Making onboarding work for both sides of the market
ThirdHome is a private travel platform where luxury second-home owners exchange stays at other high-end properties around the world. Joining the network isn't just creating an account — it's submitting your home, proving eligibility, and trusting the platform enough to actually participate.
I redesigned the end-to-end member onboarding experience to simplify a complex multi-step journey for homeowners, while ensuring the platform captured the depth of information needed to maintain marketplace quality. Because in a two-sided marketplace — no homes means no trips means no business.
💡The core tension: users needed onboarding to feel easy. The business needed it to be thorough. The solution had to do both — not choose between them.
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High-quality inventory at stake
The marketplace only works if homes meet a quality bar. Onboarding had to collect detailed property info, photos, availability, and eligibility — from brand-new users who didn't yet understand the platform.
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Cognitive overload
The existing flow asked too much at once. Users faced a dense, form-heavy experience with no guidance on why fields were needed — making it feel like a bureaucratic process, not an invitation to a luxury club.
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Post-submission black hole
After submitting, users had no idea what happened next. No visibility into review status, approval steps, or where they stood — creating anxiety, confusion, and drop-off.
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Unknown exchange model
New members didn't understand how a credit-based home exchange worked. Without in-context education, users couldn't make confident decisions — or understand the value they were signing up for.
02 — Discovery
A form problem in disguise — actually a system problem
After meeting with the Customer Success team and sitting in on Membership Experience sessions, I quickly realized this wasn't a UX problem — it was a systems problem. Onboarding didn't end when users clicked submit. That was just the beginning.
How do you collect everything a marketplace needs — without it feeling like a tax form? That tension became the core design challenge.
I mapped the full end-to-end journey across three iterations — capturing not just the user-facing flow, but everything that happened internally after submission: property review, membership approval, exchange readiness. This revealed a major gap: users were completing a form and hearing nothing. That lack of visibility created uncertainty, and uncertainty kills confidence.
Journey mapping iteration: V2 — approval states added
Journey mapping iteration: V3 — full post-submission lifecycle
🔍Key reframe: stop asking "how do we simplify this form?" and start asking "how do we design a system that guides users from submission to readiness?" That shift unlocked the solution.
03 — Process
Designing the system, not just the form
I approached this as a system design problem. Instead of optimising for one side — user or business — the goal was to balance both. That meant close collaboration with Membership Success, Sales, and Product to understand what good data looked like from the inside out.
01
Discovery
Cross-functional research & journey mapping
Sat in on Customer Success and Membership Experience sessions. Mapped the full end-to-end journey — including what happened internally after submission — to identify where friction existed both in the UI and behind the scenes. Three iterations of the flow map captured increasing fidelity of the real lifecycle.
A recurring theme across research: users didn't understand ThirdHome's credit-based exchange model well enough to make confident decisions during onboarding. They were being asked to submit a luxury home to a platform they didn't fully understand yet. The solution had to educate users in context — not before, not after, but during the flow itself.
Problem framingMental model mappingContent strategy
03
Design
Step-based flow + contextual education layer
Restructured the flow into digestible steps with clear progress indicators. Introduced an educational tooltip system — contextual callouts that surfaced platform value, explained membership benefits, and answered the implicit "why am I filling this in?" at the exact moment users needed it. Every tooltip was placed at a point of potential hesitation or confusion.
Launched to a subset of users first to measure improvements before scaling. Monitored completion rates at each step, drop-off during property listing and eligibility review, and downstream data quality as reported by Sales and Membership Success. Iterated based on live data.
A/B testingConversion trackingLive iteration
04 — Solution
Lighter on the surface, smarter underneath
The redesign transformed onboarding from a dense, form-heavy experience into a guided, step-based flow — with a built-in education layer that taught users how ThirdHome worked while they were signing up, not before or after.
Solution flow: 5-step redesigned onboarding — from registration to readiness
Account creation — simplified entry
The registration screen was stripped back to only what was needed to get started. Clean field grouping, clear labels, and a split layout with an aspirational property image on the right — setting the tone for the experience before users had even submitted a field.
Replaced a long dropdown with a visual grid of property types — reducing cognitive load while also surfacing membership benefits at the exact moment users might question the value. The tooltip on this screen explains host insurance and 24/7 emergency support, directly answering an implicit objection before it became a barrier.
