything about this other
company that you've been inconversation with for 18 months.
You know, as in sales, we wantto control everything and we
want to find out our champion,figure out our work back plan,
figure out our timelines, figureout the need, quantify the ROI,
(30:37):
put everything on paper and saythis is a watertight deal.
We know all the variables andwe have a handle on things.
But I think I would argue thatwe never that's's never a 100%.
You know math problem, likethere's always going to be an
element of unknown, there'salways going to be a dimension
and it might even that dimensionof unknown may even be unknown
(31:00):
within that organization.
They also may not really know,and that's kind of the
unsettling piece for salespeopleespecially when they come face
with that.
Why?
Why is this happening?
Why is this dragging what'sgoing on?
I think we've got to lean intothose issues in that
(31:21):
uncomfortable position.
There's a lot that can belearned there and that can make
or break a deal.
Speaker 3 (31:27):
Definitely, definitely.
Speaker 1 (31:29):
It is.
You always have to go back tothe drawing board, no matter
what project it is, whether it'snumbers based or people's based
, you know, sales basedengineering doesn't really
matter.
You have to.
Always, at some point in theprocess, when things aren't
working or you need to get overa plateau, you need to be very
willing to go back to thedrawing board and rethink every
(31:49):
assumption that you have andplay that exercise, because
that's the only way throughthose, those barriers.
Speaker 2 (31:59):
So what's the sale that you are most proud of?
May not be the biggest or thesmallest or the quickest or the
longest or the most arduous, butis there a sale that you're a
part of, that you're like, Ifeel so good about this, whether
it was the creativity to getthe deal done, or who you were
(32:20):
doing business with, or whatcame after the fact, but
whatever, or maybe somethingdifferent, but what are you most
proud of in terms of sales or aspecific sale?
Speaker 3 (32:31):
Yeah, I'll go all the way back to college for this
one.
So I worked at a student runbusiness in college.
We were a catering company oncampus and we worked with
largely academic departments,student groups, professors, you
know, symposiums that wouldhappen on campus, selling bagels
, coffee, sandwiches, reallyjust anything to make the event,
(32:54):
to bring catering to the event.
So we had a couple of reallybig contracts with some
university events and my junioryear, heading into my senior
year, when I was in theleadership position, we were
going after our biggest saleever.
It was for new studentorientation.
It was going to require us toput together something like
4,000 boxed lunches in a very,very short period of time and we
(33:18):
were a small team, we weremaybe 20 people and again we
were like this was all collegekids, the inmates ran the asylum
, there were no adults in theroom here.
So convincing academicadministrators to trust us with
such a big event Orientation isreally, when you're making the
(33:39):
sale as a university, to say,hey, you made the right choice,
you're coming to the right placefor the next four years, great
job, Welcome aboard.
You want to make the rightimpression.
And I think there are parentsat this event too, which only
raised the stakes even higher.
It wasn't just students.
So I was really really proud ofthat sale.
We made that sale in the springsemester heading out to
orientation, which happenedsometime in August later that
(34:01):
year, because it was by far themost operationally complex deal
we'd ever done in catering.
Again, this was a smallcatering operation.
So putting together somethingas complicated as 4000 box
breakfasts, we didn't have thespace for it, we didn't have the
cooler space for it, we didn'thave the hands.
We had to figure out kind ofall of these things on the fly.
(34:22):
We had to really sell the dreamof what we could do and how, by
supporting us and kind of ourstudent run mission.
By supporting us and kind ofour student run mission, the
university was going to beacting in really good faith and
kind of living out, practicingwhat they preach in terms of
supporting students and thenachieving their dreams.
And we're up against realprofessionals and you know that
(34:45):
as a, as a, it feels reallyreally good to be trusted with
something that could easily goto someone with so much more
legitimacy and credibility totheir name.
Speaker 1 (35:01):
So I was really proud of that kind of impassioned
sale that we made and theability that we were able to
pull it off.
That's always good, right.
The ones where you sell thedream and vision.
You don't have it figured outyet.
Speaker 3 (35:09):
Exactly.
Speaker 1 (35:10):
But it pushes you to figure it out.
Speaker 3 (35:12):
Exactly, exactly.
Speaker 1 (35:14):
Where did you go to college at?
Speaker 3 (35:18):
I went to Georgetown University in Washington DC.
Yeah, very cool yeah, the cityschool, so there's not a ton of
room on campus, so it's hard tofind all that space to put
together the box breakfast it isVery limited on space there.
Speaker 1 (35:30):
Yeah, Within DC.
What's the funniest sale youever have?
You ever had that.
You just keep sitting back andlaughing whenever you think
about it.
Speaker 3 (35:39):
Oh man, I don't know if I have a funniest sale itself
More than we have really funnycustomers and crazy things
happen and the characters arepretty hilarious.
