Abby Ryan has been named the new president of Crawford, a central Iowa-based trucking company, completing an intentional succession plan to take the reins from her father, Gregg.
At 26 years old, Ryan represents a young generation of leadership in an industry frequently dominated by older executives. She succeeds her father, who has served as president for 21 years since acquiring the company when it was on the brink of closure.
The transition has been months in the making, aimed at avoiding the sudden disruptions that often plague family-owned business handovers. While Gregg is stepping down from the presidency, he remains with the company to support the new leadership structure.
"For us, this is more about a title change because I’ve had the capabilities to be empowered to make the changes I’ve been looking for," Abby Ryan said. "The entire process has been super intentional, involving all the right people."
From the trash cans to the executive suite
Abby's history with the company goes back to kindergarten. After her father bought the fleet—growing it from five trucks to a peak of about 45 trucks within a few years—she would often accompany him to work. Her early responsibilities included emptying garbage cans, cleaning bathrooms, and handling basic filing.
She's spent the last 10 years formally working for the company, starting in marketing, where she developed the fleet's website and refined its brand presence before moving into accounting and operational management. Today, she manages assets, human resources, and equipment procurement, while her father handles the logistics and freight load side.
A career in trucking was not always the plan, however. Abby initially attended the University of Iowa with aspirations of becoming a dentist. During her freshman year, realizing her true passions lay elsewhere, she wrote a letter to her parents expressing her desire to return to the family business and eventually take it over.
Her parents initially rejected the idea, wanting her to find her own path and spare her from the 24/7 stress of business ownership in an industry as feast and famine as trucking.
"They were adamant that I needed to find my own way," she recalled, "and I was like, 'Okay, I’ll change your mind. I'll let you know I’m really serious about this.'"
To build her own merit, Abby became heavily involved in industry groups, graduating from leadership programs with both the Iowa Motor Truck Association (IMTA) and the Truckload Carriers Association (TCA).
"She was concerned, regardless of what she did, her work and her position would be minimized because of birthright," Gregg said. "She told me, 'The connections I made there are solely based off of myself.' She's tremendously won the respect of the team."
Future growth and cultural focus
Under the Ryans' operational leadership, Crawford has focused on a holistic approach, winning accolades such as the IMTA Image Award and fleet safety recognition. Even during market downturns, the carrier has seen organic growth, relying strictly on word-of-mouth driver referrals and unsolicited applications rather than active recruitment advertisements.
Looking forward, Abby has set a target to grow the fleet to 100 trucks over the next five years. If the business expands beyond that threshold, the strategy outlines forming separate operating units or trailer divisions to preserve the tight-knit environment that defines the carrier.
"Crawford’s niche is having everyone feel known and be known here," she said. "I want my legacy to be able to continue to empower people that maybe weren't believed in."
Contents of this video
00:00 10-44 intro: The Challenge of Succession Planning in Trucking
01:02 From Sweeping Shop Floors to Company President
03:51 Changing Career Goals
06:24 Earning Respect & Overcoming the "Birthright" Stigma
09:41 Implementing Lean Principles & Fresh Eyes in Management
11:54 Balancing Business Operations & Brand Building
13:44 Focusing on Company Culture
17:31 Scaling to 100 Trucks: Prioritizing Quality Over Quantity
21:45 The Importance of Maintaining Healthy Boundaries
Speaker 1:
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Speaker 2:
Passing the torch to the next generation is one of the biggest challenges a family-owned trucking company can face, but one Iowa carrier shows how intentional planning turns a standard title change into a masterclass in business continuity. Hey everybody. Welcome back. I'm Jason Cannon and my co-host on the other side is Matt Cole. Succession planning in the trucking industry is notoriously tricky. Too often transitions happen during a sudden medical emergency or a scramble following a death because an owner was too prideful to give up the seat. But central Iowa-based Crawford Trucking shows what happens when a transition is built on a decade of careful, thoughtful preparation.
Speaker 3:
Joining us today are Abby Ryan and her father, Greg, to talk about how Abby went from sweeping the shop floor to officially transitioning into the role of company president.
