Traveler & Travel Advisor Reviews: 4.9 out of 5 stars  

If you’ve already traveled with us, there’s a good chance you’ve met Jeff Wills as he has been on the ground at many of our events over the past 19 years that he has been part of the Roadtrips team. We wanted to help you get to know Jeff a little better, and share some of his insight about our company.

Jeff first started here in 1997, when Roadtrips was a very different company. For a start, there was only President Dave Guenther and one other employee, so Jeff signed on as employee number three. “I’d recently moved back to the city and my goal was to work in sports or music, so I started with this smaller company in order to help it grow. I wanted to ride the bubble as it got bigger, and my plan worked out,” he says.

Back then, all Roadtrips did was hockey and baseball tours. “Most of our advertising was placing ads in the Baseball or Hockey News, and people would call for a brochure, then they’d call back and buy. We’d get 100s and 100s of people to Toronto Maple Leafs getaways or Montreal Canadiens Getaways, so we were the biggest hockey tour company, but as we grew we just added more and more sports,” he says, “Soon after the internet was generating most of our leads and I was in change of that, which helped me grow with the company.”

Jeff has always been a big hockey fan, so Roadtrips was a natural fit from the start. “I was excited to join the company, and I hadn’t even traveled a lot before joining Roadtrips. I felt right from the beginning that I was part of a pretty amazing company.” It didn’t take long for Roadtrips to grow, and in 2000 the company moved to a big new office space that was way bigger than required, but they soon filled it. “We were up to seven employees at that point and just kept growing,” says Wills.

Incidentally, Dave Guenther got his start running Spring Break trips and bus trips to concerts when he was still at university. “We started out when we were all pretty young and grew up as a company,” Wills says. “I’ve been here 19 years but the company has changed so much that it has kept it interesting. You definitely don’t get bored around here, that’s for sure!”

A turning point for Roadtrips in terms of their focus was the 2006 World Cup in Germany, where they did a lot of business. “At that point we’d done other international events, but this really pushed us. People had become a little more comfortable booking their own trips within North America on their own, but going overseas was where they required a little more assistance,” he says. (This has been especially evident recently in places like Brazil, where there are so many differences with language etc.)

Wills is obviously very happy with how Roadtrips continues to grow, and has a few ideas as to why they are market leaders. “Really it is all about the level of support that our guests get on the ground. There’s something to be said for under-promising and over-delivering,” he says. “We deal with transportation and hotels, and people aren’t left alone. There’s a lot of personality that comes with our trips, as well as our high-touch service model.”

When you quiz Wills on his top adventures as part of the Roadtrips team, he says that going to that 2006 World Cup in Germany was pretty amazing. “We were based out of Frankfurt, and at that point I was only a passing soccer fan, but being part of that atmosphere you realize that an event like that is more of a cultural exchange than just going to a sporting event,” he says. “In the city there’s a game every few days, and the countries are all partying together in the streets. I really got hooked on soccer at that time, so that was a big deal.”

As a “crazy Philadelphia Flyers fan” whose uncle was an original Flyer when the team started in 1967, getting to see them play in the Stanley Cup Finals in Philadelphia a couple of times has been incredible for Wills. “Seeing your team win in their home city with the fans going completely bonkers, it was just so much fun,” he says.

“The 2012 London Summer Games was pretty special, and getting to live in London for almost a month – which is what we do when working these big events – you feel like you’ve figured a city out and that you really understand a place, you’re not just traveling as a tourist. I really enjoy that,” he says.

Wills is really looking forward to several major events, such as the America’s Cup in Bermuda next year, the Winter Games in South Korea in 2018, The World Cup in Russia, “and then Tokyo in 2020. I don’t know that any of these places were on my bucket list, but it is so neat to do these events have the opportunity to visit these places like this, at this level,” he says. “I look forward so much to the cultural exchanges that come with these trips.”

Also exciting is the way that Roadtrips is continuing to expand their offerings to guests. “As a company we’re adding more and more services, and it feels like we just get better with every event. I honestly feel like we’ve developed some kind of secret sauce when it comes to sports travel, and we are trying to apply that to other things and I’m excited to see where that takes us,” Wills says.

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