June 4, 2025 • 33 mins
TMSA’s On the Move Podcast – Featuring Lexi Farris
In this episode of TMSA On the Move, we sit down with Lexi Farris, Director of Strategy at Upwell and a speaker at the upcoming TMSA ELEVATE Conference. With a career rooted in sales and business strategy, Lexi brings a sharp, insightful perspective to the complex challenges facing transportation and logistics companies today.
She shares how her experience on the front lines of sales has informed her approach to high-level strategy, and how leaders can stay agile in an industry that’s constantly evolving. Lexi also gives us a preview of her ELEVATE session and what attendees can expect to learn.
Check out the Transportation Sales and Marketing Association (TMSA) website or engage with us on LinkedIn.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:25):
Hello everyone, welcome to On the Move, a show
where we share transportation,sales and marketing success
stories.
I am Jennifer Karpis-Romain,executive Director of the
Transportation Marketing andSales Association, which is a
trade nonprofit educating andconnecting marketing and sales
professionals in the space, andtoday on the show, I'm excited
to have Lexi Ferris, who is theDirector of Strategy at Upwell.
(00:48):
Welcome to the show, lexi.
How you doing today.
I'm good.
Thanks for having me, jen.
I'm excited to have you on theshow.
We met a few weeks ago and soit's been great to get to know
you, and we started talking andI was like, oh, you should
immediately come on the show,because I feel like there's so
many things that we can talkabout.
So I do want to start with yourcareer journey.
(01:09):
So how did you get intotransportation and logistics and
then what led you to yourcurrent role at Upwell?
Speaker 2 (01:15):
Sure.
So I actually got my start inlogistics through Worldwide
Express, so their truckloadoffice happens to be local here
in Kansas City, so it washonestly a really great place to
launch my career.
I had like the opportunity towork directly on the customer
side, so with shippers,specifically like enterprise
level customers, so that gave melike a front level seat, you
(01:39):
know, to everything that wasgoing on.
One of the really cool thingsabout Worldwide, too, is like
they have like suchcomprehensive training, so they
really just like throw you intothe industry but they teach you
as you go.
So I thought that was reallygreat.
Like, for example, when Istarted there, that was when
ELDs were coming out and soeveryone was in this panic and
(01:59):
I'm like why is everyone in thispanic?
Like technology, this is cool,this should be great.
And it wasn't until like monthslater that I understood like
what those ELDs were reallygoing to do for the space and
like what kind of disruptionwhether positive or negative
that was going to do.
So I spent four years there andthen I actually jumped into
startup life.
(02:20):
I joined a company called Denimand they are aintech company
focused on like helping brokersand carriers with like their
cash flow problems.
Um, I wore many hats across therevenue organization, you know,
I was ultimately their directorof sales and, like, denim will
always hold a special place inmy heart because it's how I got
into startups, it's how I like,found my passion, that's what I
(02:41):
love doing and that's when Ilearned, like you can work
outside the box a little bit,and it was, you know, fast paced
, high growth where I had theopportunity to lead, like
go-to-market strategy, salesefforts, work closely with
customers, things like that.
It just like deepened myappreciation for the ex, you
know, the industry.
Um, and then that journeyeventually led me to my second
(03:02):
startup, upwellwell, where I nowserve as the director of
strategy.
How I got here?
I was following Charlie Dahoney, one of our founders and CEO,
on social media.
I was, like immediately drawnto, like what he was building.
I recognized like right awaythat, like this was something
that had like high potential,high growth, something I wanted
to be a part of.
And so, long story short, Ireached out to Charlie, shot my
(03:25):
shot and here I am.
The rest is history.
Speaker 1 (03:29):
I love that.
I do think there's somethingabout like the hustle and bustle
of a startup that that's justso fast paced.
Like I can get really bored.
I always laugh because TMSA hasbeen here for over 100 years
now but because I took over acouple of years ago new
management, new structure, it'svery much kind of like that
startup feel, that small, youknow, headquartered kind of feel
(03:50):
, and but there is something toit because you don't get bored
and you get to put your hands ineverything and you get to
expand yourself and expand yourbrain.
Like I love how you said oh,you get to think outside the box
because do, because you have to, because sometimes the box
isn't even there so you have tomake it.
Speaker 2 (04:07):
So the thing that I always say is, like you just got
to be scrappy, like, bring outthe scrappiness.
That's how you get through astartup life.
Speaker 1 (04:17):
Now that you are at Upwell, can you tell us kind of
what Upwell does and how youhelp your clients tackle their
challenges?
Speaker 2 (04:24):
Sure, so we are focused on fixing like a very
overlooked but really painful,you know part of the freight
logistics lifecycle.
So we focus on accountsreceivable.
We're building like aninfrastructure to automate, you
know like invoice submission,document matching,
reconciliation, so logisticscompanies can get paid faster.
(04:46):
We do this through acombination of like AI and LLMs,
large language models and likerules-based logic.
My cat wants to join thismeeting Perfect To extract
standardized like informationfrom like free documents,
whether it's like an email, pdf,scanned paperwork, e, edi files
.
Um, again, sorry for the cat,everyone loves animals, so I
(05:09):
know, right, I mean, he justwants to be freight famous.
Um, our system, as you know,like map that data to like payer
requirements.
It flags discrepancies andensures invoices are like fully
audit ready before they ever goout the door.
So it's a space that's beenunder invested in for decades
and we're changing that bygiving you know back office
(05:32):
teams the tools they need tomove with like more speed and
precision and, you know, speedup their processes.
Speaker 1 (05:40):
I think that's fantastic.
One of the things I talk a lotabout is just the alignment at
companies, and it's not justsales and marketing teams.
And when you think about thecustomer experience, the piece
people never include which Ialways like go on my soapbox and
talk about is the billingprocess, because your sales team
can be the best, your customersupport people can be the best,
(06:01):
but you want a consistentexperience, and if your billing
process is super painful, peopleare going to remember that too,
and it's always a piece of thatpuzzle that Noah talks about.
So I think that's great thatyou guys were like no, this is a
pain point, we can solve it.
This is where we're focusing it.
I like that because you'reright.
Like not, that isn't always afocus.
It's always you know, oh, howcan we streamline things in
(06:24):
other areas?
But people need to get paid.
People need to pay their bills.
It's the basic piece.
Speaker 2 (06:31):
I mean it's definitely overlooked because
you know it's not like thesexiest thing to focus on.
But at the end of the day, ifyou don't focus on it, it can
have some pretty bad you knowoutcomes for you Absolutely, and
so through your experience inthe industry you've held roles
in both sales and strategy.
Speaker 1 (06:48):
So how has your experience in sales kind of
shaped how you approachstrategic decision-making today?
Speaker 2 (06:55):
Yeah, I think you know the experience in sales is,
in my opinion, almost needed torun any sort of like strategy
role.
It grounds you in like the realworld customer needs and like
you find out what actually movesthe needle, because you're
talking to these customers everyday.
You know when you're in salesyou're on the front line, you're
(07:16):
hearing objections, you'reseeing like where messaging
maybe isn't hitting and you'relike the one that can provide
that like direct feedback loop,and so that's kind of what
taught me how to like cutthrough the noise.
You know, like ideas like thatlook good on paper but aren't
something that, like a team canimplement, is not going to do
anything.
So being in sales has made melike incredibly outcome oriented
(07:38):
and strategy like it's easy toget caught up in, like the
framework and the long termplanning, but the sales
background reminds me that, likeevery decision like ultimately
needs to support like revenuegrowth, customer satisfaction or
like operational efficiency.
So I try to bring that samelike you know, thought process
towards action and clarity intolike strategic planning, like
(08:00):
how will this land with thecustomer?
Will this empower the salesteam?
Is you know, is this solvinglike an actual problem?
