CW

Systems Administrator • Cybersecurity • Cloud

Cayden Woo

Security-first systems administration across Windows & Linux, networking, automation, and AWS.

Windows Server Linux Active Directory Hyper-V Networking Microsoft 365 Automation AWS

About

Experienced Systems Administrator with a strong focus on cybersecurity, server administration, and network architecture across both Windows and Linux environments. I specialize in building, securing, and maintaining reliable infrastructure, with hands-on experience in automation, performance optimization, and problem resolution.

I bring a security-first mindset to IT operations, applying best practices in system hardening, access control, and network segmentation while continuously expanding my cloud skill set, particularly within AWS environments.

I am committed to continuous learning and hands-on experimentation, staying current with emerging technologies to design practical, forward-thinking solutions. I perform well both independently and in leadership roles, combining technical depth with a collaborative, problem-solving approach.

I believe effective communication is the backbone of success, and my arsenal includes not only technical prowess but also strong interpersonal skills and public speaking abilities. I thrive both working solo and in leadership roles, bringing a problem-solving mindset to the table or fostering a collaborative environment.

Tampa Bay Area, FL

What I work on

  • Server administration (Windows + Linux)
  • Security hardening, access control, segmentation
  • Identity & access (AD, GPO, DNS)
  • Virtualization (Hyper-V, VirtualBox)
  • Network + security ops (firewalls, VPNs, switches)
  • Automation (PowerShell, Python)
  • AWS fundamentals + cloud security

Experience

System Administrator

MicroImaging Source, Inc. • 03/2024 – Present

  • Administer Windows & Linux servers (AD, GPO, DNS, Hyper-V).
  • Maintain infrastructure: firewalls, switches, wireless networks, and VPN connections.
  • Deploy/manage Microsoft 365, endpoint protection, and backups for security/compliance.
  • Provide end-user support and training for hardware, software, and cloud services.
  • Automate routine tasks with PowerShell and Python scripts.
  • Lead IT projects including SaaS migrations and vendor negotiations.

Projects

Mail Server Administration

Oct 2023 – Present • MXRoute

  • Started up mail hosting through a third-party vendor (MXRoute) and administered resources.
  • Configured users and security filters; migrated DNS records and SSL certificate from an existing domain.

Skills: Email Hosting • DNS Management • System Administration

Static Website Hosting

Oct 2023 – Present • AWS S3 + CloudFront

  • Developed a custom AWS-built solution in S3 focused on redundancy, global availability, and reliability.
  • Managed compute/resources and console operations; configured CloudFront distribution and logging.

Skills: AWS • Cloud Computing • Project Planning

Home Cybersecurity Lab

Jun 2023 – Present • VirtualBox + pfSense + Kali

  • Built a virtualized environment using VirtualBox.
  • Deployed pfSense for firewalling, network segmentation, NAT, internal LANs, and rule design.
  • Performed offensive testing with Kali Linux and hardened endpoints with Windows 11.
  • Administered a Linux server and practiced service hardening and isolation.
  • Gained hands-on exposure to blue-team and red-team concepts.

Skills: Virtualization • Linux • Cybersecurity • Pen Testing • Networking

Centralized Firewall Management & Audit

Sep 2023 • AWS VPC (Demo)

  • Audited and managed security groups to identify and reduce public exposure.
  • Customized a Zero Trust model for a centralized firewall and created a WAF approach.

Skills: Firewalls • Amazon VPC • Cloud Security • AWS

S3 Ransomware Simulation / Detection

Sep 2023 • CloudFormation + CloudShell + Athena

  • Used CloudFormation and CloudShell to simulate an attack scenario targeting S3 buckets.
  • Detected activity via Athena queries (CloudTrail, VPC Flow Logs, Route 53 queries) and responded with IAM controls.

Skills: AWS • IAM • Cloud Security • Cybersecurity

Education

Pasco-Hernando State College

A.S. Cybersecurity & Information Technology • 08/2023 – 08/2026 • GPA: 4.0

Coursework: Computer Forensics, Ethical Hacking, Information Security, Network Security, Wireless & LAN Security, Database Programming & SQL, Intrusion Detection.

Certifications

AWS Certified Cloud Practitioner

11/2023 – 11/2026

CompTIA Network+

01/2025 – 01/2028

Contact

Email is best.