Meet the small but mighty team behind your favourite road trips!
founder
The woman who started it all! Jessica got the idea for this company after creating a scavenger-style road trip as a gift for her parents. Armed with a laptop and a printer, she launched the company in January 2020 from her living room floor - did we mention she was six months pregnant with her first son at the time?! Today, she focuses on the big picture and helps guide the team through new launches and business ideas.
Fun fact: Jess used to teach English in North Korea!
director of operations
Jessica (JB) keeps the wheels turning at Guess Where Trips. She leads the day-to-day operations of the business: turning big ideas into action, building timelines, overseeing marketing campaigns, managing fulfillment centres, and making sure the website (and everything else) stays up to date. From big-picture planning to the tiniest details, JB helps keep the entire team organized, aligned, and moving forward.
Fun fact: her chiweenie works security for the team, unpaid and, frankly, undeserving of the title.
Product Manager
Hannah joined the team in 2023, and since then has helped to grow our brand in so many different directions. From product launch strategy to research & development (and even writing our new Detour Diaries book!), she continues to find new ways to improve our road trip products for our customers. She has a meticulous eye for detail, and the best dance moves on the team.
Fun fact: Hannah went to Italy for professional dance training, and now she directs/choreographs musical theatre productions across London, ON!
MARKETING & PARTNERSHIP COORDINATOR
Sydney was Guess Where Trips’ very first hire - you probably recognize her from our Instagram reels! As our Marketing Coordinator, she keeps all of our marketing efforts aligned and on track. Sydney truly embodies the Guess Where Trips voice, brand, and spirit, which shines through in everything she creates.
Fun fact: Sydney once lived in Liverpool and is known to hop on a plane for the occasional long weekend back there.
Customer experience coordinator
Jessi-Rae is our Store Manager and the friendly face behind so much of what we do day to day. She leads all things in-store while also overseeing customer service and wholesale, making sure every customer and retail partner has a great experience with Guess Where Trips. Jessi-Rae works closely with both Jessicas to keep operations running smoothly and ensure the magic carries from our team to every road trip that goes out the door.
Fun fact: Jessi-Rae competed in figure skating growing up, still plays competitive soccer (despite breaking her leg playing last year!)
Fulfillment Manager
Brian is the powerhouse behind our fulfillment operations. As our Fulfillment Manager, he handles everything from printing and assembling each road trip to tying them up and sending them off to our shipping partners. He also keeps a close eye on inventory to make sure we’re always stocked and ready for your next adventure. If a Guess Where Trip makes it to your doorstep, it’s because Brian made sure it got there.
Fun fact: Brian worked for Apple for over a decade, and is our go-to tech guy.
Packaging specialist
Janet works alongside Brian to make sure every trip is assembled and tied together with care. From tucking in the booklet to the final bow, she brings a steady hand to every package.
Fun fact: Janet actually started out as Jess's kids' nanny, pitching in during our busiest Christmas seasons — and she's been part of the GWT family ever since.
FREQUENTLY ASKED QUESTIONS
We design one-day surprise road trips where the destination isn't revealed until it's time to hit the road.Pick a trip based on what interests you most (think scenic hikes, cute cafés, quaint small towns), then follow your self-guided itinerary as the day unfolds. We've planned a full day of hidden gems, roadside stops, local favourites, and unique experiences you might never have discovered on your own. It's a chance to explore somewhere new and make lasting memories - right in your own backyard.
A physical trip comes in the mail as 5 sealed envelopes: a "Before You Go" guide, plus 4 surprise stops you open one at a time as your day unfolds. Since it ships, it takes a few days to arrive.
A digital trip has the same 5 sections, sent instantly to your inbox after checkout. Since it's all one document, just go section by section and try not to peek ahead.
You won't know the exact destination ahead of time, but you'll have a good sense of the area:
Shipping speeds vary based on location. We ship out of Markham, ON and Detroit, MI, and estimate 4-10 business days - those closer to our shipping locations may receive them sooner, while those on the west coast or in rural areas may experience slight delays.
Need it sooner? A faster shipping option is available at checkout for an extra fee.
Can't wait at all? Try our digital road trips!
Our trips make a great gift! If you're sending it straight to the recipient, please share the tracking link you receive once it ships, as we aren't able to include any notes in the package - while we love a good surprise, receiving an unmarked delivery with no idea who it's from isn't as fun.
Gift cards cover any physical road trip. If used toward a digital trip, the remaining balance stays on the card. Gift cards are priced slightly higher than a single trip to account for tax at redemption. Gift cards are redeemed at checkout.
