0:00

Welcome to episode seven of the Last

0:02

Sell , where we dive into

0:04

the sales game with

0:06

stories from industry leaders . I'm

0:09

your co-host , Kevin Hill , here

0:11

with Richie Daigle , as always

0:13

. How are you doing today , Richie ?

0:15

Yeah , doing great , doing great . This was

0:17

episode seven . Yeah

0:19

, we're moving along Kerry Jablonski

0:22

, ceo of Trucker Tools , along

0:30

Carrie Jablonski , ceo of Trucker Tools , really fantastic , individual , super smart . Yeah , I'm

0:32

always impressed when I'm hearing Carrie talk

0:34

and just having conversations with

0:36

her Super approachable , you know , just great

0:39

person to chat with . Was excited to have her on

0:41

the show and

0:45

she had great stories . She delivered . She came through with some

0:47

really good stuff . Yeah , what

0:49

were your big takeaways from this one ?

0:51

The importance of channel sales right and learning

0:54

that early , Learning the

0:56

difference between retail or knocking on

0:58

each door and then having

1:00

sellers in line with different channels

1:02

and different markets to

1:05

push the product . So I think that was a

1:07

really big lesson

1:09

that she learned very early and

1:11

it's probably one

1:13

of the keys to her success

1:15

, as well as working on

1:17

selling yourself and what to do and what

1:19

not to do .

1:21

Yep and listening to her talk about the difference

1:23

between working smarter and not harder

1:25

. You know , I think everybody

1:27

in the sales a lot of people

1:30

in sales are real quick to beat their

1:32

chest about how hard they grind . You

1:34

know how hard I work . Oh , I put in 100

1:37

hours this week and I made 10,000

1:39

cold calls . And I'm a grinder

1:41

. I'm just a worker when it comes down to it

1:43

, and part of me when I hear that is like how

1:46

much of that is necessary , you

1:49

know , is that the best way ? Are

1:52

you maximizing your impact that

1:54

way , or is there a better way to where you

1:57

can grow your impact by leveraging

2:00

other sources or channels ? You

2:02

know , and Kerry figured that

2:04

out quite early , earlier

2:06

than most people probably could guess-

2:09

you

2:11

better believe it , she really has .

2:13

And also , another key point that

2:15

is really interesting is

2:18

the discussion around questioning

2:22

your assumptions . Right , once you get

2:24

to a stalled deal , deal to be able to go

2:26

back to the drawing board . Take

2:29

all your assumptions and question them all

2:31

and try a different tact , because

2:34

every company is different . Every bureaucracy is different

2:36

. She goes into detail about that and I think

2:38

that's a very important uh lesson

2:41

. You know , put your pride aside , question

2:44

what you've been doing on this deal and change

2:46

it if necessary .

2:48

And learn and analyze things after

2:50

the fact . I mean , you are

2:53

going to see whether

2:55

you win or lose a deal . You're

2:57

going to learn and see way more

2:59

information and details about that

3:01

deal after it's done

3:03

or not done or like closed in some

3:06

fashion . Then you are in the middle of it period

3:08

, like you're never going to be able to

3:11

identify all the levers and variables

3:13

when you're in the midst of it , and even

3:15

after the fact you'll see more of them , but probably still

3:17

not all of them , and so you have to

3:19

have that humility in place to where

3:22

you know you never turn off the

3:24

curiosity faucet , so to speak

3:26

.

3:27

You're exactly right , and with that

3:29

said , gopayhawk . So

3:31

if you're collecting invoices , you're

3:34

trying to get paid quickly . You need a credit card

3:36

processing and a

3:38

payment processing company to help you out

3:40

. Gopayhawk is that company

3:43

. You can go to wwwgopayhawkcom

3:47

, sign up for

3:49

a demo and kind of see how

3:51

everything works and claim

3:54

your $250 credit with

3:56

GoPayHawk . Tell them that you got

3:58

it from the last sell and

4:01

they will set you up with that deal

4:03

. But without any further ado again , let's

4:06

get straight to the

4:08

podcast .

4:09

Let's get into it . So

4:14

, carrie , I'm embarrassed to ask , but I

4:17

have to ask what is the right way

4:19

to pronounce your last name , because people butcher my

4:21

last name frequently and

4:23

I want to make sure I hear from you like the

4:25

correct pronunciation I

4:28

appreciate you asking that it is pronounced

4:30

exactly as it's spelt jabonski

4:33

jabonski got

4:35

it because I think I butchered

4:37

your name on a .

4:38

Put that coffee down at a freight race

4:41

event , even after I asked you . I think I

4:43

got on camera and still , but burst

4:45

for whatever .

4:46

I forgive you . We're all good .

4:52

And we're yeah , and so

4:54

where ? Where are you sitting today , carrie

4:56

, like where ? Remind me where you're based out of .

4:59

I'm based out of Chicago , so I I'm

5:01

at my office here in a bit of a odd

5:04

phone booth , which

5:06

is why , if you're watching us , the video might look a little strange , but

5:08

I'm I'm just in the heart of Chicago right now

5:10

nice , nice

5:13

are you always from Chicago ? or have you

5:15

moved to different places , or yeah

5:18

, I have , um , I've been in Chicago for

5:20

somehow this is , I

5:22

think , coming up on five years , which

5:25

is wild that I've been through five

5:27

Chicago winters and they really have not

5:29

been as bad as they say they are . And

5:32

I know everyone said this winter in particular

5:34

has been really warm . But even

5:36

the last four were not horrible

5:38

. But that's probably because I'm from Boston originally , so

5:40

I'm very used to it and I would take

5:42

cold temperatures over several feet

5:44

of snow and fortunately

5:46

get a lot less snow out here than we do

5:49

in New England , so it's

5:51

been easy . But yeah , I've lived . I've actually

5:53

lived all over . I grew up in New Jersey

5:55

and then mostly Massachusetts , right outside Boston

5:57

, and then went to college

5:59

down in DC , spent some time in DC and

6:02

then lived abroad , briefly in

6:04

Jakarta , indonesia , and then for a while

6:06

in Mexico City before I came

6:08

to the Midwest . So I've been in Central Time now

6:11

for seven or eight years and

6:14

Chicago is currently home .

