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STORY
I have spent 25 years at the intersection of enterprise strategy and human decision making. It started in 2001 when I founded Gaddis Events, a Microsoft preferred executive engagement firm that grew to 25 people and became one of the most trusted names in CXO engagement. Over 16 years I built the CIO Summit brand from the ground up into a waitlist only series of 58 executive summits, coaching Microsoft executives on exactly what Fortune 500 technology leaders needed to hear and designing every experience around the real challenges CIOs faced, not around a vendor's product timeline. That work taught me something that has never left me. The companies that earn lasting trust are the ones that show up with clarity, credibility, and a genuine plan for advancing their customer's business. After closing Gaddis Events I moved inside Microsoft's Azure Data and AI organization, where I spent nearly four years as a sales enablement and business manager supporting global sellers on Azure SQL modernization. I led the development of a telemetry driven seller dashboard that gave visibility into 34,000+ accounts and influenced $20B+ in annual revenue. I championed AI powered licensing tools used by 4,000+ sellers and delivered over 120 global enablement sessions driving thousands of monthly seller engagements. What I brought to that work was not just operational discipline. It was 16 years of understanding how the buyers on the other side of those seller conversations actually think. What drives me is the translation. From data to insight. From insight to action. From complexity to clarity. I have always believed that the most powerful thing you can do for a seller is give them the right intelligence, framed for the right audience, at exactly the right moment. That belief has shaped everything I have built. Away from the work, you will find me in the Pacific Northwest forest most weekends. The woods are where I process, create, and reconnect with the instincts that make the work better. I am also a practicing visual artist who independently produces graphics, video, and creative assets, a dimension of who I am that shows up directly in the quality and creativity of everything I build professionally. Wondergeist is where all of it lives. The strategy and the art. The enterprise and the forest. The career and the person behind it. If any of this resonates with what you are building, I would love to connect.
EVIDENCE
Resume One Page Summary
Video Introduction 80 Seconds
Master Resume Two Pages Detailed
Portfolio

PORTFOLIO

[1000's of photos in the works - stay tuned]

Every weekend, the woods. Every week, the work. Diane Gaddis finds her sharpest thinking at the intersection of wild places and complex problems.
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About
Diane Gaddis

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