EPISODE 603: Selling Tech-Driven Shipping, Freight, and Delivery Services with Arrive Logistics Sales Leader Will Diaz

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Today’s show featured an interview with Will Diaz, VP of Business Development at Arrive Logistics.

Find Will on LinkedIn.

WILL’S TIP:  “Whether you’re a sales representative or you’re a sales leader, I think you really need to dig deep on being intentional. I think everyone needs to look at themselves in the mirror and say, “Am I doing enough to be intentional with my outreach? Am I being intentional with my follow up? Am I getting out of my office as a sales leader and walking my sales floor? Do I know my reps? Do I know their background? Do I know what makes them tick? Do I understand their circumstances?” 


Fred Diamond: We’re talking today with Will Diaz. He’s the VP of Business Development at Arrive Logistics, and they’re a third party logistics firm. They offer proprietary freight brokerage technology to carriers and shippers across the United States. Will, you lead a team of 1,700 sales professionals. Now, first of all, thanks for being on the show. It’s great to see you. 1,700 sales professionals, tell us what they do. What does the sales organization look like?

Will Diaz: Fred, first off, thanks for having me on the podcast. Our sales team here at Arrive is working across a plethora of maybe 6,000, if not more than 6,000 shippers daily and carrier partners, over 70,000 carrier partners that currently help all of our clients across everything from retail to building some materials and supplies. If you think about third party logistics, we are largely the intermediaries that sit between the transaction of a trucking company needing a load to move themself from Chicago to Atlanta, and a shipper needing to get that load from their distribution center in Chicago to their distribution center in Atlanta to transfer product and get it to the stores where you can purchase anything from diapers, and food and beverage, and chemicals, and anything that you need, cleaning supplies.

Ultimately third party logistics is the bedrock I would say and some of the backbone of the US economy, an unseen industry until everything is not on the shelves. Every single day our team here is really looking to not only acquire new clients, but also dig in and develop relationships with all of our current partners to figure out what are they doing today, what do they need tomorrow, and how ultimately can we help them meet their long-term objectives.

Fred Diamond: I’m fascinated to get into this conversation, because we’ve interviewed sales leaders from technology all the way from the IBMs and from Googles of the world, Apple Computer, Amazon Web Services, Salesforce, et cetera. I’ve interviewed sales leaders from hospitality, Hilton, Kimpton Hotels, et cetera, a lot of professional services. But you’re the first, in the logistics industry. What makes sales in the third party logistics industry different from what people might think of in traditional sales roles?

Will Diaz: In our business and in our industry, it’s a very execution based sale. Not only are you having to acquire the client but you are selling a service. We don’t own the trucks, we don’t own the warehouses, we don’t own the freight. But we have to actually step into the shoes of our shipper and actually be their resource, be their consultant, be their confidant in the market to make sure that we’re putting their freight on the right partners that actually should be hauling it, and that they’re qualified to do so. The difference there is that the sale doesn’t get stopped and get passed off to an execution team or an operations team.

Now, at Arrive, we’ve got a ton of infrastructure and support that helps all across the value chain for our partners. But at the end of the day, there is always essentially one throat to choke, and that is your representative, and that’s your individual who is all day working on your behalf to help execute your strategy and get your goods from, as I said, whether it’s port to DC, DC to store. There’s a lot of things that go along the chain there. I think that’s probably the biggest difference is that we not only acquire, but then we have to execute on a daily basis. There’s an old saying in our industry, and for people that listen to the podcast who are from our industry, you’re only as good as your last load. That means that what just happened could easily impact the ability to continue to grow with a client. Really being steadfast and consistent separates how you can be in the market for your shipping partners.

Fred Diamond: Having done so many interviews with people in high tech and software, et cetera, we know generally what the career pathway might be. Tell us what your career path was. Again, you’re the VP of BD, business development, at Arrive Logistics. How did you get to this point? Give us a little bit of a peak briefly into your career process.

