Writers of Silicon Valley

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].

Do you enjoy the podcast? Please leave a review!
👉 Buy Margo's book, "Good Job", at her website
👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.
👉 Sign up to our UX writing newsletters
How to ace your design interview
Interviews are horrible. No one likes them. But does it have to be that way?
Margo Stern's new book, Good Job, takes on design interviews - both for candidates and for the people creating the interview process. She goes into great detail about how to actually ace a design interview, and for hiring managers, how to design an interview process that treats people like human beings.
We delve into all sorts of great discussions about interviews. How to ace them, what they get wrong, and what companies need to do to make the interview process better for designers. 
Enjoy!
What we talked about:
✅ Why interviewing is a separate skill from doing the job
✅ How candidates can prepare through self‑reflection, rehearsal, and storytelling
✅ Why the STAR method works (and why most people use it badly)
✅ The real reason case studies fall flat and how to make yours a story, not a status report
✅ How to research a company without crossing the line into oversharing
✅ The advantages extroverts have in interviews and how introverts can level the field
✅ How candidates can show genuine interest without being performative
✅ How to read red flags in interview processes (ghosting, unclear expectations, chaotic loops)
✅ The danger of applying to too many jobs and why "less, but better" works for both sides
✅ The key questions both candidates and interviewers should ask
Where to find Margo:
📖 Margo's website

Do you enjoy the podcast? Please leave a review!
👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.

Do you enjoy the podcast? Please leave a review!
👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.
👉 Sign up to our UX writing newsletters
Ditto 2.0 is here, and wants you to rethink product content
Five years ago, Ditto launched as one of the first tools built specifically for managing product copy at scale. Now? It's powering content systems for some of the biggest design teams in tech and it just relaunched with a major update.
In this episode, I catch up with co-founders Jess and Jo about what they've learned since founding Ditto, what it's like to rebuild a product from the ground up, and why strong content systems are more essential than ever especially in the age of AI.
Learn what these founders are hearing from the heads of design teams about content, why systems thinking is more important than ever, and why they're optimistic about the future of content design.
What we talked about:
✅ How Ditto's vision has changed (and stayed the same)
✅ Why rebuilding the product from scratch was the right call
✅ What they've learned from working with dozens of enterprise teams
✅ How to support content systems in companies with messy, legacy infrastructure
✅ What sales has taught them about communicating the value of content
✅ How AI is shaping expectations—and where it actually adds value
✅ Why more content designers should think like founders
Where to find Ditto:
📖 Ditto
Do you enjoy the podcast? Please leave a review!
👉 Our new course, Advanced UX Content for Product, is out! Use PODCAST20 to get 20% off.