How a billion-dollar sales leader gets buyers to notice you — Will Jenkins (Journey, $235M exit)

I think it's also okay to understand that you can't be on chapter 10 while you're still on chapter one, right? Like, it's the first page of the book, and you need to really work through that phase before you can be something else. And it's easy to compare yourself to where other organizations may be or where you want your business to be long term and skip crucial steps that you have to do to get to chapter 10.

Welcome back to another episode of the Revenue Reimagined Podcast. We are stoked to have with us today Will Jenkins, who is the founder and CEO of Journey. Why am I stoked? Because this isn't your typical B2B SaaS. Journey is a freight brokerage focused on recruiting, consulting, and training in the freight brokerage space. Will spent the past 16 years building businesses and cultivating sales talent. Having successfully hired and trained hundreds of sales professionals, prior to starting Journey, he co-founded and helped build the freight brokerage Molo Solutions, which was acquired by ArcBest in 2021 for nearly $235 million. Grew to over 900 employees and nearly one billion in annual revenue. And what I love most is that Will, you also serve on the board of some Chicago charities—my favorite city—C4 Chicago, Greater Chicago Food Foundation, and ATF. And you actively consult and invest in startups. You're an adviser and mentor to various entrepreneurs, sales professionals, and founders. So give Dale some damn help on this show, man.

That's funny. I appreciate it. Welcome to the show.

Thanks for joining the show. And what a story you can tell. So tell the audience a little bit about your journey, your current journey, and how you sold through that process and the evolution of starting Journey. Your new venture. Why it was important for you to sell one and then join and start another one.

Yeah, so I'll actually take y'all back a little bit further because my roots are in direct B2C sales. My first job ever was selling Cutco kitchen cutlery at 18. And yes, it's the best thing that ever could have happened to me. I had a friend recommend me for the job. I went in for an interview. I was like, "Oh, I don't know. I've never done this before. But like, maybe I'll do well." And I ended up doing incredibly well. Made a ton of money. But during my four years in college, I sold Cutco every summer, ran an office for them, learned the fundamentals of building a book of business, objection handling. I ran an office that did about $140K in revenue my sophomore into junior year. So I was like 20 years old with three receptionists, a group of assistant managers, 100 sales reps. It was a lot of fun.

So that got me prepared to get into entrepreneurship and get into sales in general. My first job out of college was with Kimberly-Clark Professional. So I learned really high-level B2B sales, multi-million dollar deals, things of that nature. And then that prepared me to get into transportation sales. The first role I had was more transactional, kind of quick sales opportunities. Then I transitioned to the side I spend most of my time on today, which is B2B sales and transportation—essentially selling services to large organizations, from SMB up to Fortune 500, positioning to move freight from point A to point B.

I say that to say it was important to get that experience, understand those sales cycles, understand how to position what we do to different decision makers at an organization. We were incredibly successful. I got a chance to learn this from 2014 through 2017. Then me and my business partners started a new company in July of 2017—Molo Solutions. And that's where the rubber meets the road, right? That's where things started to get really intense. You really have to figure out your new brand. Nobody knows who you are. How do you create a cohesive go-to-market motion that gets companies who would never pay attention to you to pay attention to you?

And now having the opportunity to start from zero again, obviously with seven years of experience having built, scaled, and exited a company successfully, it's a little bit easier this time. But those fundamentals of the go-to-market motion, I think, are key. Because we do a lot of consulting in my current business, Journey, and often times we're helping different stages of organizations figure out how to get their customers to pay attention to them. But if you've never done that from scratch, it's really hard to conceptualize. Like, "I don't know what to say or how do we differentiate ourselves? There's XYZ amount of competitors." So longwind answer for me to say each step has taught me a lot of how to execute that motion.

It's so funny to me because what you just articulated is exactly what we should hear founders say on the B2B SaaS side over and over again, right? Like, you articulated exactly what you need to do to build a company: Who do you reach out to? Why should they pay attention to you when you are a no-name? And sadly, on the SaaS side, we see a lot of "build it and they will come," right? Like, "I'm going to build this great product and people are just going to show up." When they don't know about it, that doesn't work.

