Chris Osterhout

Chris Osterhout is the Chief Strategy Officer at Diagram, where he advises organizations on digital transformation, AI-driven experience strategy, enterprise content ecosystems, and long-term technology planning. With deep expertise in digital experience platforms, CMS modernization, personalization, and first-party data strategy, Chris helps organizations navigate complex technology decisions while aligning digital investments with business outcomes.

Over the course of his career, Chris has led countless CMS migrations, platform upgrades, and enterprise modernization initiatives across healthcare, higher education, manufacturing, membership organizations, and enterprise B2B organizations. His experience spans platforms and ecosystems including Optimizely, Umbraco, HubSpot, Microsoft Azure, and emerging AI orchestration technologies.

Chris is known for bridging the gap between executive leadership and technical execution. He works closely with leadership teams to simplify complex digital ecosystems, evaluate composable and AI-enabled architectures, and develop practical strategies that balance innovation with operational realities.

His current areas of focus include AI-enabled workflows, enterprise personalization, first-party data orchestration, and the long-term impact of generative AI on digital operations, customer engagement, and organizational structure. Recognized for his practical and business-focused approach, Chris brings a rare combination of strategic vision, platform expertise, and operational understanding to organizations navigating digital change.