Like is this something weshould spend time on, so like
and sure like.
It taught me to thinkstrategically practically and
that's made me a better partneracross, like go-to-market
strategies with product teamsand leadership teams, things
like that.
Speaker 1 (08:22):
I think it's really important that you what you were
saying and it makes me thinkabout how sometimes we can see
strategies that are built thatare more theoretical than
actually like being able toexecute on.
So how do you make sure thatyou're not like, oh, this is the
strategy, this is the plan, butactually then make it
successful for your sales teamsto be able to then take it out
(08:43):
out, sell, move forward with itabsolutely.
Speaker 2 (08:50):
I mean, it's a big distinction, right?
Because, like, just because itlooks great, sounds great, again
like if it can't be executedlike it's essentially useless.
So for me, like you, the numberone thing is like you really
have to have alignment with thesales team from day one.
So, like before you even putanything to paper, you need to
spend time.
Or I spend time like seeing howthey're selling, like what's
working, where are they gettingstuck?
What objections are theyhearing?
What is missing, like is ittools?
(09:12):
Is it messaging, like whatneeds to be changed.
And then I also look at like thefull funnel to like what is the
data telling us, like dealvelocity, win rates, conversion
points, like it gives me like aclear picture of where strategy
can like actually move theneedle.
And then, when I'm building astrategy, I'm constantly asking
myself things like is this goingto be helpful for the rep?
(09:34):
Or like is it just more noise,like is it going to complicate
the sales process?
So, again, I focus on likeclarity, simplicity, enablement,
whatever the levers are, andjust make sure they're clear and
actionable.
And then, after that's built,you know you can't just like
pass it off from there becausethe strategy doesn't work again
unless it's executed it'sworking.
So I'll make sure I like joinsales calls, enablement sessions
(09:57):
, training sessions, juststaying really close, regularly
checking in what's sticking,what still might need to be
adjusted, things like that, justto make sure you know the sales
team's like fully equipped andsupported.
Speaker 1 (10:09):
I think that's really sound just advice for anyone
that is either building salescollateral or working in sales,
or even on the marketing side,going into those sales calls,
listening to the process, makingsure that what you're doing is
what's being executed on, andsame with like.
When I was in marketing, Iliked going on sales calls, I
(10:29):
liked going to trade shows andhearing how the sales team
pitched it, because you want,you know that messaging to align
and so if you're not doing thatyou're going to, there's going
to be just a mismatch on like,what you're saying on the
marketing side versus what getsexecuted.
And then same with like, theactual building of the strategy.
So I think that's great.
Speaker 2 (10:46):
Totally there's.
I think there's this connectionthat sometimes people don't
think about, which is howclosely, like marketing and
sales teams need to worktogether, because if one is
putting on a different messagethan the other, then like
there's misalignment, likethere's no clarity on what the
actual you know point or whatwe're trying to get across as,
like a company, I think that'stoo really true on like the
(11:12):
capacity side of things too.
Speaker 1 (11:13):
Like if there's certain routes or certain
functions that you really wantto be selling, if your marketing
doesn't know that, then theymay be promoting the things you
don't have capacity for, whichis terrible.
And then, like on the tech sideof things, or if you're
expanding new products, newcapabilities, having a proper
roadmap because I know that wasthe thing that had happened to
(11:33):
me in the past when I worked intech they'd be like, okay, we're
launching a new product.
I'm like okay, but like whatdoes it do?
Like what problems do we set?
Like you know, we need a littlebit of a ramp up, and so we got
way more sophisticated in that.
But because I feel likesometimes then I'll be like just
hand it off, like let's startpromoting, but we need to know
basically, why are we doing it?
When is it?
And like when is it being betatested versus when is it
(11:54):
actually ready for launch foreveryone, because those are
different things too.
And like how you market message.
Speaker 2 (12:00):
So I think that alignment is incredibly
important across all those teamsyeah, and I think that brings
in another whole part of thepuzzle is like your product team
, which I didn't really mention,but like they have to be on the
same page too.
Like if we're marketing thingsthat like aren't on the roadmap
or we're selling things thatlike is not what our focus is
right now too, like that notonly creates, like this
(12:20):
misalignment with your customers, but it also like internally,
it's like what is the focus?
Speaker 1 (12:28):
And if everyone's focusing on different things,
then like you're never going toget to the same end goal,
Absolutely.
What are some of the biggestshifts happening right now in
the industry that sales andstrategy leaders need to be
paying attention to?
Speaker 2 (12:39):
That's a good question.
I think there's so many and Ithink that's what's like so
exciting in this industry islike everything changes.
One of them, I would say, islike more specific to like what
I'm doing now, but I thinkthere's like this growing
recognition that operationalefficiency like extends, like
all the way through, likebilling payments receivables,
(12:59):
like most companies areinvesting in, like automating
these back end workflows,because the manual processes are
dragging down margins, they'reslowing cashflow and I think for
like a sales or strategy leader, that means you need to
highlight value in unexpectedplaces, like faster invoice
reconciliation or like lowerDSOs as like real, like return
(13:21):
on investment drivers.
The other thing that I think isbig right now is there's a ton
of M&A activity.
There's more strategicpartnerships, a push toward that
platform thinking Like peopledon't want their tools to live
in silos.
They want them to be like partof this, like larger ecosystem,
and I think that impacts how yougo to market.
Like buyers want fewer vendorsand more end to end value.
Speaker 1 (13:44):
So, like partnerships , integrations, positioning
becomes just as important aslike the product itself
(14:18):
no-transcript on the marketingand sales side, like making sure
that when those activitieshappen, that you are relaying
that to your customer and how itwill affect them.
Because if you merge or you getacquired, they're probably like
, am I, I gonna have the sameaccount manager?
Like how to like, and there'ssome of those pieces that I
(14:40):
think gets left out and peopleforget about.
A lot is just because Iremember this is totally
separate.
But we were working withsomebody and our account manager
pretty much sent us an emailthat just said they were leaving
the company, effective that day, and I was like what, what does
this mean?
Like I who is taking over ouraccount?
Like who am I supposed to callwith questions?
(15:01):
Like and, um, I knew who hermanager was and that's so I
asked, but outside of that, itwas just there was limited
communication, and so I feellike that communication plan can
be.
I know, obviously before thepaperwork's fine, you can't tell
people and that's totally fine.
But then once it's announced,make sure you have that
communication ready.
Your sales team, your marketing, your product everybody knows
(15:23):
how to answer the questions isready, especially those account
managers, so that people know,hey, we're doing this to serve
you better, and this is the waywe're going to do that.
I think that's incrediblyimportant.
Speaker 2 (15:34):
Absolutely.
In a way, it's almost like arebrand incredibly important.
Absolutely.
In a way, it's almost like arebrand.
You have to treat it like oneand make sure you have the right
communications ready to go outto the team, or, if it's
something that, like you know,affects you in a positive or
negative way, making sure you'relike relaying that message the
right way.
Speaker 1 (15:49):
Absolutely.
So I'm going to shift gears alittle bit because I'm really
excited.
So this we're when thislaunches it june 2nd or
something.
So we'll be just days away fromelevate um and you are coming
this year and you're speakingand you're um co-presenting with
kevin coombs, who's evp ofsales at chain, and you guys are
(16:10):
tackling a session called fromno to not yet turning maybes
into momentum and relationshipsinto revenue, and this was
actually a session that us attmsa really wanted to be
presented, because this is areally tough market right now
and it's really easy to get sadand want to give up and then,
you know, just be frustrated allthe time.
But that's not effective forour sales team or our momentum
(16:33):
or anything.
So building those relationships, thinking how to execute on
that and, to you know, keep abit of a positive vibe through
that can be really challenging,but it's so important now more
than ever.
So what can people expect fromthat session and why do you
think it is an important topic?