I'm curious, like, with third-party freight and freight brokering, how do you stand out? Because in B2B, it's "Oh, we have to build the best product," right? Or we have to have the sexiest marketing. But I'm curious what translates and how the hell you stand out in what I would imagine is a very, very crowded space dominated by a lot of really big players and then a million people who want to play on the field but ultimately don't get to get off the bench.

One hundred percent. You summarize the market very well. There are 21,000 third-party logistics companies, freight brokerages. And then the top 20, their annual revenue is like $40 billion. The top 20. So they dominate the space. And then everybody else in between is battling to try to gain market share.

A couple of things that we think are important when you go to market as a brokerage: First is to understand directly who you serve. So there are so many different ways to move freight, right? Like, I look at the books and stuff behind you right now. Like, those books were on a truck. That bookshelf or whatever that little credenza thing is was on a truck. Everything was on a truck or a train or a plane or a boat at some point. Now, the type of company, the manufacturer, and what they make—like, all those things are different. So you got to figure out like, "Who do I serve?" That narrows down your competition.

So an example just from companies that we work with today in consulting: we have a couple of expedited companies that we work with. So they don't care about full truckload. They don't care about what goes on the rail. They don't care about what's on a boat. They want last-minute freight. Like, it's a bleeding neck problem. It's a really big deal. And they're incredible at it, and they ignore everyone else. And as a result, it's easy for them to go to market and find companies that look like ones that are already successful. They know exactly what they're looking for.

So first, you got to identify who you serve and the modes or services that you provide. Next, if you truly want to differentiate yourself, we're in a different age of sales today. I think this is something we discounted early during our time building Molo and then learned over time: you really do have to have a strong social selling presence. And that is not to be salesy. It is to be recognizable.

So everyone that you sell to—if selling to Dale, and Dale is a buyer for a product of mine or some sort of transportation services—he's making buying decisions every day. Sends out an RFP, gets a new provider, gets a cold email, gets a cold call, and he's qualifying or disqualifying these people. If I'm never in that room and he's never considering me for a buying decision, even when I'm not selling to him, it's so much harder when I do get the opportunity. I bump into him at a conference. He's never seen my logo, never seen my name, doesn't know who I am. Scrolling on LinkedIn, never heard of us. There's no articles, no podcasts, no press, no social presence.

So there's a deliberate focus on creating buzz around your business, even when you cannot help that person directly in the moment, because eventually I'll be able to. And like, freight is, in my opinion, a very unique space to sell in because most opportunities, it's not about if, it's when. And the reason I say that is everyone that I've ever sold to in my career in transportation already had a service provider that did the exact same thing. So like, they need it. They just might not need it today. And if I'm not recognizable and I don't have any brand equity, it's almost impossible to get these people to pay attention. I'm selling against 21,000 other people.

So those are just a couple of fundamental things we think about today as you start to try to get your ICP to pay attention to you. I think one of the things you just said is, Dale's like, "Will, you shut up and let me talk." There's always a solution.

In place, right in your world, very rarely is it, "Oh, I'm brand new and I need my first transportation provider. I'm shipping somewhere with someone. Why the hell should I ship it with you?" 100% of the time. How do you keep your team, and when you're selling that kind of stuff, how do you keep them away from just total price reduction?

Yeah, that is tough, specifically for new organizations and new sales reps. So a new sales rep is trying to get a win, and they may price really aggressively to get that opportunity. There are some times where that's warranted. There are going to be really strong organizations where we try to sell the value as much as we can. And like, dude, you're just not getting in unless you are very price competitive. You have to earn your stripes, and over time you're going to be able to make money on that business. It's very common, but I think teaching people how to highlight and articulate specifics about your organization—what do you do, what services are you proficient with, what customer stories can you sell, what social proof do you have—I think this is the largest chasm for new reps to jump over.

