Ask Ollie
A travel companion to accompany your trip and help plan along the way.
BACKGROUND
MY ROLE
Product designer, responsible for discovery, research, and branding redesign of the AI tool.
TIMELINE
4 Months (April 2025 -July 2025)
TOOLS
Figma, Illustrator, Photoshop, Userinterviews.com, unmoderated testing.
With the app representing our most engaged traveler cohort and considering that driving app adoption is one of the key themes of our business strategy, it was believed that we believe that it is critical to extend the AI travel assistant experience into the app as the flagship experience to help guide user planning before their trip and direct their journey once on the trip itself.
Our vision for the AI travel assistant in the app is for it to be a travel expert, capable of providing community-backed and personalized guidance from anywhere. It should be a persistent and context-aware experience, considerate of page, content of interest, preferences, location and temporal factors to deliver personalized results.
Problem
As AI reshapes how people plan their travels, we’ve seen users turning to tools like ChatGPT, Claude, and Gemini instead of our app. Our goal was to explore how AI could enhance our experience—reducing the stress of trip planning and offering smarter support while users are on the go.
How might we help users within their planning journey with the use of AI?
CURRENT LANDSCAPE
The current landscape for the Slickdeals Extension focuses on acting as an extension (no pun intended) of the core website, There aren’t many distinguishing traits apart from the coupon auto applier in checkout.
The extension team needed to take a look stock of user pain points.
Key needs
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Access to personalized guidance from anywhere, especially while on the go
Receive personalized recommendations for hotels, attractions & restaurants
Easily save & book recommendations & guidance
Make confident, inclusive, community-backed travel decisions
Maximize their time while in-destination (including transportation & logistics)
Offer support for non-travel related questions
Final Designs
Final Designs
Entry points
A toggle approach on home gives AITA a consistent, easy-to-find location that encourages discovery without disrupting core flows. In-line entry points contextually allow the user to find relevant information and an opportunity for us to coach users on high value prompts.
Map view
Hierarchy is important within a small screen. By placing the map behind a secondary control, we help the AI summaries become the primary focus within the chat.
Sources
Each individual recommendation will display a community chip that shows the direct reviews and forum posts which helped inform the selection.
List and card view
Rather than creating a maze of text recommendations and coordinating cards at the end of the summary, we’re bringing the two together. Text recommendations sit within the same section as their cards giving users the context around the recommendation and enabling them to act on it
Prompting
Prompts will appear at the end of every AI chat response, helping the user understand the capabilities of the chat, as well as inspiring further conversation.
