Diana Shawn Barraza

Previously at Square (Block), currently shipping a first-class healthcare experience to millions of Americans. I turn ambiguity into simplicity, moving quickly with craft and strategy.

Fintech Healthcare B2C B2B AI Builder

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Featured work

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Medicare.gov · Patient appointment scheduling

Patient Appointment Scheduling Healthcare Web Responsive Mobile

Building a first-class scheduling experience for Medicare.gov patients across web and mobile.

Turning Square Checking from a pass-through account into a financial home

Growth Square Banking Insights

Leading with vision and customer jobs to be done to help Square sellers understand, move, and manage money.

Square Bill Pay dashboard with outstanding bills and email forwarding

Tackling Square Bill Pay's growth plateau post-launch

Square Bill Pay Zero to one Email Forwarding Growth

Tackled Square Bill Pay’s post-launch plateau by removing vendor setup with OCR and email forwarding, measured against the same activation funnel each release.

Square Banking Checking home and virtual debit card details

Decoupling the debit card from Checking with virtual card-first onboarding

Square Banking Debit Card Growth

Creating a faster path from account creation to usable spend through virtual card-first onboarding.

Square Bill Pay vendor acceptance: trusted invitation email through Plaid bank connect

Getting vendors to trust their first Bill Pay payment

Square Bill Pay Payment acceptance Plaid

Turned an unexpected payment notification into a trusted invitation, then made bank linking easier so vendors could complete payout.

Kiln City Events on Deckk — dark mode public deck

Deckk: Reimagining the Link-in-Bio with AI

Proof of concept AI Zero to one Solo-built

Deckk is a link-in-bio built around time-aware hierarchy and an AI studio that turns images and links into cards, making it fast enough to keep your page current.

Flyhomes Terminal Tours queue for internal tour scheduling

Automating tour scheduling so buyers could move faster

Internal Tools Automation Scheduling Real Estate

Transformed tour scheduling from manual coordination into a human-in-the-loop system that automated routine decisions and helped buyers get into homes faster.

Flyhomes mobile tour itinerary with map and confirmed showings

Redesigning home tours for a fast-moving market

Real Estate Buyer Experience Search

Mobile search experience helping buyers discover and evaluate homes faster.

Heal primary care before and after: on-demand matching vs selecting a primary care physician

From one-time visits to ongoing primary care

Healthcare Primary Care Patient Experience Medicare

Redesigned doctor selection from urgent-care booking into a PCP matching experience—building trust, meeting Medicare requirements, and increasing repeat visits.

Heal physician daily overview with monitoring alerts and review actions in iPad frame

Building Heal’s remote monitoring product from zero

Healthcare Data Visualization Health Monitoring CES Innovation Winner

Defined Heal’s remote monitoring product from zero: device reading to clinical decision, so doctors could act on chronic care between house calls.

Experience

	TRIPTK Currently building a first-class experience in healthcare for Medicare.gov	2026
	Square Senior/Staff Product Designer · Banking & Bill Pay	2023 – 2026
	Flyhomes Senior Product Designer	2020 – 2022
	UCLA Extension UX Iteration Instructor to Educator	2020 – 2022
	Vetted Petcare Senior Product Designer	2019 – 2020
	Heal (on-demand health care) Product Designer	2017 – 2019
	Freelance Product Designer	2015 – 2017