35: Brie Wolfson - Loving Attention & Ease in Craft

Full transcript and all links: ⁠ https://dialectic.fm/brie-wolfson ⁠ Brie Wolfson ( X ) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus , where she works closely with CEO Patrick O’Shaughnessy across investing and media and spearheaded Colossus Review , their new print publication known for superb long form profiles. Brie also recently joined AI-programming behemoth Cursor as Head of Employee Experience and wrote about the company’s culture . She has worked with craft-oriented software companies throughout her career, including Stripe —where she helped launch Stripe Press and the company’s planning function, among other things—and Figma , where she worked on Education. In her words, she is drawn to companies where the reality is even more impressive than the reputation, and she has publicly and privately worked with a number of the most impressive leaders in Silicon Valley on marketing, culture, and storytelling. We cover a broad range of Brie’s expertise, including craft, marketing, organizational culture, unlikely career paths, and taste, editing, and writing. This includes how AI is causing companies to become even more oriented around the empowered individual contributor and who the best of them, including company leaders, are focused on an attunement to details that she likens to “finger feel.” We also talk about why she believes marketing should be a kind of truth-telling, closing the gap between reality and perception.