Empowering Timeshare Owners Through Clarity and Trust

The Owner’s Lounge was a portal for timeshare members to manage their points, book trips, and view rewards. Over time, it became cluttered and inconsistent across systems. Members didn’t trust what they saw online because point balances were unreliable, confirmations took days, and booking felt like a gamble.

Headquarters

Headquarters

Escondido, California

Founded

Founded

2016

Industry

Industry

Hospitality

Revenue

Revenue

$200 million (2024)

Company size

Company size

5,000+

Problem Statement

Users weren’t just frustrated, they were anxious. That emotional response showed this was more than a functional problem; it was a trust problem.

“Every time I try to book, 



I feel like I’m guessing.”

Users weren’t just frustrated, they were anxious. That emotional response showed this was more than a functional problem; it was a trust problem.

“Every time I try to book, 



I feel like I’m guessing.”

Users weren’t just frustrated, they were anxious. That emotional response showed this was more than a functional problem; it was a trust problem.

“Every time I try to book, 



I feel like I’m guessing.”

Objectives

Our mission was to redesign the Owner’s Lounge to restore user confidence and autonomy.

We set out to:

  • Create a unified digital experience where owners could view points, book trips, and manage rewards in one place.

  • Reduce dependency on support staff for basic tasks.

  • Build an interface that communicates clarity, transparency, and trust.


Success would mean users feel informed, empowered, and genuinely enjoy using the platform.

Our mission was to redesign the Owner’s Lounge to restore user confidence and autonomy.

We set out to:

  • Create a unified digital experience where owners could view points, book trips, and manage rewards in one place.

  • Reduce dependency on support staff for basic tasks.

  • Build an interface that communicates clarity, transparency, and trust.


Success would mean users feel informed, empowered, and genuinely enjoy using the platform.

Our mission was to redesign the Owner’s Lounge to restore user confidence and autonomy.

We set out to:

  • Create a unified digital experience where owners could view points, book trips, and manage rewards in one place.

  • Reduce dependency on support staff for basic tasks.

  • Build an interface that communicates clarity, transparency, and trust.


Success would mean users feel informed, empowered, and genuinely enjoy using the platform.

Discovery

Approach:

We began with a combination of qualitative and quantitative research to understand not just what issues existed, but why they were happening. This included conducting twelve user interviews with timeshare owners representing a range of experience levels, analyzing three months of support chat logs containing thousands of data points, and holding stakeholder interviews with the marketing, support, and engineering teams to gain a holistic view of the challenges from both user and business perspectives.

Key Findings:

We started with 12 in-depth interviews and analyzed months of support chat logs.
The insights were emotional, not technical:

Approach:

We began with a combination of qualitative and quantitative research to understand not just what issues existed, but why they were happening. This included conducting twelve user interviews with timeshare owners representing a range of experience levels, analyzing three months of support chat logs containing thousands of data points, and holding stakeholder interviews with the marketing, support, and engineering teams to gain a holistic view of the challenges from both user and business perspectives.

Key Findings:

We started with 12 in-depth interviews and analyzed months of support chat logs.
The insights were emotional, not technical:

Approach:

We began with a combination of qualitative and quantitative research to understand not just what issues existed, but why they were happening. This included conducting twelve user interviews with timeshare owners representing a range of experience levels, analyzing three months of support chat logs containing thousands of data points, and holding stakeholder interviews with the marketing, support, and engineering teams to gain a holistic view of the challenges from both user and business perspectives.

Key Findings:

We started with 12 in-depth interviews and analyzed months of support chat logs.
The insights were emotional, not technical:

35%

owners abandoned bookings midway through.

40%

of all calls were just to confirm point balances.

60%

described the experience as stressful or confusing.

User Insights & Needs

Clarity — understand points, values, and options at a glance.

Control — manage bookings without relying on staff.

Trust — feel confident that the system works as intended.

We mapped user emotions throughout the process — anxiety peaked during booking and confirmation. That became our north star: reduce anxiety through design clarity.