Speaker 2 (16:51):
Yeah, I'm excited not only to speak but also to
attend.
I've actually never been to aTMSA elevate event, so this will
be a first for me, which isreally exciting.
So I'm excited to meet you inperson too.
But I think the title of thesession says a lot of it.
Like from no to not yet.
So it's about recognizing in.
Like today's market, dealsrarely move in like a straight
(17:13):
line anymore.
Buying cycle is longer,decision makers are more
cautious and like the initial nois most the time, just like a
reflection of timing.
You know something our ceo saysa lot is like most um, sales
cycle ends in a no decision.
Like not a no, it's the nodecision.
Like they're not sure they'renot moving forward.
Or like the timing just isn'tright, um, and I think that's
(17:37):
just like a reflection of timingpriorities or like lack of
clarity.
So I really don't believe, mostof the time, that it's just
this big lack of interest.
What people can expect from thissession is just like a real
tactical conversation.
We're going to talk about howto, you know, reframe objections
, how to stay top of mindwithout being pushy, how to
build relationships that will,like eventually turn into
(17:58):
revenue, even if it takes longerthan you'd like.
So, again, like you said, Ithink this topic is really
relevant right now because theteams that are winning in this
market are the ones who know howto like build that trust, build
those relationships.
They have patience and they'reconsistently like building that
momentum.
Speaker 1 (18:14):
Absolutely.
There is still time to register.
If you are thinking, hey, maybeI should go.
Absolutely, join us Austin,texas, june 8th through 10th,
and I'm really excited about it.
So I'm going to pivot somewhereelse too, which was part of why
I wanted you to come on theshow, because when we were
talking in the past, a couple ofcouple weeks ago we were
(18:37):
talking about what it's like tobe a female in the industry and
that there's spaces for there'sa ton of now, um groups for
women in the industry the womenin logistics, um supply chain,
um, women in trucking, all thatand they're lovely and I
participate, I go to women intrucking, I do all that stuff.
But part of it is we want tomake sure, as women in the
(18:59):
industry, we're not justparticipating in those things,
that we're being acknowledged asjust a professional in the
space.
And I know that's somethinglike.
When we started talking, werealized that we were both
pretty passionate about, becauseit can feel like that sometimes
, that it's like, okay, now wehave all these powerhouse women,
but I just want to be apowerhouse human.
That's it.
(19:19):
And how do you think that theindustry, our male colleagues,
how can we better be positioningthat message now that we are
getting recognition that thereare really great females in the
industry.
But how can we pivot and makesure that it's not just that
we're women, we're just great,awesome people?
Speaker 2 (19:36):
awesome people.
Yeah, absolutely, um, excuse me, like you said, I think there's
definitely been progress,especially in like the 10 years
that I've been around in thesales and logistics space here.
But I think, ultimately, like,when it comes to creating space
for, like women in logistics andsupply chain, um, the next step
(19:58):
is making sure like we're notjust like inviting women into
the room but we're elevatingthem into like leadership roles
and decision making roles, likegiving them a seat at the table,
and I think the biggest part ofthat is empowering women to
believe that they belong there.
And I think that's a bigmissing piece of the puzzle.
And, you know, I'll be honest,I've not always been the best
(20:19):
example of that Like for years,like I've stayed in the
background, avoided speaking upin like large settings, past
opportunities to my team.
You know, like this is thefirst podcast I've ever done,
for example.
Speaker 1 (20:32):
I know you talk about this.
Speaker 2 (20:35):
Super awkward for everyone listening because it is
my first time.
But you know, it wasn't that Ididn't care.
It's that I didn't know that,like I was the person someone
could or should or wanted tohear from.
But I realized that if I wantmore women to step up into
leadership roles, like I need toshow up as one too.
So, again, that's why I'msaying yes to podcasts like this
(20:55):
, that's why I'm doing thespeaking event with you and yeah
, I mean it feels a littleuncomfortable sometimes because
but ultimately, like, visibilitymatters and if I can push
myself to step up, maybe ithelps someone else see that they
can too.
Or it'll help you know, a malein a different company to push
maybe a female that is in aleadership position or one
(21:17):
that's on the path to be in oneto do the same thing.
And, like you said, I don'twant to be known as a woman in
logistics.
I want to be known for thevalue I bring.
But to get there we need tokeep building the systems, the
confidence, the community thathelps more women believe that
like they do belong at the top.
Speaker 1 (21:35):
Yeah, I think, from what I see, there's more and
more women coming into theindustry but, not as many that
are rising up and that is thepiece.
And so I loved when you werelike, yes, I will accept this
podcast, I will speak at yourshow, especially on the sales
strategy side.
Marketing is a little bitdifferent.
(21:55):
It is more female leaderfocused and heavy, but we need
to get there in all areas of thebusiness and I do think part of
that is, yeah, like I love, youare the director of strategy
and so people are going to seeyour name attached to that and
be like oh, there is careerpaths and there are teams that
can believe in that.
And I do think that havingthose conversations with our
(22:17):
male counterparts believe inthat.
And I do think that havingthose conversations with our
male counterparts it's not likedon't just check a box and hire
a woman to your team skill, likemake sure she's growing her
skills and that there's aposition, like you said, as seat
at the table and having thoseconversations.
And yes, like I want to makesure we don't have a disconnect
between where we're not havingthose conversations with men in
the room, like I even wastalking about this yesterday on
(22:37):
a different podcast, but myhusband works in manufacturing
and there's like a I forget whatit's called, but it's basically
supporting women inmanufacturing and he's a part of
the group and I was surprisedand I was like why?
And he was like I can't likereally be married to you and
watch everything that you do inyour career in almost all male
dominated spaces and then be amale.
(22:57):
That's not supporting the women.
And he's like cause, you alwayssay the men have to be
supportive and have to likeleave space at the table and be
part of the conversation.
I was like, oh, that's good,you, you clearly listen when I
go on rants at home, that'sgreat, but I loved them seeing
that in action and I do thinkthat that's part of what needs
to happen.
Like there needs to be.
Like there needs to be.
Like I love when there is like awomen in logistics lunch and
there is men in there becausethey're supporting the cause and
(23:20):
they're not like afraid to be,like yes, we love the women in
the space.
They're awesome, you know, andso I feel like that kind of
dialogue is really important too, because if we're not having
the conversations, then we'rejust because you don't want to
just be in a room full of peoplejust like you saying the same
things.
That's not where change happens.
It's when you're having thoseconversations and you're able to
push the needle further.
Speaker 2 (23:42):
Yeah, and I think a step further is I think it'd be
great to see a man lead one ofthese organizations.
I know that's not the point wewant women in these like
leadership roles but I think itwould be great to have more of
like a male presence in theseorganizations, so not just
people that you know like attenda lunch or jump on a podcast
with someone who's like very,very heavily involved in like
(24:04):
the events that are going on,like the one that's maybe like
helping create theseopportunities or connect women
to the right places, things likethat.
Speaker 1 (24:12):
Yeah, I think that kind of stuff is important.
Or like I would love to see,like I love mentoring younger
females to help like cause kindof what you said.
I didn't always take theopportunity, I didn't always
advocate, like I want to helpthem navigate that in a way that
I may have not at the beginningof my career, but I also feel
like our male, like ourleadership males, should mentor
(24:36):
younger women too and just belike this is what I did, and
then vice versa, like I wouldlove to mentor like a younger
male coming into the industrytoo and having that, like it
shouldn't just be woman to womanto do those things and you can
also have like multiplementorships.
So if I'm mentoring one personand she is a female to help her
learn how to advocate forherself, I could also mentor a
(24:57):
younger male, teaching him howto be more adaptive and more
open to different types ofpeople on a leadership team or
how to, you know, grow togetheror things like that.
Like it doesn't have to be justone type of thing.
In fact, it's better when it'sdiversified in that way.
