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524: The First 90 Days Just Got Faster

June 26, 2026

The first 90 days have always mattered. Now AI is making them faster, sharper, and a lot less forgiving. In this episode, Drew talks with Paige O'Neill (Culture Amp), Scott Gordon (HG Insights), and Ali McCarthy (Asset-Map) about what it takes to start strong in a new CMO role. They explore how to pressure-test what you heard in the interview process, align quickly with the executive team, assess the team you inherited, and decide where marketing can create the most meaningful impact. The con...

523: The CMO Job Search Is a Two-Way Street

June 19, 2026

Some CMO opportunities look promising right up until you stop asking, "Can I land this?" and start asking, "Can I actually win at this company?"  In a market that is warmer than it was a year ago but still unforgiving, Hugh Marshall of Heidrick & Struggles argues that CMOs need to approach the search with two-way diligence. The offer matters, but so does knowing whether the company, CEO, board, investors, and growth expectations are aligned enough to support real success.  With that recru...

522: AI, SDRs, and the New GTM Engine

June 12, 2026

The go-to-market model most teams are optimizing may be the very thing AI is making obsolete.  Too often, the buyer experience feels like a relay race nobody asked to run. AI is already proving there's a faster, straighter path to answers, value, and outcomes, making the old model a lot harder to defend.  In this episode, Drew talks with Amanda Kahlow, founder of 1mind, about why many of today's go-to-market assumptions deserve a fresh look. Using the rise of AI SDRs as a starting point, ...