Michael Free

Linux Debian Ubuntu Windows Server

LXC Docker Ansible Terraform

Gitea Git Bash Python PowerShell

Markdown MkDocs Confluence Jira

Visual Studio Code Chocolatey Kubernetes

Experience

IT Technician / System Administrator

Public Sector (2021 - Present)

  • Spearheaded an automation-first strategy using PowerShell, Ansible, and Python, reducing manual workloads and improving team efficiency by over 70% in key areas such as user onboarding and software deployment.
  • Automated Active Directory and Office 365 onboarding/offboarding, cutting provisioning time by 70%.
  • Developed 80+ standardized software deployment packages using PowerShell App Deployment Toolkit (PSADT) for consistent, silent rollouts.
  • Built a custom Python/PowerShell framework for remote domain migration of PCs, eliminating the need for on-site visits.
  • Created automated Windows 10 deployment images and post-install configuration scripts, reducing setup time from days to minutes per device.
  • Automated routine maintenance (log cleanup, service restarts) and audit reporting (license usage, inactive accounts) with Ansible and PowerShell.
  • Scripted comprehensive Active Directory audit reports using PowerShell to monitor user accounts, device compliance, group memberships, and licensing alignment.
  • Implemented OpenVAS vulnerability scanning across public and staff networks, proactively identifying and remediating critical risks.
  • Led organization-wide SSL/TLS implementation, replacing insecure self-signed certificates with CA-signed certificates across internal applications, websites, and services that previously operated without encryption.
  • Automated certificate deployment and renewal using Ansible playbooks to ensure continuous compliance.
  • Introduced Yubikeys for IT team multi-factor authentication and migrated credential storage from spreadsheets to a centralized password management solution.
  • Conducted full IT asset inventory via custom PowerShell scripts, pulling hardware and software data directly from Active Directory.
  • Migrated IT asset tracking from spreadsheets and JIRA Assets to Snipe-IT, establishing a centralized, searchable inventory database.
  • Built a custom Python-based kiosk application that interacted with Snipe-IT’s REST API to streamline asset operations. The kiosk featured barcode scanning via webcam to perform fast check-ins, check-outs, and label printing, reducing manual data entry and improving inventory accuracy.
  • Created and maintained PowerShell modules (SnipeItPS) to automate inventory reporting, audits, and bulk updates directly from Active Directory and other IT systems.
  • Led migration from Spiceworks to JIRA Service Management (and later to osTicket) with zero downtime, including parsing and importing a decade of historical ticket data using a custom Python script.
  • Assisted in the rebuild of a Windows Domain Controller and developed Group Policy Objects (GPOs) for organization-wide user and device management.
  • Deployed and managed Windows/Linux virtual machines on VMware vSphere and assisted with Azure cloud deployments using LXD containers.
  • Migrated digital signage infrastructure to a cost-effective, automated solution using Home Assistant, reducing support calls and energy consumption.
  • Managed vendor, reseller, and distributor relationships for procurement of software/hardware assets and technical support.
  • Prepared technical reports, project proposals, and capital/operating expenditure plans for management and stakeholders.
  • Provided daily Tier 1–3 support for 150+ users and 250+ systems, including public-access PCs and specialized equipment.
  • Built and maintained an internal knowledge base using BookStack, documenting systems, procedures, and projects.
  • Engineered a custom digital signage platform using Debian, preseeding, custom .deb packages, and Ansible for centralized management.
  • Coordinated and technically supported a live HAM radio event with the International Space Station, streamed via OBS Studio and covered by local media (CTV, CBC).
  • Piloted package management solutions (Chocolatey, WinGet) to automate software updates and accelerate Windows 11 deployment.

Tier 3 Platform Support Specialist

Cybersecurity Vendor (2020 - 2021)

  • Provided Tier 3 technical support for a security-focused SaaS platform, troubleshooting complex issues within Linux-based virtual appliances (CentOS/Ubuntu), network configurations, firewall rules, and virtualization environments.
  • Investigated and validated security alerts, analyzing false-positive Common Vulnerability and Exposures (CVEs) to maintain platform accuracy and customer trust.
  • Diagnosed and resolved issues with the OpenVAS (Open Vulnerability Assessment Scanner) engine, including logging, configuration, and performance optimization.
  • Responded to and triaged security incidents generated by the platform, providing initial analysis and recommending mitigation steps to customers.
  • Served as a critical liaison between customers and engineering teams, escalating software bugs, feature gaps, and technical roadblocks to drive product improvements.
  • Created and maintained technical documentation, runbooks, and training materials to onboard new team members and improve team readiness.
  • Managed support workflows and customer communications using JIRA and Zendesk, ensuring clear tracking and timely resolution of cases.
  • Collaborated proactively with engineering and product teams to communicate edge-case scenarios and user feedback, contributing to platform usability and support process enhancements.

