$0K
Revenue impact, one quarter
0x+
Lift in acquisition funnel
Onboarding completion rate
0
Sides of the marketplace, both happy
01 / Overview

Making onboarding work
for both sides of the market

ThirdHome is a private travel platform where luxury second home owners swap stays at other jaw dropping properties around the world. Here is the thing about joining though: it is not "create an account and you're in." You're submitting your actual home, proving you qualify, and trusting a platform enough to hand over the keys. That is a big emotional ask, and the old onboarding treated it like a tax return.

So I rebuilt the whole end to end member onboarding experience. The goal: make a genuinely complex multi step journey feel light for homeowners, while still capturing the depth of information the platform needs to keep marketplace quality high. Because in a two sided marketplace the math is brutal. No homes means no trips, and no trips means no business. Both sides have to win or nobody does.

💡 The core tension I kept circling back to: users needed onboarding to feel effortless, the business needed it to be thorough. My job was to refuse the tradeoff and design for both at once.
🏡

High quality inventory was on the line

The marketplace only works if every home clears a quality bar. So onboarding had to pull detailed property info, photos, availability, and eligibility out of brand new users who did not yet know how any of this worked. No pressure.

🧠

Cognitive overload, the greatest hits

The old flow asked for everything all at once. A dense wall of form fields with zero explanation of why any of it mattered. It felt like paperwork at the DMV, not an invitation into a luxury club.

The post submission black hole

You hit submit and then... silence. No review status, no approval steps, no sense of where you stood. Cue the anxiety, the support tickets, and the quiet tab closing that we call drop off.

📚

Nobody understood the exchange model

New members had no mental model for how a credit based home exchange actually works. Without education built right into the flow, people could not make confident calls, or even see the value they were signing up for.

02 / Discovery

A form problem in disguise.
Actually a system problem.

After a few sessions with Customer Success and some time sitting in on Membership Experience calls, the real shape of this became obvious. This was never a "make the form prettier" problem. It was a systems problem. Onboarding did not end when someone clicked submit. That click was the starting line, and the whole back half of the journey was invisible to the user.

How do you collect everything a marketplace needs without it feeling like a tax form? That one question became the entire design challenge.

I mapped the full end to end journey across three iterations. Not just the user facing screens, but everything happening behind the curtain after submission: property review, membership approval, exchange readiness. The map made the gap impossible to ignore. People finished a form and then heard nothing, and that silence quietly killed their confidence. Drag through the iterations below and you can watch the map grow as I learned more.

Interactive Journey map, three iterations deep

Each pass added fidelity. V1 captured the happy path, V2 surfaced the approval states, and V3 mapped the full post submission lifecycle. Tap through to see how the thinking evolved.

User onboarding flow map
V1. First pass at the flow, mapping the screens a homeowner actually touches. Useful, but it stopped at submit and missed the part of the journey that was breaking trust.
🔍 The reframe that unlocked everything: stop asking "how do we simplify this form?" and start asking "how do we design a system that walks people from submission all the way to readiness?" Different question, completely different solution.
03 / Process

Designing the system,
not just the form

I treated this as a system design problem from day one. Rather than optimizing for one side of the market and quietly hurting the other, I went after both at the same time. That meant getting genuinely close with Membership Success, Sales, and Product to understand what "good data" actually looks like from the inside out.

01
Discovery
Cross functional research and journey mapping
I sat in on Customer Success and Membership Experience sessions and mapped the full end to end journey, including everything that happened internally after submit. Three iterations of the flow map captured the real lifecycle at increasing fidelity, which is where the actual friction was hiding.
Stakeholder interviews Journey mapping Internal workflow audit
02
Definition
Naming the education gap
One theme showed up everywhere: people did not understand ThirdHome's credit based exchange model well enough to make confident decisions while onboarding. They were handing a luxury home to a platform they had not wrapped their heads around yet. The fix had to teach in context. Not before, not after, but right inside the flow, exactly when the question popped into their head.
Problem framing Mental model mapping Content strategy
03
Design
Step based flow plus a contextual education layer
I broke the flow into digestible steps with honest progress indicators, then built a tooltip system that surfaced platform value and answered the unspoken "wait, why am I filling this in?" at the precise moment of hesitation. Every tooltip earned its place by sitting at a real point of confusion, not just decorating the screen.
Progressive disclosure Contextual tooltips Information architecture Accessibility
04
Validation
Controlled A/B rollout, because opinions are not evidence
I shipped to a subset of users first so I could measure before scaling. I watched completion at every step, drop off during property listing and eligibility review, and downstream data quality as reported by Sales and Membership Success. Then I iterated on live signal rather than vibes.
A/B testing Conversion tracking Live iteration
Interactive How I kept scope creep from eating the launch

The moment a project goes cross functional, the wish list explodes. Here are real requests that landed on my desk mid project. Sort each one the way I did: ship it now, park it for later, or politely kill it. The goal was protecting a focused V1, not saying yes to everything.

📨 Incoming requests
In scope for V1 0
Nothing yet. Start sorting.
Parked for later 0
Good ideas go here to wait their turn.
Cut with love 0
Saying no is a design decision too.
04 / Solution

Lighter on the surface,
smarter underneath

The redesign turned onboarding from a dense form slog into a guided, step based flow with a built in education layer that taught people how ThirdHome works while they signed up, not in a help doc they would never open. Rather than stack a dozen static screenshots on you, I rebuilt the actual flow as something you can walk through yourself. Click through every step below and watch the contextual education do its job.

Interactive prototype Walk the redesigned onboarding flow

Seven steps, each one carrying just enough information to keep momentum and just enough education to build trust. Use the steps, the arrows, or just keep tapping Next.

