Problem
The current digital experience is not aligning with the premier Inspirato brand. Prospects have a hard time understanding what Inspirato sells and why they should buy it, and members struggle to find and book their trips without the help of the Care team.
Insights
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The areas in which we found the most oportunities:
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Search
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Navigation
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Trip Planning
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Content/Value Prop
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Account
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Onboarding
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Communications
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Personalization
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Self-Service
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Skip to Journey Map - this is where to find a more comprehensive view of all insights in one place
Impact
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Led the team to prioritize and create a roadmap, and facilitated action on Design and Development for a full incremental .com redesign.
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This project is currently in phase 1 of development.
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(Skip to Results): Designs created by the Design team, from the research​​
Objectives
Research Goals & Questions
Uncover needs, motivations, and behaviors of .com users.
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​What are the prospect and member journeys​?
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What are prospects and members trying to accomplish when they come to our website?
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Discover and define all areas of opportunity for a website redesign.
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What are the known problems, do they still ring true today or are there new problems to consider?
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What patterns or themes exist?
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Obtain buy-in from key stakeholders to move forward with a redesign.
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Why is now the right time? What stands in our way if anything?
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Are there barriers or considerations?
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What is the business appetite for a full, partial or incremental redesign?
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Facilitate ideation and prioritization for a future state vision.
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What is the business appetite for each area of opportunity? Should we include everything?
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What is the impact and effort for each feature idea within each area of opportunity?
Business Goals
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Increase bookings
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Increase membership
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Retain current members
User Goals
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Find and book trips more efficiently, less stress
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Make memories on vacation, just worry about showing up, all planning and logistics should be seamless
Methods
Part 1: What do we know, where are the gaps?​
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Research Review (45+ Studies from the past 3-4 years)
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Why this method: review what we know first, to identify any gaps in knowledge and not repeat research unnecessarily.
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Heuristic Analysis
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Why this method: We knew we wouldn't be able to meet with members during Phase 1, so we wanted to supplement the research review with our own evaluation of the website, to look for any existing violations of design heuristics.
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Analytics & Heat Mapping
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Why this method: To understand behaviors (browsing, clicking, abandonment, etc) for a larger percentage of the user base.
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Interviews/Workshops - Stakeholders & Customer Facing Employees
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​Why this method: We wanted to capture multiple perspectives throughout the organization, and learn about buying behaviors, customer problems/satisfaction, and how our products were sold and marketed, from customer facing employees and stakeholders.
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Unmoderated Usability Testing
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Why this method: We identified a gap in knowledge around the prospect journey, what the Inspirato value prop is to prospects, how they make travel booking decisions, and what would compel them to learn more about Inspirato. I hypothesized that there might be confusion around what exactly we were selling and why they should buy Inspirato over just reserving an accommodation with a competitor.
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Best Practices & Competitor Inspiration
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Why this method: To get inspiration and understand what competitors in the travel space are doing to potentially solve some of the same problems we had found.
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Part 2: Insights to Action
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Journey Mapping
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Why this method: Visualize what we've learned, look for gaps in our knowledge, and understand what parts of the user journey are most impacted.​
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Stakeholder Ideation & Prioritization Workshops
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Why this method: We wanted to prioritize what areas to include in our future state vision, so that we weren't designing for areas the business wasn't interested in.
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ABOUT INSPIRATO
Inspirato is a vacation subscription service, offering a collection of exclusive luxury vacation rentals and travel experiences. Every member gets to use Inspirato's professional concierge and trip planning services, and is assigned their own Care team.
Inspirato Users
Inspirato Members
Ranging from the wealthy elite to well-to-do families, Inspirato members are passionate about travel, appreciate the value they receive from their memberships, and enjoy the most unique and exclusive experiences.
Public Users
These are users who browse the public view of inspirato.com. They may create a free account, or they may just be curious about what Inspirato has to offer and are trying to learn more.