6:17

All those places sound cold until you got to

6:19

Indonesia and Mexico City . So how did

6:21

you deal with that ? That had to have been a

6:23

bit of a shock dealing with that sort of heat

6:25

in the summertime .

6:27

Yes , indonesia was very

6:29

, very hot . There is no

6:31

sugarcoating that . Mexico City is actually

6:33

at elevation in quite a bit . It's

6:36

50% higher than Denver

6:38

is . It's about a mile and a half of elevation , around

6:40

75,000 , 8,000 feet . So

6:44

it can get warm but it's

6:46

not hot Like . Dc

6:48

is probably the hottest place

6:51

I've lived for a long period of time . You

6:53

know it just gets gross and sticky in

6:56

the middle of the summer . There Mexico City

6:58

was pretty , you know , get up

7:00

to 75-ish , but never

7:02

significantly higher

7:04

than that ?

7:06

Where were you doing in Mexico City ?

7:08

I was working for Uber , so I

7:10

worked on ride

7:13

sharing and Uber Eats in Latin America

7:15

and Mexico City was the home

7:17

office , so I spent about a year

7:19

and a half there , working all across

7:21

the region , but based in Mexico .

7:24

What's different about living abroad ?

7:27

Oh , I mean it's

7:29

such an awesome experience for

7:32

anyone who has the good fortune to

7:34

be able to do it . It

7:37

sounds so obvious and cliche

7:40

, but it does Just

7:43

. It expands the way you think about

7:45

the world and it's like as someone who

7:47

just lived in america my whole life and

7:49

had not traveled abroad extensively I

7:54

it just opens up your eyes to like there are these

7:56

other massive regions of the world

7:58

where everything is

8:00

done differently and handled differently

8:03

. And , yeah

8:06

, I just felt like it was like a little piece of my brain

8:08

was unlocked to realize , oh my God , there is a

8:10

massive , massive world out there , far beyond

8:12

just what's going on in America day to day . So

8:14

kind of that still

8:16

impacts me today when I think about it From a day

8:18

to day perspective , though , it

8:21

is really humbling to feel

8:23

like you never quite are on

8:25

the inside . There's always going to

8:27

be some sort of cultural difference . I had

8:29

wonderful , wonderful , wonderful colleagues in

8:31

Mexico who were so welcoming . It was a really global

8:33

crew . It was not just Mexicans , it was all

8:35

over Latin America and all over the world . So

8:38

it was really fortunate to have a really diverse group

8:40

of friends there . But yeah

8:43

, just , you're just kind of constantly aware that

8:45

this is not my , my

8:47

home , and , uh

8:49

, that can be exhausting

8:52

after a while do you still travel a

8:54

fair amount ?

8:55

do you still try to travel internationally to kind

8:57

of scratch that itch , or , yeah

9:00

, the country yeah , the last

9:02

time I left the country was in the fall

9:04

.

9:05

I was down in Chile and in

9:07

Argentina . Actually , my

9:09

boyfriend is doing a graduate degree

9:12

and he was able to spend some time abroad as part of that

9:14

, so he was in Santiago for an

9:16

extended period of time . So I went down to visit him

9:18

and then we went to Argentina over

9:20

Thanksgiving , which was really awesome

9:23

. Highly recommend to

9:25

anyone who's never been . It's beautiful

9:27

. We're actually there for the

9:29

presidential election , which is really interesting . Don't

9:32

have any big international

9:36

trips on the books this year . Lots of

9:38

domestic travel . Now . I've

9:41

been home for the last two weeks , but starting

9:43

next week I'll be hitting the road

9:45

every single week of April . So getting

9:48

ready for that .

9:49

So , speaking of travel , if

9:52

there's one place that you can go

9:54

for vacation , like

9:56

one last vacation , like where are you

9:58

going ? Your favorite destination

10:01

, either someplace that you've been before , that you want

10:03

to go back to , or if

10:05

you just have one more vacation left , where

10:07

in the world are you going to go ?

10:10

That is such a hard question . My

10:13

mind initially went to Maine . Actually

10:15

, I grew up

10:17

in New England . I grew up going to Maine a

10:20

lot and in the summertime it's so

10:22

, so beautiful . Uh , I think Maine

10:24

slogan on their license plates is the

10:26

way life should be . So probably

10:28

go up to Lake Sebago and Maine and spend

10:31

some time on the lake Just enjoying the summertime there

10:33

.

10:34

And follow up question what is your favorite

10:36

beverage ? Could be alcoholic , non-alcoholic

10:39

. What ?

10:40

what does it ?

10:42

like to sip on .

10:43

Oh man , okay , I'll do . I

10:46

love chocolate milk . What

10:48

is it ? Fair Life chocolate milk . It's so delicious

10:51

I often crave that . My

10:53

go-to drink is a hazy IPA , though A

10:56

good hazy is tough to beat for me

10:58

.

10:59

Okay , so imagine fast

11:02

forward into the future . You're

11:04

done working . You know

11:07

work is way behind you and you are . What

11:09

was this lake in Maine ? You said Lake Sebago

11:11

.

11:12

Lake Sebago yeah .

11:13

You were at Lake Sebago . You still

11:15

have the chocolate mustache , you know , from

11:17

the chocolate milk that you just finished

11:20

. You just , you know , forgot to wipe it . But it's been long enough

11:22

so that the hazy IPA that you have

11:24

in your hand doesn't feel like it's

11:26

going to be some weird mix of chocolate milk and hazy

11:28

IPA . But you're sitting here on the

11:30

side of the lake and work

11:32

is done . You're retired , you're

11:35

living life the way it should be in

11:37

Maine and you're thinking back

11:39

. You're just having a moment of looking back

11:41

over the course of your career . What was the

11:43

last sale , what

11:45

was the last thing that you ever sold , or what

11:48

was the last project that you worked

11:50

on in your professional career before

11:52

retiring ?