Account creation screen
Account creation, simplified entry
Stripped registration back to only what you need to get going. Clean field grouping, clear labels, and an aspirational property image on the right that sets the tone before you have even typed a thing.
Property type selection with tooltip
Property type, visual picks over dropdowns
A long dropdown became a visual grid, which lowers cognitive load and looks the part. The tooltip here explains host insurance and 24/7 emergency support, answering an objection right where it would otherwise stall someone.
Property description with savings tooltip
Description, where data entry becomes a value moment
While naming their property, users see a tooltip surfacing 90 to 95% savings with ThirdHome versus rental rates. A boring field quietly turns into a reason to keep going.
Rental link screen with comparison tooltip
Rental link, meeting people in their own mental model
For anyone already renting on Airbnb or VRBO, a tooltip frames why ThirdHome beats traditional rental platforms, dropping the ask into context they already understand.
Property address with map
Address, with a map to confirm
A full map preview lets people visually confirm their location landed correctly. Fewer errors, more confidence, and a moment that feels right for a luxury home. You are placing your property on a world stage, not typing a postcode.
Property amenities screen
Amenities, grouped and scannable
Clear category groupings and a progressive "view more" pattern show common options first and expand on demand. Higher completion on amenity fields, less time stuck on the screen.
Post submission thank you confirmation
Submitted, and no black hole in sight
This is the screen that fixed the original problem outright. Instead of silence after submit, members land on a confirmation that sets expectations ("we'll reach out in 24 to 48 business hours") and hands them somewhere to go next: travel preferences, browse properties, the help center, and a member story. The post submission lifecycle, made visible.

Educational tooltips, confidence at every step

The single biggest gap in the original flow was that people did not understand ThirdHome's model well enough to answer with confidence, or to see the value in what they were giving up. So I built a contextual tooltip system that dropped relevant, specific education at every point of hesitation. Not generic help text. Targeted, timed, trust building copy.

💬 Tooltips were not decoration, they were a trust building layer. Each one sat at a specific moment of friction and answered the unspoken "wait, why?" before it became a reason to bail.
A/B mindset Education layer, on versus off

This is the experiment in miniature. Flip between the control (no education) and the variant (contextual tooltips) and watch how completion holds up across the steps where users used to drop. Bars are directional, measured against a controlled baseline.

Account created
Property type
Description entered
Eligibility review
Fully submitted
Control: education absent, friction loudest right where context was missing.
💰 Value education

Reinforcing ROI during description entry

The savings tooltip on the description step in the prototype above was the one I most wanted live data on. It converts a dull data entry moment into a reminder of why this is worth it.

🏆 Competitive framing

Competitive context at the rental link step

For users coming from Airbnb or VRBO (the rental link step above), the comparison tooltip reframes the ask inside the model they already trust, so it never feels like a leap of faith.

Key design decisions

Contextual education, not upfront onboarding

Instead of a tutorial nobody reads before the flow, I embedded education at the exact point of need through tooltips, inline guidance, and contextual callouts. People learned how ThirdHome works by doing, not by studying.

Progressive disclosure

Each step showed only what mattered right now. Fields were grouped logically and prioritized so nobody got hit with the full complexity of the process in one go.

Visual inputs over free text

Property type, amenities, and resort selection became visual or checkbox based inputs. Less effort for the user, and noticeably cleaner, more consistent data for the business.

Post submission lifecycle design

I designed clear post submission states so people always knew where they stood. The confirmation screen (the final step in the prototype above) sets a 24 to 48 hour expectation and routes people to travel preferences, browsing, and support. That alone deflated the black hole feeling and cut the anxious "what happened to my application?" tickets.

05 / Results

Onboarding that worked
for the whole marketplace

By treating onboarding as a shared workflow between user and business, and layering in education that built confidence at every step, the experience got better across the board. Better for users, better for internal teams, and better for the bottom line. That last part is the one that gets you budget for the next project.

$250K
Revenue impact within one quarter of tracking the redesigned experience.
3x+
Lift in the acquisition funnel as more qualified homeowners completed full onboarding.
Measured against a controlled A/B baseline
↓ Drop-off
Lower abandonment at property listing, eligibility review, and identity verification.
Biggest gain at the property submission step
📊 The biggest wins landed exactly where users used to have the least context: property type selection and description entry. Drop education at those moments and completion follows. The A/B data said so, not me.

Beyond the numbers

Improved

Internal data quality

Structured inputs and guided fields meant the data coming in was more complete and actually usable, which cut manual follow up for Sales and Operations and sped up member approval.

Reduced

Confused support contacts

Contextual tooltips and clear post submission states meant people understood both what they were doing and what came next. Far fewer "what happened to my application?" messages.

Validated

Education as a conversion lever

Tooltips were not a nice to have. They measurably improved completion at the steps where they appeared, proving that an informed user is a confident user.

Delivered

A reusable A/B framework

I left behind a repeatable, documented experiment framework that the team could point at future onboarding and activation work across the platform.

06 / Takeaways

What I carry
into every project

Education is a design decision, not an afterthought
People who do not understand what they are signing up for will not finish, no matter how clean the UI is. Dropping contextual education at the exact moment of hesitation beat any amount of upfront explanation, and I had the A/B numbers to back it up.
Design for both sides, not just the user
In a two sided marketplace, optimizing for one side always creates a mess on the other. The breakthrough was treating onboarding as a shared workflow where user ease and business completeness were co equal requirements, never a tradeoff. Protecting that balance is also how you survive scope creep.
Luxury does not mean complexity. Simplicity is the premium feature.
Designing for a premium audience never means piling on more. The biggest win here was making a complex multi step process feel genuinely painless, which, when you think about it, is exactly what a luxury experience is supposed to feel like.