Product Modernization

Modernize the work. Multiply the impact.

Modernize the work. Multiply the impact.

How I transformed my teams legacy scheduling tools into faster, clearer workflows, while keeping our existing users patterns top of mind.

How I transformed my teams legacy scheduling tools into faster, clearer workflows, while keeping our existing users patterns top of mind.

WT & TG have been a staple softwares for TEAM Software since their formation in 1989. WT is a comprehensive ERP (Enterprise Resource Planning) system focused on financial and workforce management for North American cleaning/security contractors. TG is a workforce management and operational tool primarily focused on real-time attendance, scheduling, and service delivery, popular in international markets. Long story short, not a lot of design was put into their creation, and since the 90’s, small patches have been added but it was in need of a facelift. The reality is, a lot more goes into the redesign than just a facelift. We wanted to fix the pain points for our users, improve the usability, and design a new product that still feels familiar, and intuitive to our power users. Sounds simple enough, right?

$300M → $400M

$300M → $400M

$300M → $400M

Revenue Growth

Revenue Growth

Revenue Growth

5× Faster

5× Faster

5× Faster

Filling Schedules

Filling Schedules

Filling Schedules

21st Century

21st Century

21st Century

Look & Feel

Look & Feel

Look & Feel

THE LEGACY PRODUCT

No designers present, nothing off limits

No designers present, nothing off limits

No designers present, nothing off limits

Both WT and TG were built without a designer. They are powerhouses of the security and cleaning software, and the power users can fly through the product with only their keyboards. However, because there were no designers present for the first 30 years, engineers built everything to work the way they thought it should work. New users find it incredibly confusing, modern patterns don't exist, everything requires jumping between multiple screens and we've frankenstein'd this product together with features tacked on.

WT Schedule board. The old design on the top. modernized design on the bottom

WT Schedule board. The old design on the left, modernized design on the right

TG Schedule board. The old design on the left, modernized design on the right

TG schedule board. The old design on the top. modernized design on the bottom

THE PROBLEM & COMPLEXITIES

Why this was genuinely difficult

Why this was genuinely difficult

Why this was genuinely difficult

WT and TG were entering the mid 2020's looking like a Windows 95 product. Companies are popping up yearly that are vying for our customer base, offering software that was built with todays standard of modern design. That means modern patterns, modern components, less gradients, and a product that you can figure out without reading a paper manual. In business terms, we have a large pool of legacy users, who have been with us for decades, but we aren't keeping up with the new softwares. Our competition are taking any of our potential new customers and some of our existing customers are getting fed up with promises of modernizing year after year, and are leaving. We need to keep retention high, and offer a modern suite of software that attracts new customers. Simple as that, right? Well our product has over 3 decades of features tacked on, which means the rules & permissions for our Schedule boards are very deep. Certain operations are nested with other features, manually changing the billing code effects how much a company has to pay their employee, which effects the weekly budget, their over-time, could trip exceptions on the shift because certain certifications are not checked-off, this would trigger further validation errors and require multiple steps to manually complete for a seemingly "simple" change. Let me show you some of the more "fun" features of our legacy product:

Very unusual patterns exist in our legacy product. For example, clicking on a field with a drop down opens the container


  • However, double clicking the dropdown opens a different container….sometimes

  • This pattern is unusual, and exists in only 2-3 other places across 600+ screens

  • This is just an example of the many complexities that were tacked onto screens over decades, and is not friendly to users


Below you can see just 4 of the 15 tabs that control the schedule data. Changing one single field can have drastic results on a users schedule board.

The challenge wasn't really that our scheduling UI was old. The deeper problem was that we had built up 30 years of business rules and workflows around it. Users had learned how to work around the system, and those workarounds had become part of the product. So our goal wasn't to redesign everything. We needed to modernize the workflow while preserving the parts of the system that users relied on.