Speaker 1:
He bought the company 21 years ago, so it wasn't going to go on. And what I knew is he'd always worked for a different trucking company and close to our house and he had good hours. I'd see him a lot. So then when he first bought the company, I was like, "Well, dad's gone all the time because he's now building a new foundation." And so a lot of times if my mom couldn't watch me or something during the day or she was out, I'd be at work with him. And that meant time to put you to work, whether that's emptying the garbage cans, cleaning the bathrooms. I know especially during COVID, you couldn't really get cleaners. So a lot of times I'd come in over the weekends to kind of help out. And that was just here and there. But once I got to, I always say it's been 10 official years that I've worked here at Crawford, legal years, because obviously when -
Speaker 4:
That'd be 26.
Speaker 1:
Yeah, I'm 26. So 10 legal years, but before that, the trash cans doing whatever he asked me filing if I needed to. I started in accounting.
Speaker 4:
Well, actually marketing.
Speaker 1:
Well, marketing. I'd always been doing their marketing and I really thought I knew what I was doing. I would spend hours on Photoshop and then I would show my dad something and I'd be like, "Wow, look at this. I made something really good." And he'd be like, "Well, that's not really the vision we're looking for. I think you can do better." And at the time I was like, "How dare you say this? I spent four hours doing this and looking back, I've saved some of the images. They're terrible." So I'm glad he never really tooted my horn if it wasn't deserved because I definitely got better. And then I know one time I was getting ready to go to college, he had told me that summer I needed to make us a new website. I don't think we had one at the time anymore. He said, "You need to make a website." So I thought he was kind of joking and I was going to college in a week, freshman year and he was like, "How's that website coming?" And I was like, "Oh, you're serious." He was serious.
So I had spent that whole week building up a website, working with somebody to get it up and launched. So that really started how do you brand a company? So I think that helped me hone in to what is Crawford's brand and help -
Speaker 4:
Who we are.
Speaker 1:
Who we are telling the story. We've always had the brand and what we've done, but being able to put it pen to paper and be able to showcase that brand I think is where it really helped me have that aha moment. I was never going to work for the company going forward. I was just going to do it during high school and college and I was going to be a dentist. I went to Iowa to be a dentist. Well, year one, I was taking a class that kind of talks about, do you want to be in the medical field? Is it for you? Yada, yada. Well, one, I don't really like saliva, so that's a bit of bear to entry for me. So I recognized that. And then you had to write a paper at the end of it saying, yes, I'm going to keep going this way.
Or what is it that I'm more passionate about?
Speaker 2:
Greg initially acquired Crawford Trucking 21 years ago when it was just a five-truck operation facing a shutdown. Now Greg's built that up into a stable of a 45-truck fleet, but it wasn't always the plan for Abby to take over.
Speaker 1:
I really sat with it and I was like, I don't think I really want to be a dentist. I don't know why I ever thought I wanted. I think I was a fear of a dentist, so I was like, I'm going to overcome that fear by being a dentist. So then I wrote him a paper, him and my mom saying I'd actually really like to come back and work for the family business. I'm very proud of what it stands for. I've worked here for years and I love the people that make Crawford who it is. I'd like to come back and maybe take over one day. So I wrote this whole letter and they called me and they're like, absolutely not. And I was like, well, that's fine if you say I can't come work for you, but I'm still going to go work in business, so take it or leave it.
And they were adamant that I needed to find my own way. I wasn't going to work for them. And I was like, okay, I'll change your mind. Let you know I'm really serious about this. This isn't a fail safe. I want this. So lo and behold, here I am. I was very serious about it. It was something I'm super passionate about. The people here are family to me. Many of
Speaker 4:
Them have watched her grow up.
We are truly blessed to have long-term employees both in the office, the shop, driving capacity. We've got long-term customers, long-term vendor relationships. So a lot of the individuals that Abby is now leading have literally known her since she was five years old and they've watched her up. And one of the things that's been really refreshing to me through all this is how readily they embraced her. When she first came on board full-time and we decided to go down the path, and I want to back up. The reason why her mom and I both said no, I bought a company that was going to shut down. It was a very small company. I changed the culture. Well, within a couple years I had it built up to about 45 trucks, went from five to about 45 and put in a lot of hours. And we really wanted, like may parents, better for our kids.
