Holiday

Swap

Holiday

Swap

Redesigning the home listing tools and experience to enhance home conversion rates.

Introducing personalization to help ensure retention of new and recurring users for the new Publisher’s Clearing House digital eco-system.

Role:

Product Design Consultant - Interim Head of Design

Contributions:

Design Leadership — UX Strategy — Product Design - Research

Team Management — UX Strategy — User Experience — Design Leadership — Product Design

Team Management — UX Strategy — User Experience — Design Leadership — Product Design

Core Team:

Matthew Davey - Chief Product Officer

Nikola B. - Lead Engineer

Peter F. - Engineer

Sander Eentalu - Chief Tech. Officer

Client

background

Holiday Swap Group is a home swapping service that has grown and evolved into a full home-booking platform that caters to a global community of travelers, in only six years (similar to AirBnB).

Challenge
& solution

As Holiday Swap (HS) expanded, they realized that their offering of tools for hosts either non-existent or subpar. HS responded by developing advanced tools and features, essential for retaining their current users and attracting new ones, while preserving their competitive edge in the industry.

We redefined holiday swaps business strategy by marrying HS business and HS hosts needs. This led us to introduce a list of features and experiences that are geared to empower Hosts to hit their goals. This led to a boost in home listings and the overall advocacy for hosting on HS. First up on the list, was the new home listing flow and it’s sub-features.

The results:

The results:

The results:

61%

61%

Reduction of home listing drop rates, within the first two months since new flow and features were launched.

35%

35%

Increase of re-lists from existing hosts, as they found the new features very helpful.

39%

39%

Overall net new hosts list a home on to the platform.

18%

18%

Of hosts found the save drafts feature convenient, and went back to finish their listing uploads.

How it was done:

How it was

done:

I used two main research tactics to better understand HS hosts and get to the bottom of why they were dropping off during the home listing flow. First, I created and sent out a survey to discover why users were feeling discouraged. After the surveys were in, I followed up with users of interest, conducting interviews and walking them through the current flows and documented their experiences.

Our users were very vocal and honest, they gave me great feedback that allowed me to create

some insights and form a plan of attack on how to optimize and enhance the listing flow.

While we were running the survey,
I spearheaded a an initial phase of research that consisted of an extensive comparative and competitive analysis to understand the retention methodologies of companies that PCH considers as direct and indirect competitors.

While we were running the survey, I spearheaded a
an initial phase of research that consisted of an extensive comparative and competitive analysis
to understand the retention methodologies of companies that PCH considers as direct and indirect competitors.

“I have to do too much to get my listings up”

“I have to do too much to get my listings up”

“It’s annoying that I can’t save my progress”

“It’s annoying that I can’t save my progress”

“Felt too long and tedious to complete”

“Felt too long and tedious to complete”

“I won’t want to do this again”

“I won’t want to do this again”

“I keep getting lost scrolling up and down”

“I keep getting lost scrolling up and down”

“Why is it so difficult to add images”

“Why is it so difficult to add images”

I also wanted to know what the industry standards were when it came to this kind of experience and flow, so I performed a competitive analysis to understand how the top companies and competitors were doing things.

While we were running the survey,
I spearheaded a an initial phase of research that consisted of an extensive comparative and competitive analysis to understand the retention methodologies of companies that PCH considers as direct and indirect competitors.

While we were running the survey, I spearheaded a
an initial phase of research that consisted of an extensive comparative and competitive analysis
to understand the retention methodologies of companies that PCH considers as direct and indirect competitors.

Creating the right journey

Creating the right journey

I created an initial flow that had everything the business needed to collect from users in order to build out their listing. Implementing user-centric thinking, best practices, and everything I learned in our research, I re-imagined the overall information architecture and design patterns that would be presented to the users during their time engaging with the home listing flow.


We saw immediate improvement with users who tested the new experience flow, yet we were still not reaching the range of success that we were striving for. Users were pleased with the how intuitive the experience felt, but still felt it was very long and mentioned they would possibly save their progress and return at a later date. This caused concern as some of the users that tested our new experience were already hosts with our competitors.

After two rounds of iterations and testing, my team and I held a workshop with the key stakeholders in order to go through users feedback and

figure out what information and functionality could be seen as secondary importance and be stripped away from the primary flow. This would enable us to deliver the shortest listing experience to users who wanted to list their homes on HS.

After two rounds of iterations and testing, my team and I held a workshop with the key stakeholders in order to go through users feedback and

figure out what information and functionality could be seen as secondary importance and be stripped away from the primary flow. This would enable us to deliver the shortest listing experience to users who wanted to list their homes on HS.