And organizations, as they start to tell their story, they are successfully transacting with someone today, and they would sing your praises if you knew how to articulate it. Not just that you move freight from point A to point B—sure, but what do you do that's above and beyond that makes them continue to buy from you? Because they're better sales reps than you'll ever be. Like, they're paying you right now. They're voting with their dollars. And so when you teach people how to articulate those stories that sometimes they take for granted, I think that's the best way to get away from price discounting and to provide the fact that this Apples-to-Apples comparison loves what we do for these reasons, and that's from them. It's just so much easier to get people to be comfortable with you.

And it's got to be a huge reputation thing. Like, once you get the business, you've got to hold on to it. Because, like you said, they've got to ship somehow, some way.

Totally. And if you start making some mistakes, like it's a snap, man. Like, go find someone else. It's a cutthroat industry. You may get one shot, and if that driver shows up late on a Saturday for that one shipment they gave you a chance with, like, I'm sorry, you're done. It's tough.

Yeah. So Dale, I was telling Will way back in my early days, I actually worked for a 3PL for a period of time, and it's exactly that. Like, you mess up that first shipment, even if you mess up that tenth shipment, like, I'm never going to ship with you again. And like, most of the world, in the consumer side, I'd imagine we think of shipment as like, "Oh, it's going to be FedEx, UPS, or the Amazon truck that comes to my door." We don't think about the 3PLs of the world and like everyone else. And to your point, like, everything that's on this started somewhere. It's all together here, but where the hell did it get there?

Totally. How do you drive that differentiation? You know, sure, we're going to get it from point A to point B, and like, sure, we have space on the truck and our trucks are newer and they break down less or whatever it is. Like, how do you really work with folks to drive differentiation in your space?

So one of the things that we do currently at Journey is help people articulate their stories. So part of our consulting business—not only do we build out go-to-market strategy and teach people how to figure out their ICPs and come up with the right messaging, but we actually go in and do production-level work to get them to tell the story. So we'll go into a facility with a client and record. We'll look at their trucks. We'll talk about all these unique things that they do, spin that into short little social bites that their reps can sell. Now they've got social media content. Their execs can use it. Their sellers can use it. They've got collateral to go for days.

And I truly—and this is a hill I'll die on—like, if you don't find a way to articulate your story in multiple different ways and really dive in there, it's just hard to get people to go like, "Okay, you—everyone, like you said, everyone's got the best trucks and they're on time and their rates are good." But show me what it is you actually do. I have to be able to feel that some way. I need to be able to see that as the truth. Because no one's showing up to Home Depot telling them that we're going to be late and our rates are going to be high. It's just like, "I'm not going to do that. They're not going to buy." So you have to find a way to validate that. And the easiest way is to get what's in your head and what your customers have said about you and actually be able to tell stories.

But like, y'all see this today with how people sell on LinkedIn. There's a couple different ways to do it, but some people just don't know how to tell stories, and people buy stories. They don't really buy stats. Like, I'm a big proponent of the sales process just being a long story.

And I don't know if y'all have ever read those books back in the day—Goosebumps—where you would get to a page and it's like, "You pick your own adventure. If you want to go down the left, you go to page 74. You go right, you go to page 90." That's what sales is. But that story, it's up to you to articulate that.

So I think most companies have a really hard time creating what the story is because like they don't know who they are.

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Yeah, stories. Like, we talk about it all the time. Like, no one wants to buy from this scripted person who I can tell you that. It's the way Dale sells, right? Like, I can tell you that the way you need to do this is because of this, and the problem I'm going to solve is that you've got to put yourself in that buyer's shoes. You have to feel that pain, and you have to bring this relevant story together that shows that you deeply understand the problem they're facing and that you have a solution that could solve it.