Will Diaz: It’ll go right into the Arrive story, but for me, actually I graduated 2006 from IU in Bloomington. I’m a Hoosier as we get ready for March Madness. From there I actually went and worked in real estate for a year. Saw the writing on the wall of 2007 and what was to come in 2008 and thought I could use a career change. I really didn’t know anything about freight brokerage or third party logistics. Most of my friends that actually were at a company that we all matriculated at Arrive from in Chicago, Illinois, we had no idea what we were getting into. But I started as a business development representative. I started just learning from a mentor, understanding what a shipper was, what a carrier was. You have a language that’s used in our industry pretty frequently. You figure that out really quickly. But then from there, it’s a lot of on-the-job training. There’s not really a roadmap for every client. Every client has very different needs. Every vertical that you’re working in, every consumer space, retail space, distributor, manufacturer, importer, exporter, everything is a little bit different. You have to be dynamic, almost like a chameleon. You morph your way around. Eventually you start to get comfortable and really confident in your sales voice.

Then from there I worked my way up. I spent about eight years at my first company in Chicago. We actually ended up getting acquired by a publicly traded firm at the time. Then I took that pause in my career for about a year and a half to really start to say, “Is this what I want to do?” I quickly figured out that when I was out of logistics, the world moved a lot slower than what I was used to. I was yearning to get back in. Matt Pyatt and Eric Dunigan, our CEO and president of Arrive, approached me about an opportunity to consult and get our Chicago office started, helped our leadership team there, get that off the ground. We’ve built that into our second hub location. We’re actually headquartered here in Austin, but we have our second hub location in Chicago. From there took a team and then ultimately took a promotion to Austin to lead our BD team as the VP of BD here in Austin in 2019. From there, I’ve doubled down on all of the things I learned along the way and took best practices and realized there’s always more to learn. I don’t think I’m a finished product. I don’t think any of us probably think we are. That constant wanting to get better and to learn has just led to more opportunities. When you get thrown into fires, you just have to figure stuff out. That’s largely what’s happened for me.

Fred Diamond: You mentioned when you left logistics the first time around that the pace of what you were then doing was much slower. When you have all these moving parts in the sales process, I got to imagine a lot of it is so fast-paced because it’s, I’m not going to say urgent, but it’s like, “Okay, I got an empty truck. Can you help me out?” type of a thing. Talk about the day of a sales professional at Arrive and talk about the pace. Then the follow up question is going to be for third party logistics like these, what skills are you looking for? Again, if you have 1,700 people reporting to you, I got to imagine you’re constantly hiring or constantly looking for people to bring on. Talk a little bit about the pace of sales in your industry or for your company, and then what kinds of people are you looking for that can handle that pace?

Will Diaz: The day in the life of a rep here is very consistent, but also very dynamic depending on the client need and the book of business that you’re working on. The vast majority of the day will get started diving into your current portfolio of accounts, what their needs are for the day, what freight do we have that is already covered and we’re actually looking at the operational support that’s needed to execute that load for the day. Any orders that might have come over overnight that we have to quickly get ready and get going and find coverage for early in the morning. Then from there we always try to encourage, especially here at Arrive, that all of our reps are taking time to continuously be putting in sales activity and sales effort into pipeline development, looking at their current actives, looking for opportunities to expand.

From there they will jump on anywhere from initial outreach and engagement calls, to needs assessments, and then ultimately into demonstrations of our technology, or demos of a specific service mode that we’re actually bringing to market. At Arrive, we now not only do drive in full truckload, we ship reefer and produce and cross-border Canada and Mexico drayage services. Every one of those different clients have different needs. Every single day you’re just telling the Arrive story and you’re really educating and informing people about who we are, what we’re doing, how we’re doing it, and ultimately that just leads to new opportunities. If you’re engaging the right accounts that have the right revenues and they’re in the right verticals, theoretically you’re already 80% of the way home. You just need to find the right decision maker and have consistent outreach and follow up. That’s from the sales process, essentially how they’re spending 85% of their time.

In terms of our talent and acquisition and retention of new talent and what we look for, freight is the ultimate team sport. Third party logistics, in our model, we have what’s called the Chicago Split model, which means that we’ve got people on BD, my guys and my sales reps who are out there acquiring freight. We also have a carrier sales or carrier procurement team who is out there sourcing freight onto our carrier partners and we match those two things up together. You’re never doing it all by yourself. Being collaborative, communicative is very, very important. Those are two very good skills that I look for. I’m looking generally for people who, have they demonstrated that they’re in a leadership position. If they’re from a university program, were they in the fraternity just partying, or did they actually take a leadership role? Were they an athlete? Did they take anything? Did they work during college? All of those things are good understanding points of pressure that I know that we can build off. They’re good foundational layers, I would call them.