11:54

I sold my own company . That's got

11:57

to be it . I built

11:59

something and I took it all the way through to a sale

12:01

. So TBD is exactly what that

12:03

is going to be . But I

12:06

would love to be a founder someday , start

12:09

something and fully see it off

12:11

on my own .

12:14

I take it as a next chapter in your life

12:16

. Right , that's down

12:19

the road and something that you're thinking

12:21

about eventually .

12:23

Exactly exactly . I'm a long ways away from that

12:25

right now . I've got my hands full

12:27

and really loving what we're building with trucker

12:29

tools . But it's always

12:31

been a dream of mine to start my own business

12:33

and sell it . And it could be . It could

12:35

be big , it could be small , it could be , I

12:38

think you know , owning a bookstore or something like

12:40

that . It would be an absolute blast and

12:43

dream . So TBD

12:45

exactly what it is , but it's something that I have built

12:47

with a team of people I really care about

12:49

.

12:50

Do you always have ? I find myself

12:52

with various ideas that are

12:55

bouncing around in my brain . From time to time

12:57

I share some of these ideas with Kevin

12:59

or with other friends . I'll say do

13:01

you think this could work ? Or like , what are your thoughts

13:03

on this ? And other friends I'll say do you think this could work ? Or

13:05

like what are your thoughts on this ? And do you feel the same way . Do you constantly have like

13:07

little micro ideas that are always like

13:10

I wonder if this could be something , or I wonder

13:12

if it's this , and do you criticize ? Like

13:14

what do you do with those ideas ? Like what

13:16

, what do you have to ? What does an idea have to do

13:18

to be something that you would act upon ?

13:21

yeah all the time . And then sometimes

13:23

I realize I've just invented something that already exists

13:25

. Like I think I invented

13:27

railroads . The other day when I was like what if

13:29

, instead of having to drive

13:32

, you could just put something on

13:34

a box and it would move on a preset

13:37

rail , I was like , oh , that is a train , so

13:39

we already have that . Good thing , we already have

13:41

that going . So , yes , I do , I

13:43

do think about that all the time and talk about all the time

13:46

. Um and uh

13:49

. The nice thing about at work at

13:51

least you know , we have the resources to be able to

13:53

build and move fast at trucker tools , that when

13:56

it's kind of within the context of freight

13:58

tech , I'm able to execute really quickly on those

14:00

things , um , which is really really fulfilling

14:02

. But I I have them all the time , just kind

14:04

of walking down the street and talking to friends .

14:07

Do you have an angle or something that would really

14:10

create excitement ? Because we all talk to entrepreneurs

14:12

every single day in

14:14

what we do and I

14:16

find some really great ideas , right , people

14:19

have some really great ideas . They're executing those

14:21

, but it's

14:23

just not in my wheelhouse , right

14:26

. Nothing that I would want to drop everything

14:28

and go spend 60

14:31

80 hours a week , but you

14:33

know I have a lot of respect for them , but I have

14:35

my own little wheelhouse that I'm always looking

14:37

for something that you know

14:39

it's like a bug you get bitten

14:41

by the bug and go all in . Do

14:43

you have any kind of

14:45

lanes or things

14:48

that always pique your interest ?

14:50

Yeah , so I mean , obviously , anything in

14:52

brokerage tech right

14:54

now is really interesting to me and

14:56

I'm really interested in particular around how

14:58

we're evolving . I think there's a lot of SaaS products

15:00

obviously developed in the brokerage space

15:02

over the last let's call it five to seven years

15:04

, but we're really moving into the era of DAS and

15:07

data products and how data products can be augmented

15:09

on top of those SaaS products . So that's something I'm thinking a

15:11

lot about right now at at

15:14

work itself . Outside

15:16

of , I mean , I have tons of other

15:18

interests beyond what

15:21

. What we're doing at Trevor tools and in freight

15:23

tech . I would love , I

15:26

love the idea of building something around community

15:28

for women and empowerment for women . So I think a lot

15:30

about what are things I could be doing there and how could I support

15:32

um women with them

15:34

developing their own careers . Um

15:36

, I , I

15:38

really like I would love to start

15:41

at like a . I live in a neighborhood without a great bagel

15:43

shop . I would love to start a bagel shop . You

15:45

know there's there's a lot of like very kind of brass

15:47

tacks businesses too that I

15:50

, I , I think I

15:52

would love to execute out on beyond the realm of like just

15:55

software right now .

15:57

Yeah , I love that there's certain , like small

16:00

businesses that are more community oriented , like

16:02

a breakfast restaurant or a coffee

16:05

shop or a bookstore or , you

16:08

know , a bed and breakfast

16:10

or in some beautiful location

16:12

or something like that . That are kind of lifestyle businesses

16:15

, that are kind of attractive as well .

16:17

Exactly , exactly , so , if you think

16:19

back in time .

16:20

What was the first sale

16:22

in

16:27

time ? What was the first sale ? And this could be you selling an idea or a concept , or it

16:29

could be selling something as part

16:31

of a fundraiser when you're in high school

16:33

or middle school or something . But what is

16:35

the first idea or

16:37

item that you ever remember

16:39

selling ?

