Futuristic Humanoid Robot
Futuristic Humanoid Robot
Futuristic Humanoid Robot

The Challenge & Process

Tripping needed help. As a vacation rental platform, it competed in a crowded marketplace, but the site had never received dedicated UX design attention. Every page—from the homepage through search results to individual listings—needed a complete redesign.

This was my first UX role, and the responsibility was significant. As the sole designer (aside from my manager), I would directly impact the entire user experience. The challenge was exciting and somewhat daunting.

I started with a comprehensive UX audit, identifying the most critical areas for improvement. The vacation rental search and discovery process needed to work seamlessly—users comparing multiple properties had to quickly assess options and find the right fit. Information density was a key consideration: rental listings contain lots of details (amenities, pricing, location, availability), but overwhelming users would hurt conversion.

The interface needed to work across mobile and desktop. More users were searching for rentals on mobile devices, but desktop still dominated bookings. The responsive design had to accommodate both contexts without compromising either experience.

During the redesign process, an unexpected problem surfaced through user research: photo quality. Unlike major platforms like Airbnb with professional photography, Tripping relied on user-contributed images. Quality varied dramatically—some properties had beautiful photos, others had dark, blurry, or poorly composed images. Poor photos degraded the browsing experience and likely hurt conversion rates, even for properties that were actually great.

This became an opportunity for creative problem-solving. Working with our engineering team, we explored using machine learning to rank images by quality. The ML system could analyze photos and display the best ones first, giving each property the strongest possible first impression.

The Challenge & Process

Tripping needed help. As a vacation rental platform, it competed in a crowded marketplace, but the site had never received dedicated UX design attention. Every page—from the homepage through search results to individual listings—needed a complete redesign.

This was my first UX role, and the responsibility was significant. As the sole designer (aside from my manager), I would directly impact the entire user experience. The challenge was exciting and somewhat daunting.

I started with a comprehensive UX audit, identifying the most critical areas for improvement. The vacation rental search and discovery process needed to work seamlessly—users comparing multiple properties had to quickly assess options and find the right fit. Information density was a key consideration: rental listings contain lots of details (amenities, pricing, location, availability), but overwhelming users would hurt conversion.

The interface needed to work across mobile and desktop. More users were searching for rentals on mobile devices, but desktop still dominated bookings. The responsive design had to accommodate both contexts without compromising either experience.

During the redesign process, an unexpected problem surfaced through user research: photo quality. Unlike major platforms like Airbnb with professional photography, Tripping relied on user-contributed images. Quality varied dramatically—some properties had beautiful photos, others had dark, blurry, or poorly composed images. Poor photos degraded the browsing experience and likely hurt conversion rates, even for properties that were actually great.

This became an opportunity for creative problem-solving. Working with our engineering team, we explored using machine learning to rank images by quality. The ML system could analyze photos and display the best ones first, giving each property the strongest possible first impression.

The Solution & Impact

The redesigned platform delivered a modern, scalable interface that transformed how users discovered vacation rentals on Tripping.

The homepage established clear visual hierarchy and guided users into search quickly. I designed the search and filtering experience to help users narrow options efficiently without feeling overwhelmed by choices. Rental information architecture became more scannable—key details like price, location, and standout amenities were immediately visible, with additional details accessible when users wanted to dive deeper.

The responsive design adapted intelligently between mobile and desktop. On mobile, I prioritized browsing efficiency and quick property comparisons. Desktop layouts took advantage of larger screens to show more detail and enable easier multi-property comparison.

The ML-powered image ranking solution was particularly impactful. Instead of displaying user-uploaded photos in arbitrary order, the system analyzed and ranked images by quality. Properties were now represented by their best photos first—well-lit, properly composed images that showcased spaces effectively. This seemingly simple change had measurable effects on user engagement.

Visual design modernized the entire platform. Clean layouts, contemporary typography, and thoughtful use of whitespace made the information-dense content more digestible. The interface felt current and trustworthy, essential qualities in the vacation rental marketplace where users are committing significant money to properties they haven't seen in person.

The redesign improved both engagement metrics and conversion rates. The ML image ranking was particularly effective—properties looked better, users browsed longer, and more browsing sessions converted to bookings. The modern interface helped Tripping compete more effectively in a marketplace dominated by larger, better-funded competitors.

For me personally, this project was formative. As my first UX role, it taught me how to lead a comprehensive redesign, balance competing priorities, and collaborate with engineering on creative solutions to unexpected problems. The image quality challenge—and our ML solution—demonstrated that good UX design sometimes means solving problems that aren't immediately obvious in the initial brief.

Next project.
Next project.

Mobile Design

Next project.
Next project.

Mobile Design

Next project.
Next project.

Mobile Design

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Tripping

In my time at Tripping, I took on the challenge of redesigning Tripping's entire vacation rental platform as the sole designer on the team. The product had never received dedicated UX attention, requiring a complete overhaul from homepage to listing pages. Working with my manager, I crafted a modern interface that presented rental information clearly while ensuring scalability across mobile and desktop. An unexpected challenge emerged: user-contributed photos varied wildly in quality, degrading the browsing experience. Collaborating with engineering, we implemented an innovative machine learning solution that ranked and displayed images by quality, resulting in measurable improvements in engagement and conversion rates.

Type

Mobile Design

Type

Mobile Design

Client

Luminor Lighting Co.

Client

Luminor Lighting Co.

View all

View all

Tripping

In my time at Tripping, I took on the challenge of redesigning Tripping's entire vacation rental platform as the sole designer on the team. The product had never received dedicated UX attention, requiring a complete overhaul from homepage to listing pages. Working with my manager, I crafted a modern interface that presented rental information clearly while ensuring scalability across mobile and desktop. An unexpected challenge emerged: user-contributed photos varied wildly in quality, degrading the browsing experience. Collaborating with engineering, we implemented an innovative machine learning solution that ranked and displayed images by quality, resulting in measurable improvements in engagement and conversion rates.

Type

Mobile Design

Client

Luminor Lighting Co.