Never-ending monday 9 am problem

Sarah's coffee was getting cold. Again.

It was 9:17 AM on a Monday, and her Chrome browser was choking under fifteen open tabs – each has different client's expense reports. As a partner bookkeeper at Mitchell & Associates, this was her routine. But today was different. Today, I was with her in Zoom Meeting, watching this daily routine unfold.

"It's like being an air traffic controller," she jokes, "but with receipts instead of planes."

This wasn't just Sarah's story. This was the daily reality for thousands of accounting partners using Pleo's platform. And it was a problem worth solving.

So, what I am supposed to do here?

When I joined Pleo as a freelance designer, the initial brief seemed straightforward — Refresh the partner portal's brand. But as I sat with Sarah that Monday morning, I realized we were solving the wrong problem.

A day in the life — Multiple screens, multiple clients, multiple headaches

My role? Figure out why accountants weren't using our Partner Portal, and fix it. Simple, right?

Just a preview :)

Getting down to the business

Getting to know our partners meant getting uncomfortable. We scheduled virtual 1-1 meetings, shadowed bookkeepers, and asked a lot of questions that made us squirm:

• "Why do you avoid using our portal?"
• "What makes you choose to open another tab instead?"
• "When was the last time you actually spent more than two minutes here?"

I realized we were dealing with something far more fundamental—a crisis of cognitive load.

The traditional playbook of sitting with users wasn't an option in 2020. So we got creative:

1. Virtual Shadowing: Using screen sharing, we watched 12 accountants go through their morning routines. The tab chaos was just the beginning.

2. Digital Journey Mapping: Through Miro sessions with users, we mapped out their actual workflows versus what we thought they were doing.

Unburying the real insights

One particularly enlightening moment came during a user shadowing session, we noticed partners opening the same client's account multiple times in different tabs. Why? Because they were trying to compare data across different time periods or categories.

"Watch this," said Sarah. She proceeded to demonstrate her morning routine of opening tabs, arranging them in a specific order, compares last month's expenses with this month's while keeping an eye on their wallet balance. "I've gotten pretty good at this window management," she laughed, "but I shouldn't have to be."

Remote workshop outputs revealing common patterns of friction

Numbers from data analysis with Amplitude & MixPanel Page analytics told an even more compelling story:

• 70% of partners used the portal solely as a gateway to client accounts.
• Partners spent up to 5 hours weekly just managing tabs (that's 260 hours yearly!)
• Average time spent was less than 2 minutes per session.
• Only 30% actively referred new clients—a figure lower than many politicians' approval ratings.

Making sense of the chaos

After three weeks of virtual sessions, patterns emerged:

1. Context Switching Was Killing Productivity - Accountants had to constantly compare multiple clients instead of focusing on one.
2. Critical Information Was Buried - Crucial info like missing receipts and low balances was buried behind clicks.
3. Our Mental Model Was Wrong - We designed for sequential workflows, but accountants worked in parallel, monitoring all clients at once.

tl;dr Partners themselves creating their own ad-hoc dashboards to group similar clients

Raw and real — Partner feedback that shaped our direction

What's the MVP?

The transformation began with a simple question — What if the Partner Portal could be more than just a gateway? What if it could be a command center?

We designed the new portal around three core principles:

1. Visibility Without Overwhelm
   • Created a unified dashboard showing key metrics and recent activities across all clients, instead of multiple client tabs.
   • Added partners requested features – low wallet balances, missing receipts, expenses ready, and pending actions.

The new dashboard — Everything important at a glance

2. Proactive Problem Solving
   • Implemented smart filters that actually matched partners' mental models that allowed partners to — Group clients by status, Sort by urgent actions needed, Create saved views for different workflows.
   • Added wallet balance alerts to prevent payment disruptions

Smart Filters that work the way accountants think

3. Contextual Intelligence
   • Designed a drawer system that maintained context from main page while diving into specific client details.
   • Built smart notifications with opt-in email notifications that understood partner priorities.

Quick-access drawer maintained context while showing details with overlay design instead of tabs

Measuring Success

After releasing the new client page, we tracked performance between the old and new versions. By the second month, the new page outperformed the old by over 100%. By the third month, while the gap narrowed, the new page still had more views and engagement.

Tracking data comparison

• 20% increase in feature usage, frequency, and time spent in the portal.
• 16% rise in new partners within the first three months.
• 17% boost in partner client referrals during the same period.

But perhaps the most telling metric wasn't in our analytics—it was in the words of our partners,

Nothing is quite "final", is it?

Of course, not everything worked perfectly at first. We noticed partners struggling with the client assignment process – they didn't realize they needed to be assigned to a client before managing their account. Our first solution? Tooltips. They were beautiful, clear, and... completely useless because nobody hovers long enough to read tooltips. Classic designer mistake !

Sometimes the smallest details need the most attention - Ft. Disabled State

So we flipped the script. Instead of "Access Denied," we added "Click to Get Assigned." Simple. Direct. It worked.

Also, Conveying clear, helpful error messages guides users to a solution, not just stating the problem (UX 101).

Want to know more about how I conducted multi-lingual remote usability interviews?
Get in touch to schedule a presentation.