Why Onboarding at an AI-Native Company Broke Her Definition of Fast with Lindsay O'Brien

Episode notes

What does it actually look like to onboard at a company where AI isn't a nice-to-have, but the operating system? And why does inserting AI into a workflow without thinking first make that workflow worse, not better? Pragmatico Head of Marketing Lindsay O'Brien shares her experiences on what changed for her two months into a fully AI-native company after spending the last year as one of the earliest marketers building Claude skills for brand guidelines. The conversation gets into what actually gets evaluated in an AI-native interview process, why mandating AI adoption through shame backfires, and the Claude skill Lindsay built that plans an entire marketing event end to end. Lindsay also makes the case for why a unique point of view has to come before any AI workflow, and why skipping that step is the real reason so much AI-assisted content reads as forgettable.

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