The Helicopter CCO: Breaking Silos & Building Trust w/ Anthony DeShazor

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/

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🎙️ 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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