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Background: A nonprofit that facilitates sharing more than $30,000,000 in medical expenses per month launched a UI featuring online bill submissions in 2015. By 2020, it had never been significantly updated.

Problem: Bill validators were frustrated with the limitations of the validating interface. Members endured excessive and unclear communications about their bills. Complicated, redundant workarounds led to costly inefficiencies
Objective: Bill validators needed the ability to select valid reasons for rejecting bills. External users needed appropriate messaging about the status of their bills. Call Center staff needed to be freed to serve members more efficiently.

What I did: Significantly influencing
 the project's overall trajectory, I collaborated with business leaders, PMs, engineers, designers, and BI in requirements gathering, implementation, QA Testing, and troubleshooting user flows, API emails, and UI changes. I also partnered with Call Center and Training leadership to facilitate the implementation of related process changes.

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outgoing email trends presentation cover


  • What are user expectations when onboarding with a complex developer tool, whether they use it for work or personal projects?

  • Where are users experiencing confusion?

  • How do new-to-platform users interpret the terminology we use in the onboarding flow and within the UI? Are these intuitive, too abstract, or misaligned with their mental models?

  • Where are users getting stuck? How do they find help? At what point do they give up?

  • Where are the moments of delight?

"We've been waiting 7.5 years for this! I'm almost in tears. Thank you!" 

Bill Validator

I used Lucidchart to illustrate to leaders the pain points and costly inefficiencies.

process map prior to staff and member UI changes


This project lasted 23 months from the time I began researching the problems to project completion. The amount of time this project took reflects the resource constraints nonprofits commonly face, a global pandemic and resulting prioritization strains in a healthcare setting, and business requirements that necessitated a broader scope to the project than leadership originally expected.

frustrated person at laptop

Staff and members were
constantly frustrated by the confusion and inefficiencies.


  • On my own, I conducted informal one-on-one conversations with internal users.

  • I collected qualitative data from direct external user feedback (emails, support ticket interaction notes, and feedback reports), allowing me to empathize with each person involved (staff-side and member-side).

  • Over time, I studied the quantity of automated and call center staff emails we sent daily, weekly, and monthly.

  • As an SME, I understood the issue on both micro and macro levels and provided insight to the team based on this knowledge for the duration of the project, from initiation to closing.


  • What leaders originally thought would only be internal tooling changes and updated email content necessitated UI updates that would coincide with email notifications. 

  • With the global pandemic in full swing, priorities for nonprofits remained a tough balancing act, lengthening the time to project completion. This project was no exception to that.

  • Prioritizing clear communications while following legal constraints regarding PII and PHI required ingenuity.

  • Translating some requirements from a functional group to engineers where the terminology was easily misaligned required additional patience, active listening, and clarity in communication.

  • Testing limitations required several days of tedious manual testing.


One unique challenge was persuading the team to shift how we approached the language of the problem. Members received alarming "Problem Alerts" for issues that were not problems. 


  • The concept of "submission errors" allowed users to differentiate the issues with their bills, reducing user anxiety.

  • Additionally, the change allowed us to quantify the number of bills rejected by validators, which laid the foundation for future improvements.

old bill problem email

After: Clear explanation, details user needs to understand the issue, improved CTA.

Before: vague and frequently wrong information caused unnecessary alarm for users.

new bill problem email

We had to initiate interim process changes while the cross-functional project team was spread thin due to the pandemic and common nonprofit constraints. It was not at all ideal, but it was still an improvement.

interim explanation email
Requirements gathering

Aligning on requirements was a cross-functional effort.


Addressing this multi-dimensional issue resulted in the reduction of confusing and redundant touchpoints with members by tens of thousands per month.

  • Qualitative-focused follow-up conversations with internal users and call center leaders

  • Quantitative data from our automated email service over a period of several weeks following the changes

  • Quantitative and qualitative data from CRM regarding contacts made about this issue following the changes.

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