simondai.com
Oak Street Health (CVS)
Redesigning Clinical Documentation
Where It Matters Most
Clinicians weren’t using our system.
They wrote notes.
Used third-party tools.
Did everything but document in
Canopy — Our in-house EHR{Electronic Health Record}.
Because documentation didn’t fit the flow —
it disrupted it.
We didn’t fix a feature.
We rebuilt a habit.
I led end-to-end product design for Canopy’s new documentation experience — from mapping clinical needs to prototyping, testing, and delivery. The goal wasn’t just usability, but adoption: to create something clinicians would actively choose, instead of relying on workarounds.
Team:
One Product Designer (myself), One Product Manager, Two Clinical Operations Leads, One Engineering Lead, Backend & Frontend Developers, Partners from Compliance & Data Security
Timeframe:
March –
September 2023
Context & Challenge
The problem wasn’t missing documentation.
It was a system built without real users in mind.
Canopy’s documentation flow had no UX research, no real-world testing, and no alignment with how clinicians work.
Templates were rigid.
Input points were unclear.
And no one trusted what came out.
So clinicians found their own ways
— and the system got left behind.
Research & Strategy
We visited 8 clinics across the U.S.,
interviewed 20 clinicians, surveyed over 30 patients,
and ran workshops to unpack real documentation habits.
The goal wasn’t empathy — it was pattern recognition.
We weren’t collecting quotes.
We were mapping tension:
When do people hesitate?
Where does info get repeated?
What breaks across roles?
This became our blueprint — not for screens,
but for rebuilding flow, ownership, and trust.
Current Product &
Pain Points
After weeks of interviews and observation, we saw the same behavior patterns emerge across clinics:
After weeks of interviews and observation, we saw the same behavior patterns emerge across clinics:
Notes were fragmented across systems and people
No clear handoff or continuity between team members
Documentation had become an afterthought invisible in the care journey, and invisible to the team.
Strategy & System Design
We didn’t redesign documentation.
We redefined what it means to document.
In the old system, writing was a solo task delayed, isolated, and rarely reused.
In the new system, documentation became a shared layer of care captured at the right moment, structured for others, and trusted across roles.
This wasn’t about better UX.
It was about making records reliable, reusable, and human-aware.
When the same data means different things to different teams
— the system isn’t a tool, it’s a barrier.
System Outputs
We translated clinical behavior into a modular design system:
Progressive Prompts — guiding context, not just fields
• Shared Components — reusable across visit types and roles
• Smart Defaults — based on care stage and user type
The result wasn’t a form. It was a framework — one that surfaced what mattered, when it mattered.
When the same data means different things to different teams
— the system isn’t a tool, it’s a barrier.
Interaction & Prototyping
Prototypes were built to validate not layout, but behavior.
We simulated full care journeys — capturing how documentation moved across people, timing, and context. These sessions revealed friction points invisible to surveys.
Design decisions emerged from these insights. We optimized cursor defaults, field hierarchy, and cross-role visibility. Each adjustment served a functional goal: to reduce hesitation, avoid duplication, and allow entry without interruption.
A journey was mapped
— but decisions kept falling through the gaps.
Testing & Iteration
Two rounds of remote testing with clinicians surfaced gaps in both interface logic and content perception. Click paths alone were insufficient; we traced narrative breakdowns and usage discontinuities.
Some patterns led to structural revisions — such as collapsing low-priority steps or merging handoff modules. Others shaped micro-copy, tooltip timing, and autosave logic.
We tracked changes in behavior: time to first entry dropped 22%, completion rate per session increased 31%, and over 65% of testers preferred the new model without being prompted.
Outcomes & Impact
Within 90 days of launch, documentation rates rose 45%. Hand-off time between nurses and physicians decreased by 30 seconds per visit. The number of records completed during visits — rather than after — tripled.
But more than metrics, we observed behavioral integration: clinicians stopped reaching for paper. They stayed in Canopy. The habit we rebuilt was now organic.
Designed for decision, not display.
Structure guides trust.
Reflection & Continuity
This project reshaped more than a workflow. It redefined what good documentation looks like — timely, structured, and shared.
We proved that trust doesn’t come from training. It comes from respecting user rhythm, from embedding systems where people already work.
Months after launch, Oak Street Health was acquired by CVS Health. Since then, the design foundation has informed roadmap work across mobile, API and AI-assisted modules.
Though I’m no longer with the team, I still care deeply about its future. Because when you redesign how people document care, you shape how they remember it — for every patient that comes after.
Hi-fi design emphasized clarity through flow
— structure, not visuals, shaped trust.
As of 2024, the system is still running
— and evolving with AI.
That means something.
It means the foundation we built was resilient enough to last, and flexible enough to grow.
I left the company long ago.
But I still think of this project — not as a success story,
but as a benchmark.
The product interface is under confidentiality. What’s shown here is a simulated version.
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This page marks a pause, not the end. © 2025 Simon.