Josh Olliff

Orlando, FL | On-site

• Architected global Secure Boot certificate renewal across a 550+ endpoint worldwide fleet; independently executed a phased 30-day rollout with 97.8% first-pass success and zero downtime, then manually remediated the remaining endpoints.
• Architected an enterprise-wide Windows 11 upgrade (23H2 -> 25H2) across the 550+ endpoint global fleet using an 18-tier staged deployment ring model; independently executing rollout with a 99.3% incident-free rate across 300+ completed deployments.
• Engineered 40+ Intune Win32 application packages, including complex driver deployments, using custom PowerShell detection logic, PSADT automation, and endpoint remediation scripts for legacy installers.
• Managed Cisco Secure Endpoint threat detection and incident response across the global fleet - alert triage, threat investigation, and endpoint isolation.
• Used Microsoft Defender Advanced Hunting with custom KQL queries to identify external domains bypassing DMARC and assess sender risk patterns.

Lakeland, FL | Hybrid

• Architected a Windows Update Ring deployment strategy across the enterprise Intune environment, achieving a ~35% increase in fully updated workstations within 3 weeks.
• Designed and implemented an AutoPilot provisioning strategy, reducing deployment time and eliminating manual onboarding overhead.
• Audited and remediated GPO/Intune configuration profile conflicts across enterprise infrastructure, improving endpoint stability.
• Remediated pentest findings via MDM (Addigy/Intune) policy and bash/PowerShell scripting, improving security posture and compliance.

Dimondale, MI | Hybrid

• Sole architect/administrator of Skymint's Azure environment - virtual networking, site-to-site connectivity via Meraki vMX, and on-prem-to-Azure IaaS server migration.
• Solely managed enterprise VMware infrastructure and NetApp storage environment, including maintenance, patching, and migration for Linux and Windows guest OSes.
• Architected and administered Intune for 500+ devices, including Win32 app packaging, and built AutoPilot to streamline onboarding; developed Intune apps to deploy 25+ printers via scripting.
• Migrated SQL database to a standalone SolarWinds server; transitioned settings from Server 2012 to Intune/Entra.
• Set up Entra hybrid sync for all users and devices; administered Microsoft 365 including custom Teams call queues; managed Veeam server backups and user data retention.
• Promoted from IT Systems Administrator to IT Systems Engineer within 6 months.

• Engineered and maintained network and data security measures with vendors and personnel.
• Deployed Windows Server infrastructure and used Group Policy to manage access for 600+ users.
• Played a key role in a company-wide POS migration and led creation of Skymint's Incident Response Plan.
• Developed custom Crystal Reports for manufacturing and compliance initiatives.

Los Angeles, CA | Hybrid

• Deployed and managed Windows Server 2016 (Hyper-V) - Active Directory, Print Services, DNS, SQL Server.
• Served as Global Administrator for Microsoft 365 - SharePoint, OneDrive, Exchange Online, Teams.
• Single-handedly architected and executed migration from Toshiba VoIP to Microsoft Teams, including number porting and auto-attendant configuration.
• Sole engineer on implementation of an in-house ticketing system, securing executive and end-user buy-in.

• Delivered desktop and infrastructure support; resolved real-time issues for the Executive Leadership team.
• Supported guest Wi-Fi and connectivity for external visitors at the Palevsky Center.

Foster City, CA | On-site

• Migration Team: Used LANDesk for hardware/software inventory; led XP -> Windows 7 migration for 5,000+ employees including imaging and customized software deployment.
• User Account & Data Services: Administered Linux SFTP access, RSA token provisioning for VPN, and triaged 500+ IAM incidents/requests monthly.
• Help Desk Analyst: Authored IT globalization documentation; advanced from Tier 1 to Tier 2 as part of the IAM team.

Orlando, FL | On-site

• Frontline IT support for 65,000+ students, faculty, staff, and alumni in a high-volume help desk environment.
• Provisioned and synchronized LDAP/Active Directory access in compliance with FERPA and UCF security standards.
• Supported campus-wide migrations from GroupWise to Exchange and XP to Windows 7.