THE SOLUTION IMPACT

300% faster, fewer clicks, more time back

300% faster, fewer clicks, more time back

Jumping ahead, the solution here is to create a modernized version of the schedule board. This includes building a contract page, the physical schedule board, the functionality that we learned is most sought after and helpful for moving the needle for our customers. They want faster, with less back and forth, and ultimately, more time back in their busy schedule to focus on what matters most, running their business. Below shows a before and after of both contract creation, and schedule filling. The left image is the before, the right is the after. But how we got there is the design journey I went on that I'll outline in the following sections.

TG Contract creation

TG Schedule creation

300% Faster

300% Faster

Filling Schedules

Filling Schedules

Filling Schedules

5x

5x

Fewer Clicks

Fewer Clicks

Fewer Clicks

8+ Hours

8+ Hours

Saved per week

Saved per week

Saved per week

THE DESIGN PROCESS

Discovery, testing, prototyping, delivery

Discovery, testing, prototyping, delivery

I won't go into too much detail here on the depth of the design process. I have another case study where I speak to the collaborative team structure I piloted teaming up with one PM, one engineer, and one designer (myself). We collaborated on countless figjam boards, brain storming sessions, user discovery, interviews, rapid prototyping, co-creation with our users, and ultimately, our delivery. That can be found here if you're interested in reading more about it: Empowered Product Teams

Discover

Define

Design

Test

Test

Deliver

a collage of figma sections outlining the discovery work just fro the schedule board creation. Between figjams and design whiteboarding, there was an unruly number of arrows drawn, stickies created, and highlights made.

What our customers were saying.

What our customers were saying.

What our customers were saying.

These are their core issues

These are their core issues

These are their core issues

Open Posts

Filling open posts isn’t as quick and easy as customers would like, meaning they’re spending more time on their schedule, filling open posts.

Overtime Pay

Similar to open posts, the lack of AI integration to easily find the most suitable candidate feels like we’re not keeping up with the industry. Discovering which employees are the most suitable is easier with other products.

Poor Usability

Feels like we are wasting time with redundant steps, a high program-specific-IQ is required to efficiently use WT, and overall creates hurdles that lead to poor overall usability.

TRADE-OFFS

Compromises, trade-offs, and competing truths.

Compromises, trade-offs, and competing truths.

Like every good project, there's some design trade-offs that need to be made. Even with strong user insights and a clear understanding of pain points, solutions are shaped by business goals, legacy constraints, and the need to hit our deadlines quarter after quarter. Below are only some of the deliberate compromises that moved the product forward without losing sight of the user.

Ideal UX vs. Legacy Constraints

Ideal UX vs. Legacy Constraints

Ideal UX vs. Legacy Constraints

Push for better long-term patterns, or align with what already exists?

Push for better long-term patterns, or align with what already exists?

Push for better long-term patterns, or align with what already exists?

Legacy has color-coded symbols to mean 15 different things on the schedule card, it’s what users look to immediately. We kept color-coded symbols in the same location, but made them WCAG compliant, and added iconography and badges to give even more info at a glace.

Legacy has color-coded symbols to mean 15 different things on the schedule card, it’s what users look to immediately. We kept color-coded symbols in the same location, but made them WCAG compliant, and added iconography and badges to give even more info at a glace.

Simplicity isn’t removing complexity, but rather organizing it when it appears. Adding a user role allowed for full customization of permissions and authorization, removing the redundancies of existing permissions, fixing visual clutter and streamlining worker management.

Simplicity isn’t removing complexity, but rather organizing it when it appears. Adding a user role allowed for full customization of permissions and authorization, removing the redundancies of existing permissions, fixing visual clutter and streamlining worker management.

Simplicity vs. Flexibility

Simplicity vs. Flexibility

Simplicity vs. Flexibility

We want simple experiences for our users, but edge cases, power users, internal requirements, all add complexity.

We want simple experiences for our users, but edge cases, power users, internal requirements, all add complexity.

