At a glance

Role

Product design lead and front-end developer: brand, UI, front-end code and, since 2026, experiment design and analysis

Team

Me, a lead engineer, a product and ops lead, and the Originals lead

Scope

315 merged PRs: booking pages, editor, onboarding, dashboard, pricing, homepages, emails and three brand generations

Results

4.7x revenue growth 2021→2024 · #1 Product of the Day on Product Hunt · 4x onboarding completion · +20% calendar connections

The challenge

By late 2025 TidyCal had a growth problem hiding inside its success. Sign-ups had passed 148K a year, but 46% of booking pages had never received a single booking. A page that never gets booked produces a user who never pays, never refers anyone and quietly churns.

Two more pressures sat on top of that. The business was moving from lifetime deals to recurring revenue with TidyCal Pro, so the product itself now had to sell. And five years of features (group bookings, polls, packages, teams, payments) lived in a layout designed for a much simpler app.

To find out who we were designing for, I used AI to analyse about 20,000 live booking pages. Three segments made up 71% of users: coaches and consultants, health and wellness, and fitness and education. Only 25% of pages had a cover image. That analysis set the 2026 roadmap: get people to their first booking, and give them a reason to pay.

Three brand generations

I've rebuilt TidyCal's look three times. Each time the goal was the same: make a feature-dense tool feel simple.

2021: launch

I was consulted on the name before any design existed. Within a week I had shipped the brand, the markup and the Product Hunt images. Early on I noticed a pattern I kept designing around: even when the app wasn't what people expected, they still liked how it looked and how simple it was.

2024: TidyCal 3.0

A new logo, a pattern system and the launch page. It was our first Product Hunt launch in two years and finished #1 Product of the Day. That year I also redesigned the homepage, sign-up and integrations pages, and designed Teams, the agency tier that helped make TidyCal AppSumo's top-earning paid deal of Black Friday 2024.

2026: the redesign

I rebuilt the app's whole front end in one release, across 206 files:

• a component library with cards, badges, status labels and segmented controls
• a spacing system and a new sidebar with mobile navigation
• the booking-type editor moved into a slide-out drawer
• an admin page documenting every component

It's built utility-first with very few custom classes, so later experiments could be built in days.

Experiments: getting to the first booking

In 2026 I went from shipping designs to owning their outcomes. I designed, built, instrumented and analysed each test myself. Not every test won, and the losses taught the team more than the wins.

Onboarding V3: a loss that became a 4x win

My first V3 changed five things at once and lost to V2, so we couldn't tell why. Digging in, I found V3 recorded goal events V2 never could. I stopped the test, made tracking match across both versions, and iterated:

• cut the flow from 7 steps to 5
• reordered it to profile, calendars, video, payments
• added social proof from our own data, like “Users with a photo are 5x more likely to get booked”
• renamed “Skip” to “I'll do this later”

With clean data, V3 showed a 4x lift in onboarding completion and shipped to everyone. I then wrote the team's A/B testing guideline: one variable per test, matching instrumentation, no changing metrics after the fact.

First-booking hero

A new account's dashboard was a wall of zeros. I replaced it with a hero designed to make the path to a first booking feel like a rewarding climb: four steps with two pre-checked as a head start, a hairline progress bar, a fan of live page previews for sharing, and one-time confetti on the first booking. Measured on users who could actually see it, calendar connections rose 20% and Stripe connections 11%.

Onboarding V4: killing my own idea

After watching our CEO go through onboarding, I designed a shorter two-step wizard. Bookings were flat, but it hurt the steps that matter later: calendar connections fell 12.7%, profile photos 36.8% and Stripe connections 22.7%. We kept the control, and the post-mortem made 14-day conversion windows and power analysis team defaults.

Results

• $4M in lifetime sales and 477K sign-ups; 70% of AppSumo Originals revenue in 2024
• #1 Product of the Day on Product Hunt for TidyCal 3.0
• AppSumo's highest-earning paid deal of Black Friday 2024, with 4,335 transactions
• 53% of 2026 AppSumo sales came from upgrade links I designed inside the product
• 466 TidyCal Pro subscriptions in five months
• On G2, it outscores Calendly on ease of use: 9.8 vs 9.4

What I learned

Taste gets you to launch; measurement gets you to growth. Five years of polish built the brand. The experiments showed which polish actually moved people to their first booking.

Simplicity converts, but “simple” has to be measured. Fewer steps lost to the right steps.

Next case

BreezeDoc: from a name to a live beta in 4 weeks