16:42

Yeah , the actual item that I first ever remember

16:44

selling is I think it was , it must

16:46

have been elementary school , not even quite middle school

16:48

for me , but we would have a wrapping

16:50

paper fundraiser every year where

16:53

basically the idea was to raise money for school

16:55

by selling wrapping paper

16:58

to your parents and their friends and other people

17:00

about town . And that

17:04

is what I remember as my first introduction

17:06

to like here's how you be commercial and

17:08

um , um . And

17:11

the point I really remember is that

17:13

I think that's how I discovered channel sales , because

17:16

I remember a bunch of friends would be going door to door trying

17:19

to say hey you want some wrapping paper

17:21

, mrs So-and-so , and

17:23

I had two parents who worked . My mom and

17:25

dad both worked and went into offices by

17:36

having them sell on my behalf , by bringing in the sheet of paper that we had to take orders on and

17:38

placing it with some cookies on a conference table in the lunchroom and

17:40

having them do some of that sales

17:42

development on my behalf . So

17:44

I remember being very , very successful with that , and

17:47

everyone else around town was trying to tap

17:49

into the same people locally in the neighborhood and I was able

17:51

to . They worked downtown in the city , so I was able to

17:54

tap into those networks with people who did

17:56

not live in the town I grew up in , who were

17:58

not being inundated by , you know , tens and

18:00

dozens of middle schoolers to buy

18:02

wrapping paper , which was an exciting

18:04

realization for

18:06

me and still informs how I think about how do you

18:08

scale and get into new markets .

18:11

It's a very important lesson , isn't it ? You know they're

18:16

going to knock on every door

18:19

or you're going to get a channel partnerships

18:21

and channel sales and kind of retail versus wholesale sort of quandary

18:24

. It's very important , isn't it ?

18:26

For sure , for sure . Yeah , it's

18:30

always nice to unlock something and you're like , oh

18:32

wow , this is actually a lot easier than I thought it would

18:34

be , as opposed to me having to put in the sweat equity of going

18:36

door to door . If I can just put that on

18:38

someone else who's willing to work on my

18:40

behalf , hey , I'll take that . Work

18:43

smart , not hard .

18:45

I love that you figured all this out in elementary school

18:47

.

18:48

I mean that's , I think

18:50

I only put it like all together as a framework

18:52

later in life . Put

18:56

it like all together as a framework later in life . But uh , I do remember realizing that , oh

18:58

, I can move really fast if I just get us to someone else , to go to a different

19:01

place and talk to new people did

19:03

you ?

19:04

did you like file like a report ? Afterwards

19:06

you have to do a project of like here's why , here's

19:08

how channel sales will help you with wrapping

19:10

paper sales , and what I learned and did

19:13

you . I could just just see designing some project

19:16

in fourth grade of the

19:18

successfulness of channel sales .

19:20

I was such a nerd growing

19:22

up and absolutely loved schoolwork

19:25

and doing well and projects

19:28

. I don't think I actually had to

19:30

submit anything , but I can rest assured

19:32

that I had

19:34

plenty of other like nice posters uh

19:37

, that I that I put together for school . I really must put

19:39

together a good poster after a project , it's so

19:41

satisfying .

19:43

Did you do the , the , the like

19:47

, the folding ?

19:48

you know what I'm talking about like , the big trifolds , yeah

19:50

, yeah yeah I mean , I was so

19:52

into like projects

19:54

and I remember making a trifold

19:57

poster in my free time for

19:59

fun about weather . I must have been like

20:01

in fourth or fifth grade and , as

20:03

opposed to doing what normal kids would do on the weekend , I decided

20:06

to pull together . I don't know , I must have been reading some

20:08

book about weather . I was like , oh , I'm going to

20:10

put this into a poster format and I think

20:12

that is it's really sad to say aloud

20:14

, but um , unfortunately

20:16

how I was as a kid and I

20:19

do think it does translate into how I operate as

20:21

an adult now and that I I

20:23

think about a very structured thinker

20:25

and I like taking big , nebulous ideas

20:27

and making them very , very palatable and digestible

20:30

, and that's what those trifle posters

20:32

did for me excel

20:35

is probably a really good tool that that you like

20:38

to use quite a bit , because you can put

20:40

the numbers down in a structured format

20:42

.

20:42

You can run any scenario you kind of want to

20:45

and play around with it .

20:48

You can have my team . Google Sheets is my

20:50

love language . I love it . I use

20:52

it constantly . I run the business off of it . It's

20:55

pretty sad .

20:58

Doesn't everybody ?

20:59

Yeah , that's true . Yeah , definitely . When

21:01

I was at Uber , we were like I don't know $40

21:05

million excuse me , $40 billion business . That

21:07

company was running off of Google Sheets . Still

21:10

, it's crazy , it is

21:12

the ultimate tool for business .

21:14

It really is . It really is , um

21:18

. Going back to sales , uh , so , so there's your

21:20

first sell , what was kind of your easiest

21:22

sell that you ever wandered

21:24

into and thought it

21:26

was going to be much more complicated than it was maybe

21:29

not yeah and it just , it's

21:31

everything just clicked .

21:34

Yeah , I

21:38

think sometimes , when it comes to selling

21:41

myself , I've had a bunch

21:43

of sales where it's been easier than I expected

21:46

and I don't mean that to come off not

21:51

without humility . But I

21:53

think when I think about some job

21:55

interviews over the years and the

21:58

amount of the

22:01

stakes that I felt going into them and

22:03

then realizing if I'm going to show

22:05

up really well , if I really truly do just show up

22:07

as myself and tell stories

22:10

like from the heart , without

22:12

trying to make myself seem

22:14

like I am something I'm not , there have been

22:16

some that have clicked and

22:20

gone a lot better than

22:22

I think I expected

22:24

them to . So , yeah , when it really

22:26

comes to selling myself , I think that's because

22:29

it's a skill I've been working on now for 20

22:31

, 30 years . I've

22:34

really been able to just hone that and be

22:36

able to show up and show up authentically

22:38

.

22:39

It's essential , isn't it ? Yeah , you have to sell

22:41

yourself before you can sell anything else .

22:43

It's everything , whether it's a client , employer

22:46

, to anybody right ?

22:47

Absolutely , Absolutely . It's

22:49

one of the hardest things to do , too . It's

22:52

one of the hardest things to grasp , right how

22:54

? Do you go about it . I'm not really sure

22:56

myself . Yeah , kind of fall

22:58

into it I've spent

23:00

so much .

