Jennifer Winters has taken a long journey to join the trucking force of Newmarket Equipment.
Since the England native came across the pond to Ontario in May, the 31-year-old has been trucking across the continent, attracting attention with a popular vlog series and as one of the few women truck drivers on the road.
“Out on the road, I have felt very safe, and I felt very empowered,” Winters said, recounting coming across a woman and her daughter at a stoplight in Newmarket. “They were pointing at me and throwing their thumbs up … It was so rewarding. It really was wonderful.”
Winters has garnered more than 2,800 subscribers on YouTube chronicling her journey as a truck driver, coming from Manchester, U.K. to work in Newmarket.
She has long loved North America, travelling here regularly to take on seasonal work at camps in the United States.
But Winters said she knew she needed to find more stable, permanent employment one way or another. Having had a job driving cars from dealerships to new owners, she said an Uber driver suggested she try truck driving.
“I didn’t know that was even an accessible way for me. Especially in England, you don’t see many females driving trucks over there,” she said. “I was really taken aback when he suggested it. But I started looking into it.”
Winters said she decided to pursue it, going for a licence in England as she planned her move to North America. She failed her driving test the first three times, finally passing the fourth try.
“The pressure just really ate away,” she said. “I’m not really ashamed to admit that because there’s no shame in not passing the first time.”
After travelling across both England and North America, Winters said she just fell in love with the way of life in North America. Although she spent more time in the United States over the years, Winters said she found out getting a permanent visa would be a lot easier in Canada versus the U.S.
“It was really straightforward. I ended up getting my visa and moving over a year later,” she said. “It all kind of fell into place … I love Canada and I think it’s a fantastic country and I’m honoured to be living here and be able to contribute to the economy.”
Winters started chronically that journey via a YouTube vlog, amassing more subscribers. She said she previously studied for film and this was a way to use those skills more casually.
It has led to some great connections with others, Winters said.
"You are an inspiration to all young ladies in England and Canada," one comment on her most popular video, with more than 10,000 views, said.
“It’s sort of grown into this lovely little community to my surprise," Winters said. "I’ve actually had a bunch of people reach out to me who would like to do the same thing."
Winters went to school, got her licence in Canada and started looking for work. She described challenges getting hired with no experience, but she started calling after sending out resumes. Eventually, she got an offer for an interview with Newmarket Equipment — and when she went over to do a road test, she got the job.
“I’ve been so grateful. I struck gold when I joined that company. They’re really a family-run company, you’re not just a number, you’re a human,” she said.
Starting the job was a challenge, Winters said. But she has been able to persevere and is now driving fine.
“When I started, it was a massive shock to the system … the first time was nothing short of absolutely petrifying, honestly, but I think that’s really important because the fear keeps you safe,” she said. “It’s gotten easier as time goes on. The fear sort of starts to subside. Your confidence grows.”
Breaking into the industry as a woman has also had its challenges, Winters recounted. Although much of the community is accepting and encouraging of women truck drivers, there are still instances of sexism.
“Sexism is real in this industry. There is sort of an underbelly to trucking, where you get your old heads who think this is no place for a woman, or we’re not capable,” she said, adding she has seen it happen through the trucking radio where voices are anonymous. “As soon as someone hears your voice over the radio and they realize you’re a woman, you either get abused or you get hit on, and it was pretty eye-opening and pretty shocking.”
Still, Winters said the industry has reacted positively to her. Her driving school has invited her to events to speak about her experience in the industry, she said.
Winters started out living in Port Credit but is moving to Vaughan to be closer to the Newmarket yard she drives out from.
She said she is appreciative of Canada and intends to become a permanent resident.
“I really hope I can make a future here for myself. I just think this is an absolutely wonderful place and I’m very blessed to be here,” she said.
