Crafting Impactful Brand Stories with Kate DiLeo

I'm Jennifer Karpus-Romain , Executive Director of the Transportation Marketing and Sales Association , which is a trade nonprofit educating and connecting marketing and sales professional in transportation and logistics , and this is our first show back in the new year and I'm so excited to have our keynote speaker for the 2025 TMSA Elevate Conference , Kate DiLeo , on the show .

Welcome to the show , Kate . How are you doing today ?

So this , this year , my word is thrive , which I think is really applicable for me in terms of health and wellness , relationships with my kiddo and family and friends . And then you know , of course , business . Who doesn't want to thrive in their business ? So that's my core theme for 2025 .

So those are like to me , the four areas that I want to improve in and get better in and make sure . And I like to have at least one thing I want to achieve in and get better in and make sure and I like to have at least one thing I want to achieve in all of those areas .

And so , and then it gives me some type of focus for the year and making sure one of those things aren't left out . But I don't like to call them resolutions , because I do . I feel like you're , most people's resolutions are over by the end of January , like you give up on whatever that thing is .

So but if I'm like , okay , I want to achieve this one thing as like what is my goal as a parent this year ? Like what do I want to do ? Or what do I want to do with him , and sometimes it's like , oh , I want to take him like . We're going to take him on a spring break trip this year , and so what does that look like ? And we're taking him .

It normally includes some type of aquarium . um , because he loves the sea creatures but , that's what I like to do and so that way you know it kind of guides you through the year . I have done the keyword . I love that we had a keynote speaker . Actually it's funny , the first keynote I ever worked with she said think about a word that will will drive you .

So I've done that too and I think that's really good . So , and I think thrive is a great word , especially in the supply chain in 2024 , we all just kind of tried to survive so I love trying to go into 2025 thriving .

But I think you know , um , for me , one of the the best parts about speaking is getting to know people individually , um , and actually getting to know the companies and especially this particular blend . What I'm really excited about is the blend of marketing and sales in the room and who we have that's going to be there .

You know , sometimes , due to the nature of my work , I only speak to marketers , right . I only speak to brand professionals right . I only speak to one role or title . But I think what's going to be really fun is getting this cross section of different leaders in the room and helping everybody understand what's the common thread here .

Where's the alignment moment around , how all of you can actually come together and get aligned around this singular topic , because , at the end of the day , we're all trying to drive revenue and growth for the companies that we work for and that we serve , but I think sometimes that feels a bit nebulous and we're often very heads down in our own lanes , and so

that's what's really exciting me is helping everybody link arms as a part of what we're going to talk about at the summit .

It's one of these things that I kind of stumbled into because I just was such a nerd about my work where I was so heads down for so many years building brands and working with teams for over a decade , after working in both the agency world and actually working in corporate America , and then I started side hustling and I began building my business on the side .

And it was that in that kind of beginnings of building my business more than 10 years ago that people started asking well , can you teach us , Can you teach us ?

And so I think it started honestly , jennifer , from just the passion of sure I'll teach , sure I'll get out there , and so I started to get asked to teach in front of 10 people and then teach a webinar and then teach at a local chamber of commerce , and then and it just kind of snowballed from there and all of a sudden you wake up one day and you're like

going oh my gosh , I'm teaching at international conferences , and how did that happen ? But it's always through the lens for me of it . It's not about being the keynoter of like oh , it's the Kate show .

It's always the how do we give people the aha moments that they need , how do we teach you the practical insights that you can actually apply to the business and can you walk away with one or two or three things that you're going ? That was the thing that I can immediately go do something with .

. So last year's keynote at Elevate was talking about the power of storytelling , and I do think it's so important to be able to tell a good story , be relatable , remember who you are as a human and not just like walk in and be like . This is what I want you to buy from me . Right , because that does not resonate .

But if you're not walking into the right room , when you're not talking to the right people and you're not having those conversations at the right time , you can tell the best story and it won't get you anywhere . And so what can people expect from you in that keynote ?

Obviously we don't want to give away all the secret sauce of what you're sharing , but kind of what's one little takeaway , one nugget that will get people excited to come watch okay .

