Gary Campbell

About Me

Enterprise Technology & Business Reinvention Leader

My Work & Philosophy

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.

This includes leading organization-wide Copilot adoption, designing internal knowledge systems, building AI-assisted workflows for sales and operations, and establishing governance models that respect data privacy, security, and trust.

What Defines My Approach

Systems Thinking

Grounded in real operational constraints, I understand how systems interact and influence each other across the enterprise.

Change Management

Meeting people where they are—ensuring technology adoption through empathy, training, and continuous support.

Clear Translation

Bridging the gap between executives, technical teams, and frontline users with clear, actionable communication.

Durable Transformation

A bias toward small wins that compound into lasting organizational change and sustainable business value.

Core Competencies

AI & Machine Learning

Large Language Models, Generative AI, Microsoft Copilot Studio, AI-enabled operations

Cybersecurity

Governance Risk & Compliance (GRC), Zero-Trust Architecture, Security Awareness Training

Cloud Integration

Azure Architecture, Cloud Migration, SaaS Integration, Hybrid Infrastructure

Process Automation

Power Automate, Workflow Design, Digital Transformation, System Integration

IT Governance

IT Strategy, Project Management, Vendor Management, Budget Planning

Leadership Development

Team Building, Cross-functional Collaboration, Strategic Communication, Mentorship

Current Focus

I'm especially drawn to roles where the challenge is not inventing new technology, but re-imagining workflows, decision-making, and organizational behavior at scale.

Right now that work shows up at Outpost Natural Foods Cooperative, where I lead IT modernization for a multi-site mission-driven retail cooperative — building a phased 4-year roadmap, modernizing infrastructure and security posture, and bringing AI into operations carefully and on the team's terms.

In addition to my work at Outpost, I run Compoundry Advisors, an independent IT and AI strategy practice for mission-driven organizations.

Education

Bachelor of Information Science and Technology

University of Wisconsin-Milwaukee · 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)

Focused on the intersection of technology, security, and innovation. The program combined applied data, information security, and system design with hands-on exploration of AI, blockchain, and penetration testing. Developed a strong foundation in digital transformation strategy, data analytics, and secure process automation—skills I continue to apply in enterprise AI integration and business technology leadership.

Career Journey

20+ Years in Technology & Operations

From technology retail at CompUSA, to two decades of enterprise IT leadership at Zilli Hospitality Group, to now leading IT at Outpost Natural Foods Cooperative — my career has been defined by bridging technical complexity with business value. I've held roles spanning technical support, systems administration, digital marketing, and enterprise technology leadership. Full role history on the Work page.

Hospitality & Service Industry Expertise

Early career experience in restaurant management and operations gave me deep insight into people-driven businesses — understanding workflow, service delivery, and the critical role of technology in supporting frontline teams.

Credentials

Education

Bachelor of Information Science and Technology

University of Wisconsin-Milwaukee · 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)

Certifications

22 professional certifications spanning cybersecurity, AI/ML, cloud, project management, and leadership.

Recent:

  • SAFe Introduction · Scaled Agile · Issued Oct 2025
  • Cybersecurity Foundations: GRC · LinkedIn Learning · Issued Jul 2025
  • Machine Learning Foundations · LinkedIn Learning · Issued Mar 2024
  • AI for Business Leaders · LinkedIn Learning · Issued Feb 2024
  • Cloud Computing: Azure · LinkedIn Learning · Issued Jan 2024

Full list on LinkedIn →

Honors & Awards

  • High Honors in the Major — UW-Milwaukee, School of Information Studies (May 2025)
  • Dean's Honor List — UW-Milwaukee, multiple semesters
  • CaterSource Mixology Award Nomination — Coast Restaurant (2005)
  • Lowest Cost of Goods in Regional District — Houlihan's Restaurants, four consecutive years

Professional Organizations

  • InfraGard — FBI/private sector partnership for critical infrastructure protection · Member since Jan 2025
  • ISSA Milwaukee — Information Systems Security Association · Member since Sep 2024
  • Leading Caterers of America — Industry Participant since 2024 (panelist, 2025 Executive Summit)

Volunteering & Community

  • Big Brothers Big Sisters of America — Volunteer mentor since Sep 2025 · Active
  • Elementary School Reading Mentor — Various Wisconsin schools · 2010-2015
  • Boys & Girls Club Washington County — Hartford Lincoln location summer programming · 2013