About Bradley Gillap
System Administrator & Operations Leader
About Brad Gillap
For two decades, I've walked into organizations with broken systems and fixed them. It usually starts with the same story of servers crashing, frustrated users, and infrastructure held together with duct tape and hope. I build systems that actually work, and I make sure the people using them actually like using them.
Systems Thinker & Human-Centered Technologist
Technology is supposed to make things easier, not harder. The hardest problems I've solved weren't technical. They were about people getting what they need. Before I touch a server or write a script, I spend time communicating with and watching how people actually work. That's how I know what will actually help versus what just looks good on paper.
What I Do
I specialize in seeing around corners and preparing for problems before they arrive. When I saw Broadcom acquiring VMware, I migrated 50+ VMs to Proxmox two years ahead of the industry shift, training others, and saving significant resources while providing better tools.
I build the operational frameworks that let organizations function under pressure. Whether it's one hundred site network rollouts, a multi-million dollar build, or hitting PCI compliance standards, the goal is the same. Build systems that can handle more work with fewer headaches, and keep risk under control.
My Journey
At nineteen, I worked in and built a computer store that grew to two locations and became my region's tech community hub. Our community hosted LAN parties and our business customers taught me that technology's greatest purpose is bringing people together, not keeping them apart.
Transformations
- Turned legacy organizations with failing systems into modern, secure platforms.
- Led teams through modernization while investing in their growth.
- Anticipated industry changes and positioned organizations advantageously.
Expertise
- Built systems that withstood cyber attacks when comparators fell.
- Worked at every level from support to department management.
- Subject matter expert across government, non-profit, academia, and private sectors.
People First
When people feel safe, respected, and capable, they do their best work. When they don't, everybody suffers. That's why I care about culture as much as code, and people as much as servers. This is where great change management opportunities exist and are most beneficial. Not as a box to check but the core intention on how to keep people successfully working well together.
I invest in team members' growth and help them find growth opportunities. Many of my former colleagues and vendors reach out to me from time to time. We built relationships based on trust, mutual respect, shared success, and good humour.
Areas of Expertise
Enterprise Service Management & Fiscal Oversight:
- Directory Services Mastery: Stabilized and recovered corrupted Domain Controllers via ADSI Edit and FSMO role transfers, resolving deep seated legacy configuration errors.
- Security Driven GPO Architecture: Re-engineered Group Policy using a self documenting hierarchical structure, integrating PCI compliance markers and tags for audit readiness.
- Strategic Budgeting: Managed comprehensive hardware lifecycles and infrastructure upgrades on sub $100k budgets, outperforming departments with significantly higher funding.
- Endpoint Management: Optimized organizational deployment workflows using FOG, WDS, and WSUS, ensuring consistent imaging and patch management across all clients.
- Operational Leadership: Established a 'no rogue admin' culture through strict configuration standards, onpremise SharePoint management, and lead by example technical mentoring.
Enterprise Infrastructure & Protocol Expertise:
- Large Scale Deployment: Orchestrated a 100 site switch stack replacement (HPE Enterprise), completing a 12 month project in 8 months through script based automation.
- Hybrid Environment Mastery: Managed and optimized complex Cisco and HPE infrastructures, implementing LAGs and high density Aruba and Ubiquiti WAP deployments.
- Strategic Tooling: Migrated routing to pfSense and transitioned switching to Ubiquiti to provide the team with robust GUI based management tools without sacrificing performance.
- Security Architecture: Designed and initiated 802.1X and RADIUS implementation strategies to secure institutional network access and credentialing.
- Deep Packet Analysis: Utilized Wireshark and protocol analysis to resolve intermittent connectivity issues and optimize RF environments for high density public usage.
Security Infrastructure & Service Delivery:
- PCI DSS Compliance: Architected endpoint security via Wazuh and 300+ GPOs, elevating Windows client security to meet 87% of PCI DSS standards.
- Service Management: Introduced and trained staff on osTicket, scaling the platform from IT to cross departmental use in Facilities and Operations.
- Data Integrity: Implemented Chrome security monitoring to identify and mitigate shadow IT risks, such as unauthorized third party PDF tools.
- Security Culture: Fostered a 'reporting without judgment' environment, prioritizing constructive staff education over punitive measures like phishing baiting.
- Access Control: Spearheaded multi factor authentication (MFA) readiness and deployment strategies to secure institutional credentials.
Operational Efficiency & Process Automation:
- Efficiency Philosophy: Standardized a 'script first' culture, automating repetitive tasks across PowerShell, Bash, and CMD to maximize team bandwidth.
- Custom System Integrations: Developed clever bridge scripts to facilitate data transfer and interoperability between disparate software applications.
