Behind the Docs

Heretto
  • 5.0 (1)
  • TECHNOLOGY

Welcome to Behind the Docs — the podcast that spotlights the people who make technical content come to life. Whether you're a seasoned tech writer, content strategist, or just curious about the brains behind the docs you rely on every day, this show is for you. Each episode features real conversations with the folks who build help sites, craft user guides, and keep the content engine running behind the scenes. No jargon, just smart, engaging stories about the work, the wins, and the humans making it happen.

  1. MAR 31

    What Great Documentation Actually Means in Cybersecurity - Jeff Cross at Arctic Wolf

    Jeff Cross didn't plan to become a technical writer. He started a computer science degree, dropped out, spent a year trying to make it as a fiction writer, went back for a philosophy degree, considered academia, and then — almost by accident — realized that technical writing was the thing that made all of it make sense. Now Senior Manager of Technical Writing at Arctic Wolf, Jeff has spent years doing some of the most complex content work in the industry: documenting third-party security integrations he has no direct access to, managing a full DITA migration while keeping up with release cycles, and pulling off a content carve-out from a corporate acquisition with translated content in three languages and a hard deadline. In this episode, Jeff and Patrick talk about what it really means to do great documentation work, and why the hardest parts rarely show up in a job description. They cover: - Why the security space takes documentation seriously in ways other industries don't - What happened when a product rename turned "a" into "an" across thousands of content files - How AI helped a small team execute a DITA-to-DITA migration without outside help - The checkbox doc that nobody wanted to write — and that way more people read than expected - Why technical writing is less like writing and more like investigative journalism Plus: Patrick discovers mid-conversation that Jeff was the person who fixed the BlackBerry email signature problem that drove him personally crazy for a year.

    41 min

  2. MAR 24

    Designing Documentation for Agents, Not Just Users - Dachary Carey of MongoDB and Agent-Friendly Docs Expert

    In this episode of Behind the Docs, Ren sits down with Dachary Carey of MongoDB to explore a rapidly emerging challenge: AI agents can’t reliably read your documentation and most teams don’t realize it. Dachary shares how a deep dive into agent workflows (sparked by tools like Claude Code) uncovered critical gaps in how documentation is structured, delivered, and consumed by machines. From truncated pages and hidden content to the unexpected importance of formats like llms.txt, this conversation reveals why even well-written docs can become effectively invisible to AI systems. They also dig into: how agents actually interact with documentation (and where they fail)why technical writers are becoming essential to AI successand the growing gap between companies investing in docs and those cutting them entirely If you’re thinking about AI, content strategy, or the future of technical writing, this episode is a must-listen. Important Links: Dachary's LinkedIn: https://www.linkedin.com/in/dachary/Dachary's website: https://dacharycarey.com/The Agent-Friendly Documentation Spec: https://agentdocsspec.com/The GitHub repo for anyone who wants to contribute or leave feedback: https://github.com/agent-ecosystem/agent-docs-specThe npm tool (afdocs - for Agent-Friendly docs) that documentation teams can run to see how agent-friendly their documentation is: https://www.npmjs.com/package/afdocsThe GitHub repo for that tool for anyone who finds an issue or has a suggestion or request: https://github.com/agent-ecosystem/afdocs

    36 min

  3. MAR 17

    Docs as Systems with Manny Silva of Skyflow and Doc Detective

    In this episode of Behind the Docs, Patrick sits down with Manny Silva, Head of Documentation at Skyflow, to explore what happens when technical writing evolves into full-scale content systems. From growing up building computers to working at Apple and Google, Manny shares how his path into technical communication led to a deeply systems-driven approach to documentation. Today, as a team of one, Manny is rethinking what it means to scale docs—building automated workflows that turn Slack threads into structured drafts, enforcing style guides with AI, and creating feedback loops that continuously improve content quality. He also dives into Doc Detective, his open-source project for testing documentation like code—validating procedures, capturing screenshots automatically, and ensuring docs stay accurate as products evolve. Along the way, Manny shares insights on: why technical writers are becoming content orchestratorshow AI agents are powered by documentation at their coreand what it really takes to reduce friction in modern content operations If you’re curious about the future of documentation, AI workflows, and doc ops, this episode is packed with practical ideas and forward-looking perspective. Docs as Tests website Docs as Tests book

    37 min

  4. MAR 10

    AI Isn't the Main Character with Sara Feldman of the Consortium for Service Innovation

    In this episode of Behind the Docs, Ren welcomes back Sara Feldman, Director of Member Engagement at the Consortium for Service Innovation and longtime advocate for knowledge-driven customer experience. Sara began her career as a technical writer, spending a decade embedded with support teams before diving deeper into knowledge management through Knowledge-Centered Service (KCS). That journey eventually led her to the Consortium, where she now works with member companies around the world to explore new approaches to service innovation and knowledge management. Together, Ren and Sara discuss: How KCS helps organizations capture and reuse knowledge in real timeWhy demand-driven knowledge practices produce better documentation and supportThe rise of intelligent swarming and how it could reshape how work gets routed across teamsWhy many organizations are struggling to operationalize AI despite the hypeThe importance of structured, trusted knowledge in an AI-driven worldWhy reducing customer friction matters more than simply improving efficiency Sara also shares insights from working directly with industry leaders across customer support, customer success, and service operations—and why the future of AI success will depend heavily on strong knowledge foundations. If you’re curious about the intersection of documentation, knowledge management, and customer experience, this episode offers a thoughtful look at where the industry is heading next.

