Jesse Dudgeon

Chief Information Officer
jessedudgeon@gmail.com

Profile

Strategic IT executive with 10+ years leading modernization, cybersecurity, and operations across multi-site, mission-driven organizations. Known for building high-performing teams, translating complex problems into business outcomes, and delivering measurable impact-cost reductions, uptime gains, and safer, smarter workplaces. Combines executive leadership with hands-on expertise across Azure/M365, networking, automation, and custom application development.

Core Competencies

  • IT Strategy & Roadmaps
  • Cybersecurity & Compliance
  • Cloud Migration (Azure, O365)
  • Infrastructure Modernization
  • Automation (Power Automate, PowerShell)
  • Vendor & Contract Negotiation
  • Program & Project Management
  • Disaster Recovery & Business Continuity
  • Facilities & Physical Security
  • Stakeholder Communication

Education

Bachelor of Arts in Information Systems
Indiana Tech - May 2013

Work Experience

Iris Family Support Center
IT & Facilities Director 2020 - Present
  • Provide executive leadership for IT and facilities operations serving 100+ staff across multiple locations.
  • Own IT strategy, budget, governance, and risk management; chair/serve on safety, training, and strategic planning committees.
  • Led cloud-first transformation across Azure AD (Entra), M365, SharePoint Online, Teams, OneDrive, and Exchange Online.
  • Implemented physical security (access control, surveillance) and building systems monitoring to strengthen safety and compliance.
  • Negotiated contracts and managed vendors; improved delivery performance and reduced total cost of ownership.
  • Reduced Phishing risk by 15%
  • Converted all internal forms to digital workflows, cutting paper usage by 100 reams annually and improving processing speed by 60%.
IT Manager 2014 - 2020
  • Directed day-to-day operations, service desk, and systems administration for a 100+ user environment (multi-site).
  • Standardized onboarding and imaging to cut new-hire time-to-productive by ~50%.
  • Planned and executed migrations to cloud services with zero unplanned downtime (CRM/case management and core productivity).
  • Established IT policies/procedures, DR playbooks, and security baselines (MFA, password manager, device hardening).
  • Championed VoIP transition improving call quality/reliability while reducing telecom spend ~25%
  • Migrated 100+ users to Microsoft 365 with zero downtime, improving collaboration and reducing legacy system cost
Systems Administrator 2013 - 2014
  • Consolidated and virtualized aging on-prem servers to improve availability and manageability.
  • Connected offices via secure site-to-site VPN; deployed standardized firewalls and network services (DNS/DHCP).
  • Built internal tools for automation, reporting, and tracking to streamline operations.
  • Eliminated recurring weekly outages by diagnosing root causes, implementing infrastructure upgrades, and establishing proactive monitoring—achieving 99.9% uptime and restoring user confidence.
FCC (Adams)
Systems Administrator 2010 - 2013
  • Administered and optimized enterprise-level Windows Server, Active Directory, and Exchange environments.
  • Designed and implemented proactive monitoring systems, reducing outages by 20% and improving network performance.
  • Developed and enforced IT policies and procedures, ensuring compliance with industry standards and best practices.
  • Developed OEE tracking and multi-department budget tools to improve visibility and throughput.
Air National Guard
Air Propulsion Systems Specialist 2008 - 2014
  • Inspected, maintained, and repaired jet engines to Air Force standards.
  • Performed advanced diagnostics and overhaul procedures, ensuring 100% operational readiness during active deployments.

Key Achievements

  • Designed and launched a custom case management system (C#, ASP.NET, MS SQL) to streamline records and reporting.
  • Built a multi-purpose management platform (Laravel/PHP/MySQL) for training, volunteer hours, and fundraising tracking.
  • Created user-managed mass SMS communications via Twilio API for rapid, reliable outreach.
  • Implemented a self-service HR system, reducing manual administration and saving ~$55K annually.
  • Established a formal service desk with ticketing, knowledge base, and metrics to drive continuous improvement.

Technical Skills

  • Cloud & Identity: Azure, Azure AD (Entra ID), Intune; M365 admin (Exchange Online, SharePoint Online, Teams, OneDrive).
  • Security & Networking: Firewalls, VPN (site/client), MFA, password managers, DNS/DHCP, LAN/WAN, monitoring.
  • Modern Workplace: Device provisioning, imaging, GPO/baselines, endpoint management, collaboration suites.
  • Dev & Automation: Power Automate, PowerShell; C#, ASP.NET, PHP (Laravel), JavaScript; Git, CI basics.
  • Data & Platforms: MS SQL, MySQL; virtualization, server OS, print services; asset & inventory management.