Meet Dale Flynn, Jr. – Solving logistics challenges with heart, hustle, and a dash of fun

Behind every successful shipment is a story, and Dale Flynn, Jr., Director of Business Development at McClay’s Transportation, has plenty of them to tell. With nearly two decades of experience in sales and leadership roles, Dale brings a unique combination of strategic expertise and a passion for problem-solving to the world of logistics. From navigating the complexities of cross-border freight to fostering close relationships with customers, Dale thrives on turning challenges into opportunities.

But there’s more to Dale than his impressive professional résumé. Whether he’s kicking a soccer ball on the pitch, running for charity with colleagues, jamming to classic rock with his daughter, or spending quality time with his family, Dale embodies the values that make McClay’s a trusted and personable partner in the transportation industry.

In this Q&A, Dale shares insights into his career, his approach to logistics, and even his favorite Transformer. Let’s dive in!

Q: You had a long career in the alcohol beverage industry before transitioning to transportation and logistics. What inspired the change?

Dale Flynn, Jr.: My career journey has been a bit unconventional. I spent about 20 years in sales and leadership roles in the alcohol beverage industry, with the last 10 years managing Southwestern Ontario. I’ve always been drawn to family-owned businesses where relationships matter. I’ve known Troy and Ryan McClay for a long time—we grew up together, attended multiple events, and even collaborated professionally before I joined the transportation industry.

About two years ago, Ryan and I reconnected and discussed bringing someone on to focus on sales and marketing at McClay’s. The conversations we had just checked all the boxes for what I wanted at this stage of my life. Joining a family-oriented, close-knit team has been incredibly fulfilling. Here, you’re not just a number; you’re valued, and your voice is always heard. (Editor’s note: Dale’s got a great voice, next time we’ll have to do an audio blog).

Q: What do you enjoy most about working in transportation and logistics?

Dale: For me, it’s all about solving problems and keeping the supply chain moving. This isn’t just about shipping goods; it’s about helping businesses make better decisions. I enjoy sitting down with customers, asking questions about what they value in a carrier, and designing solutions that fit their unique needs. I don’t see us as just another carrier; I see us as partners who can help keep supply chains moving forward.

Q: Cross-border freight is an area of McClay’s expertise. What are the biggest challenges shippers face in this area?

Dale: A lot of shippers focus solely on getting the lowest rate, but that doesn’t tell the whole story. Without the right documentation—like bills of lading or commercial invoices—or an understanding of customs requirements, you risk delays and unexpected costs. We’re seeing a lot of new carriers enter the industry who may offer competitive rates but lack experience in cross-border logistics.

At McClay’s, we focus on technology—like satellite tracking—and ensuring compliance with import regulations. Our operations and dispatch teams are accessible, even after hours, so our customers can adjust timelines as needed. This means we can provide not just competitive rates but also peace of mind that shipments will cross the border smoothly.

Q: What opportunities and challenges do you see ahead for the transportation industry, especially with the new year approaching?

Dale: Tariffs and the shift to electric vehicles (EVs) are two key areas to watch. Southwestern Ontario is heavily focused on the automotive sector, so any changes there can have ripple effects. There’s some concern about potential tariffs impacting shipping, especially in the automotive industry.

However, I’ve had customers tell me their phones are ringing more since the recent election, which is a positive sign. The EV projects have been pushed back to 2026 due to infrastructure challenges, and I believe the prices of combustible engine vehicles might start to correct themselves. I’m optimistic that if we focus on each quarter and don’t get ahead of ourselves, good times are ahead. With every challenge comes an opportunity.

Q: What advice are you giving to shippers looking to move cross-border freight?

Dale: Do your homework. I find that the more information we have as carriers, the better we can serve our customers. Ask questions like: Do you have satellite tracking? What are your dispatch and operations hours? Can I connect with someone after hours if needed? Do you have fleet maintenance on-site? Am I asking for the right equipment?

The more details we know upfront, the more accurate and competitive our rates can be, and the better we can meet timelines. It’s all about open communication and collaboration.

Q: If you could change one thing about the cross-border process, what would it be?

