Careers

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

Woman taking a photo with a vintage Canon camera.

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?

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COME WORK FOR US!

Available Positions

Road Trip Rep Program (Trial Program)

Locations: Victoria, BC; Philadelphia, PA; San Francisco, CA; Austin, TX

ABOUT THE ROLE
We’re launching a trial Road Trip Representative Program. We are looking for a passionate, creative, and self-motivated individual who loves local travel and is an expert in one-day road trips within their region. This role is focused on creating and fostering community through social media platforms like Facebook Groups and Instagram, testing and refining our current Guess Where Trips (GWT) itineraries, and creating new road trip experiences.

RESPONSIBILITIES

Building Community:

  • Manage local social media accounts (Instagram and Facebook Groups) for your region.
  • Engage with local followers by sharing travel tips, road trip tricks, and itinerary inspiration.
  • Host conversations through community forums and create a sense of connection among local followers.

Content Creation:

Create and post two reels per week and share Instagram stories regularly to highlight road trips, tips, and destinations.

Provide feedback on current road trips by filming at least two locations per road trip and submitting high-quality images/videos.

Road Trip Testing:

  • Test current road trips in your area and provide feedback with the intention of improving the itineraries.
  • With the potential of creating new trips when needed 

This is a four-month, part-time, remote contract position with the potential for extension based on performance. Perfect for someone who is looking for a flexible side job to fit around other commitments. While the position is remote, you are expected to live in the area you are applying for, as local content will be required.

Compensation will be based on experience and qualifications.

Please apply here - applications submitted by email will not be accepted.