Persona

Sam

Sam

Super Boomer

Goals

Goals

Confidently plan vacations, understand point value, avoid surprises.

Frustrations

Inconsistent balances, unclear redemption rules, lack of clear confirmation.


Sam enjoys his freedom from the 9-to-5 and uses it to travel frequently. His days on vacation are relaxed but intentional — mornings spent exploring museums or historical landmarks, afternoons enjoying local cuisine or mild adventures, and evenings sharing stories with his spouse or family. He prefers guided tours or organized transportation so he can focus on experiences, not logistics.



Task Mapping

We mapped the 7 key steps of the owner journey

Login → Review Points → Book Trip → Confirm → Manage Booking → Explore Experiences → Contact Support — to uncover where trust broke down and how design could rebuild it.

Key Insights:

Emotional Peaks: Anxiety rose during booking and confirmation; relief followed clear feedback.

Main Challenges: Unclear data, fragmented systems, and delayed confirmations.

Design Opportunities: Simplify steps, show real-time status, guide with reassurance, and make support proactive.

Goal: Turn confusion into confidence through visibility, clarity, and trust.


Design Strategy & Solutions

Design Philosophy

Clarity builds confidence. Our guiding principle: make the experience feel as reliable and transparent as checking your bank account. 

Core Design Principles

  • Visibility: Show key data (balances, availability) immediately

  • Feedback: Every user action triggers confirmation or system response

  • Reassurance: Use tone, microcopy, and visual cues to convey reliability

Key Features / Solutions

  • Points Dashboard: Real-time balances, point-to-value conversion, upcoming redemptions

  • Smart Booking Flow: Filters availability based on points rather than just dates

  • Predictive Confirmation: For example, “You have enough points for 5 nights at Resort X”

  • Guided Recommendations: Suggest trips or experiences tailored by history

  • Microcopy & Tone: Swap dry system messages for empathetic feedback — “You’re all set!” instead of “Transaction complete”


Design Philosophy

Clarity builds confidence. Our guiding principle: make the experience feel as reliable and transparent as checking your bank account. 

Core Design Principles

  • Visibility: Show key data (balances, availability) immediately

  • Feedback: Every user action triggers confirmation or system response

  • Reassurance: Use tone, microcopy, and visual cues to convey reliability

Key Features / Solutions

  • Points Dashboard: Real-time balances, point-to-value conversion, upcoming redemptions

  • Smart Booking Flow: Filters availability based on points rather than just dates

  • Predictive Confirmation: For example, “You have enough points for 5 nights at Resort X”

  • Guided Recommendations: Suggest trips or experiences tailored by history

  • Microcopy & Tone: Swap dry system messages for empathetic feedback — “You’re all set!” instead of “Transaction complete”


Design Philosophy

Clarity builds confidence. Our guiding principle: make the experience feel as reliable and transparent as checking your bank account. 

Core Design Principles

  • Visibility: Show key data (balances, availability) immediately

  • Feedback: Every user action triggers confirmation or system response

  • Reassurance: Use tone, microcopy, and visual cues to convey reliability

Key Features / Solutions

  • Points Dashboard: Real-time balances, point-to-value conversion, upcoming redemptions

  • Smart Booking Flow: Filters availability based on points rather than just dates

  • Predictive Confirmation: For example, “You have enough points for 5 nights at Resort X”

  • Guided Recommendations: Suggest trips or experiences tailored by history

  • Microcopy & Tone: Swap dry system messages for empathetic feedback — “You’re all set!” instead of “Transaction complete”


Testing, Iteration & Feedback

Usability Testing Setup

  • 5 representative users tested key flows (login → review → book → confirm)

  • Moderated sessions capturing verbal feedback, time on task, confusion points

Key Results

  • Completion times improved by ~40 %

  • Users expressed relief and greater confidence

  • Participants described the experience as “clear,” “reassuring,” and “easy to follow”

