Chris Osterhout
Chief Strategy Officer @ Diagram
Chicago, Illinois, United States
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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.
Topics
Breaking Data Silos with Umbraco Compose: Practical Paths to Enterprise AI
Enterprise teams are moving fast on AI, but many initiatives stall before they reach real impact. The issue is rarely the model. It is fragmented data. Customer data sits in CRMs, product and operational data lives elsewhere, and content often remains isolated inside the CMS. Without a practical way to bring these pieces together, AI stays narrow, brittle, and hard to scale.
This session looks at why data silos remain the most common blocker to enterprise AI and how a composable approach changes the equation. Using Umbraco Compose, we will explore how structured content, external data sources, and business context can be brought together without large-scale migrations or heavy custom builds.
Attendees will see how Umbraco can act as a composition layer rather than just a content repository, enabling AI use cases like personalization, intelligent content delivery, and automation across channels. The focus is on practical architecture, low-code integration patterns, and realistic ways teams can move from isolated pilots to AI solutions that actually deliver value.
Beyond Pageviews: Using Umbraco to Power Real Personalization
Most organizations rely on third-party analytics tools like Google Analytics to make website decisions—but those tools miss up to half of your traffic and can’t connect the dots between visits and real outcomes. In this session, we’ll explore how first-party data built into your CMS can reveal what’s really happening on your site and how to act on it. You’ll see how Umbraco Engage helps teams move beyond passive reporting into real-time personalization, lead capture, and decision-ready insight. We’ll cover practical examples of scalable personalization tactics that work right away—no complex setup required. If you’re ready to make your CMS more than just a content hub, this session will show you how to turn it into a lead-generating engine.
Enterprise Readiness with Umbraco: Myths, Experiences, and the Road Ahead
As organizations look to scale their digital platforms, questions often arise about whether open-source solutions can meet enterprise expectations for security, compliance, integrations, and long-term support. In this panel, we’ll explore what "enterprise readiness" really means in the context of Umbraco—and what it does not..
Whether you’re already running enterprise-level work or just curious about moving in that direction, this session will provide clear guidance, practical insights, and a look at how Umbraco is scaling with its partners to meet enterprise demands—without losing sight of its roots in accessibility and community.
Umbraco US Business Summit 2025
Leveraging Umbraco to Create Personalized Experiences in a First-Party Data World
In an era where first-party data is becoming increasingly critical for effective digital marketing and user engagement, leveraging the right tools is paramount. This session will explore how Umbraco can be utilized to create highly personalized digital experiences using first-party data. Attendees will learn practical strategies to harness the power of Umbraco's flexible CMS capabilities, integrating data insights to drive user engagement and business growth. This talk will provide real-world examples and actionable steps to help you transition from reliance on third-party data to a robust first-party data strategy.
How to Not Screw Up Your Umbraco CMS Upgrade
Upgrading your Umbraco CMS can seem daunting, but with the right approach, you can ensure a smooth transition. This session will cover essential strategies and best practices for upgrading your Umbraco CMS, particularly focusing on migrating from older versions like Umbraco 7 to the latest versions. We'll discuss common pitfalls, how to avoid them, and how to leverage new features effectively. Attendees will leave with actionable insights on planning, executing, and optimizing their CMS upgrade to minimize disruptions and maximize the benefits of new functionalities.
Beyond the Build: How Umbraco Powers a Unified Digital Ecosystem
Umbraco is more than just a CMS—it’s the glue that holds complex digital ecosystems together. In this session, we’ll explore a real-world case study where Umbraco seamlessly connects an AMS, LMS, HubSpot, Umbraco Commerce, Umbraco Engage, Sertifier, and more.
We’ll dive into both the business impact and the architectural strategy, showing how Umbraco’s flexibility enabled deep integrations, custom commerce extensions, and first-party data orchestration. This hybrid talk will balance technical insights with real business outcomes, demonstrating how Umbraco can streamline workflows, enhance user experiences, and drive measurable success.
If you’re looking to bridge the gap between strategy and implementation, this session will challenge your perspective on how Umbraco powers more than just content—it powers transformation.
Umbraco US Festival 2025
Headless CMS: Is It the Right Choice for Your Organization?
As 'headless' gains traction, businesses debate its relevance and benefits for their unique digital strategies. This session will demystify the concept of headless CMS and explore its benefits and challenges. We will discuss how headless CMS differs from traditional and composable DXPs, and help you determine if it aligns with your organization's goals. Attendees will gain insights into the factors to consider when evaluating a headless CMS, including flexibility, integration capabilities, and total cost of ownership. This session aims to equip you with the knowledge to make an informed decision that supports your digital strategy.
Umbraco US Festival 2024
Breaking Data Silos: Practical Low-Code Solutions for Enterprise AI Implementation
Enterprises are investing heavily in AI, but many initiatives stall at the same critical point: fragmented data. Customer data lives in your CRM, operational data in your ERP, content in your CMS, and financial data in legacy systems. Without unified data access, AI models remain limited in scope, pilots fail to scale, and ROI never materializes.
This talk addresses the #1 technical barrier to enterprise AI success: data integration and orchestration.
