Jesse Dudgeon

Information Systems Leadership
jessedudgeon@gmail.com

Profile

Strategic IT executive with 12+ years of progressive leadership driving digital transformation, cybersecurity maturity, and operational excellence across multi-site, mission-driven organizations. Proven record of reducing risk, modernizing infrastructure, and delivering measurable business outcomes—including 99.9% uptime, 60% workflow acceleration, and six-figure cost savings. Blends executive strategy with hands-on technical depth across Microsoft cloud, identity, security, automation, and custom application development.

Strategic Leadership Highlights

  • Led cloud-first modernization to Microsoft ecosystem (Entra ID, M365, SharePoint, Teams, Exchange), improving resiliency and collaboration.
  • Established cybersecurity baselines and risk management practices (MFA, device hardening, phishing defense), reducing phishing susceptibility by 15%.
  • Digitized 100% of internal forms and workflows, cutting paper usage by 100 reams annually and improving processing speed by 60%.
  • Built structured service desk operations with KPIs, ticketing, and knowledge base to drive measurable service quality improvements.
  • Eliminated recurring outages through infrastructure upgrades and proactive monitoring, achieving 99.9% uptime.

Core Competencies

  • IT Strategy & Roadmaps
  • Cybersecurity & Compliance
  • Cloud Migration (Azure, M365)
  • Infrastructure Modernization
  • Automation (Power Automate, PowerShell)
  • Vendor & Contract Negotiation
  • Program & Project Management
  • Disaster Recovery & Business Continuity
  • Facilities & Physical Security
  • Executive & 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 enterprise technology, cybersecurity, facilities, and physical security operations supporting 100+ staff across multiple sites.
  • Own technology strategy, governance, risk management, and modernization roadmap aligned with organizational goals and mission delivery.
  • Direct IT and facilities budgeting, vendor strategy, contract negotiation, and cost optimization initiatives to reduce total cost of ownership.
  • Established cybersecurity posture aligned with NIST-based best practices and modern identity security standards (MFA, device hardening, access controls).
  • Led cloud-first transformation across Entra ID (Azure AD), Microsoft 365, SharePoint Online, Teams, OneDrive, and Exchange Online to improve resiliency and collaboration.
  • Reduced phishing susceptibility by 15% through awareness initiatives and technical safeguards, lowering organizational cyber risk exposure.
  • Implemented physical security (access control, surveillance) and building systems monitoring to strengthen safety, incident response, and compliance.
  • Built formal service desk operations with KPI tracking and performance analytics to drive accountability and service excellence.
  • Digitized 100% of internal forms and operational workflows, cutting paper usage by 100 reams annually and improving processing speed by 60%.
  • Serve as strategic advisor to executive leadership on technology risk, infrastructure investments, and operational scalability.
IT Manager 2014 - 2020
  • Directed IT operations, service desk, and systems administration for a 100+ user, multi-site environment.
  • Standardized onboarding, device imaging, and provisioning processes, cutting new-hire time-to-productivity by ~50%.
  • Planned and executed migrations to cloud services with zero unplanned downtime (CRM/case management and core productivity).
  • Established foundational IT governance: policies/procedures, DR playbooks, and security baselines (MFA, password manager, device hardening).
  • Championed VoIP transition, improving reliability and call quality while reducing telecom spend by ~25%.
  • Led organization-wide migration to Microsoft 365 with zero downtime, improving collaboration and reducing legacy system costs.
Systems Administrator 2013 - 2014
  • Consolidated and virtualized aging on-prem servers to improve scalability, availability, and manageability.
  • Connected offices via secure site-to-site VPN; deployed standardized firewalls and core network services (DNS/DHCP).
  • Built internal tools for automation, reporting, and tracking to streamline operations and reduce manual overhead.
  • Eliminated recurring weekly outages through root cause analysis, infrastructure upgrades, and proactive monitoring—achieving 99.9% uptime and restoring user confidence.
FCC (Adams)
Systems Administrator 2010 - 2013
  • Administered and optimized enterprise 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 aligned with industry best practices to strengthen governance and consistency.
  • Developed OEE tracking and multi-department budget tools to improve operational visibility and throughput.
Air National Guard
Air Propulsion Systems Specialist 2008 - 2014
  • Maintained and inspected jet propulsion systems under strict Air Force compliance and safety standards.
  • Performed advanced diagnostics and overhaul procedures, ensuring 100% operational readiness during active deployments in high-pressure environments.

Key Achievements

  • Designed and launched a custom case management system (C#, ASP.NET, MS SQL) to streamline records, reporting, and data integrity.
  • 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.
  • Designed and implemented a self-service HR system automating administrative workflows, reducing manual effort and saving ~$55K annually.
  • Established a formal service desk with ticketing, knowledge base, and metrics to drive continuous improvement and accountability.

Technical Skills

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