So I think that those are thepieces that I'm looking forward
to as we move along, we'regetting more momentum of these
(25:19):
things, but then, yes, how canwe actually incorporate that to
make better business practices,instead of just a celebration
that we're here Because we'rehere to stay?
So how do we?
Speaker 2 (25:28):
Absolutely.
And I will say I do feel likeI've been really lucky in this
space, like I have neveractually had a female like
leader above me.
I've always had male leadersabove me.
But I would say I mean theproof is where I'm at today in
my career, like they've reallysupported me.
I've had some really greatbosses, some really great
(25:49):
leaders, not only in just likesales and strategy departments,
but in like operationsdepartments, who have like like
when I started at Denim, like Ididn't know anything about
factoring, like someone taughtme that and a lot of that was
like at the time, our VP ofoperations.
So there are these things outthere.
You got to find the right spotand the right people to work
with yes, I the job I heldbefore TMSA.
Speaker 1 (26:14):
I had the best boss and I was director of marketing,
so I had a seat at the tableand I would be like, but we're
also a tech company that has afemale leader.
We should leverage that.
He's like you don't have yourjob because you're a woman.
I'm like, I appreciate that.
But also we can also like isthere something we can do to
leverage?
But I always appreciated thatbecause if I knew that's not why
(26:34):
I had my job, I knew that's notwhy he valued my opinion.
But I liked that he was alwayscognizant, that like that could
be something I could feel, andso he would like reiterate that
that wasn't it and I would get.
And even coming to TMSA, peoplehad asked like I took older,
like I took over for an oldermale, and so for me it's not
even being a woman, it's my agetoo.
(26:56):
I'm under 40 in executiveleadership.
In this space that's also notsomething you see all the time,
and so it's not always theeasiest thing to navigate,
because I'm learning as I go.
And.
But you have those supportsystems, you have those people
you can go to.
You have those people that willnurture you and help you, and I
do think that's incrediblyimportant, like what you're
(27:17):
saying, like I've been able tonavigate my career because I
have had these like championsfor me, which I think is really
important and great, and love tosee more of that, and so I'm
glad that you're kind of sharingyour story and getting more
visibility into that, so thatmore people feel empowered to do
the same.
Speaker 2 (27:34):
Yeah, absolutely.
I mean, you might hear my dogbarking in the background now,
but I think you know youmentioned something too.
It's like the age thing comesinto it a lot as well.
You know, like I was in theseleadership roles when I was in
my thirties, so, um, andhonestly, before that, um, in my
late twenties.
So sometimes it's like not onlydo you have to have someone
(27:57):
that's supporting you and likerespecting your opinions as you
know, a female in the industrybut they also like they're
looking at your age and like Ifeel, again, I've been really
lucky to have these leaders that, like they didn't look at me as
this younger woman who theydidn't care about their her
opinion.
Like they looked at me andthey're like, no, we want your
opinion.
Like we want to elevate you, wewant to like have your help in
(28:21):
all this decision-making.
Speaker 1 (28:22):
And again, if I didn't have the right leaders,
whether that was at WorldwideDenim and now at Upwell, I
wouldn't be where I am right now, yeah, and I think, noticing
that and that was my my old bossactually came on this podcast a
couple of weeks ago and I likeasked him all the normal
questions and things and then,but at the end I'm like I do
really want to reflect and talkabout it because people see me
(28:44):
now as the executive director ofTMSA.
He met me as a two monthspostpartum, first time mom who
refused to work in an office orfull time and he was like, yes,
sign me up.
And most people wouldn't have.
But he like through ourconversations he heard okay,
this is the vision she couldhave.
She's really like I dounderstand industry, I wanted to
(29:05):
apply different things.
Like we had really gooddialogue in our job interviews
and he could tell I waspassionate and didn't care.
He was like let's see whathappens.
And not a lot of people wouldhave taken that risk.
But the risk is okay, it worksout or it doesn't, and you
figure it out in a couple monthsand then whatever.
But I feel like it's always goodto reflect on those people who
(29:27):
did help you along the way tomake sure that we're doing the
same for other people too.
Absolutely did help you alongthe way to make sure that we're
doing the same for other peopletoo, absolutely.
So I appreciate that you had anopen dialogue around that.
I feel like some of it istrickier to have a conversation
about, because we want to besupportive and I think sometimes
people are afraid to say thewrong thing and so then they
don't say anything, which thendoesn't help anybody.
(29:48):
But yeah, I do have one lastquestion, and this is what I ask
everybody who comes on the show, and if you could go back in
time and advise a younger Lexianything and it could be
personally or professionallywhen would you go back to and
what would you say?
Speaker 2 (30:04):
I think this is more of like maybe like a general
answer, but it also works likepersonally and professionally.
So this may be like a littleunexpected coming from like
someone who's done like ageneral answer, but it also
works like personally andprofessionally.
So this may be like a littleunexpected, coming from like
someone who's done like arevenue leadership role, but I'm
definitely not that personwho's like talking about the
latest books they've read in theindustry or the ones that have
to do with, you know, strategyor sales.
(30:25):
In my free time I love to readlike, but give me something like
spicy or thrilling, likesomeone dragons over, like
something that says like 10extra pipeline title, and so,
that being said, there was onebook that stick with me, sorry.
Speaker 1 (30:40):
It's okay, we're humans.
You have a dog and a cat, it'sfine.
Speaker 2 (30:44):
You're like fairly quiet, so I'm like what's going
on today?
But, that being said, like onebook did stick with me.
It was called the Gap and theGain.
It was actually recommended tome by the CEO at Denim Bea and
it's all about like shiftingyour mindset to focus on what
you've already accomplishedrather than like obsessing over
(31:04):
how far you still have to go.
And so like it sounds simple,but it really hit me hard,
especially like in a startupenvironment where the goalposts
are like constantly moving, it'seasy to feel like you're never
doing enough or like you're notwhere you need to be.
And so if I could go back andgive me advice, it would be that
like don't live in the gap,celebrate the win and celebrate
the growth and the steps you'vetaken, even if you're not there
(31:28):
yet.
And I think that mindset hasmade me, you know more of like a
grounded leader, honestly ahappier human, and I wish I'd
learned it way earlier.
Speaker 1 (31:37):
I love that advice and it's definitely something
that resonates with me.
I know when I started here atTMSA our current board
chairperson, mark Dirks afterthat first year, I was like we
have so much more to do and he'slike you need to pause and I
really want you.
And so this is an exercise nowI do every October in like our
October in-person board meetingand I print out everything that
(31:59):
we've accomplished in the pastyear, because I don't do that.
I'm yes, I'm like okay, yeah,but we, but we didn't do this.
So this is what we have to do.
This is where I wish we were,and up until that exercise that
he forced me to do, because thenyou look at it, you're like
holy Toledo, there's so muchthat we have accomplished, so
much movement we have made, andso that definitely, I feel like
(32:21):
I need to read that book nowbecause that is something that,
like, really I'm terrible at,and even that's like yes, like I
will bulldoze through Elevateand and I will have to, like
someone will have to remind meat show to be like pause, look,
because I will just be like,yeah, okay, but this person
needs the cookie because they'retired you know, like I just oh,
it's probably me.
(32:42):
I probably need the cookie butlike I just like I just care so
much and I just, you know, keepmoving forward and you sometimes
just really forget to pause.
So I I think that's.
Speaker 2 (32:51):
Yeah, I mean I find myself like having to remind my
you know myself of that, likeweekly at least.
It's definitely a book that hasstuck with me and I think about
it a lot.
And I mean I'm not perfect.
I definitely still live in thegaps sometimes, a lot of the
times, but the point is like toat least like recognize it and
like take a moment and likereflect back.
Speaker 1 (33:13):
Love it.
