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Chris Osterhout is the Chief Strategy Officer at Diagram, specializing in digital platform strategy, CMS, DXP, eCommerce, and AI-driven digital experiences. He has led countless CMS & platform migrations, helping businesses optimize their content management systems and eCommerce platforms for better functionality and user experience. Known for his practical approach, Chris simplifies complex technical challenges and advises organizations on first-party data strategies. He helps businesses make informed technology decisions that ensure scalability, flexibility, and alignment with their goals. Chris holds Most Valuable Professional (MVP) status with multiple software platforms, recognizing his expertise in digital experience strategy, CMS, and eCommerce solutions. He currently serves on several advisory boards for leading digital platforms, where he provides guidance on go-to-market strategies, platform evolution, and orchestration capabilities.
Why Your CMS Needs to be Smarter
As AI reshapes how organizations work, control and openness are becoming critical, allowing teams to orchestrate tools, structure knowledge, and build intelligence on their own terms.
From Vision to Value: How AI Cuts Time-to-Value in Digital Strategy
Long discovery phases, unclear priorities, and a lack of execution structure delay real progress. AI has the potential to change that by speeding up how teams identify opportunities and act on them.
Headless vs. Hybrid CMS: A Guide for Organizations
This guide simplifies the key differences between headless and hybrid CMS, helping you make the best choice for your content strategy.
