CW

Systems Administrator • Cybersecurity • Cloud

Cayden Woo

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

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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 & identity: Windows/Linux administration, Active Directory, Group Policy, DNS, and virtualization.
  • Security: system hardening, least-privilege access control, and practical network segmentation.
  • Networking: firewall/VPN management, switching & wireless fundamentals, and troubleshooting.
  • Automation: PowerShell and Python for repeatable admin tasks, reporting, and operational consistency.
  • Cloud: building and supporting services in AWS, Azure, and Google — with an emphasis on secure-by-default configuration.
  • People: clear communication, documentation, and end-user support that keeps operations moving.

Experience

System Administrator

MicroImaging Source, Inc. • 03/2024 – Present

  • Administer Windows and Linux servers, including Active Directory, Group Policy, DNS, and Hyper-V virtualization.
  • Maintain network infrastructure such as Fortinet firewalls, routers, and VPN connections, as well as Ubiquiti switches and wireless networks.
  • Deploy and manage Microsoft 365 & Entra, SentinelOne EDR/XDR, NinjaOne & ConnectWise RMM, and Veeam & Macrium Reflect backup solutions to ensure data security and compliance.
  • Provide responsive end-user support and training for hardware, software, and cloud services like AWS, Azure, and Google.
  • Develop and maintain PowerShell and Python scripts to automate routine administrative tasks.
  • Lead IT projects, including SaaS migrations and vendor contract negotiations, reducing downtime and improving security posture.

Projects

Mail Server Administration

Oct 2023 – Present • MXRoute

  • Started up mail server hosting through a third-party vendor (MXRoute) and administered resources.
  • Configured users and security filters; transferred 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 resources and console operations; configured CloudFront global 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 in a demo VPC to identify public access and reduce exposure.
  • Customized a Zero Trust model for a centralized firewall and designed a WAF approach.

Skills: Networking • Firewalls • Amazon VPC • Cloud Security • AWS

Education

Pasco-Hernando State College

08/2023 – 08/2026

Associate of Science: Cybersecurity and Information Technology • GPA: 4.0

Coursework

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

Program summary

This program has equipped me with a strong foundation in information technology and cybersecurity, including hands-on experience with digital forensics, network defense, and ethical hacking. It has also strengthened my ability to adapt to evolving technologies and approach challenges with curiosity, discipline, and careful attention to detail.

Certifications

AWS Certified Cloud Practitioner

11/2023 – 11/2026

CompTIA Network+

01/2025 – 01/2028

Contact

cayden@caydenwoo.com

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