Gary Campbell

Gary Campbell

Helping systems grow into better versions of themselves — without losing what makes them worth belonging to.

Guiding organizations through AI-enabled operations, systems modernization, and human-centered transformation.

Transforming Technology Into Business Value

I work at the intersection of technology, operations, and people—helping organizations modernize how they actually function, not just what tools they use. Over the past two decades, I've led enterprise-scale transformation inside a complex, people-driven organization, guiding the evolution from legacy, on-prem systems to cloud platforms, SaaS solutions, and AI-enabled workflows.

My work consistently sits in the "messy middle": translating strategy into execution, aligning cross-functional teams, and redesigning systems so they are adopted, trusted, and sustained. AI has become a meaningful part of that work—but never in isolation. I focus on practical, human-in-the-loop applications that reduce friction, surface insight, and extend human capability rather than replace it.

Increasingly, the lever has been less about the technology itself and more about how teams coordinate, decide, and execute together. Whether the work is a Copilot rollout, an EOS operating rhythm, or a cooperative capital plan, the durable improvements come from facilitating cross-functional flow and surfacing what a system is actually optimizing for — not from the tool change alone.

AI & Machine Learning Cybersecurity Cloud Integration / Azure Process Automation Microsoft Copilot 365

Current Leadership

Director of IT

Outpost Natural Foods Cooperative · Jan 2026 - Present

Leading enterprise IT modernization across infrastructure, retail systems, cybersecurity, and AI adoption for a multi-site mission-driven retail cooperative. Stewarding a phased 4-year roadmap with discipline about what to build, what to vendor, and what to leave alone. Key work includes:

  • Built a phased multi-year IT modernization roadmap (Stabilize → Harden → Adopt → Modernize) presented to the executive team and aligned to cooperative strategy
  • Leading multi-year capital planning across infrastructure, retail systems, network, and physical security for a multi-site retail environment
  • Established operational rhythms — weekly team huddles, bi-weekly CEO check-ins, structured vendor and partner engagement
  • Advancing modern collaboration and AI workflow adoption with department-level governance and human-in-the-loop discipline

Education & Professional Development

Bachelor of Information Science and Technology

University of Wisconsin-Milwaukee · Graduated May 2025

Specializations: Cybersecurity, Artificial Intelligence, and Blockchain

Honors: Graduated with 3.9 GPA · High Honors in the Major · Dean's Honor List (multiple semesters)

22 Professional Certifications

Including SAFe Introduction, Cybersecurity GRC, and extensive Microsoft/LinkedIn Learning credentials

20+ Years Experience

From technology retail to enterprise IT leadership and digital transformation

Let's Connect

If you're working on enterprise transformation, AI-enabled operations, or technology leadership challenges and want a thinking partner, I'd welcome the conversation.

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