Work Preference
Summary
Overview
Work History
Education
Skills
Certification
Affiliations
Quote
Websites
Independent Technical Architecture & Projects.
References
Accomplishments
Civic Leadership & Community Engagement.
Software
Work Availability
Languages
Interests
Timeline
Generic
Kevin Jaggernauth

Kevin Jaggernauth

Strategic IT Consultant and Infrastructure Architect
Cunupia,West Indies

Work Preference

Work Type

Full TimePart TimeContract Work

Location Preference

HybridRemoteOn-Site

Important To Me

Career advancementCompany CulturePersonal development programsFlexible work hoursStock Options / Equity / Profit SharingWork from home option

Summary

Strategic IT Consultant and Infrastructure Architect with 15 years of experience engineering resilient, software-defined data centers and converged enterprise environments. Demonstrated success during tenure at ANSA McAL configuring robust Dell Hyperconverged Infrastructure (HCI) solutions to seamlessly bridge physical hardware with advanced virtualization. Proven expertise in designing High Availability clusters across a diverse hypervisor ecosystem, including VMware vSphere, ESXi, Citrix, and Proxmox VE. Highly proficient in unifying corporate networking with scalable telecommunications, including the architectural deployment of hosted PBX solutions. Focused on delivering Zero Trust environments that align strict cybersecurity compliance with total operational continuity.

Overview

6
6
Certificates
18
18
years of professional experience
8
8
years of post-secondary education
2
2
Languages

Work History

Strategic IT Consultant & IT Manager

Orion Automation Systems Limited
Penal, Debe, Trinidad and Tobago
06.2026 - Current
  • Formulated comprehensive cybersecurity policies and staff compliance documentation aligned with ISO 27001 standards to govern enterprise data protection.
  • Engineered corporate network migration blueprints, integrating Cloudflare DNS strategies to harden enterprise security perimeters and optimize traffic routing.
  • Architected internal AI governance frameworks and best practice guidelines, establishing secure and ethical parameters for the corporate adoption of artificial intelligence technologies.
  • Engineered domain level security protocols including SPF, DKIM, and DMARC to guarantee domain authorization and high deliverability across enterprise communications.
  • Established ITIL based IT Service Management practices and spearheaded technical bid development for high stakes institutional tenders alongside Tier 1 vendors

Freelance ICT Consultant and Contractor

Self-employed
, Trinidad and Tobago
01.2024 - 06.2026
  • Led a full network infrastructure overhaul for the Archdiocese of Port of Spain, replacing legacy hardware with fully certified structured cabling from initial assessment to commissioning.
  • Delivered Azure Entra ID identity management and hybrid cloud solutions for clients transitioning to modern secure environments.
  • Architected and deployed hosted cloud PBX telecommunications solutions to modernize client voice infrastructure and unify enterprise communications.
  • Designed and implemented IT Service Management workflows aligned with ITIL best practices to improve technical support delivery and user satisfaction.
  • Executed comprehensive systems integration and managed the deployment and lifecycle support of specialized software applications.
  • Provided strategic IT consulting services, delivering remote systems administration and targeted end user training to drive technology adoption.
  • Facilitated client workshops on Artificial Intelligence literacy, educating users on practical AI applications and business workflow optimization.

Head Of IT Operations

RE-United Farmers Alliance
07.2023 - 11.2023
  • Proven ability to develop and implement creative solutions to complex problems.
  • Developed strong organizational and communication skills through coursework and volunteer activities.
  • Organized and detail-oriented with a strong work ethic.
  • Provided professional services and support in a dynamic work environment.

Real Estate Agent

Self-employed
, Trinidad and Tobago
10.2021 - 12.2023
  • FIU Registered Real Estate Agent
  • Managed full cycle residential and commercial real estate transactions while navigating complex contract negotiations and high value client portfolios.
  • Ensured strict regulatory compliance by maintaining active registration and AML/CFT reporting standards with the Financial Intelligence Unit of Trinidad and Tobago.
  • Continued professional ICT development through the active engineering of an advanced home laboratory while building an independent real estate practice.

IT Administrator

McEnearney Business Machines, ANSA McAL Trading Limited
07.2019 - 08.2021
  • Managing Internal IT all systems
  • Management of Internal IT systems and Management of Telecommunications on Premise VoIP system
  • Company Technical Liaison for key Managed Service Providers project deployments
  • Management of all On-Premises Server Operations
  • Which Includes Active Directory, Domain Controller Management
  • Office 365 Administrator
  • Technical Lead for Migration to Cloud Hosted Voice Solution
  • Provided technical training to Internal and external customers
  • Technical Lead for Implementation and Migration to IaaS- Infrastructure as a Service Environment
  • Kaspersky Endpoint Security Cloud Administrator
  • Which entailed Remote Patch Management, Web Control, Device Control and Encryption Management
  • Remote users support
  • Certified to Deploy and Support Canon imageWARE Enterprise Management Console
  • I have successfully deployed this Solution and it is Active at a Major Service Provider and it Manages their entire Print fleet across Trinidad and Tobago
  • Instrumental in preparation and implementation of a Business Continuity Plan at the start of the SARS-CoV-2 pandemic.