Well, as a move to looking alittle into the future, if you
want to join us next weekend onthe move, I'll be interviewing
Don Friedle and really excitedfor you guys to see that
conversation and next week isElevate, so hopefully you guys
will all see us there.
Really excited for that,excited for you to come to tmsa
(33:34):
and be able to speak.
And thank you for coming on theshow today.
Yeah, thanks for having me havea good one you too.
Hello everyone, welcome to On the Move, a show
where we share transportation,sales and marketing success
stories.
I am Jennifer Karpis-Romain,executive Director of the
Transportation Marketing andSales Association, which is a
trade nonprofit educating andconnecting marketing and sales
professionals in the space, andtoday on the show, I'm excited
to have Lexi Ferris, who is theDirector of Strategy at Upwell.
(00:48):
Welcome to the show, lexi.
How you doing today.
I'm good.
Thanks for having me, jen.
I'm excited to have you on theshow.
We met a few weeks ago and soit's been great to get to know
you, and we started talking andI was like, oh, you should
immediately come on the show,because I feel like there's so
many things that we can talkabout.
So I do want to start with yourcareer journey.
(01:09):
So how did you get intotransportation and logistics and
then what led you to yourcurrent role at Upwell?
Speaker 2 (01:15):
Sure.
So I actually got my start inlogistics through Worldwide
Express, so their truckloadoffice happens to be local here
in Kansas City, so it washonestly a really great place to
launch my career.
I had like the opportunity towork directly on the customer
side, so with shippers,specifically like enterprise
level customers, so that gave melike a front level seat, you
(01:39):
know, to everything that wasgoing on.
One of the really cool thingsabout Worldwide, too, is like
they have like suchcomprehensive training, so they
really just like throw you intothe industry but they teach you
as you go.
So I thought that was reallygreat.
Like, for example, when Istarted there, that was when
ELDs were coming out and soeveryone was in this panic and
(01:59):
I'm like why is everyone in thispanic?
Like technology, this is cool,this should be great.
And it wasn't until like monthslater that I understood like
what those ELDs were reallygoing to do for the space and
like what kind of disruptionwhether positive or negative
that was going to do.
So I spent four years there andthen I actually jumped into
startup life.
(02:20):
I joined a company called Denimand they are aintech company
focused on like helping brokersand carriers with like their
cash flow problems.
Um, I wore many hats across therevenue organization, you know,
I was ultimately their directorof sales and, like, denim will
always hold a special place inmy heart because it's how I got
into startups, it's how I like,found my passion, that's what I
(02:41):
love doing and that's when Ilearned, like you can work
outside the box a little bit,and it was, you know, fast paced
, high growth where I had theopportunity to lead, like
go-to-market strategy, salesefforts, work closely with
customers, things like that.
It just like deepened myappreciation for the ex, you
know, the industry.
Um, and then that journeyeventually led me to my second
(03:02):
startup, upwellwell, where I nowserve as the director of
strategy.
How I got here?
I was following Charlie Dahoney, one of our founders and CEO,
on social media.
I was, like immediately drawnto, like what he was building.
I recognized like right awaythat, like this was something
that had like high potential,high growth, something I wanted
to be a part of.
And so, long story short, Ireached out to Charlie, shot my
(03:25):
shot and here I am.
The rest is history.
Speaker 1 (03:29):
I love that.
I do think there's somethingabout like the hustle and bustle
of a startup that that's justso fast paced.
Like I can get really bored.
I always laugh because TMSA hasbeen here for over 100 years
now but because I took over acouple of years ago new
management, new structure, it'svery much kind of like that
startup feel, that small, youknow, headquartered kind of feel
(03:50):
, and but there is something toit because you don't get bored
and you get to put your hands ineverything and you get to
expand yourself and expand yourbrain.
Like I love how you said oh,you get to think outside the box
because do, because you have to, because sometimes the box
isn't even there so you have tomake it.
Speaker 2 (04:07):
So the thing that I always say is, like you just got
to be scrappy, like, bring outthe scrappiness.
That's how you get through astartup life.
Speaker 1 (04:17):
Now that you are at Upwell, can you tell us kind of
what Upwell does and how youhelp your clients tackle their
challenges?
Speaker 2 (04:24):
Sure, so we are focused on fixing like a very
overlooked but really painful,you know part of the freight
logistics lifecycle.
So we focus on accountsreceivable.
We're building like aninfrastructure to automate, you
know like invoice submission,document matching,
reconciliation, so logisticscompanies can get paid faster.
(04:46):
We do this through acombination of like AI and LLMs,
large language models and likerules-based logic.
My cat wants to join thismeeting Perfect To extract
standardized like informationfrom like free documents,
whether it's like an email, pdf,scanned paperwork, e, edi files
.
Um, again, sorry for the cat,everyone loves animals, so I
(05:09):
know, right, I mean, he justwants to be freight famous.
Um, our system, as you know,like map that data to like payer
requirements.
It flags discrepancies andensures invoices are like fully
audit ready before they ever goout the door.
So it's a space that's beenunder invested in for decades
and we're changing that bygiving you know back office
(05:32):
teams the tools they need tomove with like more speed and
precision and, you know, speedup their processes.
Speaker 1 (05:40):
I think that's fantastic.
One of the things I talk a lotabout is just the alignment at
companies, and it's not justsales and marketing teams.
And when you think about thecustomer experience, the piece
people never include which Ialways like go on my soapbox and
talk about is the billingprocess, because your sales team
can be the best, your customersupport people can be the best,
(06:01):
but you want a consistentexperience, and if your billing
process is super painful, peopleare going to remember that too,
and it's always a piece of thatpuzzle that Noah talks about.
So I think that's great thatyou guys were like no, this is a
pain point, we can solve it.
This is where we're focusing it.
I like that because you'reright.
Like not, that isn't always afocus.
It's always you know, oh, howcan we streamline things in
(06:24):
other areas?
But people need to get paid.
People need to pay their bills.
It's the basic piece.
Speaker 2 (06:31):
I mean it's definitely overlooked because
you know it's not like thesexiest thing to focus on.
But at the end of the day, ifyou don't focus on it, it can
have some pretty bad you knowoutcomes for you Absolutely, and
so through your experience inthe industry you've held roles
in both sales and strategy.
Speaker 1 (06:48):
So how has your experience in sales kind of
shaped how you approachstrategic decision-making today?
Speaker 2 (06:55):
Yeah, I think you know the experience in sales is,
in my opinion, almost needed torun any sort of like strategy
role.
It grounds you in like the realworld customer needs and like
you find out what actually movesthe needle, because you're
talking to these customers everyday.
You know when you're in salesyou're on the front line, you're
(07:16):
hearing objections, you'reseeing like where messaging
maybe isn't hitting and you'relike the one that can provide
that like direct feedback loop,and so that's kind of what
taught me how to like cutthrough the noise.
You know, like ideas like thatlook good on paper but aren't
something that, like a team canimplement, is not going to do
anything.
So being in sales has made melike incredibly outcome oriented
(07:38):
and strategy like it's easy toget caught up in, like the
framework and the long termplanning, but the sales
background reminds me that, likeevery decision like ultimately
needs to support like revenuegrowth, customer satisfaction or
like operational efficiency.
So I try to bring that samelike you know, thought process
towards action and clarity intolike strategic planning, like
(08:00):
how will this land with thecustomer?
Will this empower the salesteam?
Is you know, is this solvinglike an actual problem?
Like is this something weshould spend time on, so like
and sure like.
It taught me to thinkstrategically practically and
that's made me a better partneracross, like go-to-market
strategies with product teamsand leadership teams, things
like that.
Speaker 1 (08:22):
I think it's really important that you what you were
saying and it makes me thinkabout how sometimes we can see
strategies that are built thatare more theoretical than
actually like being able toexecute on.