This is the secret sauce . So what we're going to talk about is transitioning from just kind of throwing everything at somebody when you first get to know them and so , for example , going well , I got to tell them this whole complex story and I've got to give them all the features and benefits of all the products we offer . And we've got to hold on .

That's telling . How do you create a brand conversation with somebody ? How do you have an actual business conversation with your messaging ? Whether somebody hits the website , whether somebody reads a one pager or a sales material piece , whether somebody calls you and gets on a sales call , how do you have a brand conversation ?

And so what we're going to teach you is how to actually write that . And how do sales people plus the marketing team talk from the same set of messaging ? That's what's so cool plus the marketing team talk from the same set of messaging . That's what's so cool and I'm going to teach it , by the way , that it's formulaic and it's not paragraphs of content .

It's very systematic and short and rhythmic and it's based on buyer psychology . And you're going to go , oh my gosh , that actually makes sense . So it's going to be fabulous , it's going to be easy , it's going to be applicable .

And it's fabulous , it's gonna be easy , it's gonna be applicable and it's gonna hopefully open up the gateway for you to simplify what you guys say to your target audiences um , well , I think that is a great lesson .

Okay , let's break it down . So I'm really excited personally for this session too , because I do . I , by nature , I'm an over-explainer because I want to make sure people have all the information , and so and it can come off either like kind of defensive or like no we just need you to say yes or no , and I'm getting you're giving way too much information .

So I think it's really great to be able to really think through that and what , what is the core of the message , what do you need to say and when do you need to say it ? So I think that's really awesome .

And one thing I'm really excited about , too , is one thing that's really important to me at a TMSA show is that we're giving the information but we're not . I don't want people to ever walk out of the show and then come back a year later and be like what I did nothing .

So I think , opening the show with you giving these really thoughtful and topical approaches and then them going through the rest of our content that we have and we have some really great sessions coming up we're filling up our main stage now and we're also working through who's going to be our breakout speakers . That are those more targeted topics Really excited .

But something new that we're doing this year with you that we've never done before is we're actually kind of holding the attendees a little bit accountable to put this into action and we're doing a follow-up workshop that will be a virtual workshop with Kate a month after I said almost at a year nope , not a year after we really don't want you to forget it one

month after and it's going to be for you to build your organization's brand , trifecta messaging to have those conversations that convert . So that way when you get back to the office you won't forget what you're doing or how you're doing it .

You'll be able to come to this session and really dive in and do those pieces of information really make it work for your session . And this is going to be on July 8th at 1 pm ET , 12 pm CT , and it'll be a 90-minute workshop with Kate . So you can add this on when you sign for it's $100 .

You can add it on when you register for Elevate or if you want to register at show . You want to see what Kate's all about . You can do that register at show or after the show . And if , even if you can't attend Elevate but you still want to dive into that workshop , you can still register for that .

But so excited , why did you decide to do this kind of one ? To punch with , us .

and you're like why did I , what did I do , what did we learn ? And so here's the thing is , you're going to get inspired . You're like what did I do , what did we learn ? And so here's the thing is , you're going to get inspired . You're going to get excited .

You will have immediate practical things in the 90 minutes that I'm on stage teaching you right there in the keynote , and I think that that's fabulous . The proof is in the follow-up .

So what I want you to think about is , okay , writing your messaging and brand for sales and marketing professionals and , by the way , it's not just marketers that hold the keys to brand , it's sales too and c-suite leaders , hello . So in order for you to do this , my friends , you're gonna have to sit down together and go what's our plan ?

Let's get on this virtual workshop and let's put some pen to paper . Can we set aside 90 minutes and start flexing that muscle of learning how to write this and revising our messaging ? It's not rip out and replace . I'm not telling you like , oh my gosh , we have to rebrand the whole organization .

The purpose of what we're going to do is to say , okay , great , what got you here is awesome . How do you help ? Do that quarter turn based on the principles you learned ? How do you tighten it up ? And that workshop is going to be really helpful for you to now take the principles and practice it , because this is a learned skill .