And it wasn't that this wasn't great. It was just it took a lot out of me. And lo and behold, she came on board and helped it be much more manageable for... We've always focused on the employee's work-life balance, but it wasn't always that way for the ownership of the president and she helped with that. I talk about how I kind of ran the company focused and conservative, but I tried to remain the best kept secret in central Iowa, I thought.
Speaker 3:
One of the biggest hurdles for any next generation leader is overcoming the stigma of birthright and earning the true respect of the team. Abby actively sought out industry leadership programs like the IMTA and TCA to build an independent network and establish her own voice outside of her dad's shadow.
Speaker 4:
When Abby came on board, I didn't want her doing things for the next 30 years because her dad said so. So I got her involved in the industry associations and she's been through the IMTA leadership program, the TCA leadership program, but I knew she would have a great impact on the company. I just didn't know to what extent so early on. She's been a driving force. I tell my wife, I said, "We've always run a really good company." But I said, "She's come on board and just take us to a whole new level." And the analogy that I use, if you ever take your kids to drop them off at the dorms in college, you go past a guy's dorm room and it's pretty plain, got an Xbox and TV and you go past these girls' dorm rooms and you see they look like they come out of better homes and gardens.
Well, that's kind of the difference of what the transition she's made. So I got to look at this and watch and she's ready. She's ready and the organization is ready for her and she's tremendously won the respect of the team. Because one of the things she told me early on was that she was concerned regardless of what she did, her work and her position would be minimized because of Birthright. So when I got her involved in the association, she said, "That's mine. Nobody can tell me that. I was given that if I get into the association.
Speaker 1:
The connections I've made there are solely based off of myself rather than that. " So I think that helped grow even more my confidence.
Speaker 4:
Well, what's interesting is now as we've moved forward through the company, how many people have come to me and people that have invested me for years and they say, "Greg, we thought you were a couple years overdue. She's ready. She's ready." And through this process, I don't know how many people have come to either her and I and said, "You know what? It's just so refreshing because we've seen instances where these types of things are given to the next generation and they say it's imperative. Where Abby's concerned, she's really earned the respect of her coworkers, customers, vendors, and they can see the real difference that she's made within the organization.
Speaker 1:
When I came full-time, I think that was one of my number one goals is to not be seen as just the boss's daughter, but to make connections and say, here, what can I do? I'll do anything and I'll help you wherever I can. " So on top of what I was doing, I would be like, "Okay, what can I do to make your job a little bit easier?" Because sometimes having fresh eyes, you realize a step could be taken out of the process. So I think they really enjoyed having a breath of fresh air a little bit. And I allude to having a great mentor who allows me the space to be able to flourish and explore and change things because a lot of people are stuck in their ways and don't want to change. Now, granted, there are some ideas I've come up with that is a big heck no, which I apreciate, but I've been allowed -
Speaker 4:
Number one, they might've been a heck no, but I came back the next day and said, you know -
Speaker 1:
There might be some merit. So we've been able to work really well with each other and that's, I think, been imperative to how this transition's gone.
Speaker 4:
I really is what's best for the company.
Speaker 2:
Greg's background is rooted in continuous improvement and quality initiatives from a previous career, which taught him that entrenched management can often stifle a company's growth. That attitude gave Abby the freedom to implement lean principles and cultural changes that have reshaped the organization's trajectory.
Speaker 4:
In my previous career, I had the opportunity to work for Barnon for a decade and they focused a lot on quality initiatives, continuous improvement and lean principles. And one of the things as we started learning about lean principles, I remember really stuck with me is entrenched management can be the biggest detriment to a company moving forward.
Speaker 1:
It can have a stifling effect. Yeah.
