Blaine Billingsley: OpenAI designer on the collaboration problem AI hasn't solved yet

Blaine Billingsley is a staff designer at OpenAI, and his path there was anything but a straight line. He studied music composition and comparative religion, played guitar in Texas for a living (he remembers checking his bank account, seeing seven dollars, and feeling pumped), then drove to San Francisco and took a data entry job at a startup. This is a preview of a premium episode. To listen to the whole thing, join our premium membership on Susbtack: https://designbetterpodcast.com/p/blaine-billingsley The engineers taught him to script his way through the work in a couple of hours, and he spent the rest of the day learning from them. From there he went on to companies big and small, including a long run on Gmail. Blaine has an allergy to corporate jargon that we found interesting. He’s known amongst his colleagues for rewriting product specs to get absolute clarity on a project, and for raising his hand in meetings to ask, “what do we really mean by ‘create a command center for work’”. We talk about why a design principle only helps if you could reasonably disagree with it, and his counterintuitive advice for working with a pushy PM: the best way to have influence is to be influenced. Then we get into how design actually works inside OpenAI. Blaine walks us through what goes into an eval, and the product design plugin he built with one engineer, whose biggest fans turned out to be the PMs and engineers who were starved for a design partner. Bio Blaine Billingsley is a member of the design staff at OpenAI, where he works on making ChatGPT a daily tool for designers and built a product design plugin focused on translation workflows like image-to-code. Before OpenAI, he was a Product Design Architect at Slack and a Staff Experience Designer at YouTube, and earlier held design roles at Airbnb, where he created a system of Host Guides, and Google, where he worked on Inbox by Gmail. He was also the sole designer at Pattern Technologies, an AI-powered sales startup acquired by Workday. Blaine studied music composition and comparative religion, played guitar professionally in Texas, and got his start in tech doing data entry at a San Francisco startup. He's known for his allergy to jargon, his love of a clear process, and his belief that a designer's job is to represent the user. Books & links mentioned Show notes Blaine Billingsley blaineb Blaine Billingsley — Design Mentor @blaineranium The Systems Bible The OpenAI Product Design Plugin Mid-air Thief Vargamae: Volume I of the Truth and Justice Pentalogy *** Premium Episodes on Design Better This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: Weekly Portfolio Club calls this summer helped our paid subscribers build portfolios that land great jobs. Experts joined us weekly to provide feedback, and we compiled lessons from each session into a portfolio design guide. We’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community. And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes. Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further. Upgrade to paid *** Learn more about your ad choices. Visit megaphone.fm/adchoices