So that's your playground with me for 90 minutes . You get to ask a ton of questions . You're going to be able to follow up with me . You're going to get a workbook . It's really going to be be helpful for you . So I highly encourage you to register for that .

Again , like Jennifer said , either prior to you know the event or with your sign up , or , if you want to register , on site and if you want to learn more about the workshop , you can click right there and you can register for elevate .

And we go to these professional development conferences and we're asked what is the roi ? What did you learn ? What is , what was your takeaway ? What are you actually doing with that information ?

And so this is tmsa's way to really help our attendees be able to do that and and elevate what you learned at our elevate conference and take that into what you're doing .

So really pumped about that when I you said something , which I love that you're like okay , when we talk about brand , sometimes our sales side just kind of like , oh well , that's not us , that's marketing , you know , or the leaders , and so I'm curious what the biggest mistakes you see in terms of brand building , and to me , like that was like a little sneak

peek , because that is definitely , to me . One of them is that maybe marketing does create , like , hold the key to it or they're in charge of it at a company , but they definitely , at the very least , shouldn't be the only people engaged in the brand . Um , they there should be a lot of stakeholders , everyone who's talking to your customers , things like that .

So is that kind of what you're seeing is a big miss that companies are doing , or what other mistakes might they be making in those brand building ?

You know , I'll tell you a quick story and I'll share this again on stage . I built the most incredible brand with a cmo of a mid-sized company . I had originally talked to the ceo and he's like , yep , full blessing , go for it , go forth , build the brand , report back out . We're like yay , you know . So we go spend eight weeks .

We build the coolest brand in the world . And they spent an arm and a leg building this brand and it was multi-layers and it was actually like we built like five sets of messaging . This thing was a big company , big brands . Okay , come back . She reports out and he hated it . And I learned a lesson early on and she ended up getting let go by the way .

And I remember going how did I put this woman in this position ? And I felt terrible . And I remember saying to myself I'll never again take a project without the CEO and founder and the heads of sales in the room , because what we recognize is that , whether we know it or not , c-suite leaders are and sales leaders hold keys and responsibility to brand . Why ?

Because your brand is your path of least resistance to revenue . Your brand is your path of least resistance to revenue . It is the promise of saying this is what we do , this is how we solve our customers' problems and this is how we're different and better than the rest .

So no's not just loyal brand loyalty , and it's not just about a cult logo and colors , and it's not just about oh , unicorns , this is the message . It's supposed to create the you get me moment with your target audiences and compel them to buy . So sales . If you're listening to this , we need you in that room . See , sweet leaders .

We need you in that room to understand how are we creating messaging that's aligning with the strategic business goals that you're setting forth ? That's the number one thing that you guys need to think about is who needs to be in that room , and don't miss the opportunity to get the right stakeholders in that room as you're developing your brand .

I taught my like theme of 2024 , when I went and spoke at different shows , was talking about alignment and brand alignment and how important that is , and I was laughing because at one of these presentations I asked for four people to come sit on stage .

And you're right , these are the people who normally don't come to these conversations , and so I pivoted , because that's what you have to do as a speaker on stage , but it actually worked better for what I was trying to say .

These are all the people that should be in this conversation , all of these people who have touch points with your customers and your prospects .

If they're not having that same engagement , same relationship , getting that same messaging , that same value , then you're missing a huge piece of it and your customers will go away because they'll start to notice , like , if your billing system is super , super clunky and they don't know how to pay their bills , they're going to get frustrated because why are you making

it hard to get money ? You don't want that . If you are , if your sales is promising things that your account managers can't actually do , there's a misalignment there .

If you are even on the opposite side of , like , your employees , if you're hiring in and you're what your HR team is actually able to achieve with your employees is not what you're putting out in the marketing for , like , job seekers and things like that . That's a misalignment .

If you're missing all these conversations internally , then how are you going to have them externally and make them effective ?

We go , build the coolest message . Well , how does that actually impact my business ? All right , you want to talk metrics ? Let's talk metrics for a second . The number one thing that you're going to see as an impact on this is the number of qualified leads or prospects that you see coming to the table . Why ?

