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Beyond the Paper: A Conversation with My Career
Charles O'Brien is a technology leader who combines executive vision with deep technical expertise. He has directed security, infrastructure, and business systems teams, guiding companies through cloud transformation, M&A integration, and PCI compliance while working effectively within a variety of regulatory frameworks.
He is skilled at identifying business needs and leading initiatives with clear roadmaps, delivery milestones, and measurable outcomes. Charles works closely with cross-functional teams to align technology with business goals and deliver results that matter.
While he stays hands-on with cloud architecture, automation, and AI using AWS and Kubernetes, Charles is most proud of building strong, engaged teams. His leadership style emphasizes clarity, empowerment, and collaboration so that people do their best work. Outside of work, he enjoys outdoor activities and exploring new technologies.
Charlie Chat is an interactive AI chatbot, trained on my resume, that lets you explore my background through natural conversation.
Type a question about my career, leadership style, technical experience, or projects and Charlie Chat will respond as if we are chatting in real time.
I built Charlie Chat to experiment with AI, demonstrate how I solve problems end to end, and create a unique way to stand out as I search for my next leadership opportunity.
Charlie Chat runs on a fully serverless backend using AWS Bedrock and Python (FastAPI). The entire architecture is deployed with infrastructure-as-code using Terraform.
Visit the Dev Journal section to see how this project was designed, built and improved over time.
Yes. I am seeking IT leadership roles focused on security, infrastructure, IT transformation or product strategy.
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