What We Don't Say

When to Quit Your Job: Real Advice From A CRO Who's Lived It


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Should you stay or quit your job? A Chief Revenue Officer who's navigated this decision multiple times shares the exact framework that could save you years of pain and regret.

CRO Carl Oliveri opens up with host Ken Roden about the "perfect job" that nearly broke him—and the hard-won lessons that changed how he thinks about career moves. This isn't generic advice from someone who's never been there. This is battle-tested wisdom from the trenches of toxic boards, misaligned cultures, and the moments when you realize you're breaking yourself for the wrong reasons.

💡 What You'll Discover: ✅ The "running away vs. running towards" framework—and why this distinction changes everything
✅ How to recognize when you're being picked apart (before your health suffers)
✅ The questions you should be asking when interviewing YOUR next boss
✅ Specific career advice for new grads, 30-somethings & people in transition
✅ Why "just push through" isn't always the answer (and when it is)

⏱️ Episode Breakdown: 0:00 The perfect job that turned into a nightmare
1:58 When you can't see you're being picked apart
3:06 Toxic boards and exits that don't feel like wins
5:23 Running away vs. running towards: the critical difference
8:37 How to flip the script and interview your boss
10:13 Career advice by life stage: grads, 30s, transitions

Guest: Carl Oliveri, CRO with 20+ years navigating leadership roles
Host: Ken Roden

Supporting: FaceIT Foundation—providing peer support that makes recovery possible.

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What We Don't SayBy Ken Roden