Data vs. Intuition

Data vs. Intuition

Data vs. Intuition

We had qualitative insights from interviews, and quantitative data from analytics. However, sometimes they don’t agree, and user feedback is narrow

We had qualitative insights from interviews, and quantitative data from analytics. However, sometimes they don’t agree, and user feedback is narrow

Our Survey says 5 steps is ideal:

Our Interviews say:

Our Interviews say:

Open shifts

Successful matches

Warnings & errors

Warnings & errors

Completed assignment

*start*

*cont*

*cont*

*cont*

Open shifts

Successful matches

Warnings & errors

Warnings & errors

Completed assignment

*start*

*cont*

*cont*

*cont*

Open shifts

Successful matches

Warnings & errors

Warnings & errors

Completed assignment

*start*

*cont*

*cont*

*cont*

“I feel lost here”

“I feel lost here”

“There’s just too many steps”

“There’s just too many steps”

Not all signals agree, but strong decisions reconcile both. We reduced the steps down from 5 to 3 despite a neutral survey result. Fewer steps garnished the same results, and saved time.

Not all signals agree, but strong decisions reconcile both. We reduced the steps down from 5 to 3 despite a neutral survey result. Fewer steps garnished the same results, and saved time.

THE FINAL RESULTS

Faster work, fewer clicks, promises kept.

Faster work, fewer clicks, promises kept.

The final design was a success, we heard incredibly positive user feedback, the business saw an uptick in bookings and projected revenue after showing these features off at the latest user conference, and our customers are finally feeling like the promises they've been hearing are being kept. Prior to working on WT and TG, I had heard countless stories of our users being promised that we'll modernize and catch up with the rest of the tech world, but the faces of our customers after seeing what we built, really was worth a thousand words.

TAKEAWAYS

What this project taught me

What this project taught me

Modernization is not a visual refresh, it is a careful rebalancing of familiarity, clarity, and forward momentum. These are the principles that guided the work.

Modernization is not a visual refresh, it is a careful rebalancing of familiarity, clarity, and forward momentum. These are the principles that guided the work.

Modernize without erasing expertise.

Modernize without erasing expertise.

The most valuable patterns in a legacy product are often invisible to new users but essential to power users. Preserving familiar signals while improving accessibility, hierarchy, and feedback let the product evolve without breaking the fluency customers had built over decades.

The most valuable patterns in a legacy product are often invisible to new users but essential to power users. Preserving familiar signals while improving accessibility, hierarchy, and feedback let the product evolve without breaking the fluency customers had built over decades.

The most valuable patterns in a legacy product are often invisible to new users but essential to power users. Preserving familiar signals while improving accessibility, hierarchy, and feedback let the product evolve without breaking the fluency customers had built over decades.

Make complexity legible, not invisible.

Make complexity legible, not invisible.

Scheduling is inherently complex. The goal was not to remove every edge case, but to organize the work around the decisions people make most often, reducing redundant steps, revealing the right context sooner, and making the next best action unmistakable.

Scheduling is inherently complex. The goal was not to remove every edge case, but to organize the work around the decisions people make most often, reducing redundant steps, revealing the right context sooner, and making the next best action unmistakable.

Scheduling is inherently complex. The goal was not to remove every edge case, but to organize the work around the decisions people make most often, reducing redundant steps, revealing the right context sooner, and making the next best action unmistakable.

Balance evidence with the reality of delivery.

Balance evidence with the reality of delivery.

Research gives teams direction, not a script. Strong product decisions reconciled analytics, customer feedback, business priorities, and legacy constraints. Then turn those competing truths into a focused release that created measurable gains for customers and the company.

Research gives teams direction, not a script. Strong product decisions reconciled analytics, customer feedback, business priorities, and legacy constraints. Then turn those competing truths into a focused release that created measurable gains for customers and the company.

Research gives teams direction, not a script. Strong product decisions reconciled analytics, customer feedback, business priorities, and legacy constraints. Then turn those competing truths into a focused release that created measurable gains for customers and the company.