Man, I don't know if I have agreat answer off the top of my
(36:01):
head for that.
Speaker 1 (36:02):
I actually care Let me ask you this You've been in
different industries, right?
We all three have.
You've been in differentindustries, right?
We all three have.
Do you find that freightbrokerage and transportation
have per capita, maybedensity-wise, the most
characters of any industry thatyou've been in?
Speaker 3 (36:23):
It is not even close, without a doubt, and I think
that's in part because you knowwe all talk about selling
service and technology and allthese things that brokerages.
But brand is such a massivepart of it when you're in a
pretty commoditized industrylike truck brokerage, you have
to it's, you know it's.
It's much like any brokeragefunction.
(36:45):
You really have to figure outhow you stand out.
So being a character andbuilding that personal brand for
yourself is, of course, youhave to back it up, like there's
no excuse for actual deliveryand service timeliness, having a
easier work with tech stack.
But I really do think that'swhy we see a higher percentage
of characters in this space,because it's just good business
(37:06):
and if you're not doing it, Ithink you're doing something
wrong.
Speaker 2 (37:10):
You're more memorable character.
Speaker 3 (37:13):
Yeah, exactly Exactly , and that's really all that
matters.
Do you come top of mind, ifyou're memorable and you give
off confidence Like there's?
There's truly nothing that youcan do to better set yourself up
from a personal brandingperspective.
Speaker 1 (37:27):
Yeah, yeah, and I agree with that by far.
The most characters naturalborn characters, you know.
Speaker 3 (37:34):
Why do you think that is?
Speaker 1 (37:36):
I think it's for many of the same reasons that you
just laid out.
You know, you have to be alittle bit different.
A lot of these characters areentrepreneurs anyway, which is a
little bit of a crazy mentality.
And yeah, you just have to be alittle bit wild and bold to to,
to make it as a freight broker.
Yeah, yeah, it seems like a lotof people say that freight
(38:01):
brokerage found them.
Speaker 2 (38:03):
You know, like I I don't know too many people that
when I asked them they're like,yeah, ever since I was in
kindergarten I've wanted to be afreight broker.
You know, like it's not the thechildhood dream of I mean I'm
sure there's that person outthere and apologies for that
person.
But a lot of people will saythat you know, oh, freight
brokerage found me and now I'mnever leaving.
(38:23):
You know, it's like a lot ofpeople just fall into this
industry one way or another andthey get stuck and I don't know
if that's because theircharacters or because it's like
which came first, the chicken orthe egg, I guess?
Speaker 3 (38:39):
Yeah, I, I, I definitely think so.
I certainly never thought Iwould be going into freight.
And here I am, three years in,and I can absolutely see why
that's the case, that once youget in you really don't get out.
Because there's I think it'sbecause there's it's such a
fragmented industry riddled withso many problems that everyone
can see potential to make adifference, to build something
(39:01):
themselves, to kind of solve aproblem that hasn't been solved
yet.
So there's just that sort offragmentation breeds opportunity
, from my perspective.
Speaker 1 (39:10):
Yep, it's full of opportunity.
There's no reason to leave.
It's a very small industry,smaller than you think and once
you start meeting everybody, theopportunities just become more
available.
Speaker 2 (39:27):
Yeah, yeah, carrie what was the sale that you
learned the most from.
If you went back and said thissale was such a meaningful and
educational experience, what wasthat sale that was most
educational?
Speaker 3 (39:45):
Yeah, I think I almost feel like you learn more
from the deals you lose than thedeals you win honestly.
Yeah, I think I almost feellike you learn more from the
deals you lose than the dealsyou win honestly.
So I think, yeah, I could talkabout a deal we won, but I
really do think the deals thatyou don't win are the ones where
you learn.
Ok, here's the gap and here'swhat we need to do to close a
(40:07):
future sale.
So I think I've learned a ton.
Really, back in the early firstcouple of weeks actually, I had
at Trucker Tools this isn't evena sale, but it was that we lost
(40:28):
a customer, a really largecustomer, top 20 brokerage, very
tech forward.
It was a huge deal, one of ourbiggest load tracking deals, and
I just started at the company.
So I had really getting up tospeed and I'm like, oh well,
this is too bad, I've got tofigure out what's going on.
So I hopped on a call with oneof their senior decision makers
and turned out that it was funto understand.
Hey, what happened here?
How did you decide to leave us?
Why don't we win this renewal?
And it was really all about ELTtracking and I'll be completely
(40:53):
honest, that was not somethingthat we had really prioritized
Back when.
When I was starting a business,you know we were always mobile
first tracking solution.
And I am so grateful that thathappened so early on in my
tenure because it was definitelylike the kick in the rear end
that I needed to say OK, we'vegot to make moves fast because
if we don't, we're not going toexist as a load tracking
(41:15):
business in a year or two If wedon't solve this massive product
gap we have now.
