The Scaling CEO

Your Strength Can Become Your Biggest Blind Spot | The Scaling CEO Podcast

20 min · 26. touko 2026
jakson Your Strength Can Become Your Biggest Blind Spot | The Scaling CEO Podcast kansikuva

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In this episode, I sit down with Stacey Epstein, CEO of Structured and former executive at SuccessFactors, ServiceMax, and Freshworks, to talk about the realities of scaling as a CEO. Stacey shares the leadership lessons she learned moving from CMO to CEO, why founders often neglect the areas they think they already understand, and how culture changes as companies grow fast. We also discuss AI, partner ecosystems, leadership pressure, scaling teams, and why AI should act as a thought partner, not a replacement for people.

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jakson The State of AI for CEOs (June 2026) kansikuva

The State of AI for CEOs (June 2026)

The signal this month is clear. The companies winning with AI have stopped running pilots and started scaling what pays. New data shows that 80% of enterprises running AI agents now report measurable return. Firms stuck on chatbots fall behind. The difference comes down to execution. This month McKinsey told CEOs to move past productivity demos and ask a harder question: how will AI change the economics of your business? IBM found that companies redesigning core functions around AI are four times more likely to hit their goals. The message to the corner office is blunt. AI is now a board-level value lever, and your P&L is where the proof lives. I host The Scaling CEO podcast. I just finished interviews with 19 leaders across industrial manufacturing, software, and private equity backed hospitality. They have settled the question of whether AI works. Now they decide faster, scale what pays, and kill what stalls. Here are the five things they do to drive ROI and protect their lead.

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