From the desk of

Winston Jordan

Agent for Change | Innovation Trailblazer | AI Enthusiast | Systems & Infrastructure Specialist

Profile photo of Winston Jordan
Open to Opportunities

Prattville, AL · winstonjordan0616@gmail.com · 334-324-4251

Summary

Results-driven IT professional with 10+ years of progressive experience in system administration, infrastructure management, and technical support. Skilled at building, securing, and optimizing IT environments that improve performance, reliability, and compliance. Adept at leading end-to-end IT projects---from planning and design through implementation and support---while maximizing resources and controlling costs.

Systems AdministrationMicrosoft 365 & AzureFortinet FirewallsVMware & VDIProject ManagementDisaster RecoveryStrategic IT PlanningDesktop & End-User Support

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Experience

Alabama Board of Medical Examiners
IT System AdministratorAugust 2022Present
Alabama Board of Medical Examiners · Montgomery, AL

Lead all IT operations for a Microsoft-centric state agency serving 55 employees, driving a comprehensive modernization effort across infrastructure, security, cloud, and end-user support.

  • Retired legacy Windows Servers and migrated critical services to supported platforms for improved reliability.
  • Installed dual firewalls with a backup ISP for full network redundancy, and deployed VLAN segmentation and public Wi-Fi isolation for improved security.
  • Hardened firewall configurations: closed unused ports, deployed VPN with SSO & MFA, and implemented network monitoring and reporting.
  • Deployed Microsoft M365 E5 Security features to strengthen identity, device, and data protections across the agency.
  • Standardized Microsoft licensing per-user, migrated shared mailboxes, and established account cleanup procedures for unused and redundant accounts.
  • Integrated SSO for key applications including Govenda, FortiVoice, Avigilon, and ThoughtSpan.
  • Implemented offsite backups and configured backup switches and UPS systems to support the agency's disaster recovery plan.
  • Implemented a new FortiVoice VoIP phone system, eliminating the legacy system, automating switchboard functions, and configuring call rollover to improve caller routing.
  • Designed and deployed an Adobe Learning Management System (LMS) from the ground up; built and published courses using Adobe Captivate and earned Adobe Professional Certification.
  • Deployed new laptops to all staff and iPads to board members, managed via Microsoft Intune for security, compliance, and lost/stolen device tracking.
  • Removed unnecessary vendor agreements (Sentinel, TeamViewer, CrashPlan) and deployed PDQ Connect for remote management, reducing costs while improving functionality.
  • Established cross-agency data-sharing initiatives for DEA, NPI, and PDMP records to improve physician record accuracy.
  • Automated common IT functions via GPOs and scripts: mapped drives, printers, and remote desktop access.
  • Conducted firewall policy and vulnerability reviews and delivered IT security training to staff.
  • Evaluated, procured, and led the agency-wide replacement of the existing CRM platform with ThoughtSpan; currently serving as Product Owner, driving adoption and ongoing enhancements.
  • Introduced an Azure-hosted web application leveraging a ChatGPT instance to enable intelligent querying of decades of legacy records, legal cases, and agency data — delivering actionable analysis and dramatically reducing research time.
Alabama Department of Examiners of Public Accounts
IT System AdministratorOctober 2020August 2022
Alabama Department of Examiners of Public Accounts · Montgomery, AL

Overhauled IT infrastructure for 185 employees, modernizing outdated systems and eliminating reliance on other state agencies.

  • Designed and implemented VMware Horizon VDI on Dell VxRail from the ground up, migrating 97% of users to the VDI solution.
  • Migrated the Microsoft 365 tenant out from under another government organization, including full email migration.
  • Configured Azure MFA SSO for applications to improve user experience and strengthen security.
  • Implemented network redundancy from ISP to Horizon server, maximizing uptime for 100+ remote users.
  • Implemented a cloud-based disaster recovery solution using AWS off-site backups and Dell Data Domain.
  • Deployed HA FortiGate firewalls with redundant ISPs to maximize uptime.
Alabama Department of Rehabilitation Services
IT System AdministratorApril 2018October 2020
Alabama Department of Rehabilitation Services · Montgomery, AL

Supported 900 users across 26 offices via Track-IT, remote tools, and on-site visits.

  • Managed a Citrix VDI environment utilizing WYSE thin clients and Chromebooks for remote work.
  • Deployed an SCCM environment to facilitate Windows 7 to Windows 10 migrations across all devices.
  • Supported 24 office locations across the state of Alabama.
  • Provided tier 2 support for local technicians as needed.
Alabama Law Enforcement Agency
IT Systems TechnicianJuly 2015March 2018
Alabama Law Enforcement Agency · Montgomery, AL

Provided technical support for 1,300 agents and staff across 300+ locations.

  • Provided critical desktop support to 1,300+ users (600 law enforcement officers, full-time remote) across Alabama.
  • Created 5-year device replacement plans: tested, procured, and deployed new end-user hardware.
  • Supported public safety equipment in over 100 physical locations.
  • Deployed laptops and desktops for 600+ officers and supported law-enforcement-specific software.
Tri County Computer Repair LLC
Business OwnerNovember 2011February 2018
Tri County Computer Repair LLC · Montgomery, AL

Founded and operated a managed IT services business serving local businesses in the Montgomery area.