Travel Behavior
Travel behavior of varies not only between mental models, but often depending on the type of trip they are taking.
Factors
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Who are they traveling with: family, partner, kids, friends, self, etc.
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What is the occasion: seasonal activity (skiing, golf), anniversary, bachelorette, relaxation, etc.
Member Search Behavior
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Search by destination: wanting to explore new destinations, typically flexible on dates, maybe retired or they can travel at any time
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Search by accommodation: have certain homes in mind and are watching for when they become available, flexible on dates
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Search by dates: have certain dates in mind, following school schedules, can likely only travel during peak times, or they're Pass members just looking to see what dates will get them the most value
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Search by estimated value: Pass members who want to get the most value out of their membership, often want trips that cost less Pass days but have high value
members Want to filter by
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Number of rooms/room types
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Number of guests
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Activities
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Trip Styles (beach/mountain/city)
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Places they have been before (filter in or out)
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Member Reviews/ Recommendations
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Price/Pass Days/Estimated Value
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Location, proximity to things to do
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Regions
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Amenities
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Direct Flights
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Safety
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Hotel Brand
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Filter out accommodations they're not interested in
How Members Plan trips
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Some members want all the planning done for them in advance, with lots of activities and options
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Some members like to plan everything on their own, they like to find deals or just go with the flow
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Some members just want a few dinner reservations, or special local recommendations that are curated and personalized
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Some members enjoy a mix of all of the above, depending on the trip they are going on at that time
The Research
Phase 1: What do we know, are there knowledge gaps
In Phase 1 we first wanted to look into the research we already had to determine how much more would need to be done. We ended up having quite a bit of useful information from the past 3+ years, and we verified and supplemented the old data with new research.
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Phase 1 Methods:
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Research Review of 45+ studies from the past 3+ years
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Heuristic Analysis
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Analytics & Heat Mapping
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Stakeholder/Customer Facing Employee Interviews
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Unmoderated Usability Test - Public Users
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Best Practice & Competitor Inspiration
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Research Review
45+ Studies from the past 3+ years
I wanted to see what we already knew, so we could focus on knowledge gaps and not waste time repeating research. I went through the repository from the past 3+ years and pulled all relevant studies into one research board. I then created a giant affinity map, categorizing all findings into themes.
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User Needs Identified
1) Users need a clearer understanding across products
2) Members need education to learn how to search and book trips
3) Users want and need more self-service
4) Members want a curated, personalized experience
5) Users need a better functioning mobile experience
"I don't often recommend Inspirato because it is too cumbersome to use the website and do business with them, I don't want to overwhelm my awesome Care team."
- Inspirato Member
Heuristic Analysis
We knew we wouldn't be able to meet with members during Phase 1, so we wanted to supplement the research review with our own evaluation of the website, to look for any existing violations of design heuristics. Two designers and I measured the current .com experience against the 10 Psychological Design Heuristics, by Susan Weinschenk, to uncover our biggest areas of design deficiencies.
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Process
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I set up a board for us with the heuristics and screenshots of the entire .com experience.
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We spent some time async adding sticky notes to the screenshots for the heuristics in violation.
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We then came together to group themes and discuss our biggest areas of opportunity.
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Heuristics that surfaced the most
#1 People don't want to do more than they have to
#6 Hold onto users' attention
#7 People crave information
#10 Unconscious processing matters - Visual System
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Top Areas of Opportunity ​
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Search & Nav
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Content/Value Prop
Analytics, Heat Mapping, Digital Observation
I wanted to see if what we found in past qualitative studies may be true for the larger user base, with quantitative data. So we looked into user behavior to learn more about how users are browsing the website, where they are going, what they are doing there, and where they might struggle (page views, clicks, device used, scrolling, rage clicking).
Tools: Heap (analytics platform), Crazy Egg (for heat mapping), Full Story (digital observation)
Top Findings
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Some members were searching for trips in the wrong subscription list, suggesting they might not understand there are different lists for different subscriptions.