Solutions Architect

McEnearney Business Machines, ANSA McAL Trading Limited
07.2017 - 01.2019
  • Technical Lead for Implementation of Group Wan Project for the subsidiary McEnearney Business Machines
  • Responsible for oversight and project completion
  • Preparing Scope of Works Documents
  • On field experience managing contractors during various projects
  • Designed and proposed server configurations to meet specific Enterprise customer requirements.
  • Supported Sales Team on site visits customers during pre-sales and post-sales process.
  • Deployment of Enterprise software solutions such as McAfee Enterprise ePolicy Orchestrator.
  • Maintained current and in-depth understanding of business processes, needs and objectives.
  • Worked with developers and engineers to realize technological solutions.
  • Worked with clients post-implementation on user testing, debugging, support and maintenance.
  • Managed project planning, resource allocation, scope, schedule, status and documentation.
  • Conducted post-sale requirements gathering, analysis and documentation.

Information Technology Technician/ Assistant

The Archdiocese Of Port Of Spain, Cathedral Of The Immaculate Conception
02.2011 - 01.2016
  • Recruited to establish the state of the then existing systems; with specific intent to identify and evaluate all critical systems
  • Deploy and manage a new information-security program and implement new computer systems and workstations
  • Design and implement security processes and procedures, provide technical assistance to staff, and provide secure remote support to staff and to the clergy
  • Provide Cyber security awareness training and implement industry best practices
  • To supervise and maintain the daily activities of the network systems in the role of a Network Administrator.

Archivist

The Archdiocese Of Port Of Spain, Cathedral Of The Immaculate Conception
02.2011 - 01.2016
  • Tasked with collecting, analyzing, digitizing and managing access to the Historical Archives and Records
  • Implemented proper access to the Historical records using a model that ensures the conservation, digitization, preservation and proper usage of the Documents
  • Ensured that the accuracy and integrity of the records are protected from data corruption and manipulation so that the records maintain their continuity and Historical accuracy using Industry standard encryption and security
  • Creation of a fully functional Network Archives System portal with assigned resources to meet workflow needs.
  • Developed classification systems to facilitate public access to archived materials.
  • Researched and recorded origins, provenance, and historical significance of archival materials.
  • Participated in team projects, demonstrating an ability to work collaboratively and effectively.

Computer Service Technician/Network Administrator

The Archdiocese Of Port Of Spain, Cathedral Of The Immaculate Conception
03.2009 - 01.2010
  • Provided secure remote and on-site support for local and international visiting Clergy members
  • Provided critical technical support in solving computer Software and Hardware related issues.
  • Responded to support requests from end-users and patiently walked individuals through basic troubleshooting tasks.
  • Maintained office PCs, networks and mobile devices.
  • Implemented network security measures to minimize data loss.

Education

Information Systems And Management

School of Business And Computer Science
Champs Fleurs
09.2015 - 04.2016

College of Business And Computer Science
Chaguanas
07.2008 - 07.2010

BorderCom International
St. Claire
02.2008 - 06.2008

Presentation College Chaguanas
Chaguanas
09.2003 - 09.2006

Chaguanas Junior Secondary
Chaguanas
11.2002 - 07.2003

Princes Town Junior Secondary
Princes Town
02.2002 - 07.2002

Cunupia High School
Cunupia, Chaguanas
09.2000 - 02.2002

Skills

Enterprise Server Infrastructure & Virtualization (VMware vSphere, ESXi, Citrix, Proxmox VE, LXC)

Zero Trust Architecture (Cloudflare, WireGuard, Tailscale ZTNA, Reverse Proxies)

Cybersecurity & Telemetry (Wazuh SIEM, Localized DNS Filtering, Threat Monitoring)

Enterprise Networking & Wireless (Cisco Wireless Controllers, TP Link Omada, FortiGate SD WAN, VLAN Segmentation)

Dell Hyperconverged Infrastructure (HCI)

Unified Communications (Cloud Hosted PBX, VoIP Architecture)

IT Governance & Strategy (ISO 27001, ITIL Frameworks, AI Governance Guidelines)

Technical Deployment & Scripting (Containerization, Code Server, GitHub Version Control)

Technical Pre-Sales & Lifecycle Implementation (Solutions Architecture, Systems Integration, Post-Sales Support)

Enterprise Endpoint & Asset Management (McAfee ePO, Kaspersky Endpoint Security, Canon imageWARE, ERP/Accounting Integration)

Certification

A+ Certified Information Technology Technician

Affiliations

  • Trinidad and Tobago Computer Society

Quote

Each small task of everyday life is part of the total harmony of the universe.
Saint Thérèse de Lisieux

Independent Technical Architecture & Projects.

