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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In an AI disrupted world, what do you do when technology is moving faster than your people? Heather Jerrehian, Silicon Valley CEO, investor, and co-author of Sail to Scale, reveals why trust, psychological safety, and human-centred leadership are now the critical skills CEOs need to navigate AI-driven disruption. For most organisations, AI doesn’t fail because the tech isn’t ready.
It fails because people don’t feel safe enough to adopt it. But for Heather, this moment became a masterclass in leading through uncertainty, navigating resistance, and bringing teams with her into the future. In this conversation with Rebecca Jenkins and Callum Jenkins, Heather explains what CEOs must understand about human behaviour, fear, change, and how to build the trust that makes transformation possible. This is not theory, it’s hard-earned insight from someone who has launched, pivoted, scaled, and exited companies at the heart of the AI revolution, including a transformational acquisition by ServiceNow. What you’ll learn in this episode:
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continue reading
It fails because people don’t feel safe enough to adopt it. But for Heather, this moment became a masterclass in leading through uncertainty, navigating resistance, and bringing teams with her into the future. In this conversation with Rebecca Jenkins and Callum Jenkins, Heather explains what CEOs must understand about human behaviour, fear, change, and how to build the trust that makes transformation possible. This is not theory, it’s hard-earned insight from someone who has launched, pivoted, scaled, and exited companies at the heart of the AI revolution, including a transformational acquisition by ServiceNow. What you’ll learn in this episode:
Why AI adoption fails inside organisations, and the hidden fears leaders aren’t addressing.
How to build psychological safety so your people don’t resist AI, but embrace it.
The leadership behaviours that create trust during periods of disruption.
How Heather’s ‘listening tour’ revealed a market opportunity that changed the trajectory of her company.
Why futurist leaders must learn the skill of bringing people with them, not running ahead alone.
The four waves of growth from Sail to Scale, and how to navigate each one without losing your team.
Why human-centred leadership is the only sustainable strategy in an AI-powered world.
CEOs, Founders, and C-suite leaders navigating AI-driven change, organisational resistance, or the complexity of leading people through disruption.
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Connect with Heather:LinkedIn: Heather Jerrehian
X: @Jerrehian
Book: Sail to Scale: Steer Your Startup Clear of Mistakes from Launch to Exit (Amazon)
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LEAD TO SUCCEED is sponsored by RJEN The Revenue Architect.
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