So how do you make sure thatyou're not like, oh, this is the
strategy, this is the plan, butactually then make it
successful for your sales teamsto be able to then take it out
(08:43):
out, sell, move forward with itabsolutely.
Speaker 2 (08:50):
I mean, it's a big distinction, right?
Because, like, just because itlooks great, sounds great, again
like if it can't be executedlike it's essentially useless.
So for me, like you, the numberone thing is like you really
have to have alignment with thesales team from day one.
So, like before you even putanything to paper, you need to
spend time.
Or I spend time like seeing howthey're selling, like what's
working, where are they gettingstuck?
What objections are theyhearing?
What is missing, like is ittools?
(09:12):
Is it messaging, like whatneeds to be changed.
And then I also look at like thefull funnel to like what is the
data telling us, like dealvelocity, win rates, conversion
points, like it gives me like aclear picture of where strategy
can like actually move theneedle.
And then, when I'm building astrategy, I'm constantly asking
myself things like is this goingto be helpful for the rep?
(09:34):
Or like is it just more noise,like is it going to complicate
the sales process?
So, again, I focus on likeclarity, simplicity, enablement,
whatever the levers are, andjust make sure they're clear and
actionable.
And then, after that's built,you know you can't just like
pass it off from there becausethe strategy doesn't work again
unless it's executed it'sworking.
So I'll make sure I like joinsales calls, enablement sessions
(09:57):
, training sessions, juststaying really close, regularly
checking in what's sticking,what still might need to be
adjusted, things like that, justto make sure you know the sales
team's like fully equipped andsupported.
Speaker 1 (10:09):
I think that's really sound just advice for anyone
that is either building salescollateral or working in sales,
or even on the marketing side,going into those sales calls,
listening to the process, makingsure that what you're doing is
what's being executed on, andsame with like.
When I was in marketing, Iliked going on sales calls, I
(10:29):
liked going to trade shows andhearing how the sales team
pitched it, because you want,you know that messaging to align
and so if you're not doing thatyou're going to, there's going
to be just a mismatch on like,what you're saying on the
marketing side versus what getsexecuted.
And then same with like, theactual building of the strategy.
So I think that's great.
Speaker 2 (10:46):
Totally there's.
I think there's this connectionthat sometimes people don't
think about, which is howclosely, like marketing and
sales teams need to worktogether, because if one is
putting on a different messagethan the other, then like
there's misalignment, likethere's no clarity on what the
actual you know point or whatwe're trying to get across as,
like a company, I think that'stoo really true on like the
(11:12):
capacity side of things too.
Speaker 1 (11:13):
Like if there's certain routes or certain
functions that you really wantto be selling, if your marketing
doesn't know that, then theymay be promoting the things you
don't have capacity for, whichis terrible.
And then, like on the tech sideof things, or if you're
expanding new products, newcapabilities, having a proper
roadmap because I know that wasthe thing that had happened to
(11:33):
me in the past when I worked intech they'd be like, okay, we're
launching a new product.
I'm like okay, but like whatdoes it do?
Like what problems do we set?
Like you know, we need a littlebit of a ramp up, and so we got
way more sophisticated in that.
But because I feel likesometimes then I'll be like just
hand it off, like let's startpromoting, but we need to know
basically, why are we doing it?
When is it?
And like when is it being betatested versus when is it
(11:54):
actually ready for launch foreveryone, because those are
different things too.
And like how you market message.
Speaker 2 (12:00):
So I think that alignment is incredibly
important across all those teamsyeah, and I think that brings
in another whole part of thepuzzle is like your product team
, which I didn't really mention,but like they have to be on the
same page too.
Like if we're marketing thingsthat like aren't on the roadmap
or we're selling things thatlike is not what our focus is
right now too, like that notonly creates, like this
(12:20):
misalignment with your customers, but it also like internally,
it's like what is the focus?
Speaker 1 (12:28):
And if everyone's focusing on different things,
then like you're never going toget to the same end goal,
Absolutely.
What are some of the biggestshifts happening right now in
the industry that sales andstrategy leaders need to be
paying attention to?
Speaker 2 (12:39):
That's a good question.
I think there's so many and Ithink that's what's like so
exciting in this industry islike everything changes.
One of them, I would say, islike more specific to like what
I'm doing now, but I thinkthere's like this growing
recognition that operationalefficiency like extends, like
all the way through, likebilling payments receivables,
(12:59):
like most companies areinvesting in, like automating
these back end workflows,because the manual processes are
dragging down margins, they'reslowing cashflow and I think for
like a sales or strategy leader, that means you need to
highlight value in unexpectedplaces, like faster invoice
reconciliation or like lowerDSOs as like real, like return
(13:21):
on investment drivers.
The other thing that I think isbig right now is there's a ton
of M&A activity.
There's more strategicpartnerships, a push toward that
platform thinking Like peopledon't want their tools to live
in silos.
They want them to be like partof this, like larger ecosystem,
and I think that impacts how yougo to market.
Like buyers want fewer vendorsand more end to end value.
Speaker 1 (13:44):
So, like partnerships , integrations, positioning
becomes just as important aslike the product itself
(14:18):
no-transcript on the marketingand sales side, like making sure
that when those activitieshappen, that you are relaying
that to your customer and how itwill affect them.
Because if you merge or you getacquired, they're probably like
, am I, I gonna have the sameaccount manager?
Like how to like, and there'ssome of those pieces that I
(14:40):
think gets left out and peopleforget about.
A lot is just because Iremember this is totally
separate.
But we were working withsomebody and our account manager
pretty much sent us an emailthat just said they were leaving
the company, effective that day, and I was like what, what does
this mean?
Like I who is taking over ouraccount?
Like who am I supposed to callwith questions?
(15:01):
Like and, um, I knew who hermanager was and that's so I
asked, but outside of that, itwas just there was limited
communication, and so I feellike that communication plan can
be.
I know, obviously before thepaperwork's fine, you can't tell
people and that's totally fine.
But then once it's announced,make sure you have that
communication ready.
Your sales team, your marketing, your product everybody knows
(15:23):
how to answer the questions isready, especially those account
managers, so that people know,hey, we're doing this to serve
you better, and this is the waywe're going to do that.
I think that's incrediblyimportant.
Speaker 2 (15:34):
Absolutely.
In a way, it's almost like arebrand incredibly important.
Absolutely.
In a way, it's almost like arebrand.
You have to treat it like oneand make sure you have the right
communications ready to go outto the team, or, if it's
something that, like you know,affects you in a positive or
negative way, making sure you'relike relaying that message the
right way.
Speaker 1 (15:49):
Absolutely.
So I'm going to shift gears alittle bit because I'm really
excited.
So this we're when thislaunches it june 2nd or
something.
So we'll be just days away fromelevate um and you are coming
this year and you're speakingand you're um co-presenting with
kevin coombs, who's evp ofsales at chain, and you guys are
(16:10):
tackling a session called fromno to not yet turning maybes
into momentum and relationshipsinto revenue, and this was
actually a session that us attmsa really wanted to be
presented, because this is areally tough market right now
and it's really easy to get sadand want to give up and then,
you know, just be frustrated allthe time.
But that's not effective forour sales team or our momentum
(16:33):
or anything.
So building those relationships, thinking how to execute on
that and, to you know, keep abit of a positive vibe through
that can be really challenging,but it's so important now more
than ever.
So what can people expect fromthat session and why do you
think it is an important topic?
Speaker 2 (16:51):
Yeah, I'm excited not only to speak but also to
attend.
I've actually never been to aTMSA elevate event, so this will
be a first for me, which isreally exciting.
So I'm excited to meet you inperson too.
But I think the title of thesession says a lot of it.
Like from no to not yet.
So it's about recognizing in.
Like today's market, dealsrarely move in like a straight
(17:13):
line anymore.