DevOps / System Administrator (Build and Release)

Online Gaming & Betting (2018 - 2020)

  • Automated infrastructure provisioning, configuration, and decommissioning across AWS, GCP, DigitalOcean, and on-premise Proxmox environments using Terraform and Ansible.
  • Built and maintained Kubernetes Helm Charts to standardize and streamline the deployment of containerized applications across development and production.
  • Collaborated with development teams to establish and enhance CI/CD pipelines and automated environment creation using open-source tooling.
  • Managed a heterogeneous environment of Linux/Windows servers, Linux/Windows desktops, and macOS systems across development and staging.
  • Conducted system hardening, vulnerability assessments, and implemented security patches in coordination with the Security Administrator to ensure compliance.
  • Created and maintained a comprehensive hardware and software asset inventory system using open-source tools for internal tracking and compliance.
  • Owned internal user lifecycle management, including account provisioning, permissions management, and access control across multiple platforms and services.
  • Developed and maintained technical documentation for system architectures, deployment procedures, and operational runbooks.
  • Contributed to scalable and reliable infrastructure supporting applications in regulated, high-availability industries including online gaming, blockchain, and casino platforms.

Datacenter Solutions Specialist (Pre-Sales)

IT Solutions Provider / Value Added Reseller (2015 - 2018)

  • Acted as a subject matter expert on Lenovo datacenter technologies, providing presales technical consultation for servers, storage, networking, and hyperconverged infrastructure solutions tailored to client business needs.
  • Designed integrated infrastructure solutions aligned with performance, scalability, and budgetary requirements, encompassing compute, virtualization, storage (SAN/NAS), and associated software ecosystems.
  • Developed comprehensive solution architectures, including technical diagrams, Bills of Materials (BOMs), and Statements of Work (SOWs) for deployments involving VMware solutions and other virtualization platforms.
  • Maintained expert-level knowledge of Lenovo’s product roadmap, certifications, and enterprise deployment best practices across server, storage, networking, and hyperconverged portfolios.
  • Collaborated with vendors, distributors, and resellers to ensure competitive pricing, product availability, and accurate configuration of solutions, including integrated stacks with key partners like VMware.
  • Validated and optimized hardware and software configurations for large-scale datacenter deployments, balancing cost, compatibility, and future scalability across compute, storage, and networking layers.
  • Provided internal enablement and maintained technical credibility through continuous self-training on emerging technologies, including advancements in virtualization, storage architectures, and hyperconverged infrastructure.
  • Served as a trusted technical resource for complex datacenter inquiries, guiding stakeholders through purchasing decisions and deployment strategies for servers, storage, networking, and integrated systems.

Technical Consultant

Digital Signage / Kiosk / ATM Solutions (2013 - 2015)

  • Collaborated with sales and development teams to deploy tailored remote device management and digital signage solutions for enterprise clients.
  • Developed and maintained XML configuration templates to integrate RS232 serial command sets into proprietary remote management software.
  • Engineered automation scripts in PowerShell, Bash, and Batch to control, monitor, and manage remote field devices across diverse environments.
  • Created technical proof-of-concepts (PoCs) for digital signage monitoring software and IoT solutions using Raspberry Pi and Arduino to demonstrate product enhancements.
  • Supported the full sales lifecycle by assisting with technical sales calls, product demonstrations, and solution implementations.
  • Researched and compiled RS232 command libraries to enable remote management and control of field-deployed digital signage hardware.
  • Translated client requirements into functional prototypes and PoCs, guiding both technical feasibility and the sales process.

Microsoft Licensing Specialist

Microsoft Support / Value Added Reseller (2007 - 2013)

  • Acted as a subject matter expert for Microsoft licensing across Canada and the U.S., providing pre-sales consultation to internal sales teams and prospective clients.
  • Interpreted and communicated complex Microsoft Use Rights, Software Assurance benefits, and licensing entitlements based on product SKUs and agreement terms.
  • Created formal, accurate quotes aligned with appropriate pricing tiers and agreements (government, education, charity, etc.) using manufacturer part numbers.
  • Maintained deep, up-to-date knowledge of evolving Microsoft licensing models and transition periods between volume licensing programs.
  • Used consultative selling to support pre-sales activities related to Microsoft Licensing Programs, products, and solutions.
  • Facilitated training sessions for sales teams on products, services, licensing, and program updates.
  • Served as a liaison between Sales and Product/Partner Management to identify opportunities for improved product, program, and partner alignment.
  • Provided frontline licensing support via Microsoft’s 1‑800‑MICROSOFT hotline, assisting business customers, partners, and resellers.
  • Researched and clarified license entitlements, downgrade rights, and compliance requirements for diverse client needs.
  • Educated non‑technical customers and small‑business owners on product availability, licensing options, and purchasing channels.

