Copilot Roll-Out
95% adoption in 2 months; +15% productivity.
About Me
Results-driven IT leader aligning technology with business goals, hardening security posture, and cultivating high-performing teams. Rolled out Microsoft Copilot to 95% adoption in two months and maintained zero ransomware incidents.
B.S. in Information Science & Technology (3.93 GPA) from the University of Wisconsin–Milwaukee; CompTIA Security+/PenTest+ studies; active InfraGard & ISSA memberships.
Career Snapshot
Senior Technology Director · Zilli Hospitality Group
2023 – Present- Directed a $400k tech budget & 10-person team; improved on-time task completion 12%.
- Deployed Azure Sentinel & SentinelOne EDR, cutting breach risk 40%.
- Drove phishing click rates from 22% to 5% with Cofense simulations & training.
IT & Marketing Director · Zilli Hospitality Group
2015 – 2023- Launched digital ad & loyalty programs, raising qualified leads 30% & sales 25%.
- Cut communication costs 20% by migrating to Microsoft Teams.
IT Director · Zilli Hospitality Group
2010 – 2015- Rolled out MFA & BitLocker on 100+ endpoints (NIST SP 800-171 compliant).
- Developed enterprise-wide risk assessment & asset management framework.
Early Career – Hospitality & Marketing
2003 – 2009Bar Manager → Marketing Manager: launched Milwaukee’s first OpenTable integration & grew beverage revenue 15%.
Speaking Engagements
- Event Technology ROI: Catersource Conference & Tradeshow, Las Vegas, NV (March 2014) – Co-presented with James Zilli on maximizing tech-investment ROI for catering businesses.
- Modern Technology – iPad & iPhone: Catersource Conference, Las Vegas, NV (April 2011) – Presented a breakout session on leveraging mobile tools for event management.
Recommendations
“Gary’s bar-manager background gives him a sixth sense for client needs—critical for IT projects that impact customers.”
“He bridges creative and technical worlds—conceives bold ideas, executes them, and tracks ROI.”
“A dedicated IT leader who supports and guides colleagues with innovative methods.”
Selected Projects
Fusion→Empower Migration
Zero-downtime ERP/CRM migration; reduced errors 30%.
Cybersecurity Tabletop
Mean time-to-response reduced 40%.
Vendor Efficiency Program
Projected $250k savings via supplier grants.
Cradlepoint Event Wi-Fi
Launched cellular-backed Wi-Fi rentals.
Interactive Copilot Training
Micro-learning for 80+ staff.
Insights & Reads
Featured LinkedIn Posts
Apple in China – Book Review
Supply-chain forecasting insights.
Read on LinkedInGraduation Milestone
First-gen bachelor reflections.
Read on LinkedInSam Walton: Made in America
Vendor partnerships & cost leadership takeaways.
Read on LinkedInOn My Bookshelf
The Psychology of Money
Behavioral finance insights.
Poor Charlie’s Almanack
Munger’s mental models & inversion.
Trillion Dollar Coach
Bill Campbell’s leadership playbook.
When Breath Becomes Air
Meaning, mortality & purpose.
The Genesis Machine
Synthetic biology future tech.
Sam Walton: Made in America
Retail strategy & partnerships.
Beyond Work
Personal Fitness
5k runs & daily Concept2 rowing sharpen focus.
Language Learning
Duolingo Russian streak spans 120+ days.
Martial Arts
Green belt in Hapkido—discipline & balance.
Volunteer Work
- Boys & Girls Club (2013)
- Rossman Elementary (2017–present)
- Humane Society Dog Walker (2022)
Professional Orgs
- InfraGard
- ISSA Milwaukee
- FUEL Milwaukee
Honors & Awards
“Best Mixology” CATIE finalist.