Speaker 4:
Always in the back of my mind, but until she came along and had some of the freedom to start improving processes and even may cultural things, I recognize she needs to have the freedom to try those things. And I've been able to support, to guide, protect the organization while developing the next generation. And she doesn't stub her toe very often, that's for sure. And I truly believe it's what's best for the organization and getting fresh eyes. We were very blessed through the process of we were able to hire a vice president to support her. That has a tremendous resume. But
Speaker 1:
More importantly for us when looking for this person, we started really defining what this looked like in December.For me when we're talking about what this person looks like, because for me, I've worked with him so closely, so I need somebody that's supportive of me, doesn't take my age or my gender to a nuisance because sometimes that could be a bear to entry. And the ability to transform themselves into our culture, not to say that we can't fix a few things, but I don't want them to come in guns ablazing and saying, "Hey, let's change all these things." So that was most important to me. They could have the best resume, but if they don't have the cultural fit, it was never going to work. So I think we've found both, which is honestly like finding a four-leaf clover. I'm really grateful for that. So I feel very supported with the people we have put in place too.
Speaker 2:
Abby manages the assets, HR, and corporate spending while Greg handles the loads and operational side, but she says her real pasion lies in brand building and transforming how people view the trucking industry.
Speaker 1:
I like being able to do both because if you're working with your number portion of the brand, it looks very different from building a cultural standpoint side. So I think being able to have both is good. For us, we've always talked about his is the operations standpoint. Now I control the assets, how the money's spent, how the equipment's being propped, all the HR related functions while he's the one that works with the load portion side. So I'm very good about Xs and Os, but I also am able to be in that. I think my favorite part of the business is definitely brand building. I like to create cultural fits. I like to come up with new programs for our company. I like to build people up and have those fun experiences with the company. So I think one thing I do really excel in happens to be building the company to have this brand and make this another level that is respected by people across the industry.
No matter what our size is, we're able to have the best fleets awards, the TCA awards. We won the Iowa Motor Truck Association Image Award. So I think one thing a lot of companies miss when they only have somebody so focused on the numbers is being able to look and say, "You know what? Let's change how everybody views what trucking is. It's not just drivers or people that are... " One of my friends like to talk about, "Oh, they drive so slow." But I'm like, "Let me tell you why they drive so slow and why you should be thankful for that. " And I was like, "You know all those Amazon packages that show up at your house, that doesn't just happen." So I think being able to be a good steward to the industry, to bring young folks into the industry as well, and just to be able to write the story of all these salt-to-earth people that often get overlooked, I think that's something I'm super passionate about.
Speaker 3:
That cultural focus has yielded massive dividends. While the industry is flooded with relentless driver and recruiting ads, Crawford hasn't had to run an ad in quite some time, relying entirely on continuous driver referrals and waiting lists.
Speaker 4:
Over the years I've heard stories of there are certain leaders that are really good at starting something. They get it to a certain point and that's kind of where their abilities cap. And then there are these people that they may not be the ones that you can get it going from day number one, square number one, but they do really, really well with an organizational scale. Now the ironic part through all this is having come from a carrier that at its max size was about 700 trucks I thought I was the later. But in reality, I bought this small company about, I think it was firetrucks when we bought it and it wasn't going to go on. And I had to essentially be the technician and wear a lot of different hats long way. I had a very strong background, but I didn't have a safety background, meaning actually working in a safety department and I had to build a safety.
So Abby, clearly we've talked about it. I got it to a point where I was comfortable. I held it there.
Speaker 1:
It stayed for about a decade. So then when I came on seriously, I said, "Hey, I'm looking for it to hit this and we have all these abilities. Our customers are asking for us to have more trucks." Our
Speaker 4:
Drivers refer drivers to us.
Speaker 1:
We have a waiting list most of the time for trucks. We have a rental in right now. We just don't have enough trucks. But again, I think that's one thing that we're so excellent at is we don't let the market tell us exactly what to do. Obviously you pay attention and you're fluent in what's going on, but we don't ride the waves. So then when the peaks are really peaking, you're not jumping ship to go find the next best thing.
Speaker 4:
We're actually growing in the down.
Speaker 1:
In the down market.
Speaker 4:
Control growth during the down market. Abby may not be that technician that can sit and fill in every desk from a coverage standpoint as in the early days I had no choice to, but she focuses a whole lot more on the holistic organization being a leader. She's a very good manager, but she's an even better leader. And I always say, I think I had it the other way. I'm an okay leader from the standpoint of I've been blessed to have tremendous people stay with me for a long time, but I think my skillset tended to be stronger on the management of processes.
