AI-Assisted Onboarding
for Lasting Engagement
Skipper is an AI-powered productivity web app that organizes your browser tabs for you.
Designed for knowledge workers, rooted in CMU research & backed by Menlo Ventures.
Overview
Problem
New users struggled to understand Skipper's value and how to organize their tabs, resulting in poor active engagement.
Solution
Redesigned onboarding with an AI-assisted folder creation flow that guides users through their first 'Skipper win' while clearly explaining key values.
Impact
63% → 96%
Onboarding completion rate
16% → 49%
Week 1 active engagement*
*Folder creation/organization, tab open from Skipper, etc.
AI assistance added
to all folder workflows in the product
Role
Head of Design (sole designer)
Responsibilities
UX/UI & Interaction Design
User Research
Prototyping & Testing
Scaling Design System
Facilitating Collaboration
Team
2 engineers + 1 PM
Timeline
1 month
Problem
Skipper's PMF depended on active engagement,
but it was stalling.
Q4 2024
Automatic Tab Save retention
→ 50% at week 8
Active engagement rate
(Tab Organization & Reopen)
→ 6% at week 8
Business Problem from the Surface
We see a dip in active engagement and we don't know why.
Low active engagement for us means weak product-market-fit.
Uncovered User Problem
"As a new user, I don't know how to organize my tabs and can't envision Skipper's ongoing value for me."
Solution 1/2
Create your first folder, effortlessly.
AI-assisted folder creation
Skipper intelligently recommends tab folders based on the user's recent browsing history.
This was a new UI component introduced to the product.
1
Skipper recommends a folder title most likely to be used frequently based on user's browsing data.
2
Then it teaches users how to easily keep folders up-to-date by adding AI-recommended tabs to them.
Either by dragging & dropping…
… or by clicking the [+ Add] buttons.
Solution 2/2
Understand Skipper's key values in 2 mins.
Previous onboarding wasn't structured around the key values
Approach: Learn by doing
To help new users understand why they need Skipper, we broke down onboarding into 3 steps, each showcasing one of Skipper's core benefits.
More focused first "Save" experience
New experience eases users into Auto Save by teaching the minimal configuration & allowing them to choose which tab to keep open.
Impact
From Passive to Active: 3x Growth
A/B test hinted a positive trend in onboarding completion & W1 engagement
The PostHog product analytics page for this experiment 3 weeks into the A/B test. The purple bar (far left) indicates the previous onboarding completion rate of 63%.
63% → 96%
Onboarding completion rate
Following our full launch, we observed a substantial increase in active engagement
16% → 49%
Week 1 active engagement*
*Folder engagement, tab open from Skipper, etc.
11% → 29%
Week 4 active engagement
Lastly, the AI-assistance was added to all folder organization flows.
Research
Teamwork to find leverage in qual & quant research
To uncover this problem…
Automatic Tab Save retention
→ 50% at week 8
Active engagement rate
(Tab Organization & Reopen)
→ 6% at week 8
I teamed up with ENG & Product to look for…
Opportunities in churned and inactive user interviews
Key behaviors to leverage from user data
