Navigating Sales Strategy in Transportation with Lexi Farris

I am Jennifer Karpis-Romain , executive Director of the Transportation Marketing and Sales Association , which is a trade nonprofit educating and connecting marketing and sales professionals in the space , and today on the show , I'm excited to have Lexi Ferris , who is the Director of Strategy at Upwell . Welcome to the show , lexi . How you doing today . I'm good .

Thanks for having me , jen . I'm excited to have you on the show . We met a few weeks ago and so it's been great to get to know you , and we started talking and I was like , oh , you should immediately come on the show , because I feel like there's so many things that we can talk about . So I do want to start with your career journey .

So how did you get into transportation and logistics and then what led you to your current role at Upwell ?

I had like the opportunity to work directly on the customer side , so with shippers , specifically like enterprise level customers , so that gave me like a front level seat , you know , to everything that was going on .

One of the really cool things about Worldwide , too , is like they have like such comprehensive training , so they really just like throw you into the industry but they teach you as you go . So I thought that was really great .

Like , for example , when I started there , that was when ELDs were coming out and so everyone was in this panic and I'm like why is everyone in this panic ? Like technology , this is cool , this should be great .

And it wasn't until like months later that I understood like what those ELDs were really going to do for the space and like what kind of disruption whether positive or negative that was going to do . So I spent four years there and then I actually jumped into startup life .

I joined a company called Denim and they are aintech company focused on like helping brokers and carriers with like their cash flow problems .

Um , I wore many hats across the revenue organization , you know , I was ultimately their director of sales and , like , denim will always hold a special place in my heart because it's how I got into startups , it's how I like , found my passion , that's what I love doing and that's when I learned , like you can work outside the box a little bit , and it was , you

know , fast paced , high growth where I had the opportunity to lead , like go-to-market strategy , sales efforts , work closely with customers , things like that . It just like deepened my appreciation for the ex , you know , the industry . Um , and then that journey eventually led me to my second startup , upwellwell , where I now serve 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 drawn to , like what he was building . I recognized like right away that , like this was something that had like high potential , high growth , something I wanted to be a part of .

And so , long story short , I reached out to Charlie , shot my shot and here I am . The rest is history .

I always laugh because TMSA has been here for over 100 years now but because I took over a couple of years ago new management , new structure , it's very much kind of like that startup feel , that small , you know , headquartered kind of feel , and but there is something to it because you don't get bored and you get to put your hands in everything and you get to

expand yourself and expand your brain . 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 to make it .

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We do this through a combination of like AI and LLMs , large language models and like rules-based logic . My cat wants to join this meeting Perfect To extract standardized like information from 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 know , right , I mean , he just wants to be freight famous . Um , our system , as you know , like map that data to like payer requirements . It flags discrepancies and ensures invoices are like fully audit ready before they ever go out the door .

So it's a space that's been under invested in for decades and we're changing that by giving you know back office teams the tools they need to move with like more speed and precision and , you know , speed up their processes .

And when you think about the customer experience , the piece people never include which I always like go on my soapbox and talk about is the billing process , because your sales team can be the best , your customer support people can be the best , but you want a consistent experience , and if your billing process is super painful , people are going to remember that too

, and it's always a piece of that puzzle that Noah talks about . So I think that's great that you 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're right . Like not , that isn't always a focus . It's always you know , oh , how can we streamline things in other areas ?

But people need to get paid . People need to pay their bills . It's the basic piece .

You know when you're in sales you're on the front line , you're hearing objections , you're seeing like where messaging maybe isn't hitting and you're like the one that can provide that like direct feedback loop , and so that's kind of what taught me how to like cut through the noise .

You know , like ideas like that look good on paper but aren't something that , like a team can implement , is not going to do anything .

So being in sales has made me like incredibly outcome oriented and strategy like it's easy to get caught up in , like the framework and the long term planning , but the sales background reminds me that , like every decision like ultimately needs to support like revenue growth , customer satisfaction or like operational efficiency .

So I try to bring that same like you know , thought process towards action and clarity into like strategic planning , like how will this land with the customer ? Will this empower the sales team ? Is you know , is this solving like an actual problem ? Like is this something we should spend time on , so like and sure like .

It taught me to think strategically practically and that's made me a better partner across , like go-to-market strategies with product teams and leadership teams , things like that .

So how do you make sure that you're not like , oh , this is the strategy , this is the plan , but actually then make it successful for your sales teams to be able to then take it out out , sell , move forward with it absolutely .

Or I spend time like seeing how they're selling , like what's working , where are they getting stuck ? What objections are they hearing ? What is missing , like is it tools ? Is it messaging , like what needs to be changed .

