Boosting User Activation & Onboarding for Explosive Growth

Ricky L. Shepherd II, AI Product Manager
8 min read
August 18, 2025

Introduction

In 2018, I was on a roll. My team and I had just launched one of the most ambitious projects of my career. A  cutting-edge marketplace for health and wellness products. It had it all: predictive insights, sleek ux design, and a recommendation engine that seemed almost human.

The problem?

Signups poured in during launch week.

Then… silence. It was a gut punch. 

Not even a month later, and activation numbers were dismal. Less than 15% of users reached the core dashboard. Churn was bleeding through the edges. Retention? Nonexistent.

I had fallen into a trap many product leaders do. I overbuilt the “wow” features and underbuilt the “welcome” experience.

This launch became my crash course in why user onboarding isn’t just a box to tick, but the growth engine itself.

A valuable lesson emerged, and became the cornerstone of my career:

“If users don’t engage right away, they may be lost forever.”

TL;DR: Boosting User Activation & Onboarding for Explosive Growth

  • Onboarding is the real growth engine:  users must reach their “Aha Moment” faster or they’ll churn. Treat activation like acquisition.
  • Design for emotion, not explanation: reduce friction, personalize the journey, and reward early wins to drive habit formation.
  • Scaling can still feel personal: segment users by intent like LinkedIn. Automate smartly, and guide every user as if your life depended on it.

Lets begin…. 

Why Onboarding Is the Real Growth Engine

In every growth conversation, we talk about acquisition, retention, and monetization. But onboarding often gets treated like a formality for a “getting started” checklist.

Meanwhile onboarding is the bread and butter between acquisition and retention. And while seldom mentioned,  It’s the narrow bridge users must cross to go from being interested to invested.

Think about it. If acquisition is your front door, onboarding is the first conversation at the threshold.

A great onboarding sequence doesn’t explain features; it builds belief. And the faster you get a user to their "Aha Moment”, the higher their lifetime value.

Take Dropbox as an example. In the early growth stage, they discovered that users who installed the desktop app and synced files within the first session had much higher retention rates than those who didn't. This became their “Aha Moment.”

Instead of bombarding new users with every possible feature, Dropbox rebuilt its onboarding to guide users toward a single core action:

  • The signup flow immediately prompted users to install the desktop app.
  • An in-app checklist rewarded users for uploading their first file.
  • A referral incentive (“Get more free storage when you invite friends”) doubled as a way to keep users actively engaged.

This mindset shift changed the question from “How do we explain our product?” to:

  • What’s the fastest way for a new user to experience the core value?
  • Where do they get stuck, and how can we solve it?
  • How can we make onboarding feel emotional, not just functional?

The result? Dropbox's focus on activation helped it grow from 100,000 to over 4 million registered users in just 15 months. Which happened without spending a ton on ads.

Dropbox revenue from 2008 to 2017 (Source: Dropbox)

The Lesson

Map your Activation Funnel like you map your Acquisition Funnel by tracking:

  • Signup to first action: users felt overwhelmed by choice.
  • First action to first win: too much friction in setup.
  • First win to habit loop: no reinforcement to keep going.

If you can’t clearly define these three steps, your activation strategy might already be in jeopardy.

Designing for the “Aha Moment”

Every product has one moment when a user finally “gets it” or says, "Ohhh… now I see why this is valuable."

The problem? Most companies take too long to get there.

When I led a product at a gaming startup, I worked with a team of experts from different areas including engineers, UX designers, data analysts, and growth specialists. Together, we used journey maps to identify the roadblocks that prevented our users from hitting that point..

We discovered:

  • Signup to First Action: users felt overwhelmed by choice.
  • First Action to First Win: too much friction in setup.
  • First Win to Habit Loop: no reinforcement to keep going.

The fix wasn’t adding more tips or popups, but instead rewriting the story we told about the product. The devil was in the details: 

  • We stripped onboarding to the essentials: No more 10-field sign-up forms. Users could signup or maintain their anonymity with a KYC (Know Your Customer). This was pivotal given that our gaming platform was a metaverse.
  • We used progressive disclosure: The game only showed what you needed at the moment, or you could fully converse with an AI NPC's to gather next steps or talk about your day (hiding advanced features until you were ready).
  • We added immediate feedback loops. Users could see their track and rewards through a simple online signup form. Inviting 3 users would trigger confetti while gaining access to early features in under 2 minutes. 

We also made the first experience deeply immersive: interactive gameplay, personalized AI NPCs, in game clubs and bartenders to ask around.

The result?

Activation rate jumped 27% in two weeks, and retention improved without touching acquisition

The Lesson

Find your 2-minute win.

  • What’s the smallest, fastest, most delightful result you can give?
  • Cut everything between sign-up and that moment.

The Behavioral Psychology of Activation

Onboarding isn’t just UX design. It's also behavioral design and something that many Product Leaders miss.

The best onboarding I’ve ever built leverages three principles:

Reduction (Frictionless First Step)

  • Every extra field, button, or decision is a leak.
  • Example: Dropbox increased sign-ups by 60% just by trimming steps.

