Open to opportunities

Bobby Howerton

@bobbyhowerton

Senior Windows/VMware systems administrator and cybersecurity professional delivering compliant, automated infrastructure.

United States

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What I'm looking for

I seek senior onsite or remote roles focused on Windows/VMware systems administration, security/compliance, automation, and mentoring teams in mission-driven environments.

I am a senior IT professional with an AS in Information Technology and a BS in Network Security and Forensics, bringing over 28 years in the Information Technology career field and 12 years focused on Microsoft Windows system administration and networking support. I specialize in systems administration, VMWare ESXi/vCenter/vSphere, Windows Server platforms, Linux, PowerShell scripting, and Python programming.

My work includes designing and implementing virtualized infrastructures, automating administrative tasks with PowerShell and Python, and enforcing compliance with DoD/DISA/ACAS/STIG/IAVA requirements. I have built on-premise Azure stacks, configured VPNs and Cisco ASA firewalls, and developed tools to scan and remediate stale VMWare network stacks to improve operational efficiency.

I have served as a subject matter expert on large federal contracts (CANES, DCGS-MC) and delivered field and desktop support across Navy, Marine Corps, SSA, TSA, and commercial clients, including leading teams and training peers. I also have experience creating Quick Reference Guides, onboarding documentation, and office continuity plans to increase team capability and knowledge retention.

I hold a renewed DoD Secret clearance, multiple CNSSI/NSTISSI certifications, and active CompTIA A+ and Security+ certifications. I seek roles where I can apply security-focused system administration, automation, and compliance leadership to mission-critical environments.

Experience

Work history, roles, and key accomplishments

Senior Microsoft Systems Engineer

Boeing IP Global

Apr 2025 - May 2025 (1 month)

Conducted site survey and standardized configuration of 200+ Cisco wireless access points, replaced legacy hardware, and staged a full system-wide upgrade to improve performance and compliance with Boeing security policies.

Wireless Cisco Compliance Validation Troubleshooting

Senior Microsoft Systems Engineer IV

Atlas Technologies

Jan 2024 - Jul 2024 (6 months)

Built a 24-server test environment, enforced CANES compliance across virtual networks, authored QRGs for Exchange 2019/Outlook, and developed PowerShell tooling to audit and clean VMware network stacks.

VMware ESXi PowerShell Virtualization Compliance CANES Troubleshooting Scripting

Senior Systems Analyst & VMWare Admin

Mandex, Inc

May 2022 - Oct 2023 (1 year 5 months)

Designed and automated a VMware ESXi virtualized infrastructure for DCGS-MC GEOINT, enforced RBAC and encryption via PowerShell, managed STIG/IAVA remediation with Nessus/ACAS, and deployed on-prem Azure Stack components.

VMware ESXi PowerShell ArcGIS STIG IAVA Nessus ACAS VPN Security Automation Azure Stack

Senior Desktop Support Technician

Bluewater Federal Solutions

Nov 2021 - Apr 2022 (5 months)

Reimaged and repaired Windows 10 systems, authored PowerShell automation for first-time sign-in and SCCM updates, and produced continuity documentation to streamline RDT&E desktop support workflows.

Desktop Support PowerShell SCCM Windows 10 Imaging Troubleshooting Documentation

Information Assurance Technician

Peraton

Apr 2020 - Jul 2021 (1 year 3 months)

Provided NMCI desktop support, developed PowerShell field tools, managed TACLANE encryption devices for secure VPNs, and monitored Nessus vulnerabilities to maintain Navy Information Assurance compliance.

Information Assurance PowerShell Nessus Desktop Support Vulnerability Management Compliance

Desktop Support Technician

Apex Systems

Apr 2019 - Apr 2020 (1 year)

Delivered NMCI desktop and field support including imaging, software repair, printer installations, hardware replacement, and ensured government asset compliance with Navy and DoD standards.

Desktop Support Imaging Printer Installation Troubleshooting Ticketing Compliance

Flying IT Technician

Abbtech Professional Services

Nov 2018 - Apr 2019 (5 months)

Led multi-city field teams to set up census field offices, deploying and testing servers, routers, switches, workstations, and VoIP phones to turn empty buildings into operational offices within three days.

Field Engineering Deploying Networking VoIP Project Coordination Systems Testing Team Leadership

Independent IT Contractor

TTS Virtual Solutions

Jul 2012 - Apr 2019 (6 years 9 months)

Managed large-scale PC/laptop upgrade projects for federal and commercial clients, maintained servers and SCCM baselines for law firms, and designed backup/DR and VPN solutions across multiple contracts.

Project Management SCCM Backup VPN Active Directory Linux Team Leadership

Helpdesk Technician

SAIC

Feb 2013 - Mar 2014 (1 year 1 month)

Provided remote support for Toyota Motor Sales, managed AD accounts, supported ESXi virtualization clients, and authored continuity documentation and knowledge-base procedures.

HelpDesk+Remote Support Active Directory Bomgar Documentation Troubleshooting Windows

Network Administrator & Technician

5 Rivers Communications

Mar 2011 - Sep 2011 (6 months)

Installed and maintained SonicWall firewalls, VPNs, Ubuntu file servers, Windows workstations, and SIP/VoIP phone systems for 70+ businesses, providing network and telephony support across East Tennessee.

Sonicwall VPN Ubuntu Windows VoIP SIP Network Administration

Windows System / Network Administrator

Logon Computer Services

May 2007 - Dec 2010 (3 years 7 months)

Maintained Windows Server infrastructure, Active Directory, and networks for newspapers and radio stations, led Server 2003-to-2008 migrations, and developed backup/disaster recovery and APT conversions.

Windows Server Active Directory Backup Networking Troubleshooting APT

Database Manager / Helpdesk Supervisor

United States Air Force

Apr 1996 - Mar 2007 (10 years 11 months)

Supervised a Tier 1 help desk, maintained ~3,000 computers and the Air Mobility Command maintenance database, and led Six Sigma studies that improved aircraft part reliability and saved assets and lives.

IT Management Database Administration Six Sigma Windows Troubleshooting Asset Management

Education

Degrees, certifications, and relevant coursework

Fountainhead College of Technology

Bachelor of Applied Science; Associate of Occupational Science, Network Security and Forensics / Information Technology

Grade: High Honors (Associate degree)

Completed an Associate of Occupational Science in Information Technology and a Bachelor of Applied Science in Network Security and Forensics, graduating in 2017 with High Honors for the associate degree.

United States Air Force (military training)

Military Training / Professional Development, Management; Network and Database Administration; Six Sigma

1996 - 2007

Completed multiple military training courses in management, leadership, supervisory training, network and database administration, and Six Sigma data analysis during service from 1996 to 2007.