Open to opportunities

Todd Gregory

@toddgregory

IT Support Specialist with 4+ years delivering SLA-driven Windows/Active Directory support and security compliance in enterprise environments.

United States

Message

What I'm looking for

I want to deliver fast, SLA-driven IT support in a Windows/Active Directory environment, automate provisioning to reduce onboarding time, and help teams maintain strong cybersecurity/STIG compliance with clear documentation and customer-focused communication.

I’m an IT Support Specialist with 4+ years of experience supporting enterprise and DoD environments, with deep strength across Windows endpoints, Active Directory, Microsoft 365, and security compliance. I’ve supported 500+ users while maintaining approximately 98% SLA compliance in Tier 1 support and delivering strong first-call resolution rates in senior DoD support.

In my recent roles, I’ve owned the day-to-day service desk and onsite desktop experience—troubleshooting hardware, software, network, printers, and peripherals—and documenting support activity with clear escalation paths. I also administer Active Directory accounts, access permissions, and group policies to support onboarding, role changes, and offboarding, including participation in on-call rotations.

My technical edge includes endpoint deployment and automation: I’ve coordinated imaging and configured secure standard builds for 150+ Windows laptops/desktops/tablets, and automated portions of user provisioning with PowerShell to reduce account setup time by approximately 30%. I’ve also built training materials and troubleshooting guides that reduced repeat help desk requests by approximately 15%.

I’m especially proud of my cybersecurity readiness work, supporting STIG compliance, patching, CAC authentication, and audit support with zero critical findings. I’ve led a team of 5 Secret-cleared IT technicians at a U.S. Navy facility and bring a disciplined, risk-aware mindset to SLAs, compliance, and continuous improvement.

Experience

Work history, roles, and key accomplishments

Current

IT Specialist

Current

RLI Insurance

Feb 2026 - Present (5 months)

Serves as first point of contact in a hybrid support model, resolving hardware, software, networking, and endpoint issues. Administers Active Directory accounts and group policies for onboarding, role changes, and offboarding, while documenting and escalating incidents within defined SLAs.

Microsoft 365 Active Directory Group Policy Desktop Support User Onboarding SLA On call Support

Computer Specialist

Osmose

Sep 2024 - Jan 2026 (1 year 4 months)

Provided Tier 1 IT support for 500+ users, handling Windows endpoint, printer, and business application issues. Performed secure endpoint imaging and managed IT asset lifecycle tracking, while creating troubleshooting guides and training materials that reduced repeat help desk requests.

Tier 1 IT Support Printers License Management Troubleshooting Training Materials

Senior Information Technology Specialist

Apex Systems/Leidos

May 2023 - Aug 2024 (1 year 3 months)

Led a team of Secret-cleared IT technicians providing network and desktop support for a U.S. Navy facility. Administered Windows Server and Active Directory for ~200 users, supported STIG/DoD cybersecurity compliance and audits, and used PowerShell to automate user provisioning tasks.

Windows Server Active Directory Group Policy system updates STIG Compliance PowerShell Network Monitoring Incident Response Outlook Email Troubleshooting

Expeditionary Airfield Technician

U.S. Marine Corps

Aug 2018 - Aug 2024 (6 years)

Maintained expeditionary aviation systems, communications equipment, and lighting systems in operational environments. Conducted preventive maintenance using technical manuals and checklists and supervised aviation support activities in high-pressure conditions.

Preventive Maintenance Safety Procedures Lighting Systems Operational Readiness Supervision

Staging Technician

Apex Systems/Leidos

Feb 2023 - May 2023 (3 months)

Imaged and configured 100+ Windows 10 laptops and desktops for a large-scale technology refresh. Resolved imaging and driver issues before deployment and maintained inventory tracking to support on-time delivery.

Windows 10 Technology Refresh Deployment

Field Operations Team Member

Strategic Campaign Sourcing

Nov 2022 - Jan 2023 (2 months)

Delivered onsite support for multifunction printers across 30+ customer sites, coordinating repair schedules and documenting tickets. Diagnosed printing and network issues (including TCP/IP and scan-to-email) and trained clients on self-maintenance and basic troubleshooting to reduce repeat service calls.

TCP IP Scan To Email Secure Printing Troubleshooting Service History Review Customer Training

Field Service Technician

Xerox

Feb 2022 - Oct 2022 (8 months)

Installed, maintained, and repaired networked printers and MFPs at 30+ client sites with high first-visit resolution. Configured network printing, scan-to-email, and TCP/IP settings for enterprise environments and diagnosed connectivity, hardware, and software issues.

Connectivity Issues Scan To Email TCP IP