23:01

I think it's such an iterative process . I mean , I've

23:03

been , I've been working on it and

23:05

in a self-aware

23:07

kind of like , oh , I'm trying to think about how do I sell myself

23:09

, what is the value I can bring to a group ? Since

23:11

I was 18 and getting a job in college

23:14

I've been I've

23:16

been going through just this constant process of thinking okay

23:18

, what is my story ? How have I gotten to where I am

23:20

? What were the major inflection points ? And

23:26

now , how do I use that to talk about what value I can bring moving forward ? It's something I've been

23:28

working on for well over 20 years now .

23:30

Yeah , because you do . You have to leave out

23:32

all the boring parts or the non-essentials

23:35

, right the least dramatic points

23:37

, and really hone in on those inflection

23:39

points .

23:41

Exactly .

23:41

To bite sides . Sound bites

23:44

almost Exactly exactly .

23:46

Just like a weird contradiction that's

23:48

with selling yourself , right , because if I walk into

23:51

a meeting and I'm like Kevin

23:53

Carrie , let me tell you about

23:55

how amazing Richie is and

23:57

this is like Richie is just incredible you

23:59

won't even believe it . You , I

24:02

feel like you're both like all right , how quickly

24:04

can I leave ? Like how

24:06

long do I have to stay ? This guy is making my

24:08

skin crawl . I want to run away . So

24:10

, like this , this whole idea of selling yourself

24:12

, the more you do it straightforward

24:15

, forward , the worse it is . But

24:18

then you have to be like indirect , you have to be

24:20

more kind of I

24:23

don't know objective in how you talk about

24:25

different milestones and then

24:27

also more value and other people focused

24:29

. I feel like as authentic

24:31

and you have to be , authentic about

24:34

those things as well , in order to come off as authentic . You know , and

24:36

it's about those things as well , in order to come off as authentic .

24:38

And it's kind of like when you're selling a product and you come in

24:40

and you just vomit

24:42

features and benefits . It

24:45

covers everything . It's

24:47

the same thing , right ? People

24:49

just tune out because it's too much , they're not

24:51

interested in it . I think

24:53

you have to share things that people are

24:55

interested in and have kind of

24:57

given you a clue that they're interested

24:59

in this , or they have a past

25:02

experience in X and you share

25:04

your experience with that and

25:06

make it sound impressive , I suppose

25:08

. But keep it short and sweet in a lot

25:10

of respects .

25:11

Yeah , and I think you have to do discovery

25:13

as well . When you're thinking about how do I sell myself

25:15

much like when you're selling a software product , for example

25:17

figuring out , ok , what actually

25:20

matters to this other person and this all sounds

25:22

so nefarious when I'm saying it , but it

25:24

really does just come down to being curious about

25:26

other people and understanding what their motivations

25:28

are , why they care , why

25:30

they're there , and

25:36

then the more you can figure that out , the more you can tailor your own story to really hit the high

25:38

points that are there , similar high points , and I think that's also

25:40

a really effective .

25:41

if you go back to yourself right if

25:43

you have 10 features right , and we've all

25:45

been buyers of , of technology or

25:48

anything right ? Maybe

25:50

I just only care about one thing and I go

25:52

into something . I don't care what else it does

25:54

, does it do this and

25:56

that's where you start , and then you can kind

25:58

of add on things after that , but

26:00

that's where and that's discovery right yep

26:02

, totally , totally it's a

26:05

.

26:05

There's a little bit of a nuance there , right , if I walk

26:07

in trying to prove something , it's

26:10

I'm gonna the conversation that

26:12

everything's going to go one direction . If I walk in with a curiosity mindset , then

26:14

the conversation that everything's going to go one direction . If I walk in with a curiosity mindset

26:16

, then the conversation everything's

26:18

going to go it's going to have a completely different

26:20

trajectory . I

26:23

feel like that's kind of what . What we're getting

26:25

at and what you might be alluding to a little bit , carrie , is like

26:27

how do you ? You don't necessarily want to prove something

26:29

, but sometimes , being

26:31

curious , you're

26:36

going to prove things naturally along the way , when you're

26:38

not even trying to just from asking good questions .

26:40

Yeah , and everyone wants to be asked questions

26:42

about themselves and their experiences . The more you can

26:44

make someone feel like you care and you're interested , you'll

26:47

be so much more effective at what you're , whatever you're trying to accomplish

26:49

so what would

26:51

kind of go in a different direction ?

26:54

The hardest , most

26:56

difficult , you know

26:58

, pull your hair out frustrating

27:01

, emotionally draining

27:03

sale what was that

27:06

? What sale kind of was

27:08

most difficult in all of those ways .

27:23

Yeah , so many come to mind that it's hard to narrow it down to a single one . I think we've

27:27

had a couple in my time at

27:29

trucker tools that have been well

27:32

over a year and a half in the making

27:34

and I think those , those

27:38

are the hardest ones

27:42

because

27:44

they require so much patience and realize

27:46

, like you can , you can want to be

27:48

doing everything in your power to

27:50

bring something to

27:53

life and I myself

27:55

can see , okay , if we just do these five things , get

27:57

these people on board , like let's just do

28:00

it , we could do that all , we'd have it all done by friday

28:02

this week . Why would there not be a reason to sell

28:04

and realizing , or reason to sign

28:06

, realizing that , uh

28:08

, they're very , very real internal

28:11

politics , that a lot of the customers that we sell

28:13

to which are freight brokerages , and

28:15

that those need to be respected

28:17

and given time to develop

28:19

, and that the process of getting buy-in is not

28:21

something that a third party can come in and do , because

28:24

it's going to destroy trust between the people

28:26

at the organization . So

28:28

I can think of one

28:30

in particular that we sold just

28:33

a couple of months ago . That was well over an 18-month

28:35

sale and we

28:38

just kind of kept running into the same wall

28:41

of not

28:43

being able to get our solution , our

28:46

low-tracking solution , prioritized by the

28:49

decision maker . So

28:52

what we ended up having to do is find a couple of different

28:54

champions within the organization who were willing

28:56

to go to the mat for us and really exert

28:58

their own power of influence . Even though we had a direct line

29:01

with the decision maker , nothing we said was

29:03

ever actually going to make a difference . We

29:06

really had to equip these people who are at slightly

29:08

lower levels within the organization to influence

29:10

up and really use data more than

29:12

anything to make the business case

29:14

for what we were trying to do . So

29:17

I think any sale like that

29:20

, where it just feels like this

29:22

is it logically does not make sense to not

29:24

do this . We're going to save you money , we're going to give you higher levels

29:26

of service , but you don't want

29:28

to hear it from me , you've got to hear it from someone else are

29:30

the most frustrating because

29:32

, yeah

29:35

, sometimes you know corporate politics

29:37

are annoying and silly , but

29:40

they really do matter in the power , dynamic and

29:42

culture of organizations and they have to be respected .