Dale: Definitely more lanes and bridges. Border wait times can be a real bottleneck, and adding infrastructure would go a long way in improving timelines and reducing stress for everyone involved. We’re hopeful that the Gordie Howe Bridge, once completed, will provide a third crossing into Michigan and help alleviate some of these issues.

Q: Outside of work, how do you challenge yourself?

Dale: Soccer is my passion. Even at 42, I still play at a reasonably competitive level—well, when I’m not sidelined by injuries! Being active keeps my energy levels up and pushes motivation in all areas, including work.

I also enjoy running, which helps me clear my head and think about what’s going on both professionally and personally. Recently, I participated in a charity running event called “Running with the Bulls” (Editor’s note: No actual bulls involved, it’s just a name) with colleagues, including Tristan McClay, Ryan’s son. Funny story—we tried to promote the event on Facebook, but it flagged our post for violating community standards because it thought we were actually running with bulls! (Editor’s note: See?)

Another activity I enjoy is playing Wallyball with colleagues every Wednesday night. It’s similar to volleyball but played in a squash court where you can use the walls. It’s a great way to build team spirit and connect outside of the office.
But most importantly, I love spending time with my family—my wife Stephanie and our 13-year-old daughter Marley. Whether we’re traveling, going down to the lake, or just hanging out at home, family time keeps me grounded.

Q: Tell us more about your relationship with music. Got a logistics playlist that gets you going?

Dale: Absolutely! I love old rock and roll—bands like AC/DC and Nirvana are staples for me. It’s funny because Guitar Hero got me back into some of the music I grew up with. Now, Marley is learning guitar, and it’s amazing to see her get into the music I grew up with. It’s great to bridge generations through music, and feels like a special connection we share.

Q: Now for the really serious, hard journalism questions: Who is your favorite Transformer, and if you were one, what would you transform into?

Dale: My favorite Transformer is probably the classic choice—Optimus Prime (Editor’s note: To be fair he is both optimal and prime, so it’s a good choice). But if I could transform into anything, I’d choose an airplane to speed up timelines! Dealing with border crossings and timelines can be stressful, so being able to fly over would certainly help. (Editor’s note: Classic logistics answer. A+)

Q: Which movie best captures the vibe of cross-border logistics? Some options might include Sicario, No Country For Old Men, Traffic, From Dusk Till Dawn (that’s the one with George Clooney and vampire strippers).

Dale: I’d have to go with “Over the Top” (1987) starring Sylvester Stallone. Sometimes in logistics, you feel like the underdog facing a big challenge, but with perseverance and determination, you overcome obstacles. It mirrors the ups and downs of navigating cross-border shipping. You might start off unsure, but when you persevere and get that shipment delivered on time, it’s a real victory. This movie really couldn’t be a better fit when you really think about it. It’s about an arm-wrestling truck driver, after all… (Editor’s note: Given that the other options suggested were all extremely NSFW, this was a very solid choice).

Q: We hear that office culture is important at McClay’s. Can you share more about that?

Dale: Absolutely. We have a great team here, and we try to foster a friendly and collaborative environment. Colleagues take turns bringing in snacks and treats, which is always a hit. Sometimes I bring leftovers home for Marley, and she jokes about wanting to come to work with me because of the great food! She says we eat the best food at work. We also enjoy some friendly banter and jokes among the team. It’s important to have that camaraderie and not take things too seriously all the time.

Q: We noticed you include “Jr.” on your business cards. Is there a story behind that?

Dale: Yes, there is. I’m named after my father, who is also known in the same circles and has connections with the McClay family. To avoid confusion—since we look somewhat alike and share the same name—I include “Jr.” on my business cards and sign-offs. When I was younger, I wasn’t too keen on it, but now I’ve embraced it. It’s become part of my professional identity. (Editor’s note: Dale still looks totally young and hip, probably all that soccer).

At McClay’s, problem-solving isn’t just part of the job—it’s who we are. Dale Flynn, Jr. and the team thrive on turning challenges into opportunities, ensuring that every shipment gets where it needs to go. Whether it’s leveraging technology for smoother cross-border shipments, fostering strong customer relationships, or building a vibrant team culture, Dale embodies the spirit of McClay’s Transportation.

Ready to see how we can help your business? Reach out—or connect with Dale on LinkedIn!