License Management

Modernizing VMware's licensing tool

Project Details

As lead product designer, I drove the design initiative of demystifying a complex license management tool on the VMware customer portal.


Usability testing


Adobe Analytics


10 months



The Team

Lead Product Designer (Myself)
8 Engineers
Product Manager
Design Manager
Design Consultant
Senior Product Manager

Collaboration Partners

Customer Connect Product Team
Customer Connect Engineering Team
Connect Support Product Team
Global Support Director
Research Consultant


250% increase
in CSAT score

8% reduction
in support tickets

17% increase
in session length

12% increase
in engagement


License Management

VMware’s license management tool allows customers with perpetual licenses to organize, upgrade, and edit their license keys. It is an essential part of the Customer Connect portal, ranking as the third most visited page. Despite its importance, the tool was experiencing several issues.

Over the years, customers expressed their frustrations through feedback comments, support tickets, and even spreadsheets documenting their pain points. With FullStory user session replays, we watched customers struggle with the UI, failing to complete tasks due to convoluted workflows and a lack of user-centric design.

Existing Issues


No product oversight

Set & Forget

Infrequently updated

Old tech stack

Dated functionality

Outdated UI

Clunky and inconsistent

Project Ask

Identify and implement research-based, low effort/high impact improvements

This was a design-driven initiative, allowing us to set our own objectives. We chose to pursue small UX wins to quickly deliver changes without getting bogged down in a months-long overhaul. We wanted to focus on fast updates that could produce measurable results like higher CSAT and lower support ticket count.


Current State

To gain a more in depth understanding of  the license management tool, I leveraged our Pacesetter community for research participants. My design partner and I conducted 30-minute user interviews with 5 customers over the course of a week, learning how they engage with the current state experience.

I observed how participants performed tasks like finding and editing license keys, navigating through the folder tree system, and utilizing the search feature. Using Dovetail, we tagged and categorized recurring feedback like ease of use, challenges faced, workarounds, and frequently used features.

5 users
30 minute interviews
"It is... pretty painful to validate upgrades"
- Ian, Hosting Architect
"It's all very context-based and gets confusing very quickly"
- Brandon, Virtualization Engineer


Misaligned Mental Models

The behavior of the tool simply didn’t meet customer assumptions of how modern applications operate.

The search function was limited in reach and produced poor results. Customers expected an omnisearch that browsed all available data within the tool.

The folder tree only showed one folder at a time and had a confusing multi-select function. Customers quickly got lost in the folder structure and had a difficult time understanding which folder content they were viewing.

Insufficient Details

Customers were unable to easily identify license keys or know which folder they were stored in. As a workaround, they exported data to CSVs or manually added notes.

They also had very different preferences for which details to provide in the data grids.

Upgrade Challenges

Customers struggled to find upgradable license keys. The absence of upgrade notifications forced them to rely on old purchase order emails, personal calendar alerts, and spreadsheets to stay on top of their eligible upgrades.


Ideation & Prototypes

My design partner and I quickly whipped up two clickable prototypes based on our research findings. The prototypes tested out the following features:

Dashboard for upgrades and recent activity

Permanent folder for new license keys

Folder tree that functioned like Dropbox and Google Drive

In-page folder path breadcrumbs

Enhanced data grid content

We ran another set of 45 minute usability tests with 6 customers. At first, there was confusion from some participants on how to complete the given usability tasks. Although we had built the prototypes to exhibit more modern functionality, these users had adapted to the wonkiness of the current tool. They expected a similar experience and were using learned habits and workarounds picked up throughout the years to engage with the prototypes.

Despite the initial confusion, the prototypes were well-received, with participants completing the given prototype tasks at an 87% success rate. They found the task flows simpler and more intuitive, and appreciated having stronger context about their keys and folders.

6 users
45 minute usability tests
"It's self-explanatory, in terms of what's available for upgrade and how to actually upgrade"
- Lauren, Program Manager
"I do like that I can just click into my folder and see my other subfolders"
- Chris, IT Director


Design Direction

Our two rounds of user research presented us with so many good design opportunities – too many to deliver to customers within a meaningful timeframe. In discussions with our product manager and senior leadership, we chose to push out updates in multiple phases.

For Phase One, we stayed focused on our original goal of pursuing low effort/high impact improvements, using an impact effort map to identify which changes to start with.

Over many many working sessions, my design partner and I created dozens of design proposals, testing out different layouts and combinations of our prioritized Phase One features.

Iteration Example

  • Dedicated section for upgradable keys
  • Dedicated subfolder section
  • License key tagging system
  • Support contract and expiration details

Iteration Example

  • Upgrade/downgrade info by product
  • Recent folder activity section
  • In-page folder breadcrumbs

Iteration Example

  • Tab toggling between upgradable keys and all keys
  • Data grid column for upgrade status
  • Dedicated folder for old/unused keys

Iteration Example

  • Folder tree search function
  • Tab toggling between key upgrades, support contract renewals, and all keys
  • Subfolder section with additional information

Working with Engineering

Research and designs in hand, we approached our engineering partners to conduct a UX walkthrough of our design iterations and assess  technical feasibility.

The reception to our design proposals was incredibly tepid and inspired some lively debate. Quite frankly, the engineering team did not want to touch license management. The aging tech stack and years of neglect already presented a challenge, and there was little appetite to add more work to their quarterly roadmap.

8 engineers
Lots of opinions:
The customer is at fault. They should educate themselves with the technical documentation
The proposed changes aren't functionally significant enough to add to the roadmap
The changes will negatively impact performance for larger customers

Our product manager set up weekly syncs with engineering to continue discussing our designs. As lead designer on the project, my most important responsibility during these meetings was to give a voice to our customer and prioritize good UX over documentation reading. While there were many engineers, there were only two of us designers. We had to strive harder than usual to make sure we, and the customer, were heard.

Despite the difficulty, I routinely advocated for our customers, pulling specific research examples to justify design choices and to help our engineering partners empathize with their struggles.


Speed Bumps

The engineering team tested our key proposals in the CI environment. Although much of what we designed were basic features, years of accumulated tech debt made them unattainable, forcing us back to the drawing board.

Folder Tree and Omnisearch

Updating these functions had a negative impact on performance. Large customer accounts could experience loading times of up to four minutes – unacceptable for any web tool.

Clickable Breadcrumbs

The tool's back end system could only provide plain text breadcrumbs. Clickable breadcrumbs linked to their corresponding folders was out of reach.

Upgrades Access

Customers could have hundreds of keys ready to be upgraded. Pulling them into a dashboard or dedicated section caused long loading times and even session timeouts.


We couldn't meet the customer needs exactly where they were. But could we meet them 50%, maybe 75% of the way there? More weeks of collaborative working sessions with our engineering partners helped us reach feasible compromises.


Live Today

9 months after our design team initiated this project, through weeks of research, problem solving, UI tweaking, and testing, the Phase One designs were pushed into production for all customers. There was an expected spike in support requests after the launch as customers encountered the new experience. However, this began to subside after the 8 week mark. Today we continue to monitor customer feedback and session metrics as we prepare for Phase Two roadmapping.

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