Writers of Silicon Valley

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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
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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
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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
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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)

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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
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