Then in terms of our senior hires that come into our industry from maybe previous sales experience, I’m really looking at what type of sales did they do? How successful were they? Can they describe how they attained quota, what steps or strategies did they use to uncover new business? It’s always remarkable to just put people in a spot to talk about their successes and then you just listen, and that’s worked well for me.

Fred Diamond: Back in the old days in technology, when I was at Apple Computer, we had pretty much a year’s worth of sales training and product training before we were put out into the street, if you will. Companies don’t have that much time anymore, especially a company like yours where there’s got to be work to be done, which is why you have so many people working in the sales organization. How quickly do you want to get people onto the floor to start doing sales? What are some things you’ve learned about that? Did you learn that it works like that? Or should you be doing more training ahead of time? I’m just curious, talk about that for a few moments here, Will.

Will Diaz: Fred, honestly, when we first all got started in this industry, especially when we actually first started Arrive, for our first few years, we had a yearlong training process. Now obviously, we learned a lot about that process, and some of it was too long, and people, of course, wanted to get going and get into sales faster. We’ve revamped it now. Our training and mentorship process starts with a four-week classroom, and then we go to a 16-week on-the-floor mentorship process where you’re doing everything from account management and learning how to broker freight, as well as then operations, and then into your sales development, learning how to actually sell the Arrive story and how we do our business and our industry.

They’re on the floor after the first four weeks, and they’re already getting immersed in the ecosystem. The learning by the partner sitting next to you, the guy that just did it just before you, is always happening. That’s really I think how we’ve built tremendous scale in our business. There’s a responsibility at Arrive that you will always pay it forward or pass it backward to the person coming after you. We have these lineages of a tree of success. From there, there’s this very immersive culture of, “I want to get better. I want to improve. I want to help my client. Hey, what are you doing? How are you doing it? Can I listen in on your next call when you describe this additional service mode or whatnot?” There’s a lot of collaborative learning in that first year especially.

Once people get through their first year and they’re into their 18-month mark, they really start to figure it out. At times early on in their career, they might be like, “Will,” tapping me in, “Can you jump on this call with me?” I go by their desk now and they’re like, “I don’t need you anymore. Go help the new guy.” It’s a lot of fun to really watch us not only recruit, hire, but then train and retain all of our talent. In a business that’s moving so quickly, in a business that we’ve actually grown so quickly, to have people that have bought in and then found success really just springboards everybody forward. For me, that’s why I said earlier, it’s the ultimate team sport. You need everybody, even your newest hires, to buy in. Once everybody starts going in the same direction, you can really do some dynamic things as a sales org.

Fred Diamond: One of the questions I used to ask, Will Diaz, on the Sales Game Changers Podcast when I was interviewing, well, pretty much the first couple years of the podcast, I would ask, what are the two biggest challenges you face as a sales leader? I interviewed a guy named Frank Passanante, who was the senior VP of sales at Hilton, and he said, everybody should say hiring, recruiting, it’s table stakes. Every leader, not just sales leader, is always dealing with hiring and recruiting. I haven’t asked this question in a while, but I’m going to ask it of you. With the exception of hiring and recruiting, what are the two biggest challenges that you face as a sales leader today? Again, for the people listening, we’re doing today’s interview in February of 2023. The emergency of the pandemic has passed, but there’s still a lot of things that are going to be with us for years as it relates to the results of the last three years. But what are the two biggest challenges you face as a sales leader?

Will Diaz: I would say the first one is, especially with people new to sales, it’s really understanding the opportunity cost of time. I think we have so many things that are very quickly at our fingertips, and we can get a lot of quick wins very easily and quickly in life. I think for some of us that are older, I’m an older millennial, so I know what a world was with long division and multiplication and having to learn not having a calculator, either show my work, for example. You probably, Fred, know what that’s like as well. But today, things have become so hyper instantaneous that really one of the things that was always very important for me is to just get our people to realize that we have the opportunity cost of time, things that we are investing in, whether it’s prospecting, or research, or preparation for a call, that is really going to be the secret sauce that’s going to help them move an opportunity forward.