And then I also look at like the full funnel to like what is the data telling us , like deal velocity , win rates , conversion points , like it gives me like a clear picture of where strategy can like actually move the needle . And then , when I'm building a strategy , I'm constantly asking myself things like is this going to be helpful for the rep ?

Or like is it just more noise , like is it going to complicate the sales process ? So , again , I focus on like clarity , simplicity , enablement , whatever the levers are , and just 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 because the strategy doesn't work again unless it's executed it's working .

So I'll make sure I like join sales calls , enablement sessions , training sessions , just staying really close , regularly checking in what's sticking , what still might need to be adjusted , things like that , just to make sure you know the sales team's like fully equipped and supported .

When I was in marketing , I liked going on sales calls , I liked going to trade shows and hearing how the sales team pitched it , because you want , you know that messaging to align and so if you're not doing that you're going to , there's going to be just a mismatch on like , what you're saying on the marketing side versus what gets executed .

And then same with like , the actual building of the strategy . So I think that's great .

as , like a company , I think that's too really true on like the capacity side of things too .

And then , like on the tech side of things , or if you're expanding new products , new capabilities , having a proper roadmap because I know that was the thing that had happened to me in the past when I worked in tech they'd be like , okay , we're launching a new product . I'm like okay , but like what does it do ? Like what problems do we set ?

Like you know , we need a little bit of a ramp up , and so we got way more sophisticated in that . But because I feel like sometimes then I'll be like just hand it off , like let's start promoting , but we need to know basically , why are we doing it ? When is it ?

And like when is it being beta tested versus when is it actually ready for launch for everyone , because those are different things too . And like how you market message .

Like if we're marketing things that like aren't on the roadmap or we're selling things that like is not what our focus is right now too , like that not only creates , like this misalignment with your customers , but it also like internally , it's like what is the focus ?

One of them , I would say , is like more specific to like what I'm doing now , but I think there's like this growing recognition that operational efficiency like extends , like all the way through , like billing payments receivables , like most companies are investing in , like automating these back end workflows , because the manual processes are dragging down margins , they're

slowing cashflow and I think for like a sales or strategy leader , that means you need to highlight value in unexpected places , like faster invoice reconciliation or like lower DSOs as like real , like return on investment drivers . The other thing that I think is big right now is there's a ton of M&A activity .

There's more strategic partnerships , a push toward that platform thinking Like people don't want their tools to live in silos . They want them to be like part of this , like larger ecosystem , and I think that impacts how you go to market . Like buyers want fewer vendors and more end to end value .

Because if you merge or you get acquired , they're probably like , am I , I gonna have the same account manager ? Like how to like , and there's some of those pieces that I think gets left out and people forget about . A lot is just because I remember this is totally separate .

But we were working with somebody and our account manager pretty much sent us an email that 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 our account ? Like who am I supposed to call with questions ?

Like and , um , I knew who her manager was and that's so I asked , but outside of that , it was just there was limited communication , and so I feel like that communication plan can be . I know , obviously before the paperwork'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 how to answer the questions is ready , especially those account managers , so that people know , hey , we're doing this to serve you better , and this is the way we're going to do that . I think that's incredibly important .

You have to treat it like one and make sure you have the right communications ready to go out to the team , or , if it's something that , like you know , affects you in a positive or negative way , making sure you're like relaying that message the right way .

So we'll be just days away from elevate um and you are coming this year and you're speaking and you're um co-presenting with kevin coombs , who's evp of sales at chain , and you guys are tackling a session called from no to not yet turning maybes into momentum and relationships into revenue , and this was actually a session that us at tmsa really wanted to be

presented , because this is a really tough market right now and it's really easy to get sad and want to give up

and then , you know , just be frustrated all the time . But that's not effective for our sales team or our momentum or anything . So building those relationships , thinking how to execute on that and , to you know , keep a bit of a positive vibe through that can be really challenging , but it's so important now more than ever .

So what can people expect from that session and why do you think it is an important topic ?

Like today's market , deals rarely move in like a straight line anymore . Buying cycle is longer , decision makers are more cautious and like the initial no is most the time , just like a reflection of timing . You know something our ceo says a lot is like most um , sales cycle ends in a no decision . Like not a no , it's the no decision .

Like they're not sure they're not moving forward . Or like the timing just isn't right , um , and I think that's just like a reflection of timing priorities or like lack of clarity . So I really don't believe , most of the time , that it's just this big lack of interest . What people can expect from this session is just like a real tactical conversation .

We're going to talk about how to , you know , reframe objections , how to stay top of mind without being pushy , how to build relationships that will , like eventually turn into revenue , even if it takes longer than you'd like .