Iteration Highlights

  • Simplified navigation and hierarchy

  • Added a progress bar to orient users during booking

  • Enhanced typography, spacing, and visual hierarchy for readability

  • Expanded confirmation screens to break down costs, points used, next steps

Usability Testing Setup

  • 5 representative users tested key flows (login → review → book → confirm)

  • Moderated sessions capturing verbal feedback, time on task, confusion points

Key Results

  • Completion times improved by ~40 %

  • Users expressed relief and greater confidence

  • Participants described the experience as “clear,” “reassuring,” and “easy to follow”

Iteration Highlights

  • Simplified navigation and hierarchy

  • Added a progress bar to orient users during booking

  • Enhanced typography, spacing, and visual hierarchy for readability

  • Expanded confirmation screens to break down costs, points used, next steps

Usability Testing Setup

  • 5 representative users tested key flows (login → review → book → confirm)

  • Moderated sessions capturing verbal feedback, time on task, confusion points

Key Results

  • Completion times improved by ~40 %

  • Users expressed relief and greater confidence

  • Participants described the experience as “clear,” “reassuring,” and “easy to follow”

Iteration Highlights

  • Simplified navigation and hierarchy

  • Added a progress bar to orient users during booking

  • Enhanced typography, spacing, and visual hierarchy for readability

  • Expanded confirmation screens to break down costs, points used, next steps

Challenges & Cross-Team Collaboration

Technical Integration Complexity

One of the largest hurdles was handling four separate backend systems — CRM, Booking Engine, Rewards API, Support Portal — all with different data models and update frequencies. 

Aligning Stakeholders

  • Marketing pushed for high visual polish

  • Engineering prioritized system reliability and data consistency

  • Users demanded simplicity and clarity

    My role became the bridge: ensuring decisions respected user needs while being feasible technically and aligned with business goals.

I led design reviews, presented user data to justify design trade-offs, and developed robust interaction specs for engineering to follow.

Technical Integration Complexity

One of the largest hurdles was handling four separate backend systems — CRM, Booking Engine, Rewards API, Support Portal — all with different data models and update frequencies. 

Aligning Stakeholders

  • Marketing pushed for high visual polish

  • Engineering prioritized system reliability and data consistency

  • Users demanded simplicity and clarity

    My role became the bridge: ensuring decisions respected user needs while being feasible technically and aligned with business goals.

I led design reviews, presented user data to justify design trade-offs, and developed robust interaction specs for engineering to follow.

Technical Integration Complexity

One of the largest hurdles was handling four separate backend systems — CRM, Booking Engine, Rewards API, Support Portal — all with different data models and update frequencies. 

Aligning Stakeholders

  • Marketing pushed for high visual polish

  • Engineering prioritized system reliability and data consistency

  • Users demanded simplicity and clarity

    My role became the bridge: ensuring decisions respected user needs while being feasible technically and aligned with business goals.

I led design reviews, presented user data to justify design trade-offs, and developed robust interaction specs for engineering to follow.

Final Product & Outcomes

Launch Deliverables

  • A unified, streamlined interface

  • Integrated data systems delivering consistent, accurate values

  • A clearer booking and confirmation flow

Impact Metrics (Post-Launch)

  • +28 % increase in self-service bookings

  • –35 % reduction in support calls related to points or confirmation

  • 4.6 / 5 average satisfaction score reported by owners


Launch Deliverables

  • A unified, streamlined interface

  • Integrated data systems delivering consistent, accurate values

  • A clearer booking and confirmation flow

Impact Metrics (Post-Launch)

  • +28 % increase in self-service bookings

  • –35 % reduction in support calls related to points or confirmation

  • 4.6 / 5 average satisfaction score reported by owners


Launch Deliverables

  • A unified, streamlined interface

  • Integrated data systems delivering consistent, accurate values

  • A clearer booking and confirmation flow

Impact Metrics (Post-Launch)

  • +28 % increase in self-service bookings

  • –35 % reduction in support calls related to points or confirmation

  • 4.6 / 5 average satisfaction score reported by owners