Customer Support & Retail Store Specialist
Location: London, ON
Start Date: June 2025

Guess Where Trips is looking for a friendly, organized, and travel-loving Customer Support & Retail Store Specialist to join our growing team in London, Ontario. This is a full-time role that starts with in-office training and support responsibilities (Monday to Friday, 9 AM – 5 PM) and transitions in October to managing our very first retail store at 100 Kellogg Lane.

This position is perfect for someone who’s equal parts people person and behind-the-scenes superstar. You’ll begin by learning the ins and outs of our surprise road trip products, supporting our team with customer inquiries, and assisting with day-to-day operations. Come October, you'll take the lead on managing our new retail space—ensuring it’s welcoming, well-stocked, and running smoothly—while continuing to provide excellent customer support remotely.

What You’ll Be Doing (June–September, 1540 North Routledge Park):

• Training on all of our products and processes to understand how we support our customers and operate as a business
• Responding to customer inquiries via email, phone, social media, and our website
• Helping out around the office: stocking supplies and snacks, assisting with team events, and providing general support
• Packaging, gift-wrapping, and shipping orders when help is needed
• Supporting team tasks such as travel updates, affiliate coordination, and customer experience improvements

What You’ll Be Doing (Starting October, 100 Kellogg Lane):

• Managing the day-to-day operations of our retail store at 100 Kellogg Lane
• Ensuring the store is well-stocked, visually appealing, and aligned with our brand
• Coordinating inventory and retail orders with our fulfillment and operations team
• Continuing to respond to customer emails and phone calls from the store location
• Representing the Guess Where Trips brand with warmth and professionalism to walk-in customers
• Working a flexible schedule, including evenings and weekends, to keep the store running smoothly
  

You’d Be a Great Fit If You:

• Have 2+ years of experience in customer service, hospitality, retail, or a similar role
• Are friendly, reliable, and thrive in both fast-paced and customer-facing environments
• Are highly organized and detail-oriented, with a “do what needs to be done” attitude
• Are comfortable responding to emails, DMs, and phone calls with professionalism and warmth
• Are available to work full-time in-person:
  June–September at our head office (Monday to Friday, 9 AM – 5 PM)
  Starting October at our retail store, with availability on evenings and weekends
  

Bonus: You love travel, are obsessed with Ontario road trips, or already know and love Guess Where Trips!

Perks:

• Paid training and growth opportunities within a fast-scaling Canadian travel company
• A supportive, tight-knit team that values creativity and initiative
• Employee discounts on our trips and retail products
• Occasional team outings and road trip adventures (yes, we test our own trips!)

To Apply:

Please send your resume and a short cover letter to jessica.bax@guesswheretrips.com.

Applications without a cover letter will not be considered—we want to hear why this role excites you!

Part-Time Packaging Associate

Company: Guess Where Trips

Location: 1540 North Routledge Park, London ON

Hours: Part-Time (20-30 hours per week); temporary role through summer and fall

About Us:
Guess Where Trips specializes in creating unique travel experiences through surprise road trips. Our products are designed to delight and inspire, offering customers unforgettable adventures across various destinations.

Position Overview:
We are seeking a detail-oriented and proactive Packaging Associate to join our team. This role is crucial in ensuring the efficient assembly of our products, maintaining quality standards, and supporting our operational workflow.

Responsibilities:

• Assemble products by tying 5 envelopes together efficiently and accurately.
• Monitor printers for tasks such as changing toner, staples, and paper, and clearing paper jams.
• Take proactive steps to address any issues with printers, booklet/envelope quality, or the assembly processes.
• Maintain cleanliness and organization of the packaging area.

Requirements:

• Must be able to tie a bow.
• High attention to detail and accuracy in tasks.
• Ability to work independently and take initiative to solve problems.
• Comfortable with repetitive tasks and able to meet productivity goals.
• Physically capable of lifting up to 50 lbs and performing manual tasks.
• Willingness to learn and operate envelope-stuffing machinery (training provided).
• Excellent communication skills and a team player attitude.

Preferred Qualifications:

• No experience required

Benefits:

• Competitive hourly wage.
• Flexible scheduling
• Opportunity to be part of a dynamic and growing company.
• Training provided to enhance skills in packaging and operations.
  

How to Apply:

Please send an email to Jessica at jessica.bax@guesswheretrips.com outlining your availability and interest in this position - along with a few words about why you’d be the perfect fit. Resume and cover letter not required - we are more interested in hearing directly from you!