Screen: Property type selection with contextual benefit tooltip
Educational tooltips — confidence at every step
One of the biggest UX gaps in the original flow was that users didn't understand ThirdHome's model well enough to answer questions confidently — or to see the value in what they were giving. I introduced a contextual tooltip system that placed relevant, specific education at every point of potential hesitation.
💬Tooltips weren't just helpful hints — they were a trust-building layer. Each one was placed at a specific moment of friction or confusion, answering the user's unspoken "wait, why?" before it became a reason to stop.
💰 Value education
Reinforcing ROI during description entry
While naming and describing their property, users see a tooltip surfacing "Expect 90–95% savings with ThirdHome vs. rental rates" — converting a data-entry step into a value moment that keeps motivation high.
🏆 Competitive framing
Competitive context at the rental link step
For users who already rent on Airbnb or VRBO, a tooltip explains why ThirdHome offers superior value over traditional rental platforms — contextualising the ask within their existing mental model.
Property address — map confirmation
A full map preview was added to the address step so users could visually confirm their location was captured correctly. This reduced errors, built confidence, and felt more appropriate for a luxury property — you're not just entering a postcode, you're placing your home on a world stage.
Screen: Property address with map confirmation
Property amenities — grouped, scannable, complete
The amenities screen was restructured with clear category groupings and a progressive "View More" pattern — showing the most common options first, with the ability to expand without feeling overwhelmed. This increased completion rates on amenity fields while reducing time-on-screen.
Screen: Property amenities — grouped by category
Key design decisions
Contextual education, not upfront onboarding
Instead of a tutorial before the flow, education was embedded at the exact point of need — via tooltips, inline guidance, and contextual callouts. Users learned how ThirdHome worked by doing, not by reading.
Progressive disclosure
Each step only showed what was needed right now. Fields were grouped logically and prioritised so users weren't confronted with the full complexity of the process at once.
Visual inputs over free text
Property type, amenities, and resort selection were redesigned as visual or checkbox-based inputs — reducing cognitive effort and improving the quality and consistency of data collected.
Post-submission lifecycle design
Designed clear post-submission states so users always knew where they stood in the review process — eliminating the "black hole" feeling and significantly reducing anxious support contacts.
05 — Results
Onboarding that worked for the whole marketplace
By redesigning onboarding as a shared workflow between user and business — and adding an education layer that built confidence at every step — the experience improved across every dimension: for users, for internal teams, and for the business bottom line.
$250K
Revenue impact within one quarter of tracking the redesigned experience.
3x+
Lift in the acquisition funnel — more qualified homeowners completing full onboarding.
Measured against controlled A/B baseline
↓ Drop-off
Reduced abandonment at property listing, eligibility review, and identity verification.
Highest impact at property submission step
📊The biggest wins happened at the steps where users previously had the least context — property type selection and description entry. Adding education at those exact points directly drove completion.
Beyond the numbers
Improved
Internal data quality
Structured inputs and guided fields meant data coming in was more complete and actionable — reducing manual follow-up by Sales and Operations and speeding up member approval.
Reduced
Confused support contacts
Contextual tooltips and clearer post-submission states meant users understood both what they were doing and what came next — fewer "what happened to my application?" messages.
Validated
Education as a conversion lever
Tooltips weren't just nice to have — they measurably improved completion at the steps where they appeared, proving that informed users are more confident users.
Delivered
Reusable A/B framework
Established a repeatable, documented experiment framework applicable to future onboarding and activation improvements across the platform.
06 — Takeaways
What I'd carry into every project
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Education is a design decision, not an afterthought
Users who don't understand what they're signing up for won't complete it — no matter how clean the UI is. Embedding contextual education at the exact moment of hesitation proved more effective than any amount of upfront explanation.
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Design for both sides — not just the user
In a two-sided marketplace, optimising for just one side always creates problems somewhere else. The breakthrough came from treating onboarding as a shared workflow — where user ease and business completeness were co-equal requirements, not a tradeoff.
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Luxury ≠ complexity — simplicity is the premium feature
Designing for a premium audience doesn't mean adding more. The biggest win was making a complex, multi-step process feel not painful — which, when you think about it, is exactly what a luxury experience should feel like.