    42 min

  5. MAR 3

    Clarity is the Hill with Melanie Denise Davis of Dragonfly Diva Docs

    In this episode of Behind the Docs, Ren sits down with Melanie Denise Davis — journalist-turned-technical-communication leader, AI Wrangler, and founder of Dragonfly Diva Docs. Melanie’s career spans the evolution of modern technology itself: from punch cards and mainframes to structured content and AI. She shares what it was like entering tech before technical writing was even a defined profession, helping shape the field alongside early STC efforts, and now contributing to the ISO standard defining technical communication management. Together, they explore: ✨ Why technical communicators are far more than “glorified typesetters” ✨ The difference between writing words and engineering information ✨ Why structured content is essential for AI success ✨ How technical writers are the natural curators of generative AI ✨ The importance of allies, mentorship, and resilience as a woman of color in tech ✨ Why clarity — not grammar — is the true hill to die on Melanie also discusses her role with The Content Wrangler, her work in the upcoming Women in Technology anthology, and why this may finally be the moment technical communicators step fully into their power. If you care about clarity, collaboration, and the future of AI-ready content, this episode is packed with wisdom you won’t want to miss. Helpful Links Melanie on LinkedinDragonfly Diva DocsWomen in Technical Communication

    39 min

  6. 12/02/2025

    Technical Writers Should Be Rebranded to Knowledge Engineers with Dave Koelmeyer of IDEXX

    In this episode of Behind the Docs, Patrick Bosek interviews Dave Koelmeyer, the Content Operations Manager at IDEXX. Dave shares his unexpected journey from IT support to becoming a professional technical communicator. He discusses the importance of consistency in documentation, scaling of technical content using structured content and a CCMS, and the significant role of advocacy and education to help colleagues understand the benefits of high-quality self-help content. They also touch on the future of technical content with the integration of AI and the importance of understanding business strategy and stakeholder engagement. This episode is ideal for those interested in technical communication, content management, and the evolving role of AI in documentation.

    38 min

  7. 11/25/2025

    The Philosophy of Structured Content with Jarod Sickler of Heretto

    In this special episode of Behind the Docs, Ren sits down with Heretto’s own Jarod Sickler — philosopher-turned-structured-content expert, and one of the most genuinely thoughtful voices in the documentation world. Jarod shares how a grad-school paper and a chance encounter in a Rochester coffee shop set him on an unexpected path into technical documentation (and eventually into Heretto). He opens up about the early days of learning DITA from scratch, the realities of content conversion, and why “doing life with a weight vest on” actually makes him a stronger practitioner. Together, Ren and Jarod dig into: The moment documentation shifted from “supplemental” to “part of the product”Why structured content is seeing a resurgence thanks to AIWhat new teams should actually measure before adopting a CCMSCommon misconceptions about content conversionThe coolest emerging trends in docs and in-app helpThe joy of reuse, personalization, and helping teams finally break the copy-paste cycle If you love docs, workflows, or a good origin story that starts in a coffee shop, this one’s for you.

    42 min

  8. 11/18/2025

    From Accidentally Structured to Intentionally Scalable with Sandie Markle of Blueberri

    In this episode of Behind the Docs, we sit down with Sandie Markle, content engineer and CEO of Blueberri, whose journey through food tech, structured content, and accidental content engineering is one of the most fascinating we’ve ever featured. Sandie shares how a career pivot from finance to Shanghai led her into the world of recipe platforms, shopability, metadata, localization, and the early foundations of structured content—long before she even knew what the term meant. We talk about the realities of scaling content across platforms, building teams from scratch, navigating startup chaos, and how her experience helping home cooks ultimately shaped her philosophy on documentation and user experience. We also dig into her new venture, Blueberri, where she helps food tech companies and creators turn content into scalable systems, and her upcoming book Create Once, Share Everywhere, aimed at bridging the massive gap between creators and technology. If you love content ops, structured content, or just great stories about people who carve their own path into tech, this one’s for you. Find Sandie on LinkedIn or join her book's early reader group!

    40 min
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About

Welcome to Behind the Docs — the podcast that spotlights the people who make technical content come to life. Whether you're a seasoned tech writer, content strategist, or just curious about the brains behind the docs you rely on every day, this show is for you. Each episode features real conversations with the folks who build help sites, craft user guides, and keep the content engine running behind the scenes. No jargon, just smart, engaging stories about the work, the wins, and the humans making it happen.

Information

  • Creator
    Heretto
  • Years Active
    2025 - 2026
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Heretto
  • Show Website
    Behind the Docs

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