MyAgent
Role
UX Designer
Client
Club Wyndham
Year
2025
Domain
Travel & AI
How do we get timeshare owners to understand, discover, and trust MyAgent as a useful tool for planning and booking vacations, rather than perceiving it as just another FAQ chatbot?
I organized our design strategy around four core principles that made MyAgent easier to understand, more efficient to use, and more trustworthy throughout the booking journey:
01
Made value visible
Greeting owners with suggested prompts and task-based entry points before they typed a word.
02
Minimized conversational friction
Letting users progress from a welcome message to a reservation in roughly three to five prompts using smart defaults.
03
Preserved service continuity
Ensuring owners wouldn’t lose context when escalating to a live representative.
04
Built measurement into the interface
Embedding feedback mechanisms for both AI and human interactions.
The booking experience needed to help owners book their dream vacation without recreating a long web form inside a conversation.
Product discussions prioritized moving from the welcome experience to a reservation in approximately three to five prompts, using recommendations based on the owner’s history and allowing them to review or edit details.
MyAgent needed to support human assistance without making owners restart the conversation. In the cases when AI was not enough, we allowed users to continue the conversation with a live representative.
The live representative feature enabled a seamless handoff by providing both the AI and the representative with a summary of the owner’s previous conversation.
VOYA’s original Terms of Use experience required users to accept terms before experiencing any value from the product, creating friction at a critical onboarding step. I redesigned the acceptance flow by making it seem more conversational instead of transactional. The redesign targeted a product experiencing only ~2% user engagement and was later cited internally as helping drive much higher acceptance rates and faster chat engagement by showing MyAgent’s value proposition before requesting acceptance of the terms of service.
Because the platform spanned both Club Wyndham and WorldMark, I created a brand-agnostic design that could adapt to brand-specific color palettes and typography.
Impact
Results
While this growth was heavily influenced by expanding access during rollout rather than isolated design tweaks, the data proved we had built a robust foundation.
Sep 18, 2025
2,521
Users with Access
• 114 unique chats initiated
Oct 6, 2025
13,225
Users with Access
• 268 chats, 259 searches
• First verified same-session reservation
Nov 7, 2025
75,011
Users with Access
• 12,207 user messages
• 65 same-session reservations
Conclusion
Outcome and Reflection
Seeing MyAgent evolve was an incredible journey. Working on this project taught me that AI is not always easily welcomed, especially by older individuals. Showing the value proposition quickly and allowing for human escalation is a must when dealing with transactions so that users feel more at ease.
Let’s collaborate
Seeking partners, studios, and product teams who value deliberate design over rapid output. Currently open to freelance engagements and full-time opportunities.