Writers of Silicon Valley

This is the last episode of Writers of Silicon Valley. Thank you for listening, whether you've been here since the first run or found the show recently.  I'm not going anywhere. The conversations are moving to Dash+, the weekly newsletter for UXCC members, where I'll publish shorter interviews and analysis more often.  Thank you for being a part of the podcast! 👉 Use WOSV25 for 25% off a UXCC membership. This episode: When everyone at your company can build a Claude skill, you end up with thousands of them.  Sarah Mohs and Eva Ratcliffe work on the content systems team at Intuit. When skills took off across Intuit, they turned a pile of competing skills into one content plugin that points back to a single source of truth, plus a template product teams can build on. We talk about how they did it, what went wrong along the way, and what they're doing next. (Check out their blogs on UXCC: Claude Skills for content design: inside Intuit's AI build and How we stopped outsourcing decision-making to AI) What we talked about: ✅ Why letting everyone build their own skills started to erode trust in Intuit's content system ✅ How the content plugin connects skills to one canonical source instead of copying the guidelines ✅ The domain-skill template that lets product teams add their own terms and audiences without splitting off ✅ Rewriting design documentation for a machine audience, and why voice and tone is the hardest part ✅ Writing guidance for PMs, engineers and LLMs as well as content designers Where to find Sarah and Eva: Sarah's LinkedIn:  Eva's LinkedIn 👉 Use WOSV25 for 25% off a UXCC membership.

Get 25% off workshops and courses at UX Content Collective this week, until Monday October 5! AND get 50% off if you add a second enrollment.  Content design is changing quickly - and so is the bar for getting hired. Jody Allard is the head of content design at Roblox, with a long and experienced history at companies like Microsoft and Meta. She's been writing articles on the future of the industry, and authored a new book "Writing Was Never the Job" about where content design is going. She's also spent the past year hiring content designers. What impressed a hiring manager eight months ago, she says, may barely register today. In this episode, Jody joins me to talk about what actually separates strong candidates now, why simply "using AI" is no longer enough, and why product thinking, technical confidence, and a willingness to build are becoming essential parts of the job. We also discuss the changing value of big-tech experience, the two paths emerging within content design, and why people entering the field need a much clearer picture of what the job now requires. What we talked about: ✅ What hiring managers are actually looking for from content designers right now ✅ Why simply using AI has gone from a differentiator to table stakes ✅ What separates people who use AI from people who actually identify problems and build solutions ✅ Why product thinking and proactivity are becoming essential, not optional, content design skills ✅ How content design is splitting between content engineering and traditional UX work, and what both paths now require ✅ Why experience at large companies no longer automatically carries the weight it once did ✅ What content designers can start doing today to stay competitive as the role continues to change Where to find Jody: Website "Writing Was Never the Job" on Amazon LinkedIn Get 25% off workshops and courses at UX Content Collective this week, until Monday October 5! AND get 50% off if you add a second enrollment.

⭐⭐⭐ PODCAST OFFER! Get 50% off workshops and courses at UX Content Collective until Monday, August 24. Just use PODCAST50 at checkout. ⭐⭐⭐ Dave Connis is back on Writers of Silicon Valley after a very different eighteen months. Since his last appearance, Dave has been laid off, thrown himself into experimenting with AI, built new product workflows, and started creating System Design Lab: an education platform focused on systems thinking for product and content designers. In this episode, we talk about the emotional fallout of layoffs, the strange new roles appearing in content design, what AI actually looks like when you use it every day, and how to actually prove you're a systems thinker - both in an interview, and on the job.  What we talked about: ✅ What getting laid off did to Dave's confidence, identity, and relationship with work ✅ Why trying to constantly "prove your value" can lead straight to burnout ✅ The new roles emerging around AI, including design technologists, system architects, and content architects ✅ Why today's job descriptions increasingly seem to be looking for impossible "unicorn" candidates ✅ What Dave learned from months of actually building with Claude, Figma MCP, and other AI tools ✅ Why AI workflows are much harder to make reliable than LinkedIn posts would have you believe ✅ How systems thinking helps designers define concepts, objects, attributes, and relationships before AI starts building ✅ How to demonstrate systems thinking in an interview ✅ Why Dave is building System Design Lab  Where to find Dave: System Design Lab LinkedIn ⭐⭐⭐ PODCAST OFFER! Get 50% off workshops and courses at UX Content Collective until Monday, August 24. Just use PODCAST50 at checkout. ⭐⭐⭐

Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.  Jenny Williams is one of the most experienced content designers in the world. And now she's written a novel about a content designer. Jenny's worked at places like Microsoft and Google, where's worked on AI products. She could already see that the technology was exciting, terrifying, and likely to change far more than the products being built with it - including the role of content designers themselves. Then she left tech and wrote House of Liars: a novel about writers brought to a remote island to compete for a publishing prize.  At the centre of the story is Anna, a former content designer with a complicated history with AI - and, in Jenny's words, a "warped or twisted" version of herself. Jenny joins me to talk about turning her experience in content design and AI into fiction, why the best product writing requires the writer to disappear, and what we lose when content designers stop writing words and become overseers of systems that write them. What we talked about: ✅ How working on Microsoft's AI ethics team  inspired House of Liars✅ Why the book began as a memoir and became a novel about a content designer confronting AI ✅ Why content design turned out to be the perfect job for the story's protagonist ✅ How AI has become an ethical litmus test for writers, designers, and technologists ✅ What it felt like to discover that Jenny's first novel had been used to train AI without her permission ✅ Why Jenny left tech as content design shifted from writing words to overseeing systems that write them ✅ Whether UX practitioners can challenge harmful AI decisions without putting their careers at risk Where to find "House of Liars": Website Jenny's Newsletter Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product. 

Get 25% off courses, workshops, and bundles at UX Content Collective! Ends May 29.  IT'S A "BEST OF" SERIES! We're digging back into the archives and resurfacing some of the best episodes of the Writers of Silicon Valley podcast i the conversations that have held up, and in some cases gotten more relevant since they first aired. This one's with Chelsea Larsson. She currently leads content design at Anthropic, but when this conversation happened she was at Expedia. We got into the future of content design, UX writing, how AI is reshaping the work, and why content designers shouldn't cling to old definitions. And maybe…why content designers should learn Python? Worth a second listen if you caught it the first time, and a good place to start if you didn't. Things we discuss during this episode: Generative artificial intelligence Information Architecture for the Web Open AI, ChatGPT, Gemini Python Chelsea and her stuff: Chelsea on LinkedIn Smallish Book (newsletter)

🎧 Start listening on Apple Podcasts, Spotify, subscribe on YouTube, or wherever you get your podcasts. Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.  Oleksii Tkachenko has worked across software engineering, UX, and content design, which makes him unusually well-positioned to talk about what's happening in content design right now. In this episode, we talk about the growing identity crisis inside content design: the pressure to become more technical, the race to automate workflows, and the uncomfortable question sitting underneath all of it...what parts of the craft are actually worth keeping? We explore why so much AI discourse online feels detached from reality, why many companies still don't know what they want from content designers, and why the profession risks redefining itself around tools instead of outcomes. Enjoy! What we talked about: ✅ Why LinkedIn creates a distorted picture of AI adoption ✅ The three different types of companies hiring content designers right now ✅ Why "AI curiosity" means different things at different organizations ✅ The danger of optimizing for output instead of product quality ✅ The tension between craft, speed, and automation ✅ Why content designers are becoming the "context bearers" for AI systems ✅ The risk of redefining content design around tools instead of outcomes ✅ Why some people are quietly mourning the old version of the profession ✅ The similarities between today's AI shift and the rise of UX writing years ago Where to find Adedayo: Website LinkedIn Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product. 