Because a strong message that's rooted in a correct target audience that aligns with your goals and initiatives means that the right people are going to self-select in and the wrong people self-select out a lot faster . You're not in the business of convincing , you're in the business of converting .

So your time spent spinning your wheels trying to convince the wrong ICP or the wrong target audience to try to buy from you starts to go further down , which is great , which means you're spending more time converting right type prospects . Number two close ratio and , of course , revenue .

Higher quality prospect comes into the pipeline but then dictate that higher close ratio and revenue top line . Here's the third thing I want you to think about , though . This is fascinating sales cycle improvement , bottom line improvement . Now , how does that happen ?

Well , this is fascinating , especially if you're an organization that has any sort of like direct sales person involved that has to take a call talk with a customer for a part of their sales process in any way , shape or form .

What we find is that , instead of the prospect or the customer getting on a call with you and saying so , what do you do again and what do you offer again and I guess someone could like can you walk me through from start to finish and you having to go through multiple calls and explain all the things what we see is a decrease in sales cycle .

Why is that ? Because by the time they've hit their website , your website and seen your brand message , which is very succinct , and they get on that call with you they're no longer asking you the core things of what do you do and how do you solve my deepest problem and how you're different . They're not going . I'm already sold on that .

I had this specific issue how much is it going to cost they've already self-selected in and they're in the different point in the sales cycle . That is a direct impact , and so my clients start to see going from . I had one client go from a six month sales cycle down to less than 60 days , go from a six-month sales cycle down to less than 60 days .

So this is the power of brand alignment and creating brand conversations that convert , moving away from storytelling to story selling is that all of a sudden , you see a direct top line and a bottom line impact for your organization and that's what we're going to try to talk about at the Elevate conference is what this really is going to do for your organization

from a profitability and a revenue perspective .

Yeah , jenny GUY , yes , and I think you touched on a lot of this , but I'm curious if there's like one branding myth that you wish would just die already , like one thing that when people come to you or when you speak at conferences , they keep being like well , this is the truth , and you're like , no , it's not .

That would be the advice that I would give . Her . Took me a number of years to really come to that place and really understand the power of what that did for me personally and to grow into that as a leader , as a professional , as a mother , as a partner in all those ways .

And I think it takes us all a long time and I think pieces of me are still remembering to do that . So always a good reminder , that's great absolutely well , I'm very excited for you to come take the tmsa stage . Early bird registration ends january 20th , so if you want to see kate take the stage , lock in now .

Other exciting things that are happening at TMSA we have two things going on next week . So we have our first webinar coming up on January 21st Fueling Growth , data , back Trends , transforming Transportation in Logistics so check that out . We also will have Patrick McFarlane on the move , so January 22nd and what we're talking about is getting your trade show , roi .

How do you determine what shows you're going to ? What are your strategies ? How do you get marketing and sales alliance a little bit pieces of what we're talking about at elevate too , because it is so important to have all of those things . And in case you didn't know , you can now submit for purpose , trailbla , trailblazers and Rising Stars .

Three of our categories are open and you can submit for those now . Through the end of March , submissions are free for TMSA members , so go ahead and get started .

If you have someone that's a Rising Star , been in the industry five years or less , who's really kicking butt , and you want to nominate , get those in If you have some type of sustainable program or purpose-driven program that you really want to nominate , get those in If you have some type of sustainable program or purpose driven program that you really want to

acknowledge . That's the purpose awards . And then , of course , our Trailblazer programs is the best of sales and marketing . Both Rising Stars and Trailblazers get awarded

at Elevate . So all kinds of exciting things going on here at TMSA , really kicking the year off strong . But biggest thing is Elevate's coming up , don't forget . Come see Kate take the stage and thank you so much for joining us on the show . I always love talking to our keynotes and we oops , sorry , hit an extra button .

I didn't mean to , but we just have so much going on and , like I said , we will start debuting some of our other exciting lineup that will come after you as well , but I am excited to see you in Austin and thank you for coming on the show .