  • Architecting a High-Availability virtualization cluster utilizing Proxmox VE and Linux Containers (LXC), deploying bare-metal OpenMediaVault for distributed, software-defined storage.
  • Architecting Software-Defined Networking (SDN) topologies utilizing TP-Link Omada hardware, configuring advanced WAN gateway routing, and establishing secure multi-site network linking.
  • Deploying specialized application containers and reverse proxy architectures to securely manage and route traffic to internal services, including Code Server environments and localized AI autonomous workforce instances.
  • Engineering secure, encrypted tunnels bridging on-premise infrastructure with cloud Virtual Private Servers (VPS) utilizing WireGuard and Tailscale for Zero Trust Network Access.
  • Integrating Wazuh SIEM for real-time log ingestion, host auditing, and advanced threat monitoring across logically segmented networks.
  • Developing deployment models for localized DNS filtering and secure routing services using AdGuard and Control D.
  • Developing and maintaining technical deployment scripts, network topology documentation, and infrastructure codebases across active GitHub repositories.
  • Managing direct node access and hardware configuration across complex topologies using secure tunneling alongside fundamental protocols including Telnet and SSH.

References

  • Fr. Kenneth Assing, Roman Catholic Clergyman.
  • Mrs. Jessica James Henry, Executive Assistant.
  • Mrs. Tracey Hilaire, Entrepreneur.

Accomplishments

  • Authored and published technical articles on Hashnode under the professional handle "mithrandir-dev", focusing on Zero Trust architecture, enterprise IT governance, and AI ethics, highlighted by the publication "Responsible AI in the Caribbean: Why ICT Professionals Must Engage with Ethics Now."
  • Executed a zero downtime migration from a legacy Mitel PBX hardware system to a modern cloud hosted VoIP platform for the entire ANSA McAL organization.
  • Directed the end to end network infrastructure overhaul for the Archdiocese of Port of Spain, upgrading ad hoc connectivity to a fully documented and certified CAT6 structured environment.
  • Architected foundational AI governance frameworks and ISO 27001 aligned cybersecurity policies to establish secure enterprise technology standards for Orion Automation Systems Limited.
  • Served as Technical Lead for McEnearney Business Machines on the ANSA McAL Group wide WAN project, directing the strategic design and delivery of multi site connectivity using FortiGate SD WAN, Cisco and Extreme Networks infrastructure.

Civic Leadership & Community Engagement.

Candidate for Local Government Councillor

Trinidad and Tobago 2023

  • Orchestrated comprehensive community outreach initiatives, articulating strategic platforms and public policy goals to diverse demographics.
  • Managed campaign logistics, public relations, and stakeholder engagement, demonstrating high-stakes communication, advocacy, and leadership capabilities under public scrutiny.

Software

WireGuard

VMware vSphere

Wazuh SIEM

Elastic Security SIEM

Cloudflare

TP Link Omada SDN

Tailscale

McAfee ePolicy Orchestrator

Kaspersky Endpoint Security

Delinea Privilege Manager

AdGuard and Control D

Azure Entra ID

WireGuard

Proxmox VE

Work Availability

monday
tuesday
wednesday
thursday
friday
saturday
sunday
morning
afternoon
evening
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Languages

English
Bilingual or Proficient (C2)
Spanish
Intermediate (B1)

Interests

Non-Fiction Authorship (100 Battles Every Man Must Win)

Creative Fiction Writing

Technical IT Writing (Hashnode)

Classic Literature and High Fantasy

Distance running and fitness tracking

Digital Media Production (THE CODE KJ)

Video Production and Scripting

Advanced Home Lab Engineering

Timeline

Strategic IT Consultant & IT Manager

Orion Automation Systems Limited
06.2026 - Current

Freelance ICT Consultant and Contractor

Self-employed
01.2024 - 06.2026

Head Of IT Operations

RE-United Farmers Alliance
07.2023 - 11.2023

Real Estate Agent

Self-employed
10.2021 - 12.2023

IT Administrator

McEnearney Business Machines, ANSA McAL Trading Limited
07.2019 - 08.2021

Solutions Architect

McEnearney Business Machines, ANSA McAL Trading Limited
07.2017 - 01.2019

Information Systems And Management

School of Business And Computer Science
09.2015 - 04.2016

Information Technology Technician/ Assistant

The Archdiocese Of Port Of Spain, Cathedral Of The Immaculate Conception
02.2011 - 01.2016

Archivist

The Archdiocese Of Port Of Spain, Cathedral Of The Immaculate Conception
02.2011 - 01.2016

Computer Service Technician/Network Administrator

The Archdiocese Of Port Of Spain, Cathedral Of The Immaculate Conception
03.2009 - 01.2010

College of Business And Computer Science
07.2008 - 07.2010

BorderCom International
02.2008 - 06.2008

Presentation College Chaguanas
09.2003 - 09.2006

Chaguanas Junior Secondary
11.2002 - 07.2003

Princes Town Junior Secondary
02.2002 - 07.2002

Cunupia High School
09.2000 - 02.2002
Kevin JaggernauthStrategic IT Consultant and Infrastructure Architect