Operating Systems
Linux, Debian, Ubuntu, Arch Linux, Kali Linux, Windows, Windows Server, PowerShell.
IT Support · Systems Administration · Development
Jeffrey Whitaker
Building, troubleshooting, and understanding technology from the ground up.
IT support and systems administration professional with hands-on experience across Linux, Windows, virtualization, networking, cybersecurity, and backend development. I enjoy understanding how systems work, solving difficult technical problems, and building practical solutions.
Linux Administration
Proxmox VE
Networking
Cybersecurity
Go & Python
ABOUT ME
A practical, hands-on approach to technology
My technical background spans traditional IT support, systems administration, networking, security testing, and software development. I've spent years working with computers and operating systems, troubleshooting network problems, and learning how to build and maintain reliable technical environments.
Outside my professional roles, I independently configured and maintain a multi-node Proxmox environment that hosts Linux systems, websites, security tools, and other self-hosted services. This ongoing work gives me practical experience with virtualization, storage, networking, deployment, and system troubleshooting.
I've also pursued structured backend development training, building skills in Go, Python, SQL, and application architecture. My software projects complement my infrastructure work by giving me experience with both the applications and the systems that support them.
Whether I'm resolving a connectivity issue, diagnosing a broken virtual machine, or developing an application, I approach the problem methodically and keep learning until I understand the underlying cause.
TECHNICAL TOOLKIT
Skills & Technologies
A broad technical foundation spanning operating systems, infrastructure, networking, security, and software development.
Virtualization & Storage
Proxmox VE, virtual machines, Linux containers, ZFS, snapshots, replication experiments, and recovery.
Networking & Infrastructure
TCP/IP, DNS, DHCP, NGINX, reverse proxies, dynamic DNS, TLS, port forwarding, and connectivity troubleshooting.
Security & Monitoring
Wazuh, Cowrie, SSH honeypots, SysReptor, vulnerability assessment, Active Directory security testing, Hack The Box.
Backend Development
Go, Python, Flask, REST APIs, SQL, PostgreSQL, SQLite, Git, and GitHub.
Deployment & Containers
Docker, Gunicorn, systemd, WordPress, TrueNAS, Jupyter Notebook, with additional Kubernetes and K3s experimentation.
Support & Troubleshooting
Hardware and software diagnostics, root cause analysis, technical documentation, customer service, and issue resolution.
Additional Technical Skills
OpenCV, HTML, CSS, JavaScript, virtualization troubleshooting, application deployment, and network programming.
INDEPENDENT TECHNICAL EXPERIENCE
Systems Administration & Infrastructure
Building, administering, and troubleshooting virtualized infrastructure, Linux systems, network services, and security tooling through ongoing independent technical work.
Virtualization & Linux Administration
Independently configured and maintain a multi-node Proxmox cluster hosting virtual machines, containers, websites, and self-hosted services.
- Proxmox VE and virtual machine management
- Debian, Ubuntu, Arch Linux, and Kali Linux
- ZFS storage and snapshot management
- Replication and recovery experimentation
- Operating system and service troubleshooting
Networking & Web Infrastructure
Configure and troubleshoot the network services that connect applications, virtual machines, and publicly accessible infrastructure.
- NGINX reverse proxy configuration
- DNS and dynamic DNS
- TLS certificates and encrypted connections
- Port forwarding and NAT troubleshooting
- Public-facing websites and self-hosted services
Security Monitoring & Testing
Deploy and operate security monitoring and honeypot services while developing practical penetration-testing skills in controlled environments.
- Wazuh monitoring and agent deployment
- Cowrie and SSH honeypot infrastructure
- Self-hosted SysReptor
- Active Directory security exercises
- Hack The Box penetration-testing challenges
Windows Administration
Work with Windows administration and scripting, complemented by hands-on Active Directory experience in personal lab and security-training environments.
- Windows Server
- PowerShell
- Active Directory lab environments
- Windows and network troubleshooting
Containers & Self-Hosted Services
Deploy and maintain applications and services while exploring containerization and infrastructure management approaches.
- Docker
- Kubernetes and K3s experimentation
- Plex media services
- TrueNAS and storage infrastructure
- WordPress and Jupyter Notebook
Technical Troubleshooting
Investigate problems across operating systems, virtual machines, network configurations, and application deployments using systematic diagnosis and testing.