Sometimes the need to really hammer down and focus down on individuals on time blocking, commitment to their day, the preparation of the next day when they’re finishing a day in a current mode, to me, that’s always one that just takes time and some repetition. I always tell our managers, we’re going to be like a parrot sometimes, we’re going to repeat ourselves a few times, but that’s how we’re going to get people to understand the environment and what they have to prioritize.

Then secondly, the instant gratification. Sales is a marathon, it’s not a sprint. I think right now, so many people are used to accomplishing a lot at a young age. I think a lot of people are used to winning and winning early. In sales, your first phone call is not going to get you a deal. Your first phone call in our business shouldn’t get you a load. More than likely your first 10 or 15 really should get you, “Hi, I’m Will Diaz from Arrive Logistics, and I’m calling about this, and this is what I think I’d like to discuss about you based off of my research.” But for whatever reason, a lot of people want to go right into, “Hey, we can help you. This is our value. Can we get started?”

I think ultimately when you’re in a sales business, it is a relationship business, it’s a people business. I always tell our sales reps, no one’s going to use you if they don’t trust you, but they’re never going to trust you if they don’t like you. The only way that someone’s going to like you is making a good first impression. I think those first impressions are things that we can maybe all take for granted. We know everybody knows how to make them. But at the end of the day, as a sales leader, I watch it continuously where I’ll get tapped in and be like, “Man, I really went too aggressively on the first call. The opportunity was right there. Can you come in and fix it?” I’m always happy to fix it. I’ll do everything I can. But at the end of the day, I think those are the two things, opportunity cost of time and instant gratification of acquiring an account, or acquiring an order sometimes pulls people back from getting above the freight, so to speak, and looking at the macro story and the macro-opportunity.

Fred Diamond: A young sales professional yesterday reached out to me and asked me if he should spend his own money to go to a particular conference. He said that his company pays for one conference per year, and they’re starting to do that again. He said, “There’s another one that I want to go to. My company recommended I go to this other one. Do you recommend that I use my own money to go to this other conference?” He said, “I can get the time off, et cetera.” I said, “Your career is your career.” Without knowing more about specifics, I said, “Yeah,” I said, “You need to take your career into your own hands.” Will, what are some of your suggestions for listeners today who want to take their sales career to the next level?

Will Diaz: I would say there’s a number of different resources out there. As I said when we kicked off the chat, I’m not a finished product. Every day I’m continuously wanting to learn conferences and seminars, especially if they’re in your industry and they’re close by and you can quickly drive there within a three or four-hour drive. When you’re young in your career, you just want to immerse yourself. You want to make connections, you want to obviously be available. Being available is a great way to just spring conversation and get to know people. At most conferences, everyone’s willing to talk. No one wants to stand around and do nothing. I think that’s always a very fantastic opportunity.

Quick things that people can do on the daily, and this is no advertisement, but there’s an app that I use called Blinkist, and it actually takes motivational books, career books, sales books, fiction, non-fiction, and it breaks them down into 15-minute blinks. I can audiobook those, read them in small scripts on my way to work. I actually probably listen to, if not one or two every single day. It’s everything from motivation, sales coaching, mentorship, financial, things that I’m interested in. At the end of the day, that’s just me immersing more knowledge. When I get onto a call, when I connect with somebody in person or over the phone, we can have a conversation. I know what’s going on, I know potentially different ways and strategies by which I can probably help them based on my due diligence and my homework of them and their business. I think that’s one. LinkedIn Learning has some really good, fantastic. We use LinkedIn Learning a lot here at Arrive. They do some fantastic content that’s available and you can almost search almost any topic that you want to learn about. That’s another great one.

Then I think ultimately finding a mentor. I think it’s really important to find a mentor. Sometimes here at Arrive, we assign you a mentor, people that have done it and paved the way for others before them, but not every company does it. Maybe not every company has those resources available, but I bet you if you go to your organization and you walk through the halls, and you look at the open doors, and you just start saying hello to some people, you might really start to find some people that you enjoy talking to. You might be able to pull them aside, say, “Hey, look, I know I’m not on your team, but I’ve really enjoyed talking to you, would you mind getting 15 minutes with me biweekly and can I just pick your brain as things happen and as things are going on?”

