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