Matthew Weiskopf, CISSP — Director of Engineering
With over 20 years of strategic leadership in enterprise IT and cybersecurity, I bridge the gap between executive vision and technical execution. My career blends hands-on engineering with boardroom strategy, enabling me to deliver scalable, secure, and resilient infrastructure across global environments. I’ve led complex system designs, cybersecurity frameworks, and architectural roadmaps that drive measurable business impact while empowering technical teams. What sets me apart is empathy rooted in real-world experience. I’ve built, rebuilt, and worked from the ground up and top down. Having been in the trenches, I understand the realities engineers face: late nights, complexity, and trade-offs. That perspective allows me to make decisions that resonate with both executives and technical teams, fostering trust, alignment, and long-term collaboration. My approach is grounded in proven IT strategy that boosts ROI, enhances productivity, and maximizes performance without compromising usability. I specialize in virtualization, storage, cloud, automation, networking, and digital transformation. I’m known for cutting costs while increasing capability and for solving problems others call impossible. To stay sharp, I maintain a home lab that rivals many enterprise setups. It runs over 300 virtual machines across every major operating system, including legacy platforms like DOS 6.22, Windows NT 4.0, and Slackware, alongside modern environments like Windows 11, Server 2025, Red Hat Enterprise Linux, and Ubuntu. My hypervisor stack includes VMware, Hyper-V, Proxmox, and XCP-ng. I simulate full enterprise desktop infrastructure with Horizon View VDI, Microsoft VDI, and Terminal Services. SCCM/Red Hat Satellite is fully deployed to manage hundreds of machines. Storage is delivered via vSAN, iSCSI, NFS, Ceph, and vVols. I have built clusters of segmented networks with routing and failover to mimic global sites in Chicago, London, Shanghai, and Sydney. I run SQL Server, MySQL, PostgreSQL, and Oracle Express for testing and experimentation. My ESAE environment spans multi-forest, multi-domain Active Directory with PAWs and privileged access boundaries. In the cloud, I operate a Microsoft 365 E5 Developer Tenant with Defender, Purview, Entra ID, Intune, and more.
Stackforce AI infers this person is a Cybersecurity and IT Infrastructure Leader with extensive experience in enterprise environments.
Location: Chicago, Illinois, United States
Experience: 16 yrs
Skills
- It Strategy
- Cybersecurity
- It Transformations
- It Architecture
- It Management
- It Consulting
Career Highlights
- Over 20 years of strategic leadership in IT and cybersecurity.
- Expert in driving secure, scalable digital transformation.
- Proven track record of reducing costs while increasing capability.
Work Experience
Miller Cooper & Co., Ltd.
Director, Technology & Innovation (5 mos)
ORBA
Chief Information Officer and Chief Information Security Officer (9 yrs 11 mos)
Principal Systems and Security Architect (9 yrs 11 mos)
EMPIST
Senior Systems Architect / Senior Infrastructure Engineer (3 yrs 4 mos)
Creeden & Associates
IT Manager (2 yrs 4 mos)
Self
IT Consulting / Web & Server Hosting (8 yrs 11 mos)