Careers

Guess Where Trips is looking for a friendly, organized, and travel-loving Customer Support Specialist to join our growing team in London, Ontario.

This role is perfect for someone who’s equal parts people person and behind-the-scenes superstar. From greeting walk-in customers to keeping our office running smoothly, you’ll be the go-to for both internal team needs and external customer care.

What You’ll Be Doing:

• Welcoming customers who visit our office to purchase or pick up orders
• Managing the day-to-day vibe of the office: stocking snacks, keeping supplies on hand, and helping organize team activities
• Responding to customer inquiries via email, social media, and our website
• Packaging, gift wrapping, and shipping products as needed—especially during peak seasons and holidays
• Helping colleagues with other tasks, such as travel updates and our affiliate program

You’d Be a Great Fit If You:

• Have 2+ years of experience in customer service, hospitality, retail, or a similar field
• Are friendly, reliable, and thrive in a fast-paced, people-first environment
• Love staying organized and keeping things running smoothly
• Are confident handling emails, DMs, and social messages with professionalism and warmth
• Are available to work full-time, in-person (Monday to Friday, 9 AM – 5 PM) at our London, ON office
• Bonus: You’re passionate about travel, love a good road trip, or already know what Guess Where Trips is all about!

Perks:

• A fun, flexible work environment with a tight-knit team
• Paid training and opportunities to grow with a fast-scaling Canadian travel company
• Employee discounts on our surprise road trips and retail products
• Occasional team outings and travel adventures (we practice what we preach!)

To apply, please send your resume and a short cover letter to jessica.bax@guesswheretrips.com.

Applications without cover letters will not be considered—we want to hear why you're excited about this role!

Note: We are no longer hiring for this role, but you are welcome to submit an application if you're interested in being contacted should we expand this role in the future.

Applications submitted by email will not be accepted.

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.

Applications submitted by email will not be accepted.