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Guess Where Trips

Guess Where Trips was created by Jessica Off after several years of planning travel. 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?

Come work for us!

Available Positions

The Customer Support Specialist (CSS) 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.

Responsibilities include, but not are limited to:

-Answering emails and direct messages on all social sites

-Ensuring travellers select the right surprise road trip based on their travel preferences

-Assisting our Travel Producer with the creation of new trips

-Researching potential stop ideas

-Connecting with local businesses who are included in our itineraries

-Assisting with some social media content

We’re looking for someone who:

-Has at least two years of experience in a customer service setting

-Is well versed in Canadian geography

-Has a passion for local travel and road trips

-Has a background in hospitality and/or tourism (preferred but not required)

-Has knowledge of social media platforms (Instagram, TikTok and Facebook)

-Resides around the London, Ontario area (GWT office)

-Can work 9 AM-5 PM Monday-Friday

If you’re interested, please send a cover letter and resume to