Meet the Founder
GigitekAI is led by a Microsoft 365 architect and U.S. Army veteran with over two decades of enterprise IT experience
Harry Henry Santiago
CEO & Founder
Microsoft 365 SME | Exchange Online & Email Security
Cloud Migration | M365 Enterprise Admin Expert
📍 Tampa, Florida
🎖️ U.S. Army Veteran (1993–1997)
Harry Henry Santiago is a Microsoft 365 Subject Matter Expert with 20+ years designing, securing, and modernizing enterprise messaging environments for global organizations. His core focus areas include Exchange Online, email security (Proofpoint, SPF/DKIM/DMARC), multi-tenant Azure AD administration, hybrid migrations, and PowerShell/Graph API automation.
Harry has supported environments ranging from 100,000+ user global deployments to mid-size businesses transitioning to the cloud. He brings a hands-on approach to complex infrastructure challenges — from advanced email flow troubleshooting to full tenant migrations — and serves as a trusted SME for teams that need deep Microsoft 365 expertise.
Born in Manatí, Puerto Rico, and raised in New Brunswick, NJ, Harry served in the U.S. Army as a Legal Specialist (MOS 71D) from 1993 to 1997 before transitioning into IT in the late 1990s. He founded GigitekAI in 2024 with a clear mission: build an AI-first MSP where intelligent agents function as full employees, replacing manual workflows with automation and intelligence.
Harry is actively exploring Agentic AI frameworks and AGI concepts as they apply to enterprise automation and intelligent service delivery — positioning GigitekAI at the forefront of the next wave of managed services.
Core Expertise
Microsoft 365 Architecture
20+ years designing, securing, and modernizing enterprise M365 environments. Exchange Online, Entra ID, Teams governance, and Microsoft Purview at scale.
Email Security & Compliance
Deep expertise in Proofpoint (TRAP, TAP), SPF/DKIM/DMARC, DLP policies, and email security architecture for Fortune 500 organizations.
PowerShell & Graph API Automation
Advanced automation and reporting through PowerShell scripting and Microsoft Graph API integrations — replacing manual workflows with intelligent agents.
Enterprise Cloud Migrations
Architected and executed cloud migration strategies for organizations ranging from mid-size businesses to 100,000+ user global deployments.
Hybrid Infrastructure
Expert in hybrid Exchange/Azure AD environments, multi-tenant administration, cross-forest migrations, and complex mail flow troubleshooting.
AI & Agentic Automation
Actively integrating Agentic AI frameworks and AGI concepts into enterprise IT workflows — building the AI-first MSP of the future.
Career Timeline
Associate Manager (Senior M365 Engineer)
@ AvanadeNov 2021 – Present
Delivering enterprise messaging, identity, and security solutions for clients across hybrid and cloud-native environments. Administering Exchange Online, Entra ID (AAD Connect), Microsoft Purview, and driving automation through PowerShell and Graph API.
Senior Messaging Engineer
@ Mindtree (for Realogy — Fortune 500)Mar 2020 – Sep 2021
Senior Infrastructure Engineer supporting Microsoft 365 and on-premises messaging for one of the largest real estate enterprises in the US. Managed Proofpoint Email Security, Exchange Online, Azure AD, Teams, SharePoint, and Dynamics 365 at enterprise scale.
Senior Messaging Engineer
@ Patriot Talent SolutionsJan 2019 – Dec 2019
Architected and executed cloud migration strategies to Microsoft 365, transitioning Exchange Online, Teams, and SharePoint while minimizing business disruption. Managed on-premises Exchange 2013/2016 and Windows Server AD infrastructure.
Global Messaging Consultant
@ HCL America, Inc.Oct 2016 – Nov 2018
Senior escalation engineer in a globally distributed hybrid cloud and Exchange environment supporting 100,000+ users across multiple continents. Led infrastructure consolidation, disaster recovery, and complex cross-forest migrations.
Sr. Microsoft Escalation Engineer
@ MicrosoftJul 2012 – Jul 2013
Frontline technical expert for Microsoft's Premier Support organization, resolving the most complex and high-visibility customer escalations. Engaged Fortune 500 Premier customers as a trusted technical advisor and drove product quality improvements through direct feedback loops with Microsoft engineering.
Legal Specialist (MOS 71D)
@ US ArmyMar 1993 – Jan 1997
Certified by the Judge Advocate General's Corps (JAGC) to provide paralegal and legal administrative support. Graduated from Air Assault School. Military discipline and mission-first mindset that carries through every client engagement today.
Licenses & Certifications
Technical Skills
Work Directly with the Expert
When you work with GigitekAI, you work directly with Harry — a senior Microsoft 365 architect with a track record of delivering results for Fortune 500 organizations and growing businesses alike.
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