How Raymond Conroy, a self-made truck driver, made a name for himself transporting milk across Ontario
June 5, 2018
MISSISSAUGA, Ont. — It’s a story you’ve heard time and time again in trucking.
A little boy, whose father and uncles drove big rigs across the country, catches the trucking bug, and starts a trucking company of his own.
That’s the tale of Raymond Conroy, owner and founder of Pin to Pin Express of Mississauga, Ont.
“As a child, I grew up around trucks,” he recalled. “That’s how it started. My dad and my uncles drove. I was a guys’ guy and I loved the big equipment and it was hard to stay away from. My dad always called me the Peterbilt kid when I was growing up because those were my favorite. I always liked the Peterbilts – and here I am now. Once you get involved in trucking it’s hard to get out.”
Conroy started as a driver around 1986 when he was 23 years old.
Eventually, after driving for a while, he got into dairy hauling and starting delivering milk for Parmalat Canada.
“Then they decided they weren’t going to use company drivers anymore,” Conroy recalled. “They wanted brokers. And I didn’t think I was ready for that, so I looked for another job.”
Conroy said he always kept in touch with Parmalat over the years as he hauled for other companies stateside. And finally, an opportunity came up for him to work as a broker for Parmalat.
“It was a run into Sudbury and back,” he said. “And I thought, how ironic, because as a kid, my dad’s run used to be from Sudbury and back, so I thought it was perfect. I did that linehaul and I still do that run today.”
Parmalat allowed Conroy to grow from a company driver, to a broker, to a carrier over 22 years.
Today, Pin to Pin has 12 trucks and 14 drivers working for it, hauling pasteurized, packaged milk around Ontario, mostly to grocery stories, and on occasion to distributors that go out to restaurants.
Conroy said unlike other trucking companies, he hasn’t had to worry about the driver shortage.
“I’ve never had to advertise to get drivers,” he said. “I’ve mostly hired through word of mouth. And if guys do leave me for another job, they do so on good terms and I tell them they are always welcome back if things don’t work out. And I’ve had a few guys come and go.”
After 22 years in business, Conroy said he is proud that he has some long-term drivers who’ve worked for him for more than a decade.
“When drivers leave here, it’s never to do with the company,” he said. “It’s mostly that they want to retire.”
Most of this is good luck, said Conroy, is thanks to the nature of milk hauling.
“It’s very repetitive,” he said. “Which is a good thing for most. My drivers know when they’re going to be home for dinner. But I know some people don’t like that.
Because you’re driving the same route, seeing the same customer every time you’re on the road. Some people get bored. But I’ve had luck with finding people who want that kind of thing.”
So much so, that Conroy even has some ex-employees call him when they’re on holidays with another company and ask for work.
“I think they like working for me because I know what it’s like to be in the driver’s seat,” he said. “I was a driver, and I do miss it sometimes. I think they also like that it’s a family-oriented business. I’m really approachable and I make sure to treat them right and let them know that I need them as much as they need me.”
And the Peterbilt kid has his employees driving only what he considers the best. Peterbilts, of course.
“We really do have top of the line equipment, which I think helps keep the drivers happy,” he said. “Our trucks are the next best thing to show trucks. Because I think that for drivers, the truck is your office that you’re in for so many hours a day. So why not have it be the best?”
Conroy also said that he is a stickler for safety and training. He road-tests each and every driver he hires.
“I spend a lot of money on training,” he said. “I really want to be classy out there on the road. We don’t own any trailers. And so, because my guys pull my customers’ trailers, that’s their logo on the trailer. It’s a moving billboard for them. So, it’s important my drivers drive safe and represent Pin to Pin well.”
Recently, one of Conroy’s senior drivers had his son join the business fresh out of driving school.
“We trained him for months,” Conroy said. “And now he is good to go. I can sleep well at night knowing I don’t have to worry about him.”
As the business continues to push on, Conroy says his main focus is on growth and safety.
“Safety is so serious,” he said. “One bad incident can ruin a business and we know that. So, we really take training seriously. I stay on it and I make sure all my guys know what they’re doing.”