So I love to hear that this is taking place outside of B2B SaaS. But you know, it's interesting—we talked about LinkedIn a little bit. Yeah. And LinkedIn is prolific in the B2B SaaS world, right? Like, typically most sellers live there. And I'm starting to see it become more prolific outside of B2B SaaS, whether it be freight, whether it be healthcare. We had someone on about a month ago who's in HVAC and has got millions of dollars of business coming in from LinkedIn. Have you always been a LinkedIn proponent? Is this a recent shift? And like, talk to me a little bit about how you help folks generate business specifically from that platform in a space that you wouldn't think to go to LinkedIn to drive business.

Yeah, so LinkedIn has been—I would say prior to like 2020 it was not super prevalent in the freight world. Like, people were on there, but I wouldn't say there were a ton of creators that were on there and people just like talking about their stories. That became much more prevalent during then through now.

Our team, during our time building Molo, we were always relatively active on LinkedIn, and we were able to bring business in. And some of our best customers came inbound through that. But in my current business, when I think about building a LinkedIn presence personally, I started doing it really, really actively November of 2022. At that point, I had about 2,900 LinkedIn followers. And I just started connecting with executives in freight and commenting. You know, just not selling anything. Didn't have anything to sell. We had already built Molo. We were doing our thing. We had already sold the business. So I just wanted to build a network of strong executives I could learn from. That ended up being extremely helpful when I turned the light switch on for Journey because we launched that business November of '23, about a year after I had really intentionally started building my LinkedIn presence.

I posted just about every day. And once I got comfortable with it, it was 9 a.m. and 2 p.m. every day. And I connected and engaged with people. And a stat that I gave a current client that we're doing go-to-market and sales strategy work for today, and this is wild to say out loud, but it's exactly what happened in 2024: we generated 100 qualified inbound leads through LinkedIn that came through my profile or from my profile to our organization.

Website that included five of the top 20 largest freight brokerages in North America, all of which I had zero pre-existing relationships with at the decision-making level or with the person that came inbound. So 100 qualified leads came in because we decided to build a LinkedIn presence, which to me is bananas. And I'm a big outbound sales proponent. I've been in sales my entire life. I love the cold call. I have no problem getting in there going crazy to build a pipeline. And we simply have sent zero outbound sales messages for this business because of building a LinkedIn presence. So it's very prevalent if you know how to do it.

And I also think you have to strike the balance between being helpful and honest and authentic and then being salesy. I see a lot of overly salesy stuff on LinkedIn. It's just interesting to get a different perspective, but I'm like man, that just would never work for me. That's just not my style.

I think the authentic part is so important, right? Like at the end of the day, if you are that—I don't want to say used car salesman—if you are that salesy person, your content should probably reflect it. And I'll still probably tell you to scale it back a little bit. But the most authentic business that we've got from LinkedIn, the most authentic connections I've got from LinkedIn, and I'm going to give I'll give Dale a little bit of credit, not for the content but for the idea, is give, give, give. Like I used to certainly focus on, you know, I wasn't ever a connect and pitch person, but it wasn't give. Now every one of my connections, it's engaging and it's like truly, what can I do to help you? What can I give you? I saw you posted about this. Hey, here's a resource. And that will eventually come back because listen, if you could help me with this and you're not even asking for anything, let's at least have a conversation.

So I love that authenticity part. Like you got to be yourself. And that's why I am so against ghostwriting. I don't care how good your ghostwriter is, and listen, we know people who do it and there's great people out there, but at the end of the day it's the same thing on LinkedIn as it is with cold call scripts with emails. Like I tell reps all the time, like we'll give you the script, but you got to tweak it to you because at the end of the day if I write the email and you get on the phone with Dale, we just sound different. And vice versa, like if Dale writes the email pretending to be me and they get on the phone with me, they're going to be like, dude, you're not the same person who wrote this email. You got to be off.

Much thank you for bringing that up. I'm much smarter. Or they're much smarter. No, they said I'm much smarter because they had on the phone with me. But I mean, touché. But yes, fair enough.

