App of the Year: Tiimo
10 lessons from Apple's 2025 App of the Year
Hey there, it’s Jacob at Retention.Blog 👋
I got tired of reading high-level strategy articles, so I started writing actionable advice I would want to read.
Every week I share practical learnings you can apply to your business.
Congratulations, Tiimo!
And everyone on the team who helped contribute to this achievement.
Tiimo is a planning and to-do app built for neurodivergent people.
The founders:
Who better to learn from than the App of the Year!?
Lesson 1: Differentiate
How crowded is the planner and to-do list app space? Really, really, really crowded.
But if you can differentiate and position yourselves, you can stand out.
If your app is for everyone, it’s for no one. Who are you building for?
🎙️ New Price Power Podcast Episode!Lucas Moscon is the founder of Appstack, a mobile growth and attribution mastermind, was a senior UA manager at MonkeyTaps, and advisor for huge companies like Life360.
That’s a long way of saying he knows his shit.
What you’ll learn
“Most apps don’t actually need an MMP anymore”
“Fingerprinting is BS - 90% is via IP address”
“Your iOS RoAS is probably wrong. You need to use a blended ROI”
How to correctly design conversion values for SKAN without over-engineering
Why focusing on payback windows (D60–D180) outperforms optimizing for short-term ROAS
Why probabilistic fingerprinting is still powering the ad ecosystem — and why Apple hasn’t stopped it
and more
Watch and listen here:
➡️ Spotify 🔗
➡️ Youtube 🔗
➡️ Apple Podcasts 🔗Lesson 2: Continually test the placement of critical onboarding screens
I looked at Tiimo in June 2024, so we can compare what’s changed
One of the highest drop-off points is account creation.
But. It also can be productive because it creates higher intent users.
It’s not important to make sure every single user makes it to your paywall.
It’s important that the right users who will pay make it there.
June 2024:
Previously, they had account creation right before the paywall.
Dec 2025:
Now Tiimo has account creation right after the initial welcome screen.
This can be an effective tactic because people have the most energy and intent right when they download your app.
If someone isn’t willing to create an account when they have the highest intent, do you really think they’ll pay you?
Also, this separates two large asks further away from each other: account creation and the paywall.
I bet this boosted account creation rates, decreased onboarding drop off, and improved the trial start rate.
Lesson 3: Put your users first
If you noticed above, immediately after Tiimo asks you for account creation, they ask if you’d like to receive updates.
This is atypical.
Most products just send you updates and promotions.
But this doesn’t fit with their brand or philosophy.
It would 100% build some early trust with me as a user.
Lesson 4: Have a visual identity
I wrote a little about this in July 2024:
Tiimo does such a nice job having a distinctive feel.
Their engaging and unique illustrations instantly tell who they are.
“We’re creative”, “we’re different”, “We’re full of life”
Maybe most importantly, you remember. It doesn’t just blend into all the faceless and nameless software you use every day.
It instills emotion.
If you want to be remembered, you can’t be the same as everyone else.
Not to mention the fun change of adding their little purple circle mascot person!
Old:
New:
The hands don’t really match the body, but we’ll let it go…
Lesson 5: Use simple paywall personalization
I’ve given this advice before, so if you’re still not doing it, this is your signal to launch a test.
Add simple string personalization to your paywall.
Tiimo asks new users if they’re neurodivergent.
If they say, “yes”, then they change the title on the paywall.
Simple as that.
Asks users what are your goals, something specific about their experience, or some other question that will change their user type. Then personalize the copy based on that.
I’ve rarely seen this not have a positive impact.
Lesson 6: Simplify
Tiimo has two “quiz” type questions before the paywall today.
In 2024, they had 3 questions.
Not a huge reduction, but shows their desire to simplify based on their improved understanding of their users.
Look at the difference in copy:
“This describes me best”
“Are you neurodivergent?”
A much more focused and simple message.
And their pricing was so confusing:
Who is each plan for?
$6 vs $8 is such a small amount it makes the choice harder.
It says monthly for each, but then down below it’s annual…
Let’s look at the updated paywall and plans:
ahhh, that’s better. So much easier to understand.
One plan, two price and length options, both 30 day trial (which is interesting for a monthly plan…)
Lesson 7: Keep testing pricing and packaging
We had two lessons wrapped up in one there. Simplify, and keep optimizing your pricing and packaging.
If you didn’t see, Michal Parizek, Senior Product Growth Manager at Mojo, wrote a break down on all of his pricing tests and experiments.
He boosted ARPU by 60% year over year, and had a 56% win rate on price tests compared to 14% on other experiment types.
You can go read the full post here: Pricing Experiments: The Backbone of Mojo’s Monetization Success →
Pricing is often one of your most powerful and impactful levers, so you should not ever think of your pricing and packaging as “Done.” It’s an ever-changing offer that should update as your product and user base evolves.
Lesson 8: Your product will change
I understand this one may seem a bit obvious.
“Duh, Jacob, I know my product will change.”
What I mean is that your differentiation and features and how people think of your product will change.
And it should.
“…if that’s what you meant, why didn’t you say that the first time, Jacob?”
What got you your first users, won’t be the same thing that gets you a million users.
For example, Tiimo was promoting “body doubling” in 2024
This is when you can have someone else present to help you focus. Tiimo did it very video.
In 2025 there is no mention of it:
I’ll admit it’s possible they’re using CPPs and still have one thats dedicated if you come from an acquisition source that promotes body doubling. But regardless, it’s no longer front and center.
Body doubling is a super cool feature that probably got them some early fans, but it may not have appealed to everyone.
As your audience and user base grows, your product needs to change as well to meet their needs.
Lesson 9: Make it easy on your users
I love this little feature.
I don’t know what routines I should pick. What do I do? Stare at the screen until I get frustrated and close the app? Randomly tap some to move on?
Oh wait! I don’t have to do any of that! Tiimo will “Suggest for me”!!
For some reason, having the app suggest habits for me feels so much better than me randomly tapping a few just to move.
It felt easy and smooth. Versus annoyed because I don’t know what I want.
Empathize and anticipate where your users may get stuck.
And give them a hand!
If you can show off the value in your “AI Planner”, even better.
Lesson 10: Keep on holding their hand
Do you think your product’s job is over after someone starts a trial?
Of course not.
So don’t just drop your user into some confusing home page with a million options.
This also offers you a chance to help set up the app for the new user.
Look at everything Tiimo includes in the onboarding after the paywall!
Also, let’s compare how much simpler and focused this UX got compared to what it was previously.
They broke the set up into steps at least, but it’s only half the screen, you’re distracted by the other half, there are no preset options, and it’s all very crowded text and design.
Then, look what is waiting for the user after they complete these 5 steps…another 5 setup steps!
P.S. Curious how many downloads App of the Year will get you?
Appfigures estimates ~200k downloads over Thursday and Friday after it was announced.
Lesson Summary:
Differentiate
Continually test the placement of critical onboarding screens
Put your users first
Have a visual identity
Use simple paywall personalization
Simplify
Keep testing pricing and packaging
Your product will change
Make it easy on your users
Keep on holding their hand
Want more lessons?
Well, you may have to do some of the work yourself.
Here is the Whimsical board with Tiimo today, and Tiimo from June 2024.
See their entire onboarding flow, new and old →
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