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AI Structured content Webinar

Conversational AI: The cost of ignoring structured content (webinar)

Conversational AI is everywhere, but reliable AI responses depend on reliable content. So, how do you ensure your content is reliable? In this webinar, guest Rahel Bailie, Content Solutions Strategist at Content Seriously, and host Sarah O’Keefe, Founder & CEO of Scriptorium, examined how the intersection of structured content and conversational AI has evolved. They also share practical next steps that organizations can take to create a successful AI content strategy.

Rahel Bailie: How do you know your content is ready for AI? The level 1 test is, “Is the AI agent working well?” If it’s working well, then you go to, “Why isn’t it getting the right answer?” Then, you go to the content. The content can be good or bad and can be measured in a couple of ways. Is the source content marked up well? Does it have the right semantics on it? Does it have the right metadata? Do you have a knowledge graph in the background that’s making these relationships, so that the AI can pull out the right content?

Sarah O'Keefe
May 26, 2026
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AI Content management Podcasts Structured content

Taming AI: Using AI for content conversion at scale

AI promises to transform content conversion, but what does it actually look like when you’re processing thousands of documents a day? In this episode, Sarah O’Keefe (Scriptorium) and Rich Dominelli (DCL) dig into the real-world challenges of using AI for large-scale structured content conversion.

Rich Dominelli: If you have millions of articles and you’re asking the AI, ‘What did we do for this project six months ago?” The AI has to find those articles, pull the relevant information out of those articles, summarize it, and hand it back to you. The best way of doing that is to give extra signals to the AI, structured relevant bits of information, front matter, back matter, publication date, keywords, abstract, that allows the AI to query the corpus and get the relevant chunks out of that corpus in a very quick manner. Then, it can summarize what those chunks are. So the AI almost becomes the user interface over that corpus. But to find that data in the first place, structured content is key. Structured content is key when you’re dealing with big indexes and the web, and it’s the same with AI.

Sarah O'Keefe
May 18, 2026
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AI Content delivery portal Industry insights Webinar

UI for AI: Responsible content delivery (webinar)

With AI, users are taking control over content delivery through summarization, personalization, translation, and more. But what are the risks? In this webinar, Sarah O’Keefe, CEO of Scriptorium, and Fabrice Lacroix, CEO of Fluid Topics, explore strategies and share examples of UI for AI that empower users while protecting them—and your organization—from misinterpretation, incomplete information, and compliance breaches.

As somebody who works in structured content with metadata, taxonomy, and all those other fun things, we’re telling people, you have to do the work. You have to do the work upfront because once that ingestion step happens and the AI is ingesting not structured, not consistent, not governed, not accurate, not up-to-date content, then what chance does the AI have? The AI is not going to make your content magically more accurate. It’s not magic. I mean, it can do some magic looking things, but it is not magic. Your entropy always wins. Your content will always sort of degenerate, right? So you start for your best possible, and it goes down from there. So what’s the best possible thing that you can get into your database?

— Sarah O’Keefe

Sarah O'Keefe
May 11, 2026
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AI CCMS Content management Industry insights Podcasts

Machine experience (MX): Making content work for humans and machines

Your website may look great to humans, but can machines understand it? In this episode, Sarah O’Keefe (Scriptorium) and Tom Cranstoun (Digital Domain Technologies) explore the emerging discipline of machine experience (MX). Sarah and Tom discuss what AI agents actually encounter when they visit your web pages, why microdata and metadata are critical, and what content creators must do to ensure content is consumable for both human and machine audiences.

Tom Cranstoun: Humans are looking for pictures, they’re looking for text, and they can infer. You may think, “Well, we’ve already added information on the page,” but by putting it in as microdata, it doesn’t appear on the page for the humans. It appears on the page for the machine. I think that that’s a critical distinction. We are trying to design for both. We don’t want to overload a human with information, but we do want to give the machine as much information as it can take.

Sarah O'Keefe
May 4, 2026
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AI Content governance Content management Podcasts

Who controls your content? AI and content governance

What does it actually mean to govern your content in the age of AI, and who’s really in control? In this episode, Sarah O’Keefe sits down with Patrick Bosek, CEO of Heretto, to unpack why the quality, accuracy, and structure of your content may be the most critical factors in what your users experience on the other side of an AI model.

Patrick Bosek: In today’s world, you don’t have 100% control. There are a couple of different places where this needs to be broken up. One is the end user: what they physically get and what control they have versus what control you have. Then, there’s what control you have of how the AI model is going to behave based on your information and your inputs. Whether or that model is public, like a user accessing your documentation through Claude Desktop, or private, like a user accessing your documentation through your app or website, the governance piece comes down to what control you have immediately before the model. And that breaks down into a couple of things: completeness, accuracy, and structure of the content.