29:46

They exist at all places , at all times

29:48

, with within any corporate or

29:50

bureaucracy you

29:54

do , you have to , you have to deal with it and you

29:56

have to be proactive and

29:58

creative about it .

30:00

Totally , Totally , and figuring out who can

30:02

kind of operate on your behalf . I

30:04

think is is key .

30:07

And it's someone different each each organization . You have to go in and someone different

30:09

each organization . Yeah , you have to go in and find

30:12

that .

30:13

Exactly , exactly .

30:15

It's a humbling thing , right to

30:17

come face-to-face with the

30:19

reality that you don't know everything about

30:21

this other company that you've been in conversation

30:23

with for 18 months . You

30:25

know , as in sales , we want

30:27

to control everything and we want to

30:29

find out our champion , figure

30:32

out our work back plan , figure out our timelines

30:34

, figure out the need , quantify the ROI

30:37

, put everything on paper and say

30:39

this is a watertight deal

30:41

. We know all the variables and we have a handle

30:43

on things . But I think

30:45

I would argue that we never that's's never

30:47

a 100% . You know math

30:49

problem , like there's always going to be an

30:51

element of unknown , there's

30:54

always going to be a dimension and

30:56

it might even that dimension of unknown

30:58

may even be unknown within that organization

31:01

. They also may not

31:03

really know , and

31:05

that's kind of the unsettling piece

31:09

for salespeople especially

31:11

when they come face with that . Why

31:15

? Why is this happening ? Why is this dragging

31:17

what's going on ? I

31:19

think we've got to lean into those issues in that uncomfortable

31:22

position . There's a lot that can be learned

31:24

there and that can make or break a deal .

31:27

Definitely , definitely .

31:29

It is . You always have to go back to the

31:31

drawing board , no matter what project it is

31:33

, whether it's numbers based or

31:35

people's based , you know , sales based

31:37

engineering doesn't really matter . You have to . Always

31:39

, at some point in the process , when things

31:42

aren't working or you need to

31:44

get over a plateau , you need to be

31:46

very willing to go back to the drawing board and

31:48

rethink every assumption that you have

31:50

and play that

31:52

exercise , because that's the only way through those

31:54

, those barriers .

31:59

So what's the sale that

32:01

you are most proud of

32:03

? May not be the biggest or

32:05

the smallest or the quickest or the longest

32:08

or the most arduous , but is

32:11

there a sale that you're a part of , that

32:13

you're like , I feel so

32:16

good about this , whether it was the

32:18

creativity to get the deal done , or who

32:20

you were doing business with , or what

32:23

came after the fact , but whatever

32:25

, or maybe something different , but what are

32:27

you most proud of in terms of sales or

32:29

a specific sale ?

32:31

Yeah , I'll go all the way back to college for

32:33

this one . So I worked at a student run business in college

32:36

. We were a catering company

32:38

on campus and we worked with largely

32:42

academic departments , student

32:45

groups , professors , you

32:47

know , symposiums that would happen on campus

32:50

, selling bagels , coffee , sandwiches

32:52

, really just anything to make

32:54

the event , to bring catering to the

32:56

event . So we had a couple

32:58

of really big contracts with some university

33:00

events and my junior

33:03

year , heading into my senior year , when I was in the leadership position

33:05

, we were going after our

33:08

biggest sale ever . It was

33:10

for new student orientation . It was going to require

33:12

us to put together something like 4,000

33:14

boxed lunches in a very , very short period

33:16

of time and we were a small team , we

33:19

were maybe 20 people and again we were like

33:21

this was all college kids , the

33:23

inmates ran the asylum , there were no

33:26

adults in the room here . So

33:28

convincing

33:30

academic administrators

33:33

to trust us with such

33:36

a big event Orientation is really , when

33:38

you're making the sale as a university , to say

33:40

, hey , you made the right choice , you're coming to the right place

33:42

for the next four years , great job , Welcome

33:45

aboard . You want to make the right impression . And I

33:47

think there are parents at this event too , which only raised

33:49

the stakes even higher . It wasn't just students

33:51

. So I

33:53

was really really proud of that sale

33:56

. We made that sale in the spring semester

33:58

heading out to orientation , which happened sometime

34:00

in August later that year , because

34:03

it was by far the most operationally complex

34:05

deal we'd ever done

34:07

in catering . Again , this was a small

34:10

catering operation . So putting together

34:12

something as complicated as 4000 box breakfasts

34:14

, we didn't have the space for it , we didn't

34:16

have the cooler space for it , we

34:19

didn't have the hands . We had to figure out kind of all

34:21

of these things on the fly . We had to really sell

34:23

the dream of what we could do and how , by supporting us

34:25

and kind of our student run mission . By supporting us and kind of our student

34:27

run mission , the university

34:29

was going to be acting in really good faith

34:31

and kind of living out , practicing

34:34

what they preach in terms of supporting students and then

34:37

achieving their dreams . And

34:40

we're up against real professionals and

34:43

you know that as a

34:45

, as a , it feels really really good to

34:48

be trusted with something that

34:50

could easily go to someone with so

34:53

much more legitimacy and credibility

34:55

to their name .