- DNS and DHCP configuration failures
- NAT hairpinning and connectivity issues
- Failed installations and broken VMs
- Service configuration problems
- Recovery and root cause investigation
Infrastructure as a Learning Platform
Maintaining my own environment gives me practical experience with the dependencies between operating systems, networking, storage, security, and applications. Troubleshooting failures is an important part of that process, helping me understand not just how to deploy a service, but how to diagnose it when something goes wrong.
My technical experience also includes networking and infrastructure coordination in commercial environments, alongside a professional background in technical support and customer service.
SELECTED PROJECTS
Software Development
Practical projects demonstrating backend development, networking, secure communications, application deployment, and ongoing maintenance.
TCPeeps — Encrypted TCP Chat
A client-server chat application written in Go, developed to explore network programming, encrypted communications, and concurrent application design.
- Implemented TCP client-server communication.
- Integrated TLS-encrypted connections.
- Built an interactive terminal interface.
- Continuing development of additional capabilities and operational diagnostics.
Hangman — Web Application
A browser-based Hangman game that evolved from a command-line program into a publicly accessible web application.
- Developed using Python and Flask, with randomized word selection and difficulty levels.
- Implemented score tracking and a persistent PostgreSQL leaderboard.
- Deployed on Linux using NGINX, Gunicorn, systemd, and TLS configuration.
- Maintained in active use for over a year with very little unplanned downtime.
These projects represent different aspects of my technical work: TCPeeps explores network programming and secure communications, while Hangman demonstrates full application deployment and ongoing maintenance.
CAREER HISTORY
Professional Experience
A background combining technical support, customer communication, project coordination, and independent technical development.
AI Systems Specialist / Security Researcher
- Evaluate AI model responses for quality, reasoning, instruction adherence, and reliability.
- Conduct adversarial testing and prompt-injection analysis to identify weaknesses in model behavior.
- Assess outputs against task-specific criteria and document evaluation results.
Realtor / Sales Associate
- Managed client communication, transaction documentation, and time-sensitive workflows.
- Coordinated remote meetings and digital transactions using Microsoft Teams, Zoom, and related tools.
Service Technician
- Diagnosed residential building issues and performed maintenance, repair, and replacement work.
- Explained technical findings and service agreements, obtained customer approvals, and maintained clear documentation.
Site Superintendent
- Coordinated audiovisual, networking, and infrastructure installations across commercial renovation projects.
- Managed contractors, vendors, schedules, and project documentation for projects ranging from approximately $500,000 to $4 million.
- Communicated requirements and resolved operational issues across multiple trades.
Help Desk Specialist — Dell Support Campaign
- Delivered telephone-based technical support for hardware, operating system, software, and connectivity issues.
- Guided customers through troubleshooting procedures and documented problems and resolutions.
- Developed a strong foundation in technical diagnosis, customer service, and first-contact problem resolution.
Independent Residential Contractor
- Manage residential maintenance, repair, and installation projects, including audiovisual equipment and ceiling fans.
- Diagnose practical equipment and installation problems while managing customer communication and project execution.
EDUCATION & PROFESSIONAL DEVELOPMENT
Certifications & Education
Boot.dev — Certified Backend Developer
Completed an intensive backend development program covering Go, Python, SQL databases, algorithms, concurrency, backend architecture, Git, and Docker.
Completed August 2026Hack The Box Academy — Certified Penetration Testing Specialist (CPTS)
Completed the Penetration Tester Job-Role Path, covering enumeration, exploitation, Active Directory attacks, privilege escalation, pivoting, and professional reporting.
Coursework completed · Certification exam pendingDelaware Technical Community College
Associate of Applied Science in Computer Network Engineering. Studies included networking fundamentals, TCP/IP, OSI model architecture, and computer hardware systems.
Completed June 2003Continuous Technical Development
My learning combines formal coursework, structured security training, independent infrastructure administration, and practical software development. I continue to expand my capabilities by building projects, testing configurations, and investigating real technical problems.
My Hack The Box experience has also included achieving a reported global top-1,000 ranking through hands-on security challenges.
GET IN TOUCH
Let's Talk Technology
I'm interested in opportunities involving IT support, systems administration, infrastructure, cybersecurity, and software development. If you're looking for someone who enjoys solving technical problems and learning how systems work, I'd welcome the opportunity to connect.