Jason Gayle

Cloud Architect with 25+ years of hands-on IT experience designing, securing, and modernizing hybrid infrastructure across enterprise environments. Administered and migrated workloads across AWS, Google Cloud Platform, and Azure including app hosting, web hosting, object storage, and IAM with Azure as the main platform of my job role. Currently pursuing AZ305 (Azure Infrastructure Solutions) to formalize architect-level capabilities already deployed in practice, including Zero Trust security architecture and a 30% cloud cost reduction at infrastructure scaling.

Deep expertise in Azure IaaS, Microsoft 365, Entra ID, Intune, and PowerShell/Python automation.

Azure Cloud Operator & Head of IT - Entripy (Ink Thread & Tech) - Oakville, ON

(2018-03)

• IT decision-maker and Head of IT, owning the full technology strategy, application roadmap, infrastructure investments, and vendor relationships for the company.
• Evaluate, approve, and lead implementation of all application changes and system improvements, aligning technology decisions with business objectives and operational efficiency.
• Architect and own end-to-end Azure and Microsoft 365 infrastructure for a hybrid workforce, spanning identity, endpoint, networking, and cloud application layers.
• Administered AWS and Google Cloud Platform environments including app hosting (EC2, App Engine, Cloud Run), object storage (S3, GCS), and IAM across both platforms.
• Managed GCP app deployments using App Engine and Cloud Run, handling container configuration, environment variables, scaling policies, and service account permissions
• Administered AWS S3 and GCS bucket policies, lifecycle rules, versioning, and cross-platform access controls to support application and data workloads
• Led full migration of workloads of Azure, improving performance, scalability, and operational consistency, consolidating the multi-cloud footprint into a single strategic platform
• Reduced Azure cloud costs by 30% through governance controls, resource rightsizing, tagging policy, FinOps discipline of reduce logging size and disable unused services.
• Implemented Zero Trust security model: MFA, Conditional Access policies, Entra ID governance, and Defender for Endpoint compliance.
• Deployed cloud-hosted applications using Azure App Services, Blob Storage, and Key Vault — managing the full application lifecycle.
• Engineered automated file processing pipeline with retry logic, reducing failure rate to under 1% and eliminating manual intervention.
• Built real-time monitoring and alerting systems (Teams Webhooks, dashboards, logging) reducing troubleshooting time by 80%.
• Developed AI-driven internal tools including knowledge assistants, ticket automation, and operational workflow optimization.
• Built automation solutions in Python (Flask), PowerShell, and Power Automate — reducing manual processes across IT operations.
• Managed hybrid infrastructure: VMware, Hyper-V, Azure VMs, Active Directory, and Linux-based cloud environments
• Led enterprise migration from Slack to Microsoft Teams with training, adoption tracking, and full organizational rollout
• Managed IT asset lifecycle, vendor relationships, ChromeOS device evaluation, and infrastructure roadmap planning

Senior IT Business Analyst - Dumas Contracting - Toronto, ON

(2013-09 - 2018-03)

• Led implementation of enterprise ERP systems supporting global financial and operational processes across Canada and South America.
• Designed and developed workforce management applications using C#, ASP.NET, and SQL Server.
• Built Power BI executive dashboards providing real-time operational insights for CIO and VP Finance decision-making.
• Automated operational workflows using SharePoint and mobile solutions; managed Windows Server and SaaS platforms.
• Collaborated directly with CIO and VP Finance to identify and deliver cost-saving technology initiatives.

Senior IT Technician - IT for Dentists - Toronto, ON

(2012-05 - 2013-09)

• Delivered infrastructure support across multiple dental clinics in Ontario. Networks, servers, desktops, and clinical applications.
• Implemented JIRA Service Desk, standardizing support workflows and improving response times across all client sites.

Information Technology Analyst - Vanguard Global Services - Mississauga, ON

(2010-12 - 2012-03)

• Supported logistics platforms (Ship+, Footprint) and trained off-site clients on web shipping systems across North America.
• Administered MS Exchange, IIS, Active Directory, and network infrastructure including routers, switches, and printers.
• Built SQL tables, wrote Crystal Reports, and developed C# application components for logistics data workflows.
• Provided 24/7 on-call North American system support and delivered remote assistance via VPN, RDP, and LogMeIn.

Intermediate Technology Analyst - Hudson's Bay Company (via Loop Enterprises) - Toronto, ON

(1996-10 - 2010-03)

• Team Lead for Asset Management across HBC brands (Zellers, The Bay, HBC Information Services) — managing inventory, lifecycle, and SMS distribution for the enterprise desktop fleet.
• Led VoIP project rollout for 100+ clients; co-authored Group Policy standards with Server and Security teams for Windows XP deployment.
• 2nd-level network and desktop support: project planning, deployment strategies, documentation, and training on new technologies.
• Designed and maintained intranet site for the development support team using XML, HTML, JavaScript, and Macromedia tools.

Azure Architecture, Terraform, Security, FinOps, Python, Cybersecurity - CloudAcademy (2021 - 2025)

Certification - Enterprise Network Engineer Certification - CITI College (2010 - 2011)

Certificate - Project Management: Fundamentals & Scheduling - Sheridan College (2006 - 2007)

Diploma - Computer Programming; Web Programming & .NET Application Development - Humber College (1997 - 2000)