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.

Jump into the action:
(00:00) Why project management eats as much time as the work itself
(00:32) Catching up before the show
(11:45) A full circle moment for Mark, Natalie, and Lindsay
(14:03) How to approach AI change management step by step
(16:46) The Claude Cowork token trap
(20:12) The critical thinking piece: don't outsource your point of view
(23:02) The four-step cycle for company-wide AI transformation
(27:24) The Claude skill that plans an entire marketing event
(33:33) How to pull context straight from the codebase
(36:06) Who owns the deck when anyone can make one
(43:20) Turning marketing into an assembly line
(45:26) Why a unique point of view matters more than more context
(48:07) Will AI ever feel as boring and as useful as Excel

Connect with Lindsay O'Brien: https://www.linkedin.com/in/lindsaykenders/

Produced in partnership with Share Your Genius: https://shareyourgenius.com/