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Stephen Klein

Infrastructure Specialist
Pittsburgh, PA | skier@canadabot.net | canadabot.net | LinkedIn | GitHub
01

Summary

Infrastructure Specialist with expertise in cloud infrastructure, automation, and endpoint management. Experienced in managing Microsoft 365, Azure, Entra ID, and multi-platform environments. Builds AI-augmented PowerShell automation to integrate cloud services, streamline provisioning workflows, and eliminate manual processes — reducing onboarding time by 94% and offboarding by 93%. Background in customer service and healthcare data management provides strong communication skills and attention to compliance requirements.

02

Experience

Infrastructure Specialist

Questeq · Pittsburgh, PA · Sep 2025 – Present
  • Manage Microsoft 365, Azure, and Entra ID environments for a K-12 school district
  • Built a PowerShell-based staff lifecycle system automating provisioning across eight platforms, reducing onboarding from 44 minutes to 2.5 minutes (94% faster)
  • Developed an Entra-gated web interface for team-wide access to automation tools
  • Contributing to Sophos to Microsoft Defender endpoint protection migration across the district device fleet
  • Contributing to JAMF Pro to Microsoft Intune migration for approximately 700 staff MacBooks
  • Integrate cloud services via Microsoft Graph API and REST APIs
  • Built automated password expiration tracking that generates helpdesk tickets assigned to building-specific technicians via Sherpadesk API
  • Leverage AI-augmented development to architect and build production automation

Computer Technician

North Hills School District · Pittsburgh, PA · May 2023 – Sep 2025
  • Provided technical support for district staff and students across multiple buildings
  • Managed device deployments and imaging via SCCM and PXE boot
  • Administered Active Directory, Google Workspace, and Microsoft 365 accounts
  • Deployed Fortinet networking hardware across district buildings
  • Developed utilities to streamline common technician tasks

Medical Records Technician

Allegheny Health Network · 2021 – Apr 2023
  • Maintained patient records in compliance with HIPAA regulations
  • Ensured data accuracy and confidentiality across healthcare information systems

Front End Associate

Walmart · 2018 – 2021
  • Delivered customer service in high-volume retail environments
  • Developed communication and problem-solving skills in fast-paced settings

Technical Support Specialist

MSAD #17 · Maine · 2013 – 2014
  • Provided IT support for school district staff and students
  • Troubleshot hardware and software issues across the district
03

Skills

Cloud & Identity

Microsoft 365, Azure, Entra ID, Exchange Online, Google Workspace

Automation

PowerShell, Microsoft Graph API, REST APIs, AI-Augmented Development

Endpoint Management

Microsoft Intune, JAMF Pro, SCCM, PXE Imaging

Security

Microsoft Defender, Sophos, SpamTitan

Networking

Ubiquiti UniFi, Fortinet

Virtualization & Hosting

VMware vSphere, Docker, Caddy

Monitoring

Prometheus, Grafana

04

Certifications

CompTIA A+ Google IT Support Professional Certificate
05

Education

Oxford Hills Technical School — Computer Technology 2009 – 2012