Position: Guest Services Assistant

As Roadtrips prepares for and begins to execute our 2026 events, we are seeking a passionate and motivated Guest Services Assistant to support our At Your Service Team, focused on providing excellent customer service to all booked guests.

As a Guest Services Assistant at Roadtrips, you will play a crucial role as liaison between our travel advisors and/or our direct travelers and our Product Team, who are tasked with fulfilling clients’ booked travel experiences. You will work closely with our teams to relay important trip details to our clients via phone calls and emails, as well as providing essential technical support for various customer-facing applications.

The successful applicant will work directly with our Product Team in our Winnipeg, Manitoba-based office. This is a 10-month, full-time contract position running from October 2025 through July 2026.

• Act as point of contact with clients/travel advisors for pre-event, during travel, and post-event

• Provide technical support for clients on multiple device types with apps related to travel

• Assist with drafting and proofreading client communication and travel documentation

• Manage client communication for numerous events simultaneously

• Provide important event or destination communication updates

• Assist with administration related to additional services such as tours, transportation, restaurant reservations, and other special requests

• Assist with customer fulfillment as required, including invoicing, payment collection, and processing

• Provide additional Product Team support for administrative and customer service–related tasks

• Other administrative, fulfillment, and operational tasks as required

• Excellent oral and written communication skills

• Ability to use positive language and maintain self-control while actively listening to and addressing client concerns

• Strong computer skills; previous experience working with a Mac computer as well as Microsoft 365 products an asset

• Team player who can balance competing interests and find solutions

• Ability to remain poised under pressure and resolve issues quickly and effectively

• Highly organized and detail-oriented

• Positive work ethic and adaptability

• Must be eligible to work in Canada out of the Winnipeg-based office (remote work not offered)

Roadtrips’ standard Winnipeg office hours are 8:30am–5:00pm CST.

Roadtrips is an equal opportunity employer that offers:

• Competitive pay

• A fun and exciting work environment

• The chance to travel to major sporting events

This job is a contract, term position. Compensation will be based on experience.

Please send letter of interest and CV to lauren.lehotsky@roadtrips.com