Sarah O'Keefe
March 30, 2026
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AI Structured content

Good content = good AI: The fundamentals that never change

Good content fundamentals have been the foundation of effective product content for decades, and those same principles are exactly what make content AI-ready today. In this episode, Bill Swallow and Alan Pringle explain how attending to your hierarchy of content needs is the key to AI success.

Alan Pringle: Right now, AI is not going to fix bad content problems. It is going to regurgitate that bad information, giving your end users information that’s flat out wrong. If your content at the basic source level is wrong, your AI by extension is going to be wrong. And that is the unglossy, unvarnished, hard truth that is still, I don’t think, seeping in like it should across the corporate world.

Bill Swallow: It really does come back to the fact that, despite the world changing on a day-to-day basis, the fundamentals have not changed.

Bill Swallow
March 23, 2026
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AI Industry insights Webinar

Chart your AI-ready content ops career (webinar)

In this webinar, Emilie Herman, Director of Content Operations at the Financial Accounting Foundation (FAF), shares lessons from her career journey. Through the lens of publishing services and large-scale content workflows, Emilie shows how the shift from manual processes to automation mirrors what’s happening with AI, and how these adaptation techniques apply to your content ops career.

It’s isolating when you feel like it’s all on you to figure out how to reinvent your career. Reach out and talk to people. It’s nice to make a human connection, which is very important to get past AI, but also to look at what other people are doing. Collaborate, talk things through, and acknowledge that everybody’s trying to figure things out. People want to experiment! There’s strength in numbers. If you have a manager, mentor, or someone who can help put you in the room to be part of the discussion, you feel empowered to take control of your destiny.

— Emilie Herman

Sarah O'Keefe
March 16, 2026
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AI Podcasts Structured content

Check in on AI: The true measure of success for AI initiatives

In this episode, Sarah O’Keefe and Alan Pringle explore how AI transforms content delivery from static documents into dynamic, consumer-driven experiences. However, the need for human-led governance is critical, and Sarah and Alan explore issues of accuracy, accountability, governance, and more. They challenge organizations to define AI success by its ability to deliver accurate, high-impact outcomes for the end user.

Sarah O’Keefe: The metrics that are being used to measure the success of AI are all wrong. We should be measuring the success of various AI efforts based on, “Are people getting what they need? Are they having a successful outcome with whatever it is that they’re trying to do?” The metric we actually seem to be using is, “What percentage of your workflow is using AI? How many people can we get rid of because we’re automating everything with AI?” It’s the wrong metric. The question is, how good are the outcomes?

Alan Pringle
February 16, 2026
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AI Industry insights Podcasts

From black box to business tool: Making AI transparent and accountable

As AI adoption accelerates, accountability and transparency issues are accumulating quickly. What should organizations be looking for, and what tools keep AI transparent? In this episode, Sarah O’Keefe sits down with Nathan Gilmour, the Chief Technical Officer of Writemore AI, to discuss a new approach to AI and accountability.

Sarah O’Keefe: Okay. I’m not going to ask you why this is the only AI tool I’ve heard about that has this type of audit trail, because it seems like a fairly important thing to do.

Nathan Gilmour: It is very important because there are information security policies. AI is this brand-new, shiny, incredibly powerful tool. But in the grand scheme of things, these large language models, the OpenAIs, the Claudes, the Geminis, they’re largely black boxes. We want to bring clarity to these black boxes and make them transparent, because organizations do want to implement AI tools to offer efficiencies or optimizations within their organizations. However, information security policies may not allow it.

Sarah O'Keefe
January 26, 2026
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AI Structured content Webinar

Why Cheap Content Is Expensive and How to Fix It, featuring Dawn Stevens

Will cheap content cost your organization more in the long run? In this webinar, host Sarah O’Keefe and guest Dawn Stevens share how poor workflows, inaccurate source data, and the commoditization race can undermine both product quality and brand trust. Sarah and Dawn also discuss why strategic staffing and mature content ops create the foundation your AI initiatives need to deliver reliable content at scale.

Sarah O’Keefe: I write content that’s great for today. Tomorrow, a new development occurs, and my content is now wrong. We’re down the road of “entropy always wins.” We’re heading towards chaos, and if we don’t care for the content, it’ll fall apart. So what does it look like to have a well-functioning organization with an appropriate balance of automation, AI, and staffing?

Dawn Stevens: I think that goes back to the age-old question of, “What are the skills that we really think are valuable?” We have to see technical documentation as part of the product, not just supporting the product. That means that we, as writers, are involved in all of the design. As we design the documentation, we’re helping design the UX.

Sarah O'Keefe
November 24, 2025
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AI Content pitfalls Podcasts Structured content

Futureproof your content ops for the coming knowledge collapse

What happens when AI accelerates faster than your content can keep up? In this podcast, host Sarah O’Keefe and guest Michael Iantosca break down the current state of AI in content operations and what it means for documentation teams and executives. Together, they offer a forward-thinking look at how professionals can respond, adapt, and lead in a rapidly shifting landscape.

