Everything is designed, including leadership.
Matthew Holloway has applied that principle to turn complex enterprise technology into adoption, retention, and revenue impact. A six-time founder and former design/product executive at Apple, SAP, WebMD, Shutterfly, and SnapLogic, he builds organizations that deliver value with clarity and rigor.
Through this website he shares how AI changes design leadership: agent-based workflows, decision automation, new UX surfaces, and the metrics that matter in AI-native organizations. This site highlights the principles behind that work: how AI alters problem selection, how teams design for speed and reliability, and how leadership ensures transparency, governance, and value realization. It provides concise guidance for organizations seeking to use AI not as an add-on, but as a core source of advantage.
Speaking on Design Leadership
Learn how to increase your market share, improve customer satisfaction, and establish competitive advantages. My talks explore the full spectrum of design leadership and the transformative impact of GenAI, inspiring bold thinking and meaningful change.
Start-up & Board Advisor
I have co-founded three successful start-ups, and helping nine others achieve success. Learn how I can can help you make your idea into a viable business.
Executive Coaching
Even seasoned leaders need help from time to time. Learn how I can help you reflect, focus, and grow into your potential. I can help you navigate the organizational, operational, and personal challenges to become an effective design leader.
Professional Experience
A curated snapshot of how I’ve led from the front, leveraging design to drive the business forward, while fostering mentorship, growth, and excellence, cultivating high-performing teams while advancing the practice of design.
Fine Art Portfolio
Creativity is in every facet of my life— whether its as an executive and design leader, or as a human being and volunteer. I have painted my entire life and exhibited in galleries up and down the west coast and I am fortunate to have my work in private collections around the world.
