About Bradley Gillap
System Administrator & Operations Leader
About Brad Gillap
Throughout my career, I've been lucky enough to get opportunities with organizations that had broken systems, and to help fix 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.
How I Approach the Work
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
A lot of my work is about reading where things are headed and getting ready before the change lands. When Broadcom announced the VMware acquisition, I started moving 50+ VMs to Proxmox. By the time the broader industry felt the impact, the migration was already done, the team was trained, and we had better tools at lower cost.
I build the operational frameworks that help organizations hold up under pressure. Whether it's a hundred-site network rollout, a multi-million-dollar build, or hitting PCI compliance standards, the goal stays the same: build systems that handle more work with fewer headaches, and keep risk manageable.
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
- Helped legacy organizations with failing systems move to modern, secure platforms.
- Led teams through modernization while investing in their growth.
- Read industry changes early and helped organizations prepare.
Expertise
- Built systems that held up under cyber attacks.
- Worked at every level from support to department management.
- Worked 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 and fiscal oversight.
- Directory Services: Recovered and stabilized corrupted Domain Controllers through ADSI Edit and FSMO role transfers, resolving legacy configuration errors that had built up over time.
- Group Policy: Re-engineered Group Policy into a self-documenting hierarchy, with PCI compliance markers and tags built in for audit readiness.
- Budgeting: Managed hardware lifecycles and infrastructure upgrades on a sub-$100k budget, leaning on careful planning and reuse rather than large spending.
- Endpoint Management: Standardized deployment workflows using FOG, WDS, and WSUS for consistent imaging and patching across all clients.
- Operational Leadership: Built a 'no rogue admin' culture through clear configuration standards, on-prem SharePoint ownership, and hands-on technical mentoring.
Enterprise infrastructure and protocol expertise.
- Large-Scale Deployment: Replaced 100 switch stacks across HPE Enterprise gear alongside a contracted technician, finishing a 12-month project in 8 months with script-based automation.
- Hybrid Environments: Managed Cisco and HPE infrastructures, implementing LAGs and high-density Aruba and Ubiquiti WAP deployments.
- Tooling: Migrated routing to pfSense and switching to Ubiquiti, giving the team GUI-based management tools without giving up performance.
- Security: Designed and initiated 802.1X and RADIUS strategies to secure network access and credentialing.
- Packet Analysis: Used Wireshark and protocol analysis to track down intermittent connectivity issues and tune RF environments for high-density public use.
Security infrastructure and service delivery.
- PCI DSS Compliance: Built endpoint security using Wazuh and 300+ GPOs, raising Windows client security to meet 87% of PCI DSS standards.
- Service Management: Introduced osTicket and trained staff, scaling it from IT into Facilities and Operations.
- Data Integrity: Set up Chrome security monitoring to catch shadow IT risks like unauthorized third-party PDF tools.
- Security Culture: Fostered a 'reporting without judgment' environment, focusing on constructive staff education.
- Access Control: Led multi-factor authentication (MFA) readiness and deployment to secure institutional credentials.
Operational efficiency and process automation.
- Philosophy: Standardized a 'script-first' culture, automating repetitive tasks across PowerShell, Bash, and CMD to free up the team's time.
- System Integrations: Wrote bridge scripts to move data between software that wasn't designed to talk to each other.
- User-Centric Compliance: Wrote custom toast notification scripts for update management, giving users clear reboot deadlines and honest expectations.
- Diagnostic Automation: Built automated testing and diagnostics into deployment workflows for consistent troubleshooting.
- Administrative Support: Helped office staff with Google AppScripts and Excel automation to streamline financial and data work.
Knowledge management and grant writing.
- Implementation: Launched the institution's first Wiki, building a centralized 'source of truth' that every department adopted, from HR to front-line service.
- Grant Writing: Researched and wrote grant proposals that secured funding for departmental and organizational technology initiatives.
- Collaborative Development: Brought in specialized design talent to refine the documentation's UX, keeping it usable for the long term.
- Standard Operating Procedures: Wrote technical playbooks and SOPs to keep IT and facilities operations consistent and reliable.
- Cross-Departmental Work: Turned siloed information into a shared knowledge base, which cut internal support requests and smoothed onboarding.
Diagnostic methodology and system hardening.
- Optimization: Audited server logs and Event IDs to catch and resolve underlying system conflicts before they grew, keeping OS stability and performance steady.
- Security Remediation: Rebuilt Windows File Sync services from the ground up, putting correct ACL, SACL, and DACL permission structures in place.
- Hardware: Resolved critical failures under pressure for AV meeting systems, 3D printers, and proprietary scanning hardware.
- Generalist Problem-Solving: Applied systematic diagnostic methods to mechanical, vehicle, and logistical issues that fell outside normal IT scope.
- Efficiency Gains: Cut system latency and user downtime by standardizing hardware configs and clearing out legacy configuration errors.
Capital project design and delivery.
- Design: Defined the technical infrastructure (network, server room, systems) for multi-million-dollar capital construction projects.
- Cross-Functional Coordination: Worked with GCs, PMs, and senior management to fold detailed IT specifications into the architectural plans.
- Procurement Strategy: Led the technical scope definition for RFPs to keep budgeting accurate and vendor services appropriate.
- Scalability and HA: Advised on physical design so it supported long-term network scalability and high availability (HA).
Building technical teams and community.
- Talent Pipeline: Set up and ran co-op programs, training college and high school students in real-world systems administration.
- Skill Development: Encouraged technical peers to enter external web development and programming contests.
- Community Engagement: Ran technical community gatherings that regularly filled past capacity.
- Culture: Built trust and mutual support across multi-site technical teams, which helped morale and reduced turnover.
Financial strategy and governance.
- Policy Development: Wrote and finalized organizational policies for AI usage, vehicle fleet safety, and NIST-aligned data disposal, all approved by a public board.
- Grant Writing: Researched and wrote grant proposals with detailed statistical reports showing clear value and ROI for third-party stakeholders.
- Vendor Management: Drew on 8+ years of retail and international negotiation experience to build a reliable vendor network and part ways with providers that weren't delivering.
- Cross-Departmental Collaboration: Partnered with HR and Administration to align IT strategy with institutional goals, so policies met both operational and regulatory needs.
- Fiscal Stewardship: Brought a 'value-first' mindset to procurement, using global market insight to get better pricing and terms on hardware and services.
Operational and logistical management.
- Operational Oversight: Held a temporary operations role covering building logistics, maintenance, and IT infrastructure integration with facility procedures.
- Fleet Management: Managed a small fleet of institutional vehicles, handling insurance, staff licensing, and usage and safety policies.
- Asset Planning: Ran proactive multi-year asset planning (roof, HVAC), managed contractors, and provided assessments for planned replacements.
- Resource Management: Handled resource allocation, building safety protocols, and general facility services across 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.