So , again , like you said , I think this topic is really relevant right now because the teams that are winning in this market are the ones who know how to like build that trust , build those relationships . They have patience and they're consistently like building that momentum .

So I'm going to pivot somewhere else too , which was part of why I wanted you to come on the show , because when we were talking in the past , a couple of couple weeks ago we were talking about what it's like to be a female in the industry and that there's spaces for there's a ton of now , um groups for women in the industry the women in logistics , um

supply chain , um , women in trucking , all that and they're lovely and I participate , I go to women in trucking , I do all that stuff . But part of it is we want to make sure , as women in the industry , we're not just participating in those things , that we're being acknowledged as just a professional in the space . And I know that's something like .

When we started talking , we realized that we were both pretty passionate about , because it can feel like that sometimes , that it's like , okay , now we have all these powerhouse women , but I just want to be a powerhouse human . That's it .

And how do you think that the industry , our male colleagues , how can we better be positioning that message now that we are getting recognition that there are really great females in the industry . But how can we pivot and make sure that it's not just that we're women , we're just great , awesome people ?

But I think , ultimately , like , when it comes to creating space for , like women in logistics and supply chain , um , the next step is making sure like we're not just like inviting women into the room but we're elevating them into like leadership roles and decision making roles , like giving them a seat at the table , and I think the biggest part of that is

empowering women to believe that they belong there . And I think that's a big missing piece of the puzzle . And , you know , I'll be honest , I've not always been the best example of that Like for years , like I've stayed in the background , avoided speaking up in like large settings , past opportunities to my team .

You know , like this is the first podcast I've ever done , for example .

So , again , that's why I'm saying yes to podcasts like this , that's why I'm doing the speaking event with you and yeah , I mean it feels a little uncomfortable sometimes because but ultimately , like , visibility matters and if I can push myself to step up , maybe it helps someone else see that they can too .

Or it'll help you know , a male in a different company to push maybe a female that is in a leadership position or one that's on the path to be in one to do the same thing . And , like you said , I don't want to be known as a woman in logistics . I want to be known for the value I bring .

But to get there we need to keep building the systems , the confidence , the community that helps more women believe that like they do belong at the top .

It is more female leader focused and heavy , but we need to get there in all areas of the business and I do think part of that is , yeah , like I love , you are the director of strategy and so people are going to see your name attached to that and be like oh , there is career paths and there are teams that can believe in that .

And I do think that having those conversations with our male counterparts believe in that . And I do think that

having those conversations with our male counterparts it's not like don't just check a box and hire a woman to your team skill , like make sure she's growing her skills and that there's a position , like you said , as seat at the table and having those conversations .

And yes , like I want to make sure we don't have a disconnect between where we're not having those conversations with men in the room , like I even was talking about this yesterday on a different podcast , but my husband works in manufacturing and there's like a I forget what it's called , but it's basically supporting women in manufacturing and he's a part of the

group and I was surprised and I was like why ? And he was like I can't like really be married to you and watch everything that you do in your career in almost all male dominated spaces and then be a male . That's not supporting the women .

And he's like cause , you always say the men have to be supportive and have to like leave 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's great , but I loved them seeing that in action and I do think that 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 a women in logistics lunch and there is men in there because they're supporting the cause and they're not like afraid to be , like yes , we love the women in the space .

They're awesome , you know , and so I feel like that kind of dialogue is really important too , because if we're not having the conversations , then we're just because you don't want to just be in a room full of people just like you saying the same things . That's not where change happens .

It's when you're having those conversations and you're able to push the needle further .

I know that's not the point we want women in these like leadership roles but I think it would be great to have more of like a male presence in these organizations , so not just people that you know like attend a lunch or jump on a podcast with someone who's like very , very heavily involved in like the events that are going on , like the one that's maybe like

helping create these opportunities or connect women to the right places , things like that .

I didn't always take the opportunity , I didn't always advocate , like I want to help them navigate that in a way that I may have not at the beginning of my career , but I also feel like our male , like our leadership males , should mentor younger women too and just be like this is what I did , and then vice versa , like I would love to mentor like a younger

male coming into the industry too and having that , like it shouldn't just be woman to woman to do those things and you can also have like multiple mentorships .

So if I'm mentoring one person and she is a female to help her learn how to advocate for herself , I could also mentor a younger male , teaching him how to be more adaptive and more open to different types of people on a leadership team or how to , you know , grow together or things like that . Like it doesn't have to be just one type of thing .

In fact , it's better when it's diversified in that way . So I think that those are the pieces that I'm looking forward to as we move along , we're getting more momentum of these things , but then , yes , how can we actually incorporate that to make better business practices , instead of just a celebration that we're here Because we're here to stay ? So how do we ?

