We found churn hiding in confusion.

We found churn hiding in confusion.

The Rounds had a retention problem. I traced it to confusion in their checkout and subscription flows, then rebuilt both around clarity.

The Rounds had a retention problem. I traced it to confusion in their checkout and subscription flows, then rebuilt both around clarity.

PRODUCT

Grocery delivery service

ROLE

UX designer

TYPE

Sponsored project

Contributors

CE, QL, SL

So here's how it works…

Subscribe to items individually

(2/3)

Locally sourced, sustainably packed/shipped

(3/3)

Recycle jars to close the ecosystem

The problem?

Users dropped after week one.

So I built a prototype and tested their entire product experience to figure out why.

"I didn’t even know I had ordered anything."

My research showed users weren’t frustrated by missing products, they were confused by the system. Orders, swaps, and subscriptions all blurred together.

Users felt lost in the flow: “I feel like I’m in a maze.”

4/7 new users accidentally ordered $70+ on their first delivery.

“Where’s my cart? Confusion between orders vs. subscription

Visual hierarchy and brand consistency issues deepened confusion.

PROCESS

I started with structure, not polish.

I mapped the information architecture + order and subscription flows, then simplified each based on my user testing benchmarks. Less decision fatigue. Clearer hierarchy.

Feedback pushed iteration.

My teammates' questions forced me to rebuild sections I thought were done, making the work more intentional.

LEARNING

Trying new products felt too risky.

Committing to a subscription before trying a product meant deciding frequency without knowing if you'd like it. Users faced decision fatigue, accidental orders, or canceling their entire subscription if they made a mistake.

"So what if they could buy once?"

A no-commitment first purchase removes friction and risk. You try it, you know what you like, then decide if it's worth subscribing.

I pitched it to the
Chief of Product. He pushed back.

His point was solid: subscription is The Rounds' identity. Eliminating it entirely would sacrifice their edge.

So I compromised.

Buy once for the first order. On the second purchase, auto-subscribe at that frequency. Lowers trial risk, preserves brand identity.

But ultimately, it still got rejected.

Not every solution ships. But the work taught me how to design in the middle ground, where both the user and the business have to win.

OUTCOME

Clarity wins trust, and trust wins loyalty.

These six other changes went live. Each removed a layer of confusion from checkout and subscription management.

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Compromise breeds excellent work.

The rejected concept taught me more than any approved design. Respecting constraints and negotiating with stakeholders sharpened every decision that followed.

The system became more usable.

SUS scores jumped from 27 to 79.

Users understood the service better.

Comprehension improved 1.5x.

Users rated the service significantly higher.

Sentiment doubled after redesign.

Users completed checkout faster.

Task time dropped from 45m to 15m.

FEATURED WORK

Thanks for the read. If you liked this,

check out my other work.

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SEAN

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Minneapolis