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

If you're in customer success, sales or other go-to-market motions, stick around to hear from the best. For more frameworks, tools, and automated playbooks, check out jodastech.com and subscribe to our newsletter.

🎙️ 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

_______________________________

Tools:

Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDN

Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx

Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4

Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Communication in customer success hinges not on what you say, but what your customer hears, as Kevin Metzger discovered when a casual comment about contractual obligations spiraled into a three-month recovery process with an enterprise client.

• Customer's SSL certificate expired causing application issues
• According to contracts, certificate renewal was customer's responsibility
• Kevin's off-the-cuff remark about contract terms damaged relationship
• Previously excellent customer service included clearing 150-issue backlog
• Proactive handling of day-zero security issue before incident
• Recovery process took months despite initial good relationship
• Understanding perception versus intention is critical in communication
• Consistent actions to rebuild trust more important than being right
• Later developed honest communication about miscommunication patterns
• Relationship eventually strengthened, leading to renewal of eight-figure contract
• Future of communication increasingly involves emotional intelligence as AI handles factual elements
• Different cultural contexts require additional communication awareness

📢 Guest Spotlight:

• Kevin Metzger — Customer Success Leader with 20+ years of experience, known as “The AI Assistant Guy” https://www.linkedin.com/in/kevinmetzger/
  
  
  
• Host of the Customer Success Playbook podcast
  • Apple: https://podcasts.apple.com/us/podcast/the-customer-success-playbook/id1691760422
  • Spotify: https://open.spotify.com/show/7pPPFBQZrv3HPrA75FQk2h?si=4f42fed2355c486a
    
    
    

🟣 Tools & Technologies Discussed:

• ChatGPT, Claude, Gemini — AI tools referenced for communication and content strategy
  • https://chatgpt.com/
  • claude.ai
  • gemini.google.com
    
    
    
• Notebook LM — Used for synthesizing information, content planning, and structuring timelines or papers
  • https://notebooklm.google/
    
    
    
• SalesApe.ai — AI-powered SDR tool that qualifies leads via email communication
  • https://www.salesape.ai/
    
    
    
• Sesame.com — Voice AI tool used for realistic spoken conversation with AI agents (Miles and Maya)
  • https://app.sesame.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

_______________________________

Tools:

Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDN

Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx

Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4

Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Sri Ganesan shares how bringing intensity and professionalism to implementation projects can dramatically improve customer partnerships and outcomes. The RocketLane CEO details specific strategies for setting expectations, improving communication, and catching issues before they become dealbreakers.

• Intensity means the ball is always in your court - never waiting on customers without following up
• Catch problems early through milestone-based CSAT surveys to identify even "three-star" experiences
• Escalate partnerships quickly when things go off track - it's better you escalate than the customer escalates
• Show professionalism by starting meetings on time, publishing clear agendas, and sending prompt follow-ups
• Set clear escalation paths during kickoff for both sides to maintain momentum
• Be prescriptive and challenge customer assumptions when your experience suggests better approaches
• Turn your implementation team into consultants who understand the domain, not just your product
• Align implementation decisions with executive stakeholders' organizational goals

📢 Guest Spotlight:
Sri Ganesan is the co-founder and CEO of Rocketlane, a modern PSA (Professional Services Automation) platform purpose-built for customer onboarding and service delivery. https://www.linkedin.com/in/srikrishnang/

Connect with Sri:
📧 Email: sri@rocketlane.com
🔗 LinkedIn: Sri Krishnan Ganesan
🐦X: @SriKrishnanG
🌐 Website: rocketlane.com

📚 Book Shoutouts:

• Leadership and Self-Deception – The Arbinger Institute: https://amzn.to/4mdVyeD
  
  
  

Made to Stick – Chip & Dan Heath: https://amzn.to/4kZlCt0

🌐 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

_______________________________

Tools:

Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDN

Logitech Brio 4K Webcam: https://amzn.to/3GtKsmx

Sony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4

Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W