Tourism Talks
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December 18, 2024

Cracking the Itinerary Code with Guess Where Trips

What if creating trip itineraries could be more than just a task — it could be the foundation of an empire?

That’s exactly what Jessica Off is building. After leaving her marketing job in the tourism industry, Jessica launched Guess Where Trips, a wildly creative business that reimagines how people explore. Today, her brand boasts over 100,000 Instagram followers, brings in $5 million a year, and recently scored a deal on Dragon’s Den.

In this talk, we uncover Jessica’s inspiring journey and get insider tips on how she built her wildly engaged social media following. From the art of crafting unforgettable itineraries to the single most important decision that she credits with her social media success, this is your chance to learn from one of the tourism industry’s most exciting young entrepreneurs.
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Featuring Jessica off,

Founder, Guess Where Trips

Overview

Learn how Jessica Off transformed simple trip planning into a $5 million brand, leveraging creative itineraries, immersive marketing, and powerful social media strategies.

 What you'll learn

  • Tips for building an organic social media audience
  • How to create trip itineraries that people will love (and use)
  • Collaborating on social media
  • Working with influencers
  • The value of a printed itinerary

 Created for:

  • Social media managers
  • Destination marketers
  • Content creators
  • Digital marketers
  • Business Owners
Meet Our guest Speaker

Jessica Off

Founder, Guess Where Trips
With a background in tourism marketing, Jessica got the idea for Guess Where Trips after creating a scavenger-style road trip as a gift for her parents. Armed with a laptop and a printer, she launched the company in January 2020 from her living room floor.

Today, she focuses on the big picture and helps guide the team through new launches and business ideas.
Patrick Jones - Course author
Hosted by

Conner Galway

President, eLearningU; Junction Consulting

Conner founded the digital business consulting firm Junction, based out of Vancouver BC. There, he leads a team that conducts research, develops strategy, and consults with organizations that are looking to capitalize on digital opportunities.

Conner is an advisor to tourism businesses, leads training for Destination BC, and publishes The Brief, an award-winning weekly newsletter that is read by executives at many top North American brands.