Buying cycle is longer,decision makers are more
cautious and like the initial nois most the time, just like a
reflection of timing.
You know something our ceo saysa lot is like most um, sales
cycle ends in a no decision.
Like not a no, it's the nodecision.
Like they're not sure they'renot moving forward.
Or like the timing just isn'tright, um, and I think that's
(17:37):
just like a reflection of timingpriorities or like lack of
clarity.
So I really don't believe, mostof the time, that it's just
this big lack of interest.
What people can expect from thissession is just like a real
tactical conversation.
We're going to talk about howto, you know, reframe objections
, how to stay top of mindwithout being pushy, how to
build relationships that will,like eventually turn into
(17:58):
revenue, even if it takes longerthan you'd like.
So, again, like you said, Ithink this topic is really
relevant right now because theteams that are winning in this
market are the ones who know howto like build that trust, build
those relationships.
They have patience and they'reconsistently like building that
momentum.
Speaker 1 (18:14):
Absolutely.
There is still time to register.
If you are thinking, hey, maybeI should go.
Absolutely, join us Austin,texas, june 8th through 10th,
and I'm really excited about it.
So I'm going to pivot somewhereelse too, which was part of why
I wanted you to come on theshow, because when we were
talking in the past, a couple ofcouple weeks ago we were
(18:37):
talking about what it's like tobe a female in the industry and
that there's spaces for there'sa ton of now, um groups for
women in the industry the womenin logistics, um supply chain,
um, women in trucking, all thatand they're lovely and I
participate, I go to women intrucking, I do all that stuff.
But part of it is we want tomake sure, as women in the
(18:59):
industry, we're not justparticipating in those things,
that we're being acknowledged asjust a professional in the
space.
And I know that's somethinglike.
When we started talking, werealized that we were both
pretty passionate about, becauseit can feel like that sometimes
, that it's like, okay, now wehave all these powerhouse women,
but I just want to be apowerhouse human.
That's it.
(19:19):
And how do you think that theindustry, our male colleagues,
how can we better be positioningthat message now that we are
getting recognition that thereare really great females in the
industry.
But how can we pivot and makesure that it's not just that
we're women, we're just great,awesome people?
Speaker 2 (19:36):
awesome people.
Yeah, absolutely, um, excuse me, like you said, I think there's
definitely been progress,especially in like the 10 years
that I've been around in thesales and logistics space here.
But I think, ultimately, like,when it comes to creating space
for, like women in logistics andsupply chain, um, the next step
(19:58):
is making sure like we're notjust like inviting women into
the room but we're elevatingthem into like leadership roles
and decision making roles, likegiving them a seat at the table,
and I think the biggest part ofthat is empowering women to
believe that they belong there.
And I think that's a bigmissing piece of the puzzle.
And, you know, I'll be honest,I've not always been the best
(20:19):
example of that Like for years,like I've stayed in the
background, avoided speaking upin like large settings, past
opportunities to my team.
You know, like this is thefirst podcast I've ever done,
for example.
Speaker 1 (20:32):
I know you talk about this.
Speaker 2 (20:35):
Super awkward for everyone listening because it is
my first time.
But you know, it wasn't that Ididn't care.
It's that I didn't know that,like I was the person someone
could or should or wanted tohear from.
But I realized that if I wantmore women to step up into
leadership roles, like I need toshow up as one too.
So, again, that's why I'msaying yes to podcasts like this
(20:55):
, that's why I'm doing thespeaking event with you and yeah
, I mean it feels a littleuncomfortable sometimes because
but ultimately, like, visibilitymatters and if I can push
myself to step up, maybe ithelps someone else see that they
can too.
Or it'll help you know, a malein a different company to push
maybe a female that is in aleadership position or one
(21:17):
that's on the path to be in oneto do the same thing.
And, like you said, I don'twant to be known as a woman in
logistics.
I want to be known for thevalue I bring.
But to get there we need tokeep building the systems, the
confidence, the community thathelps more women believe that
like they do belong at the top.
Speaker 1 (21:35):
Yeah, I think, from what I see, there's more and
more women coming into theindustry but, not as many that
are rising up and that is thepiece.
And so I loved when you werelike, yes, I will accept this
podcast, I will speak at yourshow, especially on the sales
strategy side.
Marketing is a little bitdifferent.
(21:55):
It is more female leaderfocused and heavy, but we need
to get there in all areas of thebusiness and I do think part of
that is, yeah, like I love, youare the director of strategy
and so people are going to seeyour name attached to that and
be like oh, there is careerpaths and there are teams that
can believe in that.
And I do think that havingthose conversations with our
(22:17):
male counterparts believe inthat.
And I do think that havingthose conversations with our
male counterparts it's not likedon't just check a box and hire
a woman to your team skill, likemake sure she's growing her
skills and that there's aposition, like you said, as seat
at the table and having thoseconversations.
And yes, like I want to makesure we don't have a disconnect
between where we're not havingthose conversations with men in
the room, like I even wastalking about this yesterday on
(22:37):
a different podcast, but myhusband works in manufacturing
and there's like a I forget whatit's called, but it's basically
supporting women inmanufacturing and he's a part of
the group and I was surprisedand I was like why?
And he was like I can't likereally be married to you and
watch everything that you do inyour career in almost all male
dominated spaces and then be amale.
(22:57):
That's not supporting the women.
And he's like cause, you alwayssay the men have to be
supportive and have to likeleave space at the table and be
part of the conversation.
I was like, oh, that's good,you, you clearly listen when I
go on rants at home, that'sgreat, but I loved them seeing
that in action and I do thinkthat that's part of what needs
to happen.
Like there needs to be.
Like there needs to be.
Like I love when there is like awomen in logistics lunch and
there is men in there becausethey're supporting the cause and
(23:20):
they're not like afraid to be,like yes, we love the women in
the space.
They're awesome, you know, andso I feel like that kind of
dialogue is really important too, because if we're not having
the conversations, then we'rejust because you don't want to
just be in a room full of peoplejust like you saying the same
things.
That's not where change happens.
It's when you're having thoseconversations and you're able to
push the needle further.
Speaker 2 (23:42):
Yeah, and I think a step further is I think it'd be
great to see a man lead one ofthese organizations.
I know that's not the point wewant women in these like
leadership roles but I think itwould be great to have more of
like a male presence in theseorganizations, so not just
people that you know like attenda lunch or jump on a podcast
with someone who's like very,very heavily involved in like
(24:04):
the events that are going on,like the one that's maybe like
helping create theseopportunities or connect women
to the right places, things likethat.
Speaker 1 (24:12):
Yeah, I think that kind of stuff is important.
Or like I would love to see,like I love mentoring younger
females to help like cause kindof what you said.
I didn't always take theopportunity, I didn't always
advocate, like I want to helpthem navigate that in a way that
I may have not at the beginningof my career, but I also feel
like our male, like ourleadership males, should mentor
(24:36):
younger women too and just belike this is what I did, and
then vice versa, like I wouldlove to mentor like a younger
male coming into the industrytoo and having that, like it
shouldn't just be woman to womanto do those things and you can
also have like multiplementorships.
So if I'm mentoring one personand she is a female to help her
learn how to advocate forherself, I could also mentor a
(24:57):
younger male, teaching him howto be more adaptive and more
open to different types ofpeople on a leadership team or
how to, you know, grow togetheror things like that.
Like it doesn't have to be justone type of thing.
In fact, it's better when it'sdiversified in that way.
So I think that those are thepieces that I'm looking forward
to as we move along, we'regetting more momentum of these
(25:19):
things, but then, yes, how canwe actually incorporate that to
make better business practices,instead of just a celebration
that we're here Because we'rehere to stay?
So how do we?
Speaker 2 (25:28):
Absolutely.
