Selling in the Age of AI - Episode 23: Steven Werley episode artwork

EPISODE · Oct 10, 2025 · 38 MIN

Selling in the Age of AI - Episode 23: Steven Werley

from Selling in the Age of AI · host Frank Somma

Quote: "There's just an invaluable skill set to being able to use AI to assist you—while still being an amazing salesperson, carrying real conversations without a robot on the other end." - Steven WerleyEpisode Summary In this insightful episode of "Selling in the Age of AI," Frank Somma welcomes Steven Werley, founder of Closable.ai and a former Army Ranger turned sales strategist. Steven shares how he helps sales teams and entrepreneurs transform inconsistent pipelines into high-performing revenue machines by integrating AI with human-centric sales leadership. From diagnosing weak points in the sales process to training AI for smarter follow-ups, Steven unveils how technology can make us better—not replace us.Key Topics & InsightsAI-Augmented Sales Coaching: Steven trains AI models to mirror his sales coaching style, dramatically reducing feedback loops by automatically reviewing sales calls and suggesting improvements.Boosting Show Rates with AI: By analyzing setter calls with AI, Steven identified friction points and rewrote scripts—resulting in a leap from a 35% to 80% show rate.Human in the Loop: Even with automation, Steven stresses the importance of human oversight to ensure authenticity and maintain trust.Reverse Prompting Framework: Steven breaks down a simple yet powerful method to train AI using best-in-class sales trainer methodologies—redefining how sales teams can level up with LLMs.Real-Time Pipeline Intelligence: AI is used to track deal velocity, identify where prospects drop off, and suggest tailored follow-ups, providing better forecasting and pipeline