I think at the end of the day, as a sales leader, when I see someone who is that intentional, that focused, that thirsty for success, I want to do everything I can to support that person. I want to go the extra mile to outreach to them and, “Hey, I know they were asking me for 15 minutes. I’m actually going to throw an extra 20 minutes onto our next 15-minute meeting, and really deep dive for them on where and how they can continue improving.” Stuff like that I think is critical. Whether you’re the mentee, or the mentor, or the sales leader, or the sales rep, there’s a ton of ways to make connections available and make connectivity possible for your own success. I would agree with you, definitely should go to the seminar.

Fred Diamond: Before I ask you for your final action step, what are people doing wrong? Again, you’re managing 1,700 people in your sales organization. Obviously you have people who are managing along the way at various levels, if you will. But what do you see people doing wrong these days?

Will Diaz: The pandemic was a very challenging time for all of us, and I think it’s been really challenging to come out of the pandemic. In our industry specifically, we never really slowed down or stopped. Actually everything accelerated during the pandemic. Right now, because everything accelerated so quickly, we had some people in our organization have a lot of quick wins and some success that now as the market normalizes, it’s kind of like you have to recalibrate, you have to refocus, you have to deep dive and look at your portfolio, look at your pipeline, because you have to work that much harder to get opportunities to become actual new business.

What I would say is where I think what some people are doing wrong is that they’re hoping for things to change or hoping for things to happen. Really, hope is not a strategy. It’s never going to be one. Right now, I think that’s the one thing that all sales leader can do, is get down and get deep with everyone across their sales org, no matter their level, whether they’re a senior rep, an entry level rep, and really be empathetic to not only who they are as an individual and to what we’ve all experienced over the last few years, but really to understand who are they today? What is the makeup of their book of business? What are the opportunities that they’re creating? If they’re not, if they’re having really a hard time struggling to get the effort and the intentionality and the attitude to develop a pipeline again, you have to deep dive there and figure out strategies that you can work with them piece by piece, not just barking at them like, “Hey, make calls.” Making calls is, again, that’s hope as a strategy. It’s not really a fluid strategy that’s going to get them new business, or your company new business.

Fred Diamond: Will, thanks for the great insights today. I appreciate it. Again, you’re the first person that we’ve had on the show in your particular industry, and you’ve given us a lot of things that we hadn’t spoken before, but I guess a lot of the challenges are very similar. You got to take your profession seriously. We talk about that all the time. It is a sale. It’s one thing that we learned over the pandemic was, especially in the beginning when things had stopped and transactions stopped and people were trying to figure out their own stuff, okay, you’re a sales professional, what does a professional do right now? Even now, again, we’re doing today’s interview, like I mentioned, in February of 2023, a lot of things have changed. There’s new technology. AI is the big thing.

Customers are still trying to figure out how do they be in this post pandemic world, because their customers are still trying to figure out, and their customers’ customers are also still trying to figure out what people want out of life, people were thinking, et cetera. You’ve given us a lot of great things to think about, and I just want to acknowledge you for those insights that you’ve shared. Give us one final thought, briefly, one specific thing that you recommend people do right now to take their sales career to the next level.

Will Diaz: Whether you’re a sales representative or you’re a sales leader, I think you really need to dig deep on being intentional. I think everyone needs to look at themselves in the mirror and say, “Am I doing enough to be intentional with my outreach? Am I being intentional with my follow up? Am I getting out of my office as a sales leader and walking my sales floor? Do I know my reps? Do I know their background? Do I know what makes them tick? Do I understand their circumstances?” There’s been a lot thrown at every single person from every industry, inclusive of sales. Right now, I think if you can be intentional and very focused on your team and their development, your customers will feel that, your people will find success, and ultimately you will get back to and focus on growth from the bottom up from every individual who ultimately will deliver a great product to your client or a great service to your client, which ultimately will lead to more business that boomerangs around.

Fred Diamond: I agree with that, and I like the way you said it too. You got to look yourself in the mirror. I had lunch yesterday with a woman, her name is Marty Holmes. She runs what’s called the Sales Education Foundation. Their whole premise is to raise the profile of professional sales at the university level. They track the universities that have sales programs, even as a major, minor, or at least a class, if you will. Their whole mission is to raise the profile of professional sales. To be successful, we believe that sales is a profession. Again, if you’re a professional, what should you be doing?

Transcribed by Mariana Badillo

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