- User Centric Compliance: Authored custom toast notification scripts for graceful update management, providing users with reboot deadlines and transparent expectations.
- Diagnostic Automation: Built automated testing and diagnostic scripts into deployment workflows to ensure consistent troubleshooting benchmarks.
- Administrative Support: Consulted on and developed complex Google AppScripts and Excel automation for office staff to streamline financial and data workflows.
Knowledge Management & Grant Writing:
- Strategic Implementation: Spearheaded the first institutional Wiki, creating a centralized 'source of truth' adopted by all departments from HR to Front Line Service.
- Grant Success: Researched and authored successful grant proposals, securing critical funding for departmental and organizational technology initiatives.
- Collaborative Development: Identified and hired specialized design talent to refine documentation UX, ensuring long term ease of use and maximum staff engagement.
- Standard Operating Procedures: Developed comprehensive technical playbooks and SOPs, ensuring continuity and reliability across all IT and facility operations.
- Cross Departmental Synergy: Transformed siloed information into a shared knowledge base, reducing internal support requests and streamlining employee onboarding.
Diagnostic Methodology & System Hardening:
- Optimization: Proactively audited server logs and Event IDs to resolve underlying system conflicts, ensuring peak OS stability and performance.
- Security Remediation: Re-architected Windows File Sync services from the ground up, implementing correct ACL/SACL/DACL permission structures.
- Hardware Proficiency: Resolved critical failures in high pressure environments for AV meeting systems, 3D printers, and proprietary scanning hardware.
- Generalist Problem Solving: Applied systematic technical diagnostic methods to resolve complex mechanical, vehicle, and logistical operational issues.
- Efficiency Gains: Reduced system latency and user downtime by standardizing hardware configurations and remediating legacy configuration errors.
Capital Project Design & Delivery:
- Architecture & Design: Architected and directed technical infrastructure (network, server room, systems) for multi million dollar capital construction projects.
- Cross Functional Coordination: Coordinated with GCs, PMs, and Senior Management to integrate detailed IT specifications into architectural plans.
- Procurement Strategy: Spearheaded Technical Scope Definition for RFPs, ensuring accurate budgeting and securing appropriate vendor services.
- Scalability & HA: Provided Subject Matter Expertise to ensure physical design supported long term network scalability and High Availability (HA).
Cultivating Technical Excellence & Community:
- Led Talent Pipeline: Established and managed co-op programs, training college and high school students in real world systems administration.
- Drove Competitive Skill Development: Organized and motivated technical peers to enter and compete in external web development and programming contests.
- Community Engagement: Organized and executed high attendance technical community gatherings, often exceeding event capacity.
- Fostered High Trust Culture: Cultivated strong community and mutual support across multisite technical teams, boosting morale and reducing turnover.
Financial Strategy & Governance:
- Policy Development: Authored and finalized organizational policies for AI usage, vehicle fleet safety, and NIST aligned data disposal, all approved by a public Board.
- Strategic Grant Writing: Researched and authored successful grant proposals, providing high detail statistical reports that demonstrated clear value and ROI to third party stakeholders.
- Vendor Management: Leveraged 8+ years of retail and international negotiation experience to cultivate a high performance vendor network while eliminating underperforming service providers.
- Cross Departmental Collaboration: Partnered with HR and Administration to align IT strategy with institutional goals, ensuring policies met both operational and regulatory requirements.
- Fiscal Stewardship: Applied a 'value first' business mindset to procurement, utilizing global tech market insights to secure superior pricing and terms for hardware and services.
Operational & Logistical Management:
- Operational Oversight: Served as Operations Manager, overseeing building logistics, maintenance, and IT infrastructure integration with facility procedures.
- Fleet Management: Managed a small fleet of institutional vehicles, organizing insurance, staff licensing, and drafting comprehensive usage and safety policies.
- Strategic Asset Planning: Directed proactive multi-year asset planning (e.g., roof and HVAC), managed contractors, and provided assessments for planned replacements.
- Resource Management: Managed resource allocation, building safety protocols, and general facility services across institutional locations.
Technologies & Tools
Current Focus
Today, I'm writing, reflecting, and continuing to learn. I've taught myself AI integrations, open source language models, and development pipelines. Not because I think they'll replace us, but because I understand them as tools that need experienced pilots.
I'm looking for culture over position, for people who value demonstrated capability over credentials, and environments where saying "I don't know" is acceptable but not trying to find out is not.
Let's Connect
Technology is about connection between systems, ideas, and people. I believe the best solutions come from sharing experiences and learning from each other's challenges.
Whether you're facing similar IT transformations or just passionate about where technology is heading, I'm always interested in exchanging stories.