Project 

Time 

Role

Challenge

Solution

Although app downloads were high, many users uninstalled soon after viewing their results. Thoughtful needed to transform these initial interactions into sustained engagement. I collaborated with the research, copy, and product teams to uncover why users disengaged and to develop strategies for maintaining long-term motivation.

How might we create a motivating and habit-forming practice that users will adopt into their daily routine?

I analyzed the user journey to pinpoint friction points and missed opportunities. UX research highlighted a key issue: users felt disconnected from the app experience after receiving their Connection Style results. While users appreciated the variety of articles, they struggled to see how the content aligned with their results or guided their next steps. The experience also demanded upfront effort without immediate reward, leading users to abandon the app.

In parallel, I noted a growing trend: users increasingly value personalized, socially aware experiences that make them feel understood. Personalization builds trust and fosters connection, which drives ongoing engagement. This hypothesis was supported by usability testing and competitive analysis of successful quiz funnels, which showed that users sought more personalized insights, recommendations, and advice tailored to their unique needs.

Web-to-mobile app customer acquisition flow 

Usability test quotes

Examples of competitive analysis of optimized online funnels.

Technical limitations made full personalization unfeasible. As a mobile-first company, Thoughtful needed to balance the diverse needs of users without overwhelming the app with excessive features. To address these constraints, we introduced granular test with a score breakdown to give deeper insights. This change encouraged more users to complete the Connection Style Test, but many still uninstalled the app after viewing their results. Realizing that more was needed to retain users, we began exploring ways to create emotionally impactful moments within the app.

Introducing granularity boosted user motivation to complete the test, sparking organic growth with 100–130 new users discovering the app in a single weekend. However, users continue to uninstall the app.

With funding deadlines approaching, I focused on mitigating risks and maximizing impact quickly. I explored strategies from Hooked by Nir Eyal, reviewed Duolingo’s A/B testing methods, and conducted a competitive analysis of top-performing gamification apps. I also gathered feedback from colleagues on their favorite apps to understand how they successfully motivated and retained users.


Gamification patterns set the stage for experimentation. Features like badges, leaderboards, and delightful animations offered low-effort, high-impact opportunities to boost engagement and retention.

Competitive analysis of top gamification apps and colleagues’ favorites.

We initially explored offering badges for adding personal information, like friends’ dates and notes, to motivate users to stay engaged. However, with my background in behavioral health, I recognized this approach was flawed. The badges prioritized business metrics over user-driven goals, risking a negative impression. Instead of rewarding tasks, I proposed using user-inputted data to provide meaningful self-reflection and deeper insights.

To realign our strategy, I focused on key questions to better understand user motivation:

• What do users truly care about?
• What meaningful challenges can we offer?
• How can we help users feel accomplished?

User motivation brainstorm

Recognizing the effort needed to get badges right, we explored other ways of creating emotionally impactful moments within the app.

Low-fidelity sketches showcasing in-app delights.

We drew inspiration from Apple Workout for completing Daily Actions, hoping the rings would provide a sense of accomplishment and keep users motivated.

I drew inspiration from Super Smash Brothers to create an ‘unlocking’ effect, aiming to evoke a rewarding feeling and sustain motivation through variable rewards.

We considered a leaderboard but scrapped it after realizing it required more scope than anticipated.

Then came the AI boom, solving two major challenges: personalizing the experience for a broad audience without cluttering the interface and delivering immediate value through deep insights with minimal input. Users engage with an emotionally supportive chatbot that fosters introspection, offering personalized insights and a daily action plan to help strengthen relationships. The emotional impact comes from users feeling truly seen and heard.

The first platform version launched in June 2023 with a healthy web-to-mobile funnel, but the mobile app faced high abandonment. Recognizing the challenge of forming new habits, my research led to a business pivot from generalized article guides to personalized content, driving deep insights and facilitating behavioral change. This pivot, once implemented, achieved the following outcomes:

43%+

Increase in Week-One Retention

230%+

Increase in Active Users (from 180 to 600+). 

130%+

Organic Growth Surge

For this project, I was tasked with uncovering why users disengaged and uninstalled the app, and developing strategies to boost long-term retention. The main challenge was sustaining user motivation long enough to kickstart a flywheel of inputting information and forming habit-building practices.

One unexpected hurdle was addressing subconscious barriers, like fear of conflict or inability to establish boundaries, that prevent users from taking action. Drawing from my background in psychotherapy, I recommended a personalized experience that encouraged introspection before engaging with others. This approach helped reduce abandonment by allowing users to diagnose their social situations and follow a prescriptive regimen.

Many of the exploratory designs didn’t go live with user feedback. If I could go back, I’d like to see how the gamification techniques would have performed. However, I’ve learned that meeting users’ internal goals is far more effective for sustaining motivation than any gamified approach. Overall, this project taught me the importance of aligning product rewards with user expectations and motivations to drive meaningful behavioral change.

THOUGHTFUL

Fixing a leaky customer funnel.

Growth • B2C SaaS • Animation

GOLD HEARTED

Rebrand a jewelry company for market fit.

Responsive • E-commerce • Visual

NETFLIX

Enhance accessibility for better control.

Feature redesign • Microinteraction

ANIMAL CARE CENTERS

Feature to reunite lost pets with owners.

Add a feature • Database • AI