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66% of members were using mobile devices, which is a significant rise, suggesting we might consider a "mobile first" strategy.
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The primary action on the website is searching for trips.
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Public users were not scrolling far past the fold on the Home page, and most often clicking on the main CTA in the hero.
Interviews/Workshops: Stakeholder & Customer Facing Employee Perspectives
We wanted to capture multiple perspectives throughout the organization, and learn about buying behaviors, customer problems/satisfaction, and how our products were sold and marketed, from customer facing employees and stakeholders. So I met with several stakeholders and customer facing employees to round out the research.
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Goals​​
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Hear from employees who talk to members on a regular basis, to learn what questions and complaints about the website they hear the most. - If we can answer these questions on the website, we could potentially save time and money on Care calls.
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Learn about buying behaviors, customer satisfaction, and known insights around our products from Customer Insights.
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Learn about how both Sales and Marketing sell Inspirato, and if they have different perspectives on how we should present content on the website.
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Add in the Trip Planning team's perspective and include this part of the user journey in the future state vision. ​
Process​
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Shadowed Customer Care calls
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Met with Customer Insights Director
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Held a workshop for Sales
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Interviewed the VP of Brand
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Reviewed all previous workshops and interviews I facilitated with the Trip Planning team (this project was on hold)
Findings
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Search/Navigation is the hardest function on the website for all users. There are members who will only find vacations by calling their Care team, because it's too confusing to do on their own.
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Prospects often don't realize this is a membership when they call and they don't understand how the memberships work with "pass days" and booking.
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Sales and Marketing have different strategies for what they want on the website - Sales doesn't want prospects searching for vacations on the website, they want prospects to have to call in. And Marketing wants to use the space to get prospects to dream about going on vacation.
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Internal processes for trip planning make it difficult for the Trip Planning team to provide personalized and curated information to build an itinerary for members.
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Recommendations
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Answer the main questions users have, throughout the website at the right times in the user journey. Make it really clear what we're selling and answer their questions about the different memberships. Users don't always make it to the FAQs, and our FAQs are still a little vague. We could save time and money on Care calls if we answer their questions on the website.
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Don't rely on prospects to call Sales to learn more. Provide the right information at the right time, and talk more about our value prop like the services and things that set us apart. Prospects like to research and learn more on their own before calling Sales, they don't want to be sold and they don't want to be on the phone for 30 minutes. Give them a reason to want to learn more.
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Create a more intuitive search experience, so we can feel comfortable with prospects (and members) searching for vacations on their own, and Care and Sales won't have to spend as much time teaching users how to search the website.
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Internal processes are out of scope for this project, but we could work on some ways to help Trip Planners make trip planning more personalized in the future state vision.
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Unmoderated Usability Testing With Public Users
Usability test on usertesting.com
- How do public users navigate the site and do they understand the content.
From the existing research, there was a gap in our knowledge around the prospect/public user journey. We know that public users, and even members have a hard time understanding everything Inspirato has to offer and the difference between subscriptions. But it was unclear if prospects and public users understand Inspirato's value prop, or what would compel them to learn more about Inspirato. I hypothesized that there might be confusion around what exactly we were selling and why they should buy Inspirato over just reserving an accommodation with a competitor.
We could be missing out on prospects who don't want to call the Sales team to learn about why they should buy Inspirato.
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Key Findings
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Public Users do understand that Inspirato is a vacation subscription service and there are two subscriptions to choose from.
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Public Users struggle to understand the difference between subscriptions. - It takes a long time for them to find the information to compare, and then they often don't explain the difference correctly.
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Public Users struggle to understand why they would pay for a subscription for travel when it doesn't seem much different than just going to a competitor and booking accommodations.
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Public Users still have several unanswered questions about the Pass subscription, after browsing the website.
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Public Users think they can book trips through the website by creating a free account, not realizing they need a subscription​
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To make buying and booking decisions users primarily rely on reviews, price, and pictures of accommodations, the most.
