In this episode of Selling the Cloud, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams.

Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer relevance, and clearer deal strategy.

This conversation also dives into the science of trust in a noisy, AI-saturated world. Cherilynn explains how the questions we ask and how we listen directly influence buyer confidence, especially inside complex buying committees. From discovery to prospecting to executive conversations, this episode focuses on how sellers and leaders can create credibility without adding more noise.

What You’ll Learn:

• AI as a Daily Sales Discipline: How a simple 15 minute daily AI prep routine helps sellers develop POVs, anticipate change, and continuously improve.
• POV Development at Scale: A repeatable framework for triangulating industry, company, and persona insights using AI.
• Making AI Revenue Relevant: Why leaders should evaluate AI through insights, context, and business impact instead of activity metrics.
• Trust in the Age of AI Noise: How better questions and deeper listening create credibility when buyers are overwhelmed with automation.
• High Connection Discovery Questions: How to use AI to reframe discovery questions that trigger trust, openness, and buyer engagement.
• Prospecting Without Pitching: Why offering value through insights, case studies, and tools beats asking for meetings.
• Navigating Modern Buying Groups: How to adapt when new stakeholders like CFOs enter late-stage conversations.
• Financial Fluency for Sellers: Why precise numbers, not rounded estimates, matter when speaking with executive buyers.

Key Topics:

• AI fluency as a mindset, not a toolset
• Daily AI routines for sellers and managers
• POV creation using LinkedIn profiles, 10Ks, and industry analysis
• Relationship selling and the science of trust
• Discovery questions that increase buyer confidence
• Avoiding buyer defensiveness and ethical AI use
• Executive conversations and CFO expectations
• Financial storytelling with insight, context, and impact

Guest Spotlight: Cherilynn Castleman

Cherilynn Castleman is an enterprise sales leader, strategic coach, and Harvard instructor focused on helping sellers become trusted advisors through AI fluency and relationship-driven selling. She is the creator of highly rated AI and sales programs available on Udemy Business and leads large learning communities through weekly live sessions and workshops.

Cherilynn is on a mission to equip one million women in sales and leadership with the confidence, fluency, and playbooks needed to thrive in modern go-to-market roles.

Resources & Mentions:

• Course: Smart Tips Sales – Master Relationship Driven Selling via AI
• Book: Post-Pandemic Selling
• Research Reference: Dr. Jane Dutton on High Quality Connections
• Concepts: AI fluency, POV selling, high connection discovery, financial storytelling

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