We identified the essential information hosts need to list their homes, which simplified the user flow by half. This allowed me more time to design more innovative ways for users to easily list their homes on HS

We identified the essential information hosts need to list their homes, which simplified the user flow by half. This allowed me more time to design more innovative ways for users to easily list their homes on HS

We identified the essential information hosts need to list their homes, which simplified the user flow by half.
This allowed me more time to design more innovative ways for users to easily list their homes on HS

Taking a closer look at the design and features

The old experience:

  • Only allowed for individual image uploads.

  • Users had to keep scrolling up and down the page to complete it.

  • There was no way to save progress.

  • Input forms didn’t meet the user’s requirements.

  • Location input was not intuitive.

The list went one...

Truth be told the original listing experience had a lot of holes and needed a complete overhaul. I took the learnings and insights from talking to users along with my competitive analysis and crafted a new interface that is baked with catered behavioral patterns that would make this experience naturally intuitive to our audience.

I also made sure that the new components created would be re-usable across different HS touch-points and flows since the team was also in the midst of developing a new digital design language for their brand.

Below you can see some of the new features that I created for the new home listing flow.

Taking a closer look
at the design and features

Taking a
closer look
at the design and features

Taking a closer look at the design and features

The old experience:

  • Only allowed for individual image uploads.

  • Users had to keep scrolling up and down the page to complete it.

  • There was no way to save progress.

  • Input forms didn’t meet the user’s requirements.

  • Location input was not intuitive.

The list went one...

  • Only allowed for individual image uploads.

  • Users had to keep scrolling up and down the page to complete it.

  • There was no way to save progress.

  • Input forms didn’t meet the user’s requirements.

  • Location input was not intuitive.

The list went one...

Truth be told the original listing experience had a lot of holes and needed a complete overhaul. I took the learnings and insights from talking to users along with my competitive analysis and crafted a new interface that is baked with catered behavioral patterns that would make this experience naturally intuitive to our audience.

Truth be told the original listing experience had a lot of holes and needed a complete overhaul. I took the learnings and insights from talking to users along with my competitive analysis and crafted a new interface that is baked with catered behavioral patterns that would make this experience naturally intuitive
to our audience.

I also made sure that the new components created would be re-usable across different HS touch-points and flows since the team was also in the midst of developing a new digital design language for their brand.

I also made sure that the new components created would be re-usable across different HS touch-points and flows since the team was also in the midst of developing a new digital design language for their brand.

Below you can see some of the new features that I created for
the new home listing flow.

Below you can see some of the new features that I created for the new home listing flow.

Media selection and uploading

Taking a
closer look
at the design and features

Taking a closer look at the design and features

Following successful trends that I saw across other experiences, I created an easy way for users to upload multiple images into the experience.

To adhere to some technical restraints we had home listers upload only 

6 images at first, but while working with the engineers, we were able create a quick patch that allowed users to upload as many images as they liked afterwards.

The new image uploading improvements favored well with the current home listers in the HS community who tested the new flow.

External API integration

Taking a
closer look
at the design and features

Taking a closer look at the design and features

Collaborating closely with the Chief Product Officer and our engineers, we ideated and executed a way for hosts that had their homes already listed else where, to easily bring them into the Holiday Swap platform.

Users just simply use their log in credentials from third party platforms to access their listings database and select the listings they would like to upload onto the HS platform.

AI powered composing

Taking a
closer look
at the design and features

Taking a closer look at the design and features

We simplified the listing process for hosts even further by introducing 

a system that uses description indicators to help draft their listing overviews. These generated listing overviews can be used as provided 

or edited as desired.

To bring this feature to life, we integrated ChatGPT, which significantly enhanced the listing creation process. During user testing, hosts were 

so impressed with this new tool that we prioritized its rollout in our development map.

Connecting the new flow to the rest of the HS experience

Connecting the new flow to the rest of the HS experience

Connecting the new flow to the rest of the HS experience

During workshops with key stakeholders, we identified several opportunities to deepen host engagement with the Holiday Swap platform. We recognized the potential to enhance listing optimization, ensure accurate home ratings, promote the HS loyalty program, and provide hosts with greater insights and control over their listing preferences.

During workshops with key stakeholders, we identified several opportunities to deepen host engagement with the Holiday Swap platform. We recognized the potential to enhance listing optimization, ensure accurate home ratings, promote the HS loyalty program, and provide hosts with greater insights and control over their listing preferences.

During workshops with key stakeholders, we identified several opportunities to deepen host engagement with the Holiday Swap platform. We recognized the potential to enhance listing optimization, ensure accurate home ratings, promote the HS loyalty program,
and provide hosts with greater insights and control over their
listing preferences.

Want to
work together?

I’m available to consult, freelance and even open to new full-time opportunities. If you think we can partner up and create something great, shoot me an email.

Contact me

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© 2025 Christian Castellanos

© 2025 Christian Castellanos

© 2025 Christian Castellanos

© 2025 Christian Castellanos

© 2025 Christian Castellanos