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Reducing time to aha! moment in B2B SaaS
A case study of Otter.ai

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Last week, I wrote about Otter.ai’s onboarding flow.
In the deep dive, I found three things they do really well:
- 🛠️ Introduce set-up tasks one by one: turn on meeting notes, sync calendar and invite team — — all covered within 5 mins from landing page
- 🍔 Give people a monetisation sandwich: paywall at start and end of onboarding to drive conversion (as well as have a freemium + free trial model)
- 📆 Have a leading indicator for activation: calendar sync is pushed so many times, likely correlating with activation & retention later on
When I was writing last week’s issue, I found there’s just so much good stuff to analyse. So, I had to do another issue 🙃
This week we go deeper into the recording tool’s activation funnel to analyse:
- How the Homepage pushes to key tasks without overwhelming
- An onboarding checklist that progressively discloses what to do
- A tutorial to get users to record ASAP
- Some cool GIF demos for prompting their chat search
And a lot more.
Here’s a summary for the busy bees out there:

Without further ado, let’s jump in.
First up, a recap of the onboarding UX on a macro level, which is crucial for how users are primed (and not overwhelmed) when they land on the homepage.
Pre-homepage UX
Last week we covered the journey from Landing page to the last paywall in detail. Zooming out, their onboarding flow goes like this:
- Landing page
- 🍔 First step = Paywall
- Account creation 1: registration
- Account creation 2: set a password
- Account creation 3: first and last name
- Set up task 1: turn on auto meeting notes