Certifications

CompTIA A+ (2013)

  • Earned CompTIA A+, validating hands-on skills in hardware, operating systems, networking, security, and technical troubleshooting.
  • Demonstrated ability to install, configure, maintain, and support end-user devices in a professional IT environment

CompTIA Server+ (2013)

  • Earned CompTIA Server+, validating hands-on skills in server hardware installation, configuration, maintenance, virtualization, and disaster recovery
  • Demonstrated ability to deploy, manage, and troubleshoot on-premises server infrastructure in enterprise environments

Microsoft Licensing Solutions for Enterprise Organizations (2012)

  • Completed Microsoft Licensing Solutions for Enterprise Organizations, demonstrating understanding of Microsoft volume licensing models, compliance, and cost optimization
  • Gained expertise in selecting and managing enterprise Microsoft licensing solutions aligned with organizational needs and governance requirements

Microsoft Licensing Solutions for Small & Medium Sized Organizations (2012)

  • Completed Microsoft Licensing Solutions for Small & Medium Sized Organizations, demonstrating knowledge of Microsoft licensing programs tailored to SMB environments
  • Developed ability to recommend compliant, cost-effective Microsoft licensing solutions aligned with business size, growth, and operational needs

Lenovo Datacenter Technical Sales Professional (2017)

  • Earned Lenovo Datacenter Technical Sales Professional (2017), validating expertise in Lenovo server, storage, and SDI portfolios and their application to customer requirements
  • Demonstrated ability to position data center solutions by workload, build basic configurations, and leverage Lenovo Systems Management tools (XClarity, XClarity Controller, CMM)
  • Validates skills in mapping customer business and technical requirements to appropriate Lenovo hardware and solution families
  • Confirms competency in building and proposing basic server and storage configurations aligned with stated use cases
  • Supports proven capability to translate technical features into value-driven solutions during technical sales and pre-sales engagements

Education

Business Mangagement Studies

Conestoga College (2009)

  • Advanced Diploma (3 years) — Developed broad understanding of business functions including finance, accounting, marketing, sales, HR, operations, and project management
  • Gained practical skills in modern management techniques and business databases, applicable to corporate, government, non-profit, and entrepreneurial environments
  • Prepared as a versatile management generalist, capable of strategic decision-making, team leadership, and adapting to evolving business needs

Skills

Automation & Scripting

  • PowerShell (including PSADT)
  • Python scripting and frameworks
  • Ansible (automation & playbooks)
  • Bash/Batch scripting
  • Terraform (infrastructure automation)

Systems & Infrastructure

  • Windows Server administration
  • Linux administration (Debian, Ubuntu, CentOS)
  • Active Directory & Office 365 management
  • Group Policy Objects (GPO) creation and management
  • Virtualization: VMware vSphere, Proxmox, LXD
  • Container orchestration: Kubernetes & Helm Charts
  • Cloud Platforms: Azure, AWS, GCP

DevOps & CI/CD

  • Infrastructure as Code (Terraform, Ansible)
  • CI/CD pipeline creation and automation
  • Software deployment automation (PSADT, Chocolatey, WinGet)
  • System hardening & vulnerability management (OpenVAS)

Networking & Security

  • SSL/TLS deployment and certificate management
  • Multi-factor authentication (Yubikeys)
  • Firewall & network troubleshooting
  • Cybersecurity incident triage and vulnerability scanning

IT Operations & Asset Management

  • IT asset tracking and inventory (Snipe-IT, spreadsheets, JIRA)
  • Digital signage/kiosk/ATM systems management
  • Ticketing & support systems (JIRA, osTicket, Zendesk)

Hardware & software auditing

  • Knowledge base creation (BookStack)
  • Technical Sales & Pre-Sales
  • Solutions architecture and consultation
  • Datacenter solutions design (Lenovo, VMware, hyperconverged infrastructure)
  • Microsoft Licensing expertise (enterprise & SMB)
  • Vendor and client relationship management
  • Proof-of-concept (PoC) creation and demonstrations

Project & Team Skills

  • Cross-functional collaboration (IT, sales, engineering)
  • Process optimization and efficiency improvement
  • Documentation, runbooks, and technical reporting
  • Project planning and execution
  • Client-facing technical consultation