The Context

Email is one of the most critical parts of the retreat experience. It’s how centers welcome guests, share arrival details, request payments, and stay connected even after the program ends.

The platform already supported all of this—automated emails, templates, personalization, and scheduling across the guest journey.

But despite having these capabilities, something wasn’t working.

The Problem

While onboarding new retreat centers, a pattern kept surfacing. What should have been a simple task—editing and scheduling emails—was consistently turning into a frustrating experience.

The root issue was the interface.

Users had to paste and edit raw HTML inside text boxes, and the system attempted to convert that HTML into a readable format. In the process, formatting—especially spacing—often broke.

“It looks perfect in my template, but completely off when I paste it here.”
“I don’t understand why I need HTML just to edit an email.”
“I avoid touching it unless I absolutely have to.”

What started as a UI inconvenience quickly became a deeper product problem—users didn’t trust the system.

Research: Hearing It Firsthand

To better understand the issue, we spoke directly with retreat centers during onboarding and support interactions.

Instead of structured usability tests, this was more observational and conversational research—watching how users actually configured emails and where they got stuck.

A few things became immediately clear.

Most users weren’t trying to do anything complex. They wanted to:

• Send the right email at the right time

• Make small edits to existing templates

• Feel confident that what they see is what guests will receive

But the current experience made even simple actions feel risky.

We saw users repeatedly copy-paste templates, tweak spacing manually, and refresh the page just to check if something broke. Some would abandon customization entirely and stick to defaults—not because it worked for them, but because it felt safer.

At the same time, Customer Success teams were stepping in frequently to fix formatting issues or help configure basic email flows.

This research reframed the problem:

The issue wasn’t missing features—it was that users didn’t feel in control.

The Opportunity

We saw an opportunity to shift the experience from technical and fragile → guided and reliable.

The goal wasn’t to add more capabilities, but to make the existing system feel intuitive and safe for non-technical users.

The Redesign

We redesigned the Email Tab around how users naturally think about emails:
when to send, who to send to, and what to send.

Instead of a blank text-heavy interface, emails became structured around clear logic—triggered by events like registration, arrival, or departure, with simple timing controls.

The biggest shift was removing the dependency on HTML.

Users could now select templates, customize them visually using a formatting toolbar, and even copy from existing templates without worrying about breaking anything. Formatting stayed consistent, and the experience finally matched expectations.

We also introduced flexibility that users had been asking for—like scheduling emails before or after key events, adding conditions (such as sending payment reminders only to guests with a balance), and sending test emails to preview changes.

“Now I can actually see what I’m doing—and trust it.”

The Outcome

The impact of the redesign was immediately noticeable.

Users who previously hesitated to edit emails began configuring them on their own. Support requests around formatting dropped, and more centers started using advanced features like scheduling and conditional emails.

Most importantly, the relationship users had with the feature changed.

What was once avoided became something they could rely on.

“I didn’t need to ask for help this time—I just set it up myself.”

Reflection

This project reinforced a simple but important lesson:

Even the most powerful systems fail if users don’t feel confident using them.

By listening to real user frustrations and removing unnecessary complexity, we didn’t just improve a UI—we restored trust in the product.

And in doing so, we turned email from a pain point into a strength.