Outrigger
Redesigning the Booking Experience for Increased Conversions and Scalability
Outrigger, a global hospitality brand, faced a high bounce rate and low conversion rate due to a fragmented online booking experience. Their existing third-party booking system forced users to re-enter travel details, leading to frustration, cart abandonment, and increased reliance on customer support.
Additionally, Outrigger’s portfolio includes both hotels and vacation rentals, each with distinct booking behaviors and challenges. The company was also undergoing a site migration and needed a scalable design solution that could support local and global expansion.
Solution //
CPG&Retail, Customer Experience
Role // Design Lead
My Role
As the Lead Product Designer, I led the research and design strategy, collaborating with marketing, engineering, and a branding agency to craft a seamless user experience that balanced business goals, user needs, and technical constraints.
Project specifications
Duration:
10 months
Tools:
Figma
Miro
Azure Devops
Business Goals & Challenges
Increase online booking rate by reducing friction in the user journey.
Minimize bounce rate and support costs by making information clearer upfront.
Improve mobile usability to match shifting user behaviors.
Ensure scalability across hotels and vacation rentals, while accommodating Outrigger’s global expansion.
Work within constraints of an existing third-party booking widget that couldn’t be fully customized.
Research
To fully understand user behavior and business pain points, I conducted:
Stakeholder interviews
To align with leadership, marketing, and operations on business priorities.Customer support deep dives
To analyze frequent issues that led users to abandon the website or call support.Google Analytics, heatmaps, and session recordings
To track user flows, drop-off points, and hesitation moments.Competitive analysis
To identify best practices in hospitality booking experiences.
Key Findings
High cart abandonment
Users either called support to complete their booking or chose a competitor due to friction in the experience.Lack of property comparison tools
Users struggled to evaluate hotels and rentals side by side, making it harder to decide.Confusing rental booking flow
Unlike hotels, vacation rentals had variable amenities and locations, leading to uncertainty about pricing, availability, and features.Unavoidable double data entry
Since Outrigger had already committed to a third-party booking system, users would still need to re-enter some details upon checkout.
These findings shaped the core design strategy: reduce friction in the decision-making phase, structure content for clarity, and ensure users enter the booking widget with confidence.
Design Approach
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Challenge:
Users needed a better way to explore hotels and rentals before entering the booking system.
Solution:
Implemented an interactive map feature to visually display all Outrigger properties in a given region, helping users see alternative options if one wasn’t available.
Simplified hotel and rental comparison by restructuring pages to highlight key differentiators (e.g., amenities, pricing, location benefits).
Defined content strategy with marketing to ensure users had all necessary details before reaching the booking widget.
Iteration & Trade-Offs:
Originally, I proposed a fully interactive map with availability filtering directly on .com, but due to backend limitations, this wasn’t possible without triggering the booking widget. Instead, we scaled down the map functionality to provide essential context, while allowing users to filter location options directly in the booking flow.
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Challenge:
The third-party system couldn’t be modified, meaning users still had to re-enter their information.
Solution:
Optimized the transition into the booking widget by pre-filling as much information as possible, reducing redundant steps.
Split decision-making into two distinct phases:On .com → Users explore properties, compare amenities, and narrow their selection.
In the booking widget → Users complete the transaction without distractions.
Collaboration & Constraints:
This required close coordination with engineering and the branding agency. Given budget constraints and skill limitations within the offshore engineering team, we adjusted the solution to work within existing technical capabilities while still delivering a meaningful UX improvement.
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Challenge:
Outrigger needed a system that worked for both hotels and vacation rentals, which had different booking behaviors and requirements.
Solution:
Designed a flexible CMS-driven system → Outrigger could create new microsites for future expansions without custom development.
Structured content modules to accommodate differences in hotel vs. rental bookings while maintaining brand consistency.
Future-proofed the design system to scale across multiple regions, adapting to different markets while keeping a cohesive experience.
Outcome & Impact
25% increase in online bookings
The redesigned experience reduced friction, leading to higher conversions.
215% improvement in engagement
More users explored and interacted with property pages, making informed decisions.
Scalable, CMS-driven infrastructure
Outrigger can now easily expand its presence in new locations without overhauling the website.
Key Learnings & Reflections
Product design is about balancing user needs with business and technical realities.
While I aimed for a fully interactive, availability-driven map, constraints forced me to scale back while still delivering value.Cross-functional collaboration is key.
This project required alignment between marketing, engineering, and branding, as well as navigating offshore development constraints.Expect and adapt to late-stage challenges.
Engineering skill limitations surfaced late in development, requiring design adjustments that preserved the user experience while remaining feasible.
Check out the live site here
Final Thoughts
This project reinforced the importance of designing for both user experience and business impact. By simplifying exploration, clarifying the decision-making process, and ensuring scalability, we created a solution that not only improved conversions but also set Outrigger up for future growth.
Team
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Design Director: Andres Herrera
Design Lead: Mei Li
Experience Director: Kelly Noah
Experience Designer: Jordan Kiehel