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 conversation also digs into how AI is changing the first-90-days playbook, from accelerating onboarding and research to raising expectations around team productivity, experimentation, and org design. Paige, Scott, and Ali share how they’re using AI, where they’re still relying on old-fashioned listening, and why the best early wins are the ones that build momentum with both the team and the business.

In this episode:

• Paige shares how she tested the interview story against reality, unlocked stalled team ideas, and used AI to speed up onboarding
• Scott breaks down how he pressure-tested pipeline goals, budgets, team sentiment, and sales alignment before resetting expectations
• Ali explains how she brought focus to Asset-Map’s many possible stories, used research to sharpen the message, and chose the first market problem to solve

Plus:

• How AI is accelerating onboarding, research, testing, and early execution
• Why early wins should build credibility without disrupting what works
• How to gauge AI readiness across your inherited team
• Why the first 90 days are your best window to challenge assumptions

If you’re stepping into a new CMO role, or preparing for one, this episode offers a practical look at how to use your early window wisely, build trust quickly, and avoid squandering the power that comes with fresh eyes.