Matthew Weiskopf, CISSP

Director of Engineering

Chicago, Illinois, United States16 yrs experience
Highly StableAI Enabled

Key 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.
Stackforce AI infers this person is a Cybersecurity and IT Infrastructure Leader with extensive experience in enterprise environments.

Contact

Skills

Core Skills

It StrategyCybersecurityIt TransformationsIt ArchitectureIt ManagementIt Consulting

Other Skills

vendor managementrisk complianceincident responseteam managementbudget managementcybersecurity awarenesstrainingAI-driven analyticsoperational efficiencystrategic initiativescollaborationsecurity frameworksbusiness continuitydisaster recoverycloud platforms

About

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.

Experience

16 yrs
Total Experience
5 yrs 2 mos
Average Tenure
5 mos
Current Experience

Miller cooper & co., ltd.

Director, Technology & Innovation

Nov 2025Present · 5 mos

  • Miller Cooper & Co., Ltd. is one of the United State's and Chicago’s most respected independent accounting and advisory firms, known for its deep commitment to middle-market businesses. With a legacy spanning over a century, the firm blends technical precision with strategic insight to help clients grow, adapt, and thrive.
  • Nationally, Miller Cooper is recognized by INSIDE Public Accounting as a “Best of the Best” firm, a designation restricted to a small circle of firms that is not calculated by revenue or headcount, and ranks 51st among the largest U.S. accounting firms. Accounting Today places the firm at 55th nationwide, while Crain’s Chicago Business ranks it as the 10th largest accounting firm in Chicago, and is the largest independent firm in the city. These distinctions reflect Miller Cooper’s excellence in client service, talent development, and operational leadership. Its multidisciplinary teams deliver audit, tax, consulting, and transaction advisory services tailored to the unique needs of privately held companies and their stakeholders.

Orba

2 roles

Chief Information Officer and Chief Information Security Officer

Promoted

Dec 2015Nov 2025 · 9 yrs 11 mos

  • ORBA is a nationally recognized certified public accounting and financial advisory firm, consistently ranked among the industry's top performers. Honors include INSIDE Public Accounting’s “Top Accounting Firms,” Crain’s “Top 20 Largest Accounting Firms in Chicago,” USA Today’s “Top Workplace,” Chicago Tribune’s “Top Workplace,” Forbes’ “Top Tax & Accounting Firms,” and Accounting Today’s “Top 100 Firms to Watch.” ORBA’s wealth advisory arm, ORBA Wealth Advisors, manages over $250M in assets.
  • As CIO and CISO, I lead both IT and cybersecurity functions across all business units, aligning technology strategy with business goals. I manage a multi-million-dollar annual budget, build and mentor high-performing teams, and drive innovation to meet evolving organizational needs.
  • I oversee vendor partnerships, procurement, and contract management, negotiating agreements that reduce costs and increase ROI. I guide enterprise risk and compliance across frameworks including NIST, CIS, GLBA, HIPAA, GDPR, CCPA, and SEC/FINRA. I lead threat detection and incident response efforts, cutting resolution time by 35% and maintaining low critical risk exposure through recurring audits, penetration tests, and vulnerability scans.
  • As Chair of the Technology Committee, I lead strategic initiatives in collaboration with executive stakeholders. These efforts have streamlined operations and enhanced alignment between technology and business goals. As a result, operational efficiency improved by 20%.
  • I also lead the firm’s cybersecurity awareness program, promoting a culture of vigilance through targeted training and engagement. This program increased phishing detection rates by 90% and strengthened our security posture through AI-driven analytics, automation, zero trust architecture, and resilient frameworks.
  • My mission is to deliver forward-thinking strategies that protect critical assets, empower teams, and enable the business to thrive.
IT strategycybersecurityvendor managementrisk complianceincident responseteam management+2

Principal Systems and Security Architect

Dec 2015Nov 2025 · 9 yrs 11 mos

  • I lead enterprise IT and cybersecurity transformations by designing and implementing modern, resilient, and high-performing environments. My approach integrates infrastructure and security into a unified strategy that supports business growth, protects critical assets, and strengthens organizational posture.
  • I architect virtualization and server ecosystems that enhance performance, reduce downtime, and support seamless integration of business applications. I design scalable storage and database environments, remote access platforms, and standardized system configurations that streamline deployment and improve user experience. My work spans hybrid infrastructure, cloud platforms, and legacy systems, ensuring agility and reliability across the organization.
  • On the security side, I implement comprehensive frameworks that safeguard sensitive data and embed governance into daily operations. I develop policies, conduct recurring assessments, and proactively mitigate risks to maintain compliance with evolving regulatory standards. I also design and maintain business continuity and disaster recovery strategies that ensure operational stability and minimize disruption.
  • I led a full rebuild of IT and cybersecurity across multiple locations, executing architecture and implementation while mentoring junior engineers. This resulted in a 50x reduction in downtime and kept total cost of ownership within budget. I deployed a cybersecurity stack that reduced incident response time by 50% and engineered SAN environments that boosted storage I/O capacity by 16,000%. I built scalable Azure and SQL environments that tripled data capacity and improved query speed by 70 percent. I directed a Microsoft 365 E5 rollout that increased productivity by 15% and developed continuity plans that achieved 99.99% uptime with zero data loss.
  • My goal is to create secure, scalable ecosystems that empower organizations to thrive in a rapidly evolving digital landscape.
IT transformationssecurity frameworksbusiness continuitydisaster recoverycloud platformshybrid infrastructure+1

