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Matthew Sheets

Engineering Leader | Healthcare & PBM Platforms | Enterprise Modernization & AI Adoption

Engineering leader with 18+ years of experience across healthcare, pharmacy benefits, retail, and payments. I lead up to 35 people across five teams at Kroger Health and Wellness, with responsibility for all operational software supporting Kroger Prescription Plans. My experience includes bringing healthcare products to market, scaling a payments business through a successful exit, and improving cost, reliability, and patient workflows.

Experience

Leadership roles across healthcare, retail, payments, and enterprise software.

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Senior Advanced Engineering Manager

2023 – Present

Kroger Health and Wellness

  • Lead up to 35 people across five teams, with responsibility for patient identity, patient communications, and all operational software supporting Kroger Prescription Plans (KPP), Kroger’s pharmacy benefit management (PBM) offering
  • Lead patient identity, healthcare data, and platform initiatives tied to 96 million patient records
  • Helped drive broad adoption of AI coding assistants and establish AI usage patterns across teams building HIPAA-regulated Pharmacy, Patient Communications, EMPI, and KPP software

Senior Engineering Manager

2021 – 2023

Walgreens Boots Alliance

  • Led teams of 9-12 engineers for a national COVID response platform delivering testing, treatment, and vaccine scheduling
  • Supported peak appointment creation rates exceeding 70 bookings per minute across the United States
  • Used Azure services and Kubernetes architecture to maintain uptime, scalability, and security for patient-facing systems under extreme load

Founder and Director of Technology

2017 – 2021

Pymt

  • Founded and built a full retail POS and payments platform used by more than 3,500 merchants across the United States and Canada before a successful exit
  • Led architecture and development of online and in-person commerce capabilities across payments, inventory, reporting, and operations
  • Designed APIs used by merchants and partners for custom workflows and integrations in payments, analytics, and business management

Featured Projects

Platforms and initiatives across payments, healthcare, and enterprise software.

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Pymt

Retail POS and Payments Platform

Founded and scaled a retail POS and payments platform for thousands of merchants across the US and Canada, spanning in-person and online commerce. Led product and platform direction through growth and successful exit.

  • 3,500+ merchants in US and Canada
  • Unified POS and payments platform
  • Merchant APIs and extensibility
PaymentsFinTechRetailAPIs

Kroger Prescription Plans (KPP)

PBM Operational Software Leadership

Lead software development management for all operational software supporting Kroger Prescription Plans, Kroger’s pharmacy benefit management (PBM) offering, while leading up to 35 people across five teams.

  • Responsibility for the full PBM operational software portfolio
  • Leadership across patient identity, patient communications, and PBM software
  • AI coding assistant adoption and usage patterns for teams building HIPAA-regulated software
HealthcarePBMEngineering LeadershipHIPAA

UAB Medicine Clinical and Operational Platforms

Healthcare Technology Systems

Led teams building clinical and operational platforms at UAB Medicine, resulting in more than eight commercially viable software products sold to other organizations.

  • Award-winning Patient Consent Platform covering all consent types, including informed consent
  • Patient pre-visit forms
  • Unity lab specimen tracking across clinics, hospitals, and community locations
HealthcareEMRFHIRApple Health Records

Books

Practical guides to enterprise software and applied AI.

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The Year of Corporate Software cover

The Year of Corporate Software

Enterprise software, modern corporate systems, and practical AI-era thinking

A published book about enterprise software, modern corporate systems, and practical AI-era thinking. Reached Amazon Top 100 Software books.

Get the Book

Get in touch

I am open to speaking opportunities, consulting, advisory work, media inquiries, and executive networking. Recruiters and hiring managers: I am happy to discuss roles in technology leadership, engineering, and product.

matt@mattsheets.com