About Bob "Masa" Matsuoka
With over two decades of experience in technology leadership, Bob "Masa" Matsuoka has established himself as a pioneer in AI systems design and implementation. His expertise spans from leading engineering organizations through transformative growth to developing cutting-edge AI solutions for enterprise clients.
The Agentic AI Journey
In 2024, Masa emerged as a leading voice in the agentic AI coding community through practical implementation, research, and knowledge sharing. As the author of HyperDev (hyperdev.matsuoka.com), a specialized publication focused on practical applications, patterns, and best practices in agentic AI coding, he has become a trusted source for professionals seeking to implement autonomous AI systems in production environments.
His work in agentic AI extends beyond theory—Masa actively develops and shares implementation frameworks for integrating AI agents into production systems, contributes open-source tools for agentic AI development, and conducts workshops on agent-based application development. Through HyperDev, he explores the intersection of human creativity and AI autonomy, documenting emerging patterns in autonomous agent architectures and prompt engineering.
Technical Leadership Philosophy
As a thought leader in the AI space, Masa combines deep technical knowledge with strategic business acumen, helping organizations navigate the complex landscape of artificial intelligence and emerging technologies. His approach to technology leadership emphasizes sustainable growth, ethical AI development, and building resilient engineering teams capable of tackling tomorrow's challenges.
From serving as Head of Product Engineering and Interim CTO at Tripadvisor (managing over 550 engineers) to founding and scaling multiple technology ventures, Masa has consistently demonstrated an ability to bridge technical innovation with executive strategy. His experience includes driving M&A technical diligence, leading global engineering expansions, and transforming legacy systems into modern, scalable architectures.
Current Focus
Today, Masa serves in multiple advisory and fractional leadership roles across various innovative startups and established organizations. This portfolio approach allows him to apply his expertise across diverse industries while continuing to push the boundaries of what's possible with agentic AI systems.
Through his writing, speaking engagements, and hands-on work with emerging technologies, Masa remains at the forefront of the AI revolution, helping organizations and individuals harness the power of autonomous systems while maintaining a focus on ethical implementation and sustainable growth.
"The real breakthrough in agentic AI isn't the technology itself—it's discovering which human tasks we should automate and which we should augment. I'm more interested in the architecture of human-AI collaboration than in the hype of full automation."