CISSP Certified

AI Strategy, Cybersecurity & Technology Leadership

27+ years helping organizations navigate technology, secure their operations, and put AI to work with practical, results-driven solutions.

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About

Building, Securing & Transforming Businesses Through Technology

As Principal Consultant at The White Rabbit Advisory Group, I help executives and leadership teams anticipate emerging trends, navigate complexity, and make confident, high-impact decisions across cybersecurity, AI, and automation.

Leveraging my CISSP credential and deep expertise in cybersecurity strategy, compliance, and risk management, I advise organizations on how to responsibly adopt AI-driven and automated solutions without increasing risk or sacrificing governance. My focus is on practical, secure implementation that improves resilience, accelerates operations, and delivers measurable business value.

With more than two decades of leadership experience in managed IT services and cybersecurity, including senior roles at BERPL Inc. and PalmTech Computer Solutions, I have built and scaled secure, high-performing technology organizations aligned tightly with business objectives.

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27+
Years in Technology
22
Years Leading PalmTech
400+
Custom Applications Built

Career

A Track Record of Building & Leading

2025 - Present
Principal Consultant
White Rabbit Advisory Group
Helping leaders anticipate emerging trends and implement AI-driven solutions with strong security foundations. Strategy, foresight, and hands-on implementation for organizations ready to modernize intelligently.
2024 - 2025
Chief Information Security Officer
BERPL Inc. ($200M Employee-Owned Company)
Led cybersecurity governance, strategy, and oversight across all divisions. Guided clients in adopting robust security practices while aligning security initiatives with growth and innovation goals.
2003 - 2025
Founder & CEO
PalmTech Computer Solutions
Built and led a managed IT and security practice over 22 years, growing it into a trusted partner for organizations across South Florida. Successfully transitioned the company to employee ownership through BERPL's ESOP.
1985 - 2004
Co-Founder & Chief Technology Officer
Voiceware Systems, Inc.
Designed and developed 400+ custom telecommunications applications for major organizations including the FBI, CIA, United Nations, MTV, Cosmopolitan Magazine, and multiple international telecom companies.

Ventures

Where I'm Focused Today

🐇
White Rabbit Advisory Group
whiterabbitadvisorygroup.com

AI strategy and implementation consulting that delivers measurable results. From AI roadmaps to MCP integrations and process automation, WRAG helps organizations bridge the gap between AI potential and real-world business outcomes.
🤖
ChuckGPT
chuckgpt.com

AI insights and education for businesses and individuals. Practical exploration of how artificial intelligence can transform operations, enhance decision-making, and drive growth in both professional and personal contexts.

Highlights

Speaking, Writing & Recognition

Speaking

Featured Speaker at Industry Events

Regularly invited to speak on cybersecurity, AI adoption, and technology strategy at industry conferences and professional organizations.

Upcoming:

🎤 AI Engineer Miami — April 20–21, 2026, Hyatt Regency Miami

🎤 IAMCP Carolinas Chapter — April 21, 2026 (Virtual) — "Experiments in AI"

View all speaking engagements →

Amazon Bestseller

Co-Author: "Under Attack"

Under Attack book cover Amazon Best Selling Author badge

Contributing author to Under Attack: How to Protect Your Business & Bank Account From Fast-Growing, Ultra-Motivated and Highly Dangerous CyberCrime Rings, published by CelebrityPress™ alongside experts trained by Jack Canfield, Brian Tracy, and Dan Kennedy.

Chuck's chapter — "Anti-Virus Software Doesn't Work: Strategies To Protect Your Business Against Increasingly Sophisticated Malware Attacks" — drew on more than two decades of frontline cybersecurity experience.

#1 Cloud Computing #1 Network & Cloud Computing #1 Computer Network Security
View on Amazon
Certification

CISSP - Certified Information Systems Security Professional

Issued by ISC2, the CISSP is one of the most respected and rigorous certifications in information security, validating deep technical and managerial competence in cybersecurity.

Beyond the Boardroom

Life at the Table

Not every high-stakes decision happens in a boardroom. Away from consulting engagements and cybersecurity strategy, Chuck Poole is a competitive poker player who brings the same calculated thinking and composure under pressure to the felt.

In 2025, Chuck won the Moneymaker Tour Pub Poker Promotion at O'Shea's in downtown West Palm Beach, earning a complete prize package including round-trip airfare, four nights at the Hilton Aruba, an invitation to the player pool party, and a $1,700 seat in the Moneymaker Tour Main Event at The Casino Aruba, part of the Caribbean Poker Series.

On Day 1A of the $300,000 guaranteed Main Event, Chuck bagged an impressive 736,000 in chips, finishing the day as the overall chip leader. He went on to finish in the money, a result that turned more than a few heads in a field of international players.

"Winning the tournament was an unforgettable experience. The energy at the tables and the camaraderie among players made it truly special. Earning the trip to Aruba and a seat in the Moneymaker Main Event was the opportunity of a lifetime."
Read the Moneymaker Tour Feature

That tournament experience inspired a new project: an AI-built poker training app. Using "vibe coding" with Claude, Chuck built a full MTT decision trainer in a single day, complete with interactive table visualizations, a GTO-based range engine generating over 1,300 unique practice hands, and personalized leak detection across 8 categories. It went from concept to live web app between morning coffee and dinner.

Try the Poker Trainer
Chuck Poole celebrating his win at O'Shea's Pub Poker in West Palm Beach
Winning the O'Shea's Pub Poker Promotion, West Palm Beach
Chuck Poole at the poker table during the Moneymaker Tour Main Event in Aruba
Building a chip stack at the Moneymaker Tour Main Event, Aruba

Contact

Let's Connect

Whether you're exploring AI strategy, strengthening your cybersecurity posture, or looking for a technology partner who delivers results, I'd like to hear from you.

chuck@whiterabbitadvisorygroup.com
561-373-2547
West Palm Beach, Florida

Latest Writing

From the Blog

After 27 Years in Tech, This Morning Changed How I Work A hands-on look at what it's actually like to run your day with an AI assistant handling the operational details.
WRAG Blog AI strategy for businesses ChuckGPT Blog Everyday AI tips and how-tos

Frequently Asked Questions

Who is Chuck Poole?

Chuck Poole is a CISSP-certified technology leader, AI strategist, and cybersecurity expert with 27+ years of experience. He is the Principal Consultant at White Rabbit Advisory Group, founder of ChuckGPT, and Amazon #1 best-selling author of 'Under Attack.'

What is Chuck Poole's professional background?

Chuck has over 27 years in technology leadership, including 22 years leading PalmTech Computer Solutions, building 400+ custom applications, and serving as CISO. He holds a CISSP certification and has built software for the FBI, CIA, and United Nations.

What is Chuck Poole's book about?

Chuck is the author of 'Under Attack,' an Amazon #1 best-seller published by Celebrity Publishing that covers cybersecurity awareness and protection strategies for businesses and individuals.

How can I work with Chuck Poole?

Chuck consults through White Rabbit Advisory Group (whiterabbitadvisorygroup.com) on AI strategy, cybersecurity, and technology leadership. He also shares free AI tips and resources through ChuckGPT (chuckgpt.com).

What is Chuck Poole's approach to AI?

Chuck focuses on practical, results-driven AI implementation — not theory. He helps organizations and individuals put AI to work with measurable outcomes, emphasizing security, automation, and real-world business value.