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Matthew Sheets

Matthew Sheets

Director of Engineering | Enterprise AI | Healthcare and Payments Platforms

Engineering leader with 18+ years of experience building and scaling enterprise platforms across healthcare, retail, and payments. I lead large engineering organizations, modernize legacy systems, and deliver secure, high-availability solutions in HIPAA and PCI environments with a practical approach to enterprise AI adoption.

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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 a 35 direct-report engineering organization supporting patient identity, healthcare data, communications, and platform initiatives tied to 96 million patient records
  • Helped design and support an AI-driven patient communications middle layer spanning SMS, phone, and email outreach
  • Reduced prescription return-to-stock by 9%, lowering waste, shipping, inventory handling, and labor costs

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 built a full retail POS and payments platform serving over 3,500 merchants across the United States and Canada. The platform supported both in-person and online commerce, with APIs that enabled thousands of merchants to create custom solutions for payments, inventory, reporting, and operational workflows. Early adopter of GraphQL. Designed key authentication and security patterns to protect PCI and PII data. Operated in highly secure PCI-regulated environments. Grew company to successful exit.

  • 3,500+ merchants in US and Canada
  • APIs for merchant extensibility
  • Payments, inventory, reporting, merchant workflows
PaymentsFinTechRetailAPIs

EMPI / Patient Identity and Personalization

AI-Assisted Healthcare Identity

Led work in AI-assisted duplicate detection, match scoring, and weighting logic for enterprise patient matching. Built merge recommendations and systems that improved business value through patient targeting and better identity quality. Healthcare personalization and analytics at scale.

  • AI-assisted duplicate detection
  • Match scoring and weighting logic
  • Merge recommendations
AIHealthcareEMPIIdentity

UAB Medicine Clinical and Operational Platforms

Healthcare Technology Systems

Led mobile and web initiatives including mobile EMR, patient self-scheduling, and eSignature platform. Worked on PDMP and analytics, built an award-winning 340B drug reconciliation system, and integrated with Cerner and Oracle Health. Strong intersection of healthcare operations, software engineering, and analytics.

  • Mobile EMR
  • Patient self-scheduling
  • eSignature platform
HealthcareEMRMobileClinical

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.

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OpenClaw and Local LLMs in Business

Coming Soon

A practical guide to enterprise AI, local models, and real business workflows

An upcoming practical guide to using OpenClaw and local LLMs in business. Covers enterprise AI adoption, local models, and real-world workflows.

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