The Helicopter CCO: Breaking Silos & Building Trust w/ Anthony DeShazor
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Anthony DeShazer shares how his protective approach to customer management earned him the reputation as "The VP of No" and how he transformed his leadership style to foster cross-functional collaboration. He reveals the journey from gatekeeping to enabling teams through a mindset shift from "No" to "Yes, and" thinking.
• Taking customer ownership to harmful extremes created organizational friction
• Solving customer confusion by requiring all teams to get "passports" to customer land
• Shifting from "No" to "Yes, but" to "Yes, and" approaches transformed team dynamics
• The customer journey must be owned by the company, not individual departments
• Creating data-driven triggers helps align teams around customer advocacy opportunities
• AI is revolutionizing how CS teams identify patterns and predict customer behaviors
• Revenue is a "full-contact team sport" requiring all departments to work together
• Executive coaching provides valuable perspective for leadership development
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🎙️ Guest: Anthony DeShazor
Chief Customer Officer | GTM & RevOps Architect | Former “VP of No”
📣 Find Anthony:
LinkedIn: https://www.linkedin.com/in/adeshazor/
📌 In This Episode:
Anthony joins Joe Di Grande on Customer [Un]Success to unpack the lessons behind earning — and evolving beyond — the title of “VP of No.” He shares how customer success leaders can go from gatekeeping to growth-enabling.
🔥 Topics Covered:
🟣 The real story behind “VP of No” and “Helicopter CCO”
🟣 How to shift from “No” → “Yes, but” → “Yes, and”
🟣 Why too many internal teams talking to the customer = chaos
🟣 Lessons on cross-functional alignment between CS, Sales & Marketing
🟣 The role of AI in building advocacy workflows
🟣 What happens when CS owns more of the GTM strategy
🟣 Self-awareness and humility in executive leadership
🟣 The importance of psychological safety on your team
💡 Shoutouts & Mentions:
- Pavilion — a go-to CS/RevOps community, Anthony is active in- https://www.joinpavilion.com/
🌐 Website
https://www.joedoestechtouch.com/
📰 Subscribe to the JDTT Newsletter –
Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter
🎙️ Be a Guest on the Podcast
Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast
🔗 Connect with Joe on LinkedIn
https://www.linkedin.com/in/josephdigrande
📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw
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Chapters
1. The VP of No: A Helicopter CCO (00:00:00)
2. From No to Yes And: Changing Leadership (00:08:44)
3. Customer Journey Ownership & GTM Alignment (00:17:37)
4. Data-Driven Customer Advocacy Strategies (00:26:05)
5. AI Applications in Customer Success (00:35:10)
6. Revenue as a Full-Contact Team Sport (00:45:17)
16 episodes