Sarah O’Keefe: How do you talk to executives about this? How do you find that balance between the promise of what these new tool sets can do for us, what automation looks like, and the risk that is introduced by the limitations of the technology? What’s the roadmap for somebody that’s trying to navigate this with people that are all-in on just getting the AI to do it?

Michael Iantosca: We need to remind them that the current state of AI still carries with it a probabilistic nature. And no matter what we do, unless we add more deterministic structural methods to guardrail it, things are going to be wrong even when all the input is right.

Sarah O'Keefe
November 17, 2025
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AI Content debt Podcasts

The five stages of content debt

Your organization’s content debt costs more than you think. In this podcast, host Sarah O’Keefe and guest Dipo Ajose-Coker unpack the five stages of content debt from denial to action. Sarah and Dipo share how to navigate each stage to position your content—and your AI—for accuracy, scalability, and global growth.

The blame stage: “It’s the tools. It’s the process. It’s the people.” Technical writers hear, “We’re going to put you into this department, and we’ll get this person to manage you with this new agile process,” or, “We’ll make you do things this way.” The finger-pointing begins. Tech teams blame the authors. Authors blame the CMS. Leadership questions the ROI of the entire content operations team. This is often where organizations say, “We’ve got to start making a change.” They’re either going to double down and continue building content debt, or they start looking for a scalable solution.

— Dipo Ajose-Coker

Sarah O'Keefe
November 3, 2025
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AI Localization Podcasts

Balancing automation, accuracy, and authenticity: AI in localization

How can global brands use AI in localization without losing accuracy, cultural nuance, and brand integrity? In this podcast, host Bill Swallow and guest Steve Maule explore the opportunities, risks, and evolving roles that AI brings to the localization process.

The most common workflow shift in translation is to start with AI output, then have a human being review some or all of that output. It’s rare that enterprise-level companies want a fully human translation. However, one of the concerns that a lot of enterprises have about using AI is security and confidentiality. We have some customers where it’s written in our contract that we must not use AI as part of the translation process. Now, that could be for specific content types only, but they don’t want to risk personal data being leaked. In general, though, the default service now for what I’d call regular common translation is post editing or human review of AI content. The biggest change is that’s really become the norm.

—Steve Maule, VP of Global Sales at Acclaro

Bill Swallow
October 20, 2025
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AI Learning content Podcasts

From classrooms to clicks: the future of training content

AI, self-paced courses, and shifting demand for instructor-led classes—what’s next for the future of training content? In this podcast, Sarah O’Keefe and Kevin Siegel unpack the challenges, opportunities, and what it takes to adapt.

There’s probably a training company out there that’d be happy to teach me how to use WordPress. I didn’t have the time, I didn’t have the resources, nothing. So I just did it on my own. That’s one example of how you can use AI to replace some training. And when I don’t know how to do something these days, I go right to YouTube and look for a video to teach me how to do it. But given that, there are some industries where you can’t get away with that. Healthcare is an example—you’re not going to learn how to do brain surgery that someone could rely on with AI or through a YouTube video.

— Kevin Siegel

Sarah O'Keefe
October 6, 2025
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AI Localization Podcasts

AI in localization: What could possibly go wrong? (podcast)

In this episode of the Content Operations podcast, Sarah O’Keefe and Bill Swallow unpack the promise, pitfalls, and disruptive impact of AI on multilingual content. From pivot languages to content hygiene, they explore what’s next for language service providers and global enterprises alike.

Bill Swallow: I think it goes without saying that there’s going to be disruption again. Every single change, whether it’s in the localization industry or not, has resulted in some type of disruption. Something has changed. I’ll be blunt about it. In some cases, jobs were lost, jobs were replaced, new jobs were created. For LSPs, I think AI is going to, again, be another shift, the same that happened when machine translation came out. LSPs had to shift and pivot how they approach their bottom line with people. GenAI is going to take a lot of the heavy lifting off of the translators, for better or for worse, and it’s going to force a copy edit workflow. I think it’s really going to be a model where people are going to be training and cleaning up after AI.

Sarah O'Keefe
August 4, 2025
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AI Webinar

Ready, set, AI: How to futureproof your content, teams, and tech stack (webinar)

Your customers expect intelligent, AI-powered experiences. Is your content strategy ready for an AI-driven world? After a popular panel at ConVEx San Jose, the team at CIDM brought the conversation online in this webinar.

AI is going to require us to think about our content across the organization, across the silos, because at the end of the day, the AI overlord, the chatbot is out there slurping up all this information and regurgitating it. The chatbot doesn’t care that, for example, I work in group A, Marianne’s in group B, and Dipo’s in group C, and we don’t talk to each other. The chatbot, the world, the consumer, sees us all in the same company. If we’re all part of the same organization, why shouldn’t it be consistent?

— Sarah O’Keefe

Christine Cuellar
June 23, 2025
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