Summary
Overview
Work History
Education
Skills
Certification
Timeline
Generic

Joshua Olliff

Orlando,FL

Summary

Results-driven IT Systems Engineer with 10+ years of experience in system administration, engineering, and technical support. Expert in Microsoft technologies including Azure, Entra, and Intune with proven ability to implement and manage complex cloud infrastructures. Skilled in Windows Server, Active Directory, VMware, and Meraki environments. Adept at executing mission-critical migrations, optimizing system performance, and providing exceptional support. Demonstrated success in automating processes, enhancing security postures, and mentoring junior IT professionals.

Overview

9
9
years of professional experience
1
1
Certification

Work History

System Administrator

ASPIRION
02.2025 - Current
  • Implemented Windows update rings in Intune, achieving 35% increase in fully updated workstations within 3 weeks
  • Spearheaded AutoPilot adoption, streamlining device provisioning and reducing deployment time by 60%
  • Created and deployed macOS packages, configuration profiles, and scripts through Intune and Addigy
  • Identified and eliminated GPO/Config profile conflicts, resolving system incompatibilities and improving performance
  • Mentored junior IT team members on Intune, Entra, and Azure best practices
  • Managed enterprise-level IT infrastructure including operating systems, security tools, applications, and servers
  • Implemented and maintained backup solutions ensuring data integrity and regulatory compliance
  • Implemented solutions for security and compliance initiatives, including remediating pentest findings on endpoints through MDM

IT Systems Engineer

SKYMINT BRANDS
10.2022 - 08.2024
  • Built out Azure environment, implementing Meraki's vMX virtual appliance for site-to-site connectivity
  • Solely managed enterprise VMware infrastructure and NetApp storage environment for 500+ users
  • Architected and administered Intune for 500+ devices, including W32 app packaging and deployment
  • Developed scripts to automatically deploy 25+ printers via Intune
  • Established Entra hybrid sync for all users and computers
  • Designed and implemented AutoPilot system alongside Intune for streamlined user onboarding
  • Migrated SQL database to stand-alone server while updating SolarWinds software
  • Managed Veeam server backups and user data retention strategies
  • Promoted from IT Systems Administrator within 6 months due to exceptional performance

IT Systems Administrator

SKYMINT BRANDS
03.2022 - 10.2022
  • Deployed Windows Server infrastructure and utilized Group Policy to manage access for 600+ users
  • Led company-wide Point-of-Sale system migration affecting 20+ retail locations
  • Created Incident Response Plan and security protocols for organizational risk management
  • Developed custom Crystal Reports for manufacturing and compliance initiatives
  • Collaborated with vendors to engineer and maintain network and data security measures

Network Coordinator

CALIFORNIA COMMUNITY FOUNDATION
12.2015 - 02.2022
  • Administered Windows Server 2016 infrastructure in Hyper-V environment
  • Served as Global Administrator for Microsoft 365 core applications
  • Engineered migration from Toshiba VoIP to Microsoft Teams, including number porting
  • Administered Citrix Workspace applications for enterprise-wide virtual desktop infrastructure
  • Provided comprehensive technical support for 85+ users both on-site and remotely
  • Implemented in-house ticketing system, gaining executive buy-in and enhancing service management
  • Delivered executive-level IT support from CEO throughout organization

Education

Associate of Applied Science - Network Services, Advanced Technology

Seminole State College of Florida
Sanford

Skills

  • Microsoft Azure
  • Microsoft 365
  • Entra ID
  • Microsoft Intune
  • AutoPilot
  • GPO
  • ActiveDirectory
  • Configuration Profiles
  • Windows Server
  • Windows 10/11
  • VMware
  • Hyper-V
  • Meraki
  • LAN/WAN
  • Firewalls
  • VPN
  • TCP/IP
  • Microsoft Teams
  • Backup & Disaster Recovery
  • Identity Management
  • Compliance

Certification

  • Microsoft Certified: Azure Administrator Associate
  • Microsoft 365 Certified: Endpoint Administrator Associate
  • Microsoft 365 Certified: Fundamentals
  • Microsoft Certified: Azure Fundamentals
  • Microsoft Certified: Security, Compliance and Identity Fundamentals
  • Microsoft 365 Certified: Security Administrator Associate

Timeline

System Administrator

ASPIRION
02.2025 - Current

IT Systems Engineer

SKYMINT BRANDS
10.2022 - 08.2024

IT Systems Administrator

SKYMINT BRANDS
03.2022 - 10.2022

Network Coordinator

CALIFORNIA COMMUNITY FOUNDATION
12.2015 - 02.2022

Associate of Applied Science - Network Services, Advanced Technology

Seminole State College of Florida

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