🎧 Start listening on Apple Podcasts, Spotify, subscribe on YouTube, or wherever you get your podcasts. Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.  Adedayo Agarau is a poet, a Stanford Wallace Stegner Fellow, and a content designer who has worked on AI search at Google and on Grok at XAI. He came to content design through web writing, a Nigerian fintech startup, a browser company, and an MFA at Iowa - not the path anyone would have predicted, and exactly the kind of path that produces someone worth listening to. We talk about what it actually means to design for a large language model: how personality gets built, why guide rails are a writing problem, why the distinction between an ideal response and just a response is what separates well-designed AI from the rest...and why content designers are the best ones to do this type of work. What we talked about: ✅ How Adedayo discovered poetry through a Nigerian social app  ✅ What it was like contributing to AI-powered Google Search  ✅ Designing voice, tone, and personality for Grok  ✅ Why the X algorithm amplifies shock value and what that does to content designers  ✅ Why AI hype creates both overclaiming and unhealthy skepticism  ✅ What engineers actually want from content designers when building AI systems ✅ The case for treating data as content, not just content as data ✅ Why designing an AI agent is fundamentally the same as writing a character Where to find Adedayo: Website LinkedIn Github Get 20% off workshops and courses at UX Content Collective. For content designers who want to upgrade their thinking, check out Advanced UX Content for Product.   

Want to learn how to use AI to build with other content designers? Join the Content Design AI Accelerator. Applications open until January 30. Why wearable tech will change content design Smart glasses and wearable devices have been "just around the corner" for years. But quietly, that's starting to change. In this episode, I speak with Carly Gray, a content designer who's spent years working on AR and wearable products, including smart glasses at North and Meta. While much of the industry debates AI and screens, Carly has been designing content for products where there's little or no screen at all. We talk about what changes when content moves off phones and into the physical world, why wearables raise entirely new design and ethical challenges, and what content designers need to start learning now if they want to stay relevant as new platforms emerge. What we talked about: ✅ How Carly moved from technical writing into content design for AR and smart glasses ✅ Why smart glasses are different from VR, and why wearability matters more than novelty ✅ Designing content with extreme space constraints (or no screen at all) ✅ Using sound, voice, and companion apps to communicate when text isn't an option ✅ Why "designing for the bystander" is as important as designing for the user ✅ What wearable tech reveals about the future skill set of content designers ✅ Why conversation design and systems thinking matter more in emerging platforms Where to find Carly: Website: carlygray.ca LinkedIn: Carly Gray Twitter: @carlygray 

THANK YOU FOR 50 EPISODES!  This is the 50th episode of Writers of Silicon Valley. Thank you for listening all this time - through my bad editing skills, a three year break, and me saying "absolutely" a lot.  It means so much that you'd tune in once, let alone 50 times. So thank you :)  As an extra 'thank you' I'm offering 35% off Advanced UX Content for Product at UX Content Collective. Use PODCAST35 at checkout :) Here's to 50 more.  Content design for AI agents Christopher Greer has been creating cool content design resources for years, but his latest is a real accomplishment: a Claude Skill that hooks into Figma and critiques UX writing.  It turns out Chris is quite optimistic about the state of the content design market.  We talk about his work at Stripe, what it actually means to design content for AI agents and internal systems - not chatbots for end users, but the infrastructure, context, and governance that sit behind them. Chris shares how content design skills translate directly into agent design, why context management is now a core capability, and how content designers can scale their influence by working closer to engineering and systems. What we talked about: ✅ Why content design skills map closely to designing AI agents and systems ✅ Context management, "context rot," and why structure matters more than prompts ✅ How content designers can scale influence through internal tools and governance ✅ Working as a content designer inside an engineering-led company like Stripe ✅ What Chris learned building and open-sourcing a Claude skill for UX writing critique ✅ Why GitHub and version control are becoming practical skills for content designers ✅ The risks AI poses to junior roles, and the strategic work that won't disappear ✅ Why qualitative judgment, taste, and human evaluation still matter Where to find Chris: LinkedIn Chris's blog Chris's Claude Skill

👉 Get up to 35% off everything at UX Content Collective until December 16! It's the end of the year, which means it's time for a little reflection.  I've picked 5 clips from the most popular episodes of the year. Have a wonderful end of the year / holiday season, and I'll see you all in 2026. Any suggestions, interview ideas? Hit me up at [email protected].