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Travel + Leisure Co

Club Wyndham Vacation Planner

Helping members and prospects discover their perfect vacation across 220+ resorts through personalized, quiz-style discovery.

Club Wyndham Vacation Planner Explore Resorts experience

Role

Design Manager

Timeline

2020 – 2022

Team

2 Designers

Platform

Web, Mobile

The Challenge

220+ resorts, endless decision paralysis

Users were having difficulty discovering resorts that would fit their ideal vacation. With over 220 resorts throughout the US, Caribbean, and Hawaii, finding the right match was time-consuming and overwhelming. Lack of personalization and social media's focus on popular destinations made the problem worse.

Destination discoverability—resort search experience with 220+ options

Challenge 01

Destination Discoverability

Users struggled to search and find resorts with over 220 options. The map and list views were time-consuming, and featured resorts weren't customized to user needs.

Product education gap—onboarding and conversion challenges for prospects

Challenge 02

Product Education Gap

Prospects coming from social media or email campaigns weren't converting. New members had limited onboarding—they didn't know where to start or what resort was right for them.

Inventory balance—popular resorts vs underutilized availability

Challenge 03

Inventory Balance

Popular resorts were increasingly difficult to book. Meanwhile, resorts with similar amenities and ratings had availability but limited visibility—a business opportunity hiding in plain sight.

Who We're Helping

Members at every stage of their journey

Users at different stages with Club Wyndham were having similar issues—from prospects researching membership to seasoned members looking to try something new.

Prospect

I'm interested in a Club Wyndham membership. What kind of vacations can I go on?

Seasoned Member

We love our beach resort. It'd be great to find a similar style resort in Orlando within our budget.

New Member

I don't know where to start. What resort is right for me?

Final design: Vacation Planner Explore Resorts quiz flow

The Solution

Different experiences for different goals

We designed the Explore Resorts experience to guide users through a series of questions to understand the type of vacation that best suits them. We created different flows for members and prospects to align with their unique goals—members get actionable booking paths, prospects get aspirational results with clear paths to membership.

Member experience—from results to bookings with actionable recommendations

Member Experience

From Results to Bookings

Member results make booking vacations easy. Users can quickly act on recommendations while being encouraged to continue exploring destinations in their results.

Prospect experience—aspirational results with clear path to membership

Prospect Experience

From Aspirational to Actionable

Prospect results are more aspirational—generating excitement and deeper understanding of the product—while making a clear path to learn more about club membership.

My Role

Design Manager

I led the design team working on the Club Wyndham website, including the owner dashboard, booking flow, and the Vacation Planner. I managed 2 designers, reviewed designs from our external agency team, and provided guidance to ensure good user experience and consistent design patterns. I worked closely with the user testing team to gather insights using high-fidelity prototypes.

Design Management Product Strategy Agency Collaboration User Testing Design Systems

Reflection

What I learned

Users enjoyed the experience but wanted it customized to them. Personalization isn't just a nice-to-have—it's what transforms a tedious search into an exciting discovery. The same content, presented differently based on user goals, creates dramatically different outcomes.

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