Empist

Senior Systems Architect / Senior Infrastructure Engineer

Jul 2012Nov 2015 · 3 yrs 4 mos · Chicago, IL · On-site

  • EMPIST is a top-ranked global IT Managed Service Provider, recognized in the prestigious Channel Futures' MSPMentor "Top 100" and CRN Security's "Top 100."
  • Based in Illinois, EMPIST is ranked #1 among Chicago-headquartered IT consultants by Channel Futures, and continues to lead the industry in innovation and client satisfaction.
  • As an experienced IT and cybersecurity professional, I have architected scalable and secure solutions tailored to global client needs, improving security posture, increasing operational efficiency, and ensuring system reliability. I led cybersecurity strategy and implementation, driving threat detection, incident response, and cross-functional collaboration.
  • I built and configured physical and virtual servers, architected storage area networks, and deployed Virtual Desktop Infrastructure. I led proactive monitoring, patching, and endpoint management to keep systems secure and stable. My ticket close ratio was the highest on the team, and I earned the best customer satisfaction reviews across all user levels.
  • I collaborated with global IT teams across time zones, using remote management tools to deliver responsive support. I ensured compliance with Service Level Agreements and Key Performance Indicators, often surpassing expectations. I worked directly with client leadership to resolve critical issues quickly and build trust.
  • In addition to technical operations, I supported presales engineering by helping craft proposals, budgets, and quotes that aligned with business goals. I mentored junior engineers, documented technical procedures, and built strong vendor relationships to improve team efficiency and knowledge sharing.
  • In short, I led enterprise IT delivery, support, and strategy across global environments while driving measurable results in performance, security, and client satisfaction.
server architecturecybersecurity strategyincident responsemonitoringpatchingendpoint management+2

Creeden & associates

IT Manager

Mar 2010Jul 2012 · 2 yrs 4 mos · Glenview, IL

  • Creeden is the world’s largest sales and marketing representative for brands selling to Ace Hardware, True Value, Do it Best, Orgill, Home Depot, Lowe’s, Grainger, Amazon, and other major distributors. Its client portfolio includes industry leaders like Stanley Black & Decker, 3M, Energizer Battery, Westinghouse, Kaba-Ilco Key Systems, Schlage, Fiskars, Liquid Death Water, SC Johnson, Legrand, and many more. If you walk down any aisle in a hardware store, chances are we represented a majority of brands on the shelf.
  • At Creeden, I led IT and cybersecurity initiatives that strengthened operational resilience and protected critical systems. I provided nationwide support for employees, including executive leadership, while managing system upgrades, migrations, and deployments. I worked closely with developers and IT staff to support proprietary applications, administer infrastructure, and drive innovation across departments.
  • I oversaw IT operations at major trade shows, supported mobile access, and maintained backup and disaster recovery systems. I helped manage budgets, asset inventories, and hiring efforts to build a capable and agile IT team. I delivered corporate training, developed technical documentation, and supported the Business Intelligence platform to improve reporting and decision-making.
  • Key accomplishments include migrating Exchange Server to Google Apps, upgrading systems from Windows XP to Windows 7, and maintaining 99.9 percent uptime across all systems. I administered Active Directory, group policies, DNS, and mobile device support. I standardized endpoint setups with corporate gold images and kept IT spend per employee 10 to 15 percent below industry average.
IT managementsystem upgradesdisaster recoveryActive Directorygroup policies

Self

IT Consulting / Web & Server Hosting

Aug 2003Jul 2012 · 8 yrs 11 mos · Illinois, United States · On-site

  • I’ve delivered IT and cybersecurity consulting services by partnering with clients to develop tailored solutions that improve operational efficiency and align with strategic goals. My work spans personal and business infrastructure, web hosting, and specialized server environments, all built with performance, scalability, and security in mind.
  • I configured, deployed, and maintained enterprise-grade server infrastructure within the world’s largest data center at 350 E Cermak in Chicago. These systems supported high availability and robust security protocols, ensuring consistent uptime and seamless scalability for demanding workloads.
  • I managed Debian Linux hosting environments using Apache, MySQL, PHP, and cPanel, supporting a very large base of websites with sub-100ms response times and over 98 percent SLA adherence. I also designed and maintained dedicated gaming servers, also on Linux, for titles like Half-Life, Half-Life 2, and the Counter-Strike series, optimizing gameplay and user satisfaction for very large player communities.
  • As an active member of the Microsoft Partner Network since 2005, I’ve stayed aligned with evolving industry standards to better support client needs and technology initiatives.
  • Whether deploying data center architecture or fine-tuning Linux environments, I focus on delivering reliable systems that meet real-world demands. My work reflects a commitment to precision, performance, and continuous learning across every layer of the tech stack.
IT consultingserver infrastructureweb hostingLinux environments

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