From Questions to Enrollments: How AI Assistants Can Cut Call Volume & Boost Applications in 30 days
Prospective students, parents, and counselors have thousands of questions, but most institutions answer them with overloaded call centers, overflowing inboxes, and hard‑to‑find web content. Meanwhile, “AI” often sounds like a multi‑year, high‑risk project that requires new tools, new teams, or a full site redesign. It doesn’t have to be that way.
This session shows how higher‑ed teams can deploy focused AI assistants on top of their existing Cascade CMS sites and tech stack to answer common admissions and student‑services questions 24/7, reduce call volume, and nudge more visitors toward starting—and finishing—applications. The emphasis is on using content you already have (program pages, FAQs, deadlines, policies) and light‑touch integrations, so most institutions can move from idea to live pilot in less than a month.
We will walk through a step‑by‑step approach: choosing the right use cases (admissions, financial aid, program discovery), curating and structuring content for AI, defining guardrails and escalation paths, and embedding assistants in your current site and channels without changing your CMS or core systems. Along the way, we will highlight real metrics institutions can track—fewer routine calls, faster answers, improved self‑service, and higher completion rates for key conversion steps. Attendees will leave with a practical blueprint they can adapt immediately for their own site
Here's Where to Start with AI Search
A Live Ask Me Anything for Marketing Teams Navigating GEO and AI Search Visibility
Panel Discussion: Ethics of AI
Join us for an engaging dialogue on the ethical implications of AI technologies in professional settings. This session brings together diverse perspectives to explore how artificial intelligence is transforming workplace dynamics and the ethical considerations this raises.
This interactive forum welcomes questions and perspectives from attendees, creating a collaborative space to consider both the transformative potential of workplace AI and the ethical responsibilities it entails. Whether you're an AI specialist or simply curious about how these technologies affect your professional life, this discussion offers valuable insights into navigating the evolving AI landscape.
Umbraco US Festival 2025
The Truth About Security In Open Source CMS – For Enterprise Leaders
In this session, you’ll hear from Zoja Antuchevič as she discusses one of Europe’s most resilient digital defence strategies in the face of growing threats tied to the Russia-Ukraine conflict. With over 15 years of experience in IT security, Zoja now serves as CEO and Partner at SolutionLab, the CREST EU Council member, and is an active member of Umbraco’s Security Team.
She’ll be joined by Emma Burstow, VP of Developer Relations at Umbraco, and Chris Osterhout, SVP of Strategy at Diagram (USA), to explore what enterprise-grade security really looks like in the open-source CMS space.
Together, this expert panel will challenge the persistent myth that open-source platforms are less secure than proprietary alternatives – and unpack what today’s enterprises should truly be prioritizing when choosing a CMS.
From encryption and compliance to transparency, architecture, and practical implementation, this session will give you a grounded, honest, and forward-looking perspective on open-source security in 2025.
2025 Webinar: Panel Discussion
How Umbraco Orchestrates Business
Umbraco Business Summit 2025 – Odense, Denmark
A panel discussion exploring how organizations can leverage the Umbraco platform to drive growth—both for their own business and for the clients they serve.
Umbraco Business Summit 2025 – Odense, Denmark
Ektron and Episerver side-by-side
Helping organizations plan the transition from Ektron to Episerver CMS
Episerver Ascend
10 Ways to Spend More Time Innovating Your Digital Experiences
Helping marketers leverage the Episerver platform to reduce time-to-market.
Episerver Ascend
How to Leverage Abandoned Carts in Episerver Commerce to Increase Revenue
Helping marketers and technologists learn tactics to calculate ROI on abandoned shopping cart recovery.
Episerver Ascend
How to not Screw up your Episerver Migration
Walking Ektron customers through the process of migrating their CMS from Ektron to Episerver.
Episerver Ascend
10 Things Ektron Customers Should Know About Episerver
Benefits of moving to the cloud for you as an Ektron customer
Episerver Ascend
Turning Website Visits Into Results
Most websites are still stuck treating every visitor the same. Same message. Same experience. Same CTA. But today’s audience? They expect more—and honestly, they deserve it.
Stop talking at your audience and start connecting with them.
Chicago, IL and Charlotte, NC
Turning Higher Ed Website Visitors into Applicants
Boost Applications by Engaging Students Where It Matters Most—Your Website
With declining enrollment and tighter budgets, higher education institutions must make every website visit count. Traditional recruitment methods alone can’t keep up with shifting demographics and rising competition.
The key to driving more applications? First-party data and personalization. In this webinar, we explore how colleges and universities can maximize their existing website traffic by implementing smarter engagement strategies and leveraging data-driven insights.
Learn how institutions are preparing for a cookieless future, integrating the right technologies, and turning prospective students into applicants with the power of personalization.
2025 Webinar
Cutting Through the Noise on Umbraco Upgrades
A Live Ask Me Anything for IT and Marketing Leaders Who Need Answers
Beyond the Click: Rethinking Measurement in AI-Driven Search
A Live Ask Me Anything for marketing and analytics leaders who know their dashboard isn’t telling the whole story
Umbraco US Festival Upcoming
Codegarden 2026 Sessionize Event Upcoming
Umbraco Partner Summit (NYC)
Umbraco US Advisory Board
Umbraco US Festival 2025 Sessionize Event
Umbraco US Festival Sessionize Event
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