I've had some really great bosses , some really great leaders , not only in just like sales and strategy departments , but in like operations departments , who have like like when I started at Denim , like I didn't know anything about factoring , like someone taught me that and a lot of that was like at the time , our VP of operations .

So there are these things out there . You got to find the right spot and the right people to work with yes , I the job I held before TMSA .

But I always appreciated that because if I knew that's not why I had my job , I knew that's not why he valued my opinion . But I liked that he was always cognizant , that like that could be something I could feel , and so he would like reiterate that that wasn't it and I would get .

And even coming to TMSA , people had asked like I took older , like I took over for an older male , and so for me it's not even being a woman , it's my age too . I'm under 40 in executive leadership . In this space that's also not something you see all the time , and so it's not always the easiest thing to navigate , because I'm learning as I go . And .

But you have those support systems , you have those people you can go to .

You have those people that will nurture you and help you , and I do think that's incredibly important , like what you're saying , like I've been able to navigate my career because I have had these like champions for me , which I think is really important and great , and love to see more of that , and so I'm glad that you're kind of sharing your story and getting

more visibility into that , so that more people feel empowered to do the same .

So sometimes it's like not only do you have to have someone that's supporting you and like respecting your opinions as you know , a female in the industry but they also like they're looking at your age and like I feel , again , I've been really lucky to have these leaders that , like they didn't look at me as this younger woman who they didn't care about their her

opinion . Like they looked at me and they're like , no , we want your opinion . Like we want to elevate you , we want to like have your help in all this decision-making .

now , yeah , and I think , noticing that and that was my my old boss actually came on this podcast a couple of weeks ago and I like asked him all the normal questions and things and then , but at the end I'm like I do really want to reflect and talk about it because people see me now as the executive director of TMSA .

He met me as a two months postpartum , first time mom who refused to work in an office or full time and he was like , yes , sign me up . And most people wouldn't have . But he like through our conversations he heard okay , this is the vision she could have . She's really like I do understand industry , I wanted to apply different things .

Like we had really good dialogue in our job interviews and he could tell I was passionate and didn't care . He was like let's see what happens . And not a lot of people would have taken that risk . But the risk is okay , it works out or it doesn't , and you figure it out in a couple months and then whatever .

But I feel like it's always good to reflect on those people who did help you along the way to make sure that we're doing the same for other people too . Absolutely did help you along the way to make sure that we're doing the same for other people too , absolutely . So I appreciate that you had an open dialogue around that .

I feel like some of it is trickier to have a conversation about , because we want to be supportive and I think sometimes people are afraid to say the wrong thing and so then they don't say anything , which then doesn't help anybody .

But yeah , I do have one last question , and this is what I ask everybody who comes on the show , and if you could go back in time and advise a younger Lexi anything and it could be personally or professionally when would you go back to and what would you say ?

So this may be like a little unexpected , coming from like someone who's done like a revenue leadership role , but I'm definitely not that person who's like talking about the latest books they've read in the industry or the ones that have to do with , you know , strategy or sales .

In my free time I love to read like , but give me something like spicy or thrilling , like someone dragons over , like something that says like 10 extra pipeline title , and so , that being said , there was one book that stick with me , sorry .

It was actually recommended to me by the CEO at Denim Bea and it's all about like shifting your mindset to focus on what you've already accomplished rather than like obsessing over how far you still have to go .

And so like it sounds simple , but it really hit me hard , especially like in a startup environment where the goalposts are like constantly moving , it's easy to feel like you're never doing enough or like you're not where you need to be .

And so if I could go back and give me advice , it would be that like don't live in the gap , celebrate the win and celebrate the growth and the steps you've taken , even if you're not there yet . And I think that mindset has made me , you know more of like a grounded leader , honestly a happier human , and I wish I'd learned it way earlier .

And so this is an exercise now I do every October in like our October in-person board meeting and I print out everything that we've accomplished in the past year , 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 then you look at it , you're like holy Toledo , there's so much that we have accomplished , so much movement we have made , and so that definitely , I feel like I need to read that book now because that is something that , like , really I'm terrible at , and even that's

like yes , like I will bulldoze through Elevate and and I will have to , like someone will have to remind me at show to be like pause , look , because I will just be like , yeah , okay , but this person needs the cookie because they're tired you know , like I just oh , it's probably me .

I probably need the cookie but like I just like I just care so much and I just , you know , keep moving forward and you sometimes just really forget to pause . So I I think that's .

I definitely still live in the gaps sometimes , a lot of the times , but the point is like to at least like recognize it and like take a moment and like reflect back .

And thank you for coming on the show today . Yeah , thanks for having me have a good one you too .