35:01

So I was really proud of that kind of impassioned sale that

35:03

we made and the ability that we were able to pull it off . That's always good , right

35:05

. The ones where you sell the dream and vision . You don't have it figured

35:07

out yet .

35:09

Exactly .

35:10

But it pushes you to figure it out .

35:12

Exactly , exactly .

35:14

Where did you go to college at ?

35:18

I went to Georgetown University in Washington DC

35:20

. Yeah , very cool yeah , the city school , so

35:23

there's not a ton of room on campus , so it's hard to find all

35:25

that space to put together the box breakfast it

35:27

is Very limited on space there

35:29

.

35:30

Yeah , Within DC

35:32

. What's the funniest sale you

35:34

ever have ? You ever had that . You just keep

35:36

sitting back and laughing whenever you

35:38

think about it .

35:39

Oh man , I don't know if I have

35:41

a funniest sale itself

35:44

More

35:48

than we have really funny customers and crazy things

35:50

happen and the characters are

35:52

pretty hilarious . Man

35:57

, I don't know if I have a great

35:59

answer off the top of my head for that

36:02

.

36:02

I actually care Let me ask you this

36:05

You've been in different

36:07

industries , right ? We

36:09

all three have . You've been in different industries

36:11

, right ? We all three have . Do you find that

36:13

freight brokerage and transportation have per

36:15

capita , maybe density-wise , the most

36:18

characters of any

36:20

industry that you've been in ?

36:23

It is not even close

36:26

, without a doubt , and I think that's

36:28

in part because you

36:30

know we all talk about selling service and technology

36:33

and all these things that brokerages . But brand

36:35

is such a massive part of it when you're in a pretty

36:38

commoditized industry like truck brokerage

36:40

, you have to it's

36:42

, you know it's . It's much like

36:44

any brokerage function . You really have to figure out

36:46

how you stand out . So being a character and

36:48

building that personal brand for yourself is , of

36:50

course , you have to back it up , like there's no

36:53

excuse for actual delivery and service timeliness

36:55

, having a easier work with tech

36:57

stack . But

37:04

I really do think that's why we see a higher percentage of characters in this space , because it's just

37:06

good business and if you're not doing it , I think you're

37:08

doing something wrong .

37:10

You're more memorable character .

37:13

Yeah , exactly Exactly , and that's really all that

37:15

matters . Do you come top of mind , if you're

37:17

memorable and you give off confidence

37:19

Like there's ? There's truly nothing that

37:22

you can do to better set yourself up from

37:24

a personal branding perspective .

37:27

Yeah , yeah , and I

37:29

agree with that by far . The most characters

37:31

natural born characters , you

37:33

know .

37:34

Why do you think that is ?

37:36

I think it's for many of the same reasons

37:38

that you just laid out . You know , you have to be a little bit different

37:40

. A lot of these characters are

37:42

entrepreneurs anyway , which is a little bit

37:45

of a crazy mentality . And

37:48

yeah , you just have to be a little

37:50

bit wild and bold to

37:52

to , to make it as a freight broker

37:54

. Yeah , yeah , it

37:58

seems like a lot of people say that freight

38:01

brokerage found them .

38:03

You know , like I I don't know too many

38:05

people that when I asked

38:07

them they're like , yeah , ever since I was in kindergarten

38:10

I've wanted to be a freight broker . You know , like

38:12

it's not the the childhood dream

38:14

of I mean I'm sure there's that person out there

38:16

and apologies for that person . But a

38:19

lot of people will say that you know

38:21

, oh , freight brokerage found me and now

38:23

I'm never leaving . You know , it's like a lot of people just fall

38:25

into this industry one way or

38:27

another and they get stuck

38:29

and I don't know if

38:31

that's because their characters or because

38:33

it's like which

38:38

came first , the chicken or the egg , I guess ?

38:39

Yeah , I , I , I definitely think so . I certainly never

38:42

thought I would be going into freight . And

38:46

here I am , three years in , and I can absolutely see why that's the case , that

38:48

once you get in you really don't get out . Because there's

38:50

I think it's because there's it's

38:53

such a fragmented industry

38:55

riddled with so many problems that everyone

38:59

can see potential to make a difference , to

39:01

build something themselves , to kind

39:03

of solve a problem that hasn't been solved

39:05

yet . So there's just that sort of fragmentation

39:07

breeds opportunity , from

39:09

my perspective .

39:10

Yep , it's full of opportunity . There's no

39:13

reason to leave . It's

39:15

a very small industry , smaller

39:19

than you think and once

39:22

you start meeting everybody , the

39:25

opportunities just become more available

39:27

.

39:27

Yeah , yeah

39:30

, carrie what was the sale

39:32

that you learned the most from . If

39:35

you went back and said this sale was

39:38

such a meaningful and educational

39:40

experience , what was that sale that was most

39:43

educational ?

39:45

Yeah , I think I almost feel like you learn

39:47

more from the deals you lose than the deals you win honestly

39:49

. Yeah , I think I almost feel like you

39:52

learn more from the deals you

39:54

lose than the deals

39:57

you win honestly . So I think , yeah , I could talk about a

39:59

deal we won , but I really do think the

40:01

deals that you don't win are the ones where you

40:03

learn . Ok , here's the gap and here's what

40:06

we need to do to close a future sale

40:08

. So I

40:10

think I've

40:12

learned a ton . Really

40:15

, back in the early first

40:18

couple of weeks actually , I had at

40:20

Trucker Tools this

40:25

isn't even a sale , but it was that

40:28

we lost a customer , a really large customer , top 20 brokerage

40:30

, very tech forward . It was a huge deal , one of our biggest

40:32

load tracking deals , and I just started at the company . So I had really getting up