And I think it's very difficult to write in somebody else's voice. But I want to go back a little bit or forward into Journey. So you sell the company and you're like, you know, this is great. I'm sure like you took a little bit of time to figure out where you want to go, what you want to do. Why Journey? Why pick this? You obviously saw some kind of gap in the market. So I think some people think I don't really have good ideas, so I'm not really sure what the next step is. But you saw this gap, so talk to us a little bit about that.

Totally. I left Molo May of 2023, which was 18 months after we sold the company. I felt really good about what we built. I always want to be an entrepreneur. And we had a handful of goals that we want to check off: get acquired, you know, hit a certain revenue threshold. We got a chance to do a billion dollars in revenue. I'm like, man, I don't know how many chances to do that again. Like, started a company that did a billion dollars in revenue. It's really cool. So those things to me taught me the fundamentals of going from zero to scale and building a business that was actually acquirable. Like, this is something that someone wants to buy because it generates enterprise value and it's something that they would like to have.

Fantastic. I am incredibly ambitious personally. I just want to go win. It's just how I'm wired. I played football in college. I am a lifelong competitor, and not in the sense of like me versus other people. I just think there are more things that I have the capability to produce and I want to see myself produce at that clip.

So I knew I was going to start Journey. I didn't know exactly what we were going to do. The nature of the business first had to be recruiting because I had to non-compete. So my non-compete was one year long. I couldn't start another freight brokerage. I couldn't invest in any freight tech or freight adjacent businesses. So I had to sit for a year. And I've got great relationships with the execs at ARC Best that executed the deal and did all that, so I'm like, I appreciate y'all, not a big deal, I'll chill for a year. And on my way out I told him, look, I'm starting a recruiting company, and then when I'm done with that we're going to do consulting and training. When my non-compete is up, like this is what I'm going to do. I'm just a transparent cat.

So I knew those were going to be parts of it, but really it just came as a necessity. Like I can't start a brokerage, so I have to go do something. And I figured, you know, there's some strong recruiting organizations in the space. I've recruited internally. I think my brand is strong enough to be able to represent some other companies. Like let's get this going.

It worked really well. I spent the summer of 2023 traveling Europe. I left the states in June, came back in September and did a little bit of a dry run on recruiting, signed clients. It worked. I was like, okay, thumbs up, this goes. Started hiring people to build out our team. And from there, when my non-compete for consulting fell off, rolled out the consulting arm. So January of last year the rest of my non-compete fell off, started the training side. And so to me it was multi-layered to be able to just kind of test the market. But I felt really comfortable that one, the expertise I had would resonate with owners of brokerages and executives of brokerages regardless of size because I ran a company at all of those sizes: zero to 10, 10 to 100, 100 to 250, 250 to 500, 500 to a billion. Like I've seen all of that done. The things that they would come to us service-wise, and I think that created a lot of confidence in the market. And so as a result of that, we were able to bring in, you know, a fair amount of business and have scaled since then.

And I think one thing you said that was super important in that process when you were starting Journey was you actually had a bigger vision and you knew you couldn't get there right away because of the non-compete. So like, there was an evolution. And I think too many times people when you're founding a company like, I want to be a billion dollar company, like that's not always the trajectory. It's like, how do I get the incremental wins to be something bigger?

We spoke with a founder a couple weeks ago and one of the things that he said was when he built his company and sold it, he always knew who he wanted to sell to before he started the company.

Yeah, so he's like, I built the company around who I wanted to sell to.

Smart. And then I reverse engineered it.

I think one of the best things I read—and I don't remember what book it was in—but essentially the concept was run your business the way a multi-billion dollar enterprise would structure it conceptually, even when you're a one-person org, because it's going to be easier to scale and easier to look at it long-term if you do that. And that's just like the way I've approached building and structuring this business, having put your hand on the stove a couple times previously and go, you know, it's hot, maybe don't do that. And that allowed me to conceptualize, okay, we're going to do recruiting, knowing that we're then going to provide consulting, knowing that we're then going to provide training. And that creates the largest moat for us against our competitors.

