Love a good surprise? Love a good road trip? Be part of Guess Where Trip's growing team!

Guess Where Trips

Our team understands how long it takes for the average trip to be planned and booked. One of our greatest joys is creating exciting itineraries that allow travellers to discover new places they would have never seen before. Our ultimate goal is to create an experience that will inspire you to step out of your comfort zone and explore your own backyard. Guess where you'll go next?


Available Positions

CTravel Support Specialist / Travel Agent CLOSED

The Travel Support Specialist (TSS) is a service fanatic, organizational wizard, road tripper, surprise lover and problem solver all rolled into one package. They know the ins and outs of our itineraries and have a passion for helping other people. Their primary role is assisting travellers throughout the booking process.


Responsibilities include, but are not limited to:

  • Answering emails and direct messages on all social sites
  • Ensuring travellers select the right surprise road trip based on their travel preferences
  • Connecting with local businesses who are included in our itineraries
  • Assisting with booking overnight trips (*TICO certification is strongly preferred)


We’re looking for someone who:

  • Has at least two years of experience working in the hospitality, customer service or tourism sector
  • Is well versed in Canadian geography
  • Has a passion for local travel and road trips
  • Has a background in booking travel (*TICO certification strongly preferred)
  • Resides in the London, Ontario area
  • Can work 8 AM – 4 PM or 9 AM – 5 PM Monday-Friday


*Being TICO certified is a requirement of the job (in order to book overnight accommodations for our travellers). If the applicant is not TICO certified, they will need to become certified shortly after starting the role. GWT will cover training costs.


Please send your cover letter and resume to