  • Performed managed IT services for local businesses, including Office 365 and Active Directory environments.
  • Built custom PCs to order and performed hardware repairs (hard drive failures, broken screens, etc.).
  • Managed client relationships and delivered hands-on technical support across a range of industries.

Projects

🤖IT Done Right – AI-Built Resume Site

Designed and shipped a fully functional, production-grade interactive resume website from scratch — with zero prior coding experience — using Claude AI as a collaborative development partner.

  • Built with Next.js 14, TypeScript, and Tailwind CSS; deployed on Vercel with a custom domain.
  • Integrated OpenAI gpt-4o-mini to power an 'Ask My Resume' AI chat widget trained on resume content.
  • Implemented CI/CD workflow via GitHub pull requests with automatic Vercel deployments on merge.
  • Featured as a live demonstration of AI-assisted development and modern IT infrastructure skills.
🎃Pumpkin Pi – IoT Home Monitoring System
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A Raspberry Pi-powered home automation and monitoring project inspired by the Marauder's Map from Harry Potter — a real-time dashboard that tracks activity and presence across the house, nicknamed 'the pumpkin house.'

  • Built on Raspberry Pi with Arduino sensors for room-level presence and environmental monitoring.
  • Designed to provide a live, map-style view of household activity — who's home, which rooms are active, and environmental conditions.
  • Demonstrates hands-on IoT skills including hardware integration, sensor data collection, and home network configuration.
  • Personal project applying enterprise infrastructure thinking (monitoring, alerting, uptime) to a home environment.
🖥️VMware Horizon VDI Deployment

Led end-to-end design and implementation of a VMware Horizon VDI environment on Dell VxRail for the Alabama Department of Examiners of Public Accounts, enabling secure remote work for 185 employees.

  • Migrated 97% of users from physical desktops to a fully virtualized environment.
  • Deployed across two vSphere environments plus one hyper-converged Dell VxRail cluster.
  • Implemented network redundancy from ISP to Horizon server to ensure zero single points of failure.
  • Reduced hardware costs and enabled seamless remote work capabilities statewide.
☁️Microsoft 365 Tenant Migration

Planned and executed a full Microsoft 365 tenant migration for a state agency, separating their environment from another government organization with zero data loss.

  • Migrated all email, SharePoint, OneDrive, and Teams data to a new sovereign tenant.
  • Configured Azure AD, MFA, and SSO for all applications post-migration.
  • Minimized downtime through careful cutover planning and staff communication.
📞FortiVoice Phone System Deployment

Implemented a FortiVoice VM-200 VoIP phone system for the Alabama Board of Medical Examiners, replacing legacy hardware with a modern, software-defined solution.

  • Deployed FortiVoice with soft clients for desktop and mobile use.
  • Configured policy-based routing to ensure call reliability and redundancy.
  • Provided staff training and documentation for the new system.
🧠Azure AI Document Intelligence Platform
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Migrated decades of on-premises file server records to Azure Blob Storage and deployed a Retrieval Augmented Generation (RAG) AI solution — based on the Microsoft PubSec Information Assistant reference architecture — enabling intelligent, citation-backed querying of legacy agency documents.

  • Ingested on-premises file server content into Azure Blob Storage, building a structured document repository for AI indexing.
  • Deployed Azure AI Search with an enrichment pipeline that chunks documents, generates embeddings, and builds a searchable index.
  • Leveraged Azure OpenAI (GPT-4) to power a conversational interface that grounds responses in agency records with source citations.
  • Enabled staff to query decades of legacy records, legal cases, and agency data in seconds — dramatically reducing manual research time.
  • Built on the Microsoft PubSec Information Assistant open-source architecture, adapted for the agency's on-premises-to-cloud data migration.
🛡️Cloud-Based Disaster Recovery

Designed and implemented a cloud-based disaster recovery solution to protect critical state data and ensure business continuity.

  • Implemented AWS off-site backups integrated with Dell Data Domain for on-premises deduplication.
  • Established recovery time and point objectives aligned with agency compliance requirements.
  • Documented runbooks and tested recovery procedures to validate the solution.

Education & Certifications

🎓Associate of Applied Science
Computer Information Systems
Trenholm State Community College
Graduated with a 4.0 GPA - Dean's List
Graduated 2017
🏅Adobe Certified Professional - Adobe Captivate
Adobe
Issued October 2024 · Expires October 2026
🏅CompTIA A+
CompTIA
Issued 2016
🏅Eagle Scout
Boy Scouts of America
Issued 2008

Skills

Platforms

Windows Server 2012-2022VMware ESXi/vSphereVMware Horizon VDIWindows 10/11MacOSChrome OS

Cloud & SaaS

Microsoft 365Azure AD & MFAIntuneSharePoint OnlineExchange OnlineOneDriveTeamsAWSDruva Backup

Hardware

Dell Servers & VxRailFortinet (FortiGate, FortiSwitch, FortiAP, FortiVoice)Cisco/Ruckus NetworkingTegile & Dell SAN

Software

Active DirectoryGroup PolicyPowerShellOffice SuiteTrack-ITAvamarCitrixWYSEAdobe Captivate

Security & DR

MFA/SSOFirewall HA PairsVPNSD-WANBackup/RestoreBusiness Continuity Planning