Recognition (Personalized Entry)

  • People lean into things that feel for them.
  • Use names, data pre-fills, or role-based flows to make onboarding relevant.

Reward (Instant Gratification)

  • Gamification works when it’s tied to meaningful progress.
  • Early success should trigger emotional reinforcement not just a “Done” message.

A great example of this is when Instagram rolled out its “Stories” feature in 2016. The company knew they couldn’t just drop a new icon at the top of the feed and expect adoption to skyrocket. Stories was a format shift for a different kind of engagement and if users didn’t create their first story quickly, they might never use it at all.

Rather than relying on flashy ads or endless announcements, Instagram honed in on a smarter rollout:

  • Visual prompts appeared at the top of the feed with animations encouraging users to “Share your first story.”
  • They reduced friction by letting users post without leaving the main feed without requiring a multi step navigation.
  • They added realtime feedback loops, like instantly showing who viewed your story, creating a small dopamine rush that encouraged repeat usage.

The results were significant. Internal metrics indicated a steep increase in activation rates from Day 1 to Day 7 for Stories. This surge wasn’t about better advertising or viral techniques; it was all about making that first creation experience so rewarding and visible that it hooked users into a new behavior loop.

When your first moments are designed to feel effortless and rewarding, you don’t need a bigger ad budget, you need a better product welcome.

The Lessons:

Use the 3 R’s Framework for every onboarding flow:

  • Reduce friction:  make the first step obvious.
  • Recognize the user:  tailor the experience.
  • Reward early wins: give feedback that feels good.

Scaling Without Losing the Human Touch

Product leaders in hypergrowth products struggle with one key challenge: scaling onboarding while preserving a personal touch.

As you jump from 500 to 50,000 users, it's impossible to give everyone a personalized tour, but you can design an experience that feels like you did.

During its rapid growth in the mid-2010s, LinkedIn tackled this issue head on. With millions of new members joining every quarter, the company discovered that dropping users onto a generic profile page was leaving value on the table.

The first experience felt cold, impersonal and users disengaged quickly.

As a response their solution was a personalized onboarding system at scale:

LinkedIn Customer Segmentation from 2009 -2014 (source: LinkedIn)

Segment first time users by intent:

  • Identify the primary goal of each new user (e.g., “Find a job” vs. “Hire talent” vs. “Grow network”).
  • Build onboarding flows that match those goals instead of one-size-fits-all tutorials.

Automate Personalization at Scale:

  • Use dynamic welcome screens, checklists based on user roles, and personalized UI copy that addresses users by name.
  • Make users feel like the product already understands their needs.

Leverage predictive triggers for engagement:

  • Monitor early user behaviors to identify those at risk of churning (e.g., users who haven't added connections after three days).
  • Send targeted nudges, such as emails, push notifications, or in-app suggestions, based on their behavior.

Use smart defaults to speed up setup:

  • Fill in profile data using signup information and integrations.
  • Suggest high impact actions to help users get started quickly (e.g., making their first connection or posting for the first time).

Create the experience of 1:1 guidance:

  • Use a conversational tone to make automated messages feel like they're coming from a real person, and provide suggestions that fit each user's situation.
  • Ensure every prompt is relevant to the user's situation, creating a personalized experience that feels tailored just for them.

The genius of this approach was that it felt like LinkedIn was personally involved in each user's welcome experience, despite being automated. This helped keep engagement high without needing manual onboarding teams to grow with the user base.

As a result, LinkedIn's onboarding improvements led to a significant increase in activation and profile completion rates, while maintaining the sense of personal investment that makes a network sticky.

At scale, “personal” is often an illusion, but this approach made it a reality.

Lessons for the Next Generation of Product Leaders

If I could go back and talk to myself in that 2018 launch, I’d say:

  • Onboarding is your silent growth channel. Just treat it like acquisition and retention rolled into one.
  • You don’t have to roll out every feature to users, just enough to win them over.
  • Track activation as aggressively as you track signups.

At KIING Studios I now learn one simple mantra:

“If users don't understand your product and experience an "Aha Moment" in the first session, they probably never will.”

We craft every flow to ensure the first five minutes sparkle. It's not just about usability; it’s about creating unforgettable moments that enchant and engage.

Closing: First Impressions Make the Growth

User onboarding isn’t pre-growth; it's the ignition.

In a landscape where acquisition costs are soaring, growth doesn’t demand a hefty ad budget. It hinges on those who transform first-time users into steadfast fans in mere minutes, not months.

If you can turn a curious visitor into a confident believer before they think about closing the tab..

YOU WIN
Ricky L. Shepherd II,  AI Product Manager

Ricky Shepherd II is an AI growth product manager passionateabout building scalable products that drive adoption, retention, and revenue. With a track record of launching high-impact features across health, fintech,and gaming, Ricky helps companies from startups to Fortune 500s leverage AI anddata points to unlock sustainable growth. Through insightful articles andstrategic frameworks, he empowers product leaders to master go-to-market,growth loops, and AI integration for next-gen user experiences.

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