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Recommendations
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The current content strategy is around helping users dream about going on vacation. This will capture their attention, but if prospects can't understand what Inspirato sells and why they should buy it in a quick browse through the site, they will likely leave and go somewhere that is less confusing. A stronger value prop that explains the Inspirato difference (the services included) and a comparison of the subscriptions at a glance, could help prospects understand why they should buy or learn more.
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People make travel booking decisions based on what real people recommend. We should consider surfacing reviews and showing prospects the member experience through the eyes and voice of the member, throughout the site.
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Consider storytelling to answer the top questions about Pass through the eyes of a member, instead of relying on FAQs. (i.e. This is Jane, this is where she's going, who she's taking there, the trip planning and services she's getting, how often she travels, and how much she loves Inspirato).
Example of competitor inspiration we added to the first presentation to stakeholders
Best Practices & Competitor Inspo
We added in best practices for travel websites and competitor inspiration to see how we compare, and where we might be falling short in the industry. This piece also enhanced our storytelling in the initial presentation to get Product leadership buy-in.
Phase 1 Results
Opportunities
10 opportunities or areas of focus were discovered:
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Search
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Navigation
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Trip Planning
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Content/Value Prop
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Account
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Onboarding
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Communications
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Personalization
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Self-Service
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Mobile Experience/iOS (this became a separate project)
DESIGN
I worked with Design to communicate the opportunities found throughout the research, and they were able to start working on some proof of concepts for the future state vision like the foundation (search/nav) and a new look and feel, while we were prioritizing the rest of the opportunities with stakeholders and Product leaders.
Phase 2: Insights to Action, Prioritizing Opportunities Throughout the User Journey
In Phase 2 we put the insights into action with ideation workshops and prioritization, to help product leaders organize the Product roadmap.
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Phase 2 Methods:
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Journey Mapping
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Stakeholder Ideation & Prioritization Workshops
Journey Mapping
In order to visualize what we've learned, look for gaps in our knowledge, and understand what parts of the user journey are most impacted, I mapped out the journeys for both Prospects and Inspirato Members.
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The Prospect Journey
The Member Journey
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Most Impactful Phases:​
​The Beginning of the Prospect Journey
​Highly impacted if public users can’t understand what our products are and why they should buy them.​
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​Finding trips
​This is the primary action members take on the website. If it’s difficult to find the right trips, members have to wait for business hours, and then call the Care team for help, instead of just booking a trip right away. They may even visit another travel website instead.​
​Planning Trips
This is one of the services that sets Inspirato apart. If members don't see value in this, they could go to a competitor to book their accommodations, instead of paying for a subscription.
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What We Learned from Journey Mapping
Creating and reviewing the journey map helped us to see what stages of the customer journey had the most opportunity. We also found that we didn't have a lot of information about the on-trip experience and how our digital products could support on-trip. So that is an area to consider for the future, but isn't top priority at this time.
Product Leaders & Stakeholders Pre-Prioritization Workshop
After all research was complete, we wanted to allow the leaders and stakeholders in Product to review the journey map and give their perspective.
What We Captured:
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What we've tried & outcomes (for each area of opportunity) - to discover what didn't work, why didn't it work, and why now
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Risks/Blockers/Considerations - so we can be better equipped to plan for success
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Business Goals - to help weigh business appetite when prioritizing
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Additional Pain Points - in case there are any we had missed
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Biggest Takeaways
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It's a good time to start thinking about a redesign because we are moving everything out of our operating system "DryFly" and into "Serenity". We could potentially develop some of the redesign work now and then move that into Serenity, instead of moving over old designs that we'll be changing.
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It still might take 1-2 years before we'll have Development bandwidth to tackle the full website redesign.
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Pre-prioritization Workshop board (partial)
Ideation Workshops & Prioritization
We wanted to prioritize what areas to include in our future state vision, so that we weren't designing for areas the business wasn't interested in. But we ran into some difficulty here and had to pivot.