40:34

to speed and I'm like , oh well , this is too bad , I've got to

40:36

figure out what's going on . So I hopped

40:38

on a call with one of their senior

40:40

decision makers and turned out that

40:43

it was fun to understand . Hey , what

40:45

happened here ? How did you decide to leave us ? Why

40:47

don't we win this renewal ? And it

40:50

was really all about ELT tracking and

40:52

I'll be completely honest , that was not something that we had really

40:55

prioritized Back

40:58

when . When I was starting a business , you know we

41:00

were always mobile first tracking solution . And

41:02

I am so grateful that that happened

41:05

so early on in my tenure because it was definitely

41:07

like the kick in the rear end

41:09

that I needed to say OK , we've got to make moves

41:11

fast because if we don't

41:13

, we're not going to exist as a load tracking business

41:16

in a year or two If we don't

41:18

solve this massive product gap we have

41:20

now . So we started really doubling

41:22

down on our ELD team and standing up an

41:24

entire organization to support onboarding and

41:26

figure out how do we do this better and different than some of our competitors

41:29

are doing . Organization to support onboarding and figure out how do we do this better and

41:31

different than some of our competitors are doing . And you know , three years later , I think we're

41:33

getting noticed all the time now for what we've built

41:35

from the ELD world . So I think

41:37

losing those sort of sales or losing

41:39

a customer is an absolute punch

41:41

to the gut because you know how hard you work to bring

41:43

them on board . But in this case I think

41:45

it was actually it ended up being good

41:48

for us because it it

41:50

led to this whole new development of

41:52

a whole new part of our product and has totally changed

41:54

our product strategy . So that's

41:56

, that's the deal I'd say I learned the most from

41:58

.

42:00

Going off on that a little bit . You know

42:02

what's the most important sales lesson or

42:05

lessons that you learned since becoming

42:07

CEO . You know things that you

42:09

didn't realize about sales before that , that

42:13

you now grasp or that you now

42:16

hold dear .

42:19

Yeah , I think

42:21

that sales is . Yes

42:24

, you know we talked about selling ourselves and

42:26

showing up well , and the interpersonal nature

42:28

of it . That is absolutely important . But

42:35

sales is a really really technical science as well , and appreciating what goes into orchestrating

42:38

a large deal where you've got five

42:40

, six , seven stakeholders involved on the customer

42:42

side , maybe two to three on your own internal

42:44

side , how

42:46

important it is to be writing a really really tight

42:49

process there , and how that

42:51

can make or break you as an organization , how

42:54

, when it comes to sales , it's not just

42:56

about kind of showing up and taking someone out

42:58

to lunch and really getting their buy-in as , oh , we're

43:00

buds . That's not what sales is about . Sales is about

43:02

building an ironclad business

43:05

case for someone to help them solve a

43:07

very , very specific problem , and

43:11

kind of that problem orientation

43:13

, as opposed to I'm selling this

43:15

whole feature and this whole product set . Now

43:17

we are selling a couple of solutions to

43:20

specific pain points has

43:22

been a big shift for me when I think about how I sell

43:24

as a CEO .

43:27

Yeah , that's fantastic . I couldn't

43:30

agree more . I mean , it's the big

43:32

sales come from specificity

43:35

. Did I say that ? Right , it's got lots

43:37

of syllables in it , but it's

43:39

being able to pinpoint an exact ROI

43:41

and make it real . And that comes out

43:43

of the exact use case . And it's

43:46

this another kind of contradictory

43:49

sort of stance where you have , on

43:51

one hand , it's not personal

43:54

right , it's not you and

43:56

your thoughts and opinions , or your customers

43:58

thoughts and opinions , it's no , there's a problem

44:00

and this problem needs to be fixed

44:02

, and either your technology does

44:05

that or it doesn't like it's one

44:07

or the other . So there's an impersonable

44:09

, impersonal aspect to it

44:11

all . But there's also a personal aspect

44:13

in that the other side has to have

44:15

trust that they can believe that what you're

44:17

saying is true and honest

44:19

and geared towards solving that problem . So

44:23

there's this weird kind of dialectical

44:26

thing happening where it's about you

44:28

and the trust and them having trust in you

44:30

, but it's also not about you

44:32

or them . It's mostly about solving a problem

44:35

.

44:36

Yeah , and that's what's going to win you . A deal is solving

44:39

that problem and doing it in a very specific

44:41

, pointed way . They're

44:44

only going to be interested in doing that if they trust you

44:46

. So that's kind of the door opener , but

44:48

it's not going to close the deal .

44:52

Yeah , I think a lot of people gauge salespeople on their likability in a lot of ways

44:54

or how good they are

44:56

at getting in front of people . But there's that

44:58

back half of it that

45:00

you actually have to fix the problem right

45:03

, yep . So you

45:05

have to actually have a good solution . People can go

45:08

have lunch with you all the time and enjoy themselves

45:10

, but if you don't have the capabilities

45:12

to fix that problem , that you

45:14

don't have the solution . That's where it

45:16

ends and it's going to end there every single time

45:18

.

45:19

Exactly , exactly .

45:21

Yeah . So , carrie , where can our

45:23

listeners find you ? How can they

45:26

get in touch with you ? How can they learn more about Trucker

45:28

Tools ? Yeah , what's the best way for people to reach you

45:30

? How can they get in touch with you ? How can they learn more about Trucker ?

45:32

Tools . Yeah , what's the best way for people to reach you ? Yeah , find me on LinkedIn Kari

45:34

Jablonski spelled like it sounds

45:36

and on Twitter as well

45:39

. Same , my handle is just my name . Or

45:41

feel free to shoot me an email at kjablonski , at truckertoolscom

45:44

. Love hearing from folks . Thank you , I had a great

45:46

time .

45:46

Yeah , thanks for joining , gary . Always a

45:48

pleasure speaking with you . Every

45:57

time I'm going to various conferences , you're always one of the people I'm hoping to run into to

45:59

say hi and catch up if we have time . So pleasure having you on this on the show and

46:01

thanks again , really enjoy the conversation

46:04

. We'll have to have you back . I feel like there's more stories

46:06

that we can dive into . So , yeah

46:09

, thanks for your time

46:11

today .

46:12

Thank you both , I really appreciate it .