Speaker 1:
And our generation work-life balance is a big thing, but that can look at so many things. So I try to really make it an environment people want to come to work for. So it's a stupid little thing, but every week I have a theme of the week. So this week it's an All-American theme and I have a dog, a little dog trinket with an American flag in its mouth. And then you're supposed to pass the award every day to somebody for X, Y, Z to help build sharing compliments to each other because sometimes it's easy in trucking, especially to stay down in some negatives. I try to make fun little things here and there or just little themes. So then today people are wearing American themed things. So just little things go a long way. You don't have to be endless deep pockets of having food trucks come in, but the little things really do matter here.
Speaker 4:
She touched upon it briefly. I'm sure you might have picked up on it. We're in an environment today. In 37 years in the industry, I have never seen as many recruiting ads as what ascend upon me and social media. We haven't run an ad for quite some time. We still have referrals coming in. We still have some unsolicited applications coming in. We do have a finishing program, so it says a lot for our culture and just truly being blessed that we're waiting for our new trucks to arrive and we have to rent trucks for people that we brought on.
Speaker 2:
Looking ahead, Abby has set highly calculated goals for the fleet and she wants to grow it up to 100 trucks over the next five years. She's prioritizing quality over rapid quantity to preserve the Crawford family culture where every single employee is known. We
Speaker 1:
Talked about that yesterday. I said, "You had president title for 21 years. There's a good chance I get to surpass you, " which is kind of interesting to think about. Goals for me, someone asked me today, what's the first thing I'm changing? And I said, "For us, this is more about a title change because I feel like I've been able to do all those. I've had the capabilities to be able to be empowered to make the changes I've been looking for. For me, I look for us to be at a hundred trucks within the next five years. We don't like to do fast growth, but for me, that's where it stops at this point of my time. That doesn't mean maybe we have a different facet of a company. I just think Crawford's niche is having everyone feel known and be known here. So I think that's something I look to do, be able to provide good jobs for good people.
It's not necessarily with very much quality over quantity here. So I just want to continue steering this trip in the right direction with creating some new positive experiences for other people. We have a training program, so I just really like to be able to give the opportunity to folks that maybe are passed up otherwise.
Speaker 4:
One of the things Abby and I have talked about is we believe what it is that really makes Crawford special is not exponentially growable. And that is we know the individuals as individuals, we know the customers. Not to say that it can't get bigger than a hundred, but I think it focuses more on operating models. So here in central Iowa, essentially 60% of our drivers are based out of central Iowa. There's 40% that are along lanes. But my long-winded way where I'm going is I know Abby's talked a lot about she sees this model being manageable for a hundred for this location and this trailer type. At some point in time, Abby has talked about a vision of if there's growth beyond a hundred in this, we develop a separate operating unit with a different trailer type. Or potentially we have opportunities with partnerships where we could potentially have another location at another place to develop the same thing, but it really is about the connections with
Speaker 1:
People.
Being grounded in our roots here. I think that's what our integrity is first and foremost and just having the value of everybody.Because a lot of times some drivers don't get to see their families very much or maybe they don't have good relationships with their families. So a lot of times we are their family here. So I do take that with a sense of pride that people are willing to come here and have the life that they've always dreamed for of themselves and being able to support them through that. So I know I have good stories of someone near homelessness and now they've been able to buy their first house. So being able to watch those kind of stories is what I want my legacy to be is being able to continue to empower people that maybe weren't believed
Speaker 4:
In. In 21 years, keep in mind, we have a lot of really long-term employees. The number of times that I've been able to hear, and I know Abby has an urgent short time here, people come to us and say, "My family, we just bought a home and never believed that was ever going to be possible." And they say, "We owe that to you guys." And I'm like every step of the way they're earning it. We're just truly grateful to get to be part of that.
Speaker 1:
I think one thing that resonated me most the other day happened here, we had to let someone go for unfortunate circumstances. But during the process he was upset that he was losing his job. But he said to us, we told him, "You have a CDL, you'll be able to get jobs elsewhere. We're just not the right fit for you. " And he said, "Well, that's the thing. All the jobs, they're not you guys. They're not jobs people want. Crawford has something here that isn't seen elsewhere." So I think even in their darkest times for somebody to come back and compliment us for what we do and what we provide here was kind of eye-opening.