And I will say I do feel likeI've been really lucky in this
space, like I have neveractually had a female like
leader above me.
I've always had male leadersabove me.
But I would say I mean theproof is where I'm at today in
my career, like they've reallysupported me.
I've had some really greatbosses, some really great
(25:49):
leaders, not only in just likesales and strategy departments,
but in like operationsdepartments, who have like like
when I started at Denim, like Ididn't know anything about
factoring, like someone taughtme that and a lot of that was
like at the time, our VP ofoperations.
So there are these things outthere.
You got to find the right spotand the right people to work
with yes, I the job I heldbefore TMSA.
Speaker 1 (26:14):
I had the best boss and I was director of marketing,
so I had a seat at the tableand I would be like, but we're
also a tech company that has afemale leader.
We should leverage that.
He's like you don't have yourjob because you're a woman.
I'm like, I appreciate that.
But also we can also like isthere something we can do to
leverage?
But I always appreciated thatbecause if I knew that's not why
(26:34):
I had my job, I knew that's notwhy he valued my opinion.
But I liked that he was alwayscognizant, that like that could
be something I could feel, andso he would like reiterate that
that wasn't it and I would get.
And even coming to TMSA, peoplehad asked like I took older,
like I took over for an oldermale, and so for me it's not
even being a woman, it's my agetoo.
(26:56):
I'm under 40 in executiveleadership.
In this space that's also notsomething you see all the time,
and so it's not always theeasiest thing to navigate,
because I'm learning as I go.
And.
But you have those supportsystems, you have those people
you can go to.
You have those people that willnurture you and help you, and I
do think that's incrediblyimportant, like what you're
(27:17):
saying, like I've been able tonavigate my career because I
have had these like championsfor me, which I think is really
important and great, and love tosee more of that, and so I'm
glad that you're kind of sharingyour story and getting more
visibility into that, so thatmore people feel empowered to do
the same.
Speaker 2 (27:34):
Yeah, absolutely.
I mean, you might hear my dogbarking in the background now,
but I think you know youmentioned something too.
It's like the age thing comesinto it a lot as well.
You know, like I was in theseleadership roles when I was in
my thirties, so, um, andhonestly, before that, um, in my
late twenties.
So sometimes it's like not onlydo you have to have someone
(27:57):
that's supporting you and likerespecting your opinions as you
know, a female in the industrybut they also like they're
looking at your age and like Ifeel, again, I've been really
lucky to have these leaders that, like they didn't look at me as
this younger woman who theydidn't care about their her
opinion.
Like they looked at me andthey're like, no, we want your
opinion.
Like we want to elevate you, wewant to like have your help in
(28:21):
all this decision-making.
Speaker 1 (28:22):
And again, if I didn't have the right leaders,
whether that was at WorldwideDenim and now at Upwell, I
wouldn't be where I am right now, yeah, and I think, noticing
that and that was my my old bossactually came on this podcast a
couple of weeks ago and I likeasked him all the normal
questions and things and then,but at the end I'm like I do
really want to reflect and talkabout it because people see me
(28:44):
now as the executive director ofTMSA.
He met me as a two monthspostpartum, first time mom who
refused to work in an office orfull time and he was like, yes,
sign me up.
And most people wouldn't have.
But he like through ourconversations he heard okay,
this is the vision she couldhave.
She's really like I dounderstand industry, I wanted to
(29:05):
apply different things.
Like we had really gooddialogue in our job interviews
and he could tell I waspassionate and didn't care.
He was like let's see whathappens.
And not a lot of people wouldhave taken that risk.
But the risk is okay, it worksout or it doesn't, and you
figure it out in a couple monthsand then whatever.
But I feel like it's always goodto reflect on those people who
(29:27):
did help you along the way tomake sure that we're doing the
same for other people too.
Absolutely did help you alongthe way to make sure that we're
doing the same for other peopletoo, absolutely.
So I appreciate that you had anopen dialogue around that.
I feel like some of it istrickier to have a conversation
about, because we want to besupportive and I think sometimes
people are afraid to say thewrong thing and so then they
don't say anything, which thendoesn't help anybody.
(29:48):
But yeah, I do have one lastquestion, and this is what I ask
everybody who comes on the show, and if you could go back in
time and advise a younger Lexianything and it could be
personally or professionallywhen would you go back to and
what would you say?
Speaker 2 (30:04):
I think this is more of like maybe like a general
answer, but it also works likepersonally and professionally.
So this may be like a littleunexpected coming from like
someone who's done like ageneral answer, but it also
works like personally andprofessionally.
So this may be like a littleunexpected, coming from like
someone who's done like arevenue leadership role, but I'm
definitely not that personwho's like talking about the
latest books they've read in theindustry or the ones that have
to do with, you know, strategyor sales.
(30:25):
In my free time I love to readlike, but give me something like
spicy or thrilling, likesomeone dragons over, like
something that says like 10extra pipeline title, and so,
that being said, there was onebook that stick with me, sorry.
Speaker 1 (30:40):
It's okay, we're humans.
You have a dog and a cat, it'sfine.
Speaker 2 (30:44):
You're like fairly quiet, so I'm like what's going
on today?
But, that being said, like onebook did stick with me.
It was called the Gap and theGain.
It was actually recommended tome by the CEO at Denim Bea and
it's all about like shiftingyour mindset to focus on what
you've already accomplishedrather than like obsessing over
(31:04):
how far you still have to go.
And so like it sounds simple,but it really hit me hard,
especially like in a startupenvironment where the goalposts
are like constantly moving, it'seasy to feel like you're never
doing enough or like you're notwhere you need to be.
And so if I could go back andgive me advice, it would be that
like don't live in the gap,celebrate the win and celebrate
the growth and the steps you'vetaken, even if you're not there
(31:28):
yet.
And I think that mindset hasmade me, you know more of like a
grounded leader, honestly ahappier human, and I wish I'd
learned it way earlier.
Speaker 1 (31:37):
I love that advice and it's definitely something
that resonates with me.
I know when I started here atTMSA our current board
chairperson, mark Dirks afterthat first year, I was like we
have so much more to do and he'slike you need to pause and I
really want you.
And so this is an exercise nowI do every October in like our
October in-person board meetingand I print out everything that
(31:59):
we've accomplished in the pastyear, because I don't do that.
I'm yes, I'm like okay, yeah,but we, but we didn't do this.
So this is what we have to do.
This is where I wish we were,and up until that exercise that
he forced me to do, because thenyou look at it, you're like
holy Toledo, there's so muchthat we have accomplished, so
much movement we have made, andso that definitely, I feel like
(32:21):
I need to read that book nowbecause that is something that,
like, really I'm terrible at,and even that's like yes, like I
will bulldoze through Elevateand and I will have to, like
someone will have to remind meat show to be like pause, look,
because I will just be like,yeah, okay, but this person
needs the cookie because they'retired you know, like I just oh,
it's probably me.
(32:42):
I probably need the cookie butlike I just like I just care so
much and I just, you know, keepmoving forward and you sometimes
just really forget to pause.
So I I think that's.
Speaker 2 (32:51):
Yeah, I mean I find myself like having to remind my
you know myself of that, likeweekly at least.
It's definitely a book that hasstuck with me and I think about
it a lot.
And I mean I'm not perfect.
I definitely still live in thegaps sometimes, a lot of the
times, but the point is like toat least like recognize it and
like take a moment and likereflect back.
Speaker 1 (33:13):
Love it.
Well, as a move to looking alittle into the future, if you
want to join us next weekend onthe move, I'll be interviewing
Don Friedle and really excitedfor you guys to see that
conversation and next week isElevate, so hopefully you guys
will all see us there.
Really excited for that,excited for you to come to tmsa
(33:34):
and be able to speak.
And thank you for coming on theshow today.
Yeah, thanks for having me havea good one you too.
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