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Who was involved:
Product team leadership, Product Managers (for a few of the workshops we also included stakeholders from Care, Sales, and Member Insights).
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What we tried to do:
Prioritize the list of areas of opportunity (i.e. search, navigation, content/value prop, communications, etc.), with level of impact and business appetite scores.
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What happened:
Everyone had different ideas of what each opportunity meant because we didn't define each one with solution ideas (i.e. Communications could mean a chat bot, a communication hub, or a carrier pigeon. If someone is thinking communications means chat bot and we don't have the business appetite to create a chat bot, they would deprioritize communications). Outside conversations among directors continued on.
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How we pivoted:
I decided to facilitate high level ideation workshops for each area of opportunity, so stakeholders could voice their ideas and better define effort and impact of features instead of opportunities. In the workshops we voted on the feature ideas for each category, and it gave us a better idea of what areas to focus on first. The Design team was able to take that information and make final decisions on how to best solve for the known pain points in the future state vision.
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Resulting Data Visualization:
We captured all pain points, themes and solution ideas for each area of opportunity in a spreadsheet. This made it easier for PMs and leadership to see everything in one place and start planning what teams would work on everything and when.
Trip Planning Workshop Example
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The 10 Themes of Trip Planning Pain Points Identified for the Workshop
Trip Planning Workshop Ideation Board (Partial)
Results - Future State Vision
From this research, ideation, and prioritization, the design team created a future state vision. The team is now testing and presenting these concepts and working with Development to make changes incrementally for the next 1 to 2 years.
A Few Examples: FSV Designs
Throughout this project, I collaborated with Design to inform them with research so they could create the following designs.
Search
Search is prioritized on the Home page, since it's the primary action. The 2 subscriptions appear in the search bar as selections, so they are now associated with the Search.
Navigation
A brief description is given for Nav items that members and public users have found confusing. And having the information about Inspirato Care and Travel Planning could help prospects understand Inspirato's value prop, and want to learn more.
Trip Planning
Members often say trip planning doesn't feel personalized, it starts too late (30 days before the trip), and members just end up planning their own trips. Since Trip Planning is one of the main services that sets Inspirato apart from competitors, this could really make or break member retention.
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We created a way for members to start giving input on their trip preferences for the trip planning, right away. This streamlines the call that happens 30 days out and makes it easier for the Trip Planning team to gather curated experiences before the call.
Onboarding
New member onboarding is a great time to start gathering information about the member, so we can serve them more personalized content throughout their digital experience. Capturing preferences is something that is currently done in a 1 hour long welcome call. These calls take a lot of Care team hours, and members don't always want to have a call before they can start booking trips.
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This new digital experience streamlines the welcome call, by gathering some basic information the Care team would normally ask. This also allows the member to start booking trips right away.
Communications
Currently all communications are through email or phone, and it's difficult for members to keep track of everything that was said.
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A communications hub where all conversations are stored, would help members find information from messages quicker and easier. This also provides them with a way to communicate without having to call in during business hours.
Account
An interesting addition to the Account is this Trip Timeline. This would help members stay on track of each step to complete before they leave for their trip. Each step would link out to that task and the member could complete each one right from the timeline. This would save them time from having to search around Account or outside of inspirato.com, for each of these things.
Learnings
Because of the nature of our business, we had to prove we should prioritize a redesign and get buy-in with this research. We then had to move quickly once we started gaining momentum and there was never a time for a proper kickoff or to gather a dedicated team of key stakeholders throughout the organization to work on this. So at times it felt a little messy and not as organized as it could have been with a kickoff and dedicated team. I also know it's not best practice to work on research projects that don't have executive buy-in, because the risk of the project ending without being prioritized is high.
In a perfect world, we would have been able to get buy-in before a lengthy research effort, and we would have spent more time organizing and planning in the beginning.
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