Speaker 3:
For any fleet owner reading or watching this who is considering handing the keys over to their son or daughter, Greg and Abby emphasized that the absolute most important rule is to maintain healthy boundaries and never let the business come between your family relationship.
Speaker 4:
Through this process, I've had a lot of chance to look at that. And as Abby and I are involved in the industry, we talk about how I'm stepping down, she's taking over. And there's a tremendous amount of people that come out of the woodwork and say just how lucky I am because in many cases, not a lot of people have somebody who wants to take their business on for the next generation. And based upon that, I've had a lot of opportunity to think about that through this. And generally speaking, I think there's two categories that predominantly that situation fits into. One is the parent was so, so, so successful that the child doesn't really need to take on those responsibilities. But the other one, and I think the one that's more common, and in the early years was really the case here, which surprised me.
And that was where the reaction came from as far as originally wanting to talk her out of it was the fact that it wasn't easy.
Speaker 1:
It's not just a nine to five day.
Speaker 4:
Yeah, it's twenty four seven, 365. So make the job, the role seem desirable to your kids.
Speaker 1:
And I think another thing I don't think he'll ever press on because I don't think he's realized, but I feel like again, it was probably eight-ish years ago for sure we decided that this is exactly where we're headed. But I think 21 years ago it all started. I don't think a magic light necessarily switched, but I was involved with the company. It was something he was proud of. It wasn't something, oh, that's just dad's job. It was something like, this is what I've built and created and something to be proud of. So I'd be brought around to things all the time and I got to really experience what we had here. So to be able to have that in the background of my mind be like, wow, that's not necessarily something you find everywhere. So I think it's been in the works forever. I mean, now the past 10 years, it's been a lot more of a teaching process.
Speaker 4:
It has. Ever since she was a little girl when I first bought the company, it didn't even have TMF. And I'd have to come in on Monday nights and Tuesday nights because I had a CPA hired part-time to do payroll. And she didn't understand why all of a sudden her dad was never home on Monday and Tuesday nights. And then explained it to her to a five-year-old, I said, "Do you know how we live in this house and we have the car and we buy groceries?" And I said, "All this stuff has to be paid for. " And I said, "Essentially, I go to work so other families can do this for their family." And I started explaining the significance of the role, the responsibility. So a lot of it is, in my opinion, being more deliberate in those areas of explaining what positive impacts we are able to make in people's lives.
I didn't make it look easy along the way though. And I think that's the biggest thing is make it something your kids want to be a part of. That'd be the biggest thing.
Speaker 1:
And just over the past decade too, he's allowed me to have say input and then be able to be a part of other industry events. So I've been able to meet a bunch of other really amazing people. He's my biggest mentor, but being able to have the facet of being able to connect with other folks from other companies, get to hear what worked for them or didn't work for them has been really instrumental in my ability to be here and having that support from others as well has been awesome.
Speaker 4:
The other thing I would also share on that is don't let the business come between our relationship. I often tell people, and I picked up on this conversation, there's two things in this world that make me choked up when I talk about. One is the company and the other is my daughter. They both mean the tremendous, I mean foundational. I love my wife, but as I always tell her, I says, "We're partners. This is my daughter who's now being a partner I guess in the business. She's my daughter first. So if there's a disagreement about something here, we're still family when
We walk out the door and we'll figure this out. We'll figure this out. " So keeping healthy boundaries, healthy relationships and not letting the business come between the family. And then really it is, if you were to... This I know I've instilled too is our number one responsibility is to protect the Crawford family. And that's something here that we have is a lot of companies will talk about that. The people that are with us long-term here, they'll oftentimes be talking about, "Yeah, you hear that a lot, but here it is a thing. We protect the Crawford family."
Speaker 2:
That's it for this week's 10:44. You can read more on ccjdigital.com. While you're there, sign up for our newsletter and stay up to date on the latest in trucking industry news and trends. If you have any questions or feedback, please let us know in the comments below. Don't forget to subscribe and hit the bell for notifications so you can catch us again next week.
