There are some elements of our business and training that are really scalable. We create content, people license it. We've got a couple of tools that people use to train their reps. We create it, they license it, we don't have to be there. But that's like a slow burn. You got to build their credibility and get it going, and after a while that will overtake the active services like placements and consulting. But it was phased on purpose.

So I'm saying it's a marathon, not a sprint, right? Like sure, you want to be a billion dollar company. I'd love to sell Journey for, you know, $20 million, but what do we have to do to get there first? Because if the goal is how do we be a billion dollar company or how do we sell for $20 million, like you're going to have a problem. There's steps you have to take little by little to get there. Knowing what those steps are and taking, for lack of better terms, the baby steps to get the bigger steps and building those foundation blocks very similar to building a good house.

Market motion. I think those are really, really important. I totally think it's also okay to understand that you can't be on chapter 10 while you're still on chapter one, right? It's the first page of the book, and you need to really work through that phase before you can be something else. It's easy to compare yourself to where other organizations may be or where you want your business to be long term and skip crucial steps that you have to do to get to chapter 10 or wherever you mean. You need a foundation before you get to repeatability.

Crazy thought.

Yeah, crazy thought. It's mindboggling to me. I just don't understand.

Well, you shared a ton of awesome knowledge. This half hour went by really fast. Looking down at the time, I would love to jump into some rapid fire before we let you go.

Let's do it.

All right. Early bird or night owl, sir?

I am an early bird. How early? I will be up typically by five, sometimes a hair before that. But that's when my brain is the sharpest. What time do you go to bed?

I'm normally in bed by 9:00, maybe 9:30.

Yeah. So if you weren't doing logistics and freight moving and you had to do some kind of trade, what kind of trade would that be?

Okay, so I don't know if this necessarily is a trade, but I love working out. I probably would be, if it couldn't be freight or some other stuff that I have domain expertise in, I just love working out. So I probably would be like a trainer or something like that. I do not like doing trade work myself personally, so I don't have one that I would enjoy doing.

I hate working out. I wish I liked it. I am on day 3 weeks and every day, every little step. And I woke up, and Dale probably hears me say this more often than not, but like this morning I was like, "Oh, I don't want to do this," and I forced myself to go out of the house and go do it.

Yeah, those are the days that are the best.

Things they are, but it's frustrating, man. Like, I've been doing everything right, and I haven't lost a damn pound. That's the worst part.

In the beginning, it'll come. It'll come.

Speaking of not losing a pound, favorite guilty pleasure snack?

I love Tony, and I believe the chocolate is like Chocofelli or something like that. It's a brand. I think they're from Amsterdam or something, but their chocolate is incredible. And they have one that is chocolate and caramel, and I love it so much that it is not allowed in my home any longer because I will eat all of it.

Very good. Last question, let's wrap it up. Dream vacation destination?

Okay, so I've traveled quite a lot and checked a lot of them off. The last two that I'm super passionate about getting to are Australia or Japan. I've not been to those two, but I spent summer of '23 in Europe and did 22 cities and 10 countries and saw a lot. It was a lot of fun.

Nice. Love that. Yeah, my son wants to go to Japan. I think it'd be awesome to do that before he graduates.

That would require you to take a vacation, Dale.

That is true, which is very against all that you do.

I don't know if it's against. It's just we're building something.

Will knows. I sure do. I get it.

Wow. If you know, you know. I get it. He says that because I travel more than anyone, but I work when I travel.

Will, thanks so much for joining, man. We appreciate it. This was extremely insightful. Where can people learn more about Journey?

So we are really active on LinkedIn. My LinkedIn is Will Jenkins, wcj, and our LinkedIn is Journey. The handle is Journey Delivers. Our website is JourneyDelivers.com, and all of our social media presence, all of those are at Journey Delivers, and then mine for Instagram and all those are Will Jenkins wcj. So website, LinkedIn, very active on both of those.

Awesome, man. Thanks, Will. We appreciate it.

Yep, thank you very much. Good to see y'all.