So we started really doublingdown on our ELD team and
standing up an entireorganization to support
onboarding and figure out how dowe do this better and different
than some of our competitorsare doing.
Organization to supportonboarding and figure out how do
we do this better and differentthan some of our competitors
are doing.
And you know, three years later, I think we're getting noticed
all the time now for what we'vebuilt from the ELD world.
(41:36):
So I think losing those sort ofsales or losing a customer is
an absolute punch to the gutbecause you know how hard you
work to bring them on board.
But in this case I think it wasactually it ended up being good
for us because it it led tothis whole new development of a
whole new part of our productand has totally changed our
product strategy.
So that's, that's the deal I'dsay I learned the most from.
Speaker 1 (42:00):
Going off on that a little bit.
You know what's the mostimportant sales lesson or
lessons that you learned sincebecoming CEO.
You know things that you didn'trealize about sales before that
, that you now grasp or that younow hold dear.
Speaker 3 (42:19):
Yeah, I think that sales is.
Yes, you know we talked aboutselling ourselves and showing up
well, and the interpersonalnature of it.
That is absolutely important.
But sales is a really reallytechnical science as well, and
appreciating what goes intoorchestrating a large deal where
(42:39):
you've got five, six, sevenstakeholders involved on the
customer side, maybe two tothree on your own internal side,
how important it is to bewriting a really really tight
process there, and how that canmake or break you as an
organization, how, when it comesto sales, it's not just about
kind of showing up and takingsomeone out to lunch and really
getting their buy-in as, oh,we're buds.
(43:00):
That's not what sales is about.
Sales is about building anironclad business case for
someone to help them solve avery, very specific problem, and
kind of that problemorientation, as opposed to I'm
selling this whole feature andthis whole product set.
Now we are selling a couple ofsolutions to specific pain
(43:21):
points has been a big shift forme when I think about how I sell
as a CEO.
Speaker 2 (43:27):
Yeah, that's fantastic.
I couldn't agree more.
I mean, it's the big sales comefrom specificity.
Did I say that?
Right, it's got lots ofsyllables in it, but it's being
able to pinpoint an exact ROIand make it real.
And that comes out of the exactuse case.
And it's this another kind ofcontradictory sort of stance
(43:50):
where you have, on one hand,it's not personal right, it's
not you and your thoughts andopinions, or your customers
thoughts and opinions, it's no,there's a problem and this
problem needs to be fixed, andeither your technology does that
or it doesn't like it's one orthe other.
So there's an impersonable,impersonal aspect to it all.
(44:11):
But there's also a personalaspect in that the other side
has to have trust that they canbelieve that what you're saying
is true and honest and gearedtowards solving that problem.
So there's this weird kind ofdialectical thing happening
where it's about you and thetrust and them having trust in
you, but it's also not about youor them.
(44:33):
It's mostly about solving aproblem.
Speaker 3 (44:36):
Yeah, and that's what's going to win you.
A deal is solving that problemand doing it in a very specific,
pointed way.
They're only going to beinterested in doing that if they
trust you.
So that's kind of the dooropener, but it's not going to
close the deal.
Speaker 1 (44:52):
Yeah, I think a lot of people gauge salespeople on
their likability in a lot ofways or how good they are at
getting in front of people.
But there's that back half ofit that you actually have to fix
the problem right, yep.
So you have to actually have agood solution.
People can go have lunch withyou all the time and enjoy
themselves, but if you don'thave the capabilities to fix
(45:13):
that problem, that you don'thave the solution.
That's where it ends and it'sgoing to end there every single
time.
Speaker 3 (45:19):
Exactly, exactly.
Speaker 2 (45:21):
Yeah.
So, carrie, where can ourlisteners find you?
How can they get in touch withyou?
How can they learn more aboutTrucker Tools?
Yeah, what's the best way forpeople to reach you?
How can they get in touch withyou?
How can they learn more aboutTrucker?
Speaker 3 (45:32):
Tools.
Yeah, what's the best way forpeople to reach you?
Yeah, find me on LinkedIn KariJablonski spelled like it sounds
and on Twitter as well.
Same, my handle is just my name.
Or feel free to shoot me anemail at kjablonski, at
truckertoolscom.
Love hearing from folks.
Thank you, I had a great time.
Speaker 2 (45:46):
Yeah, thanks for joining, gary.
Always a pleasure speaking withyou.
Every time I'm going to variousconferences, you're always one
of the people I'm hoping to runinto to say hi and catch up if
we have time.
So pleasure having you on thison the show and thanks again,
really enjoy the conversation.
We'll have to have you back.
I feel like there's morestories that we can dive into.
(46:07):
So, yeah, thanks for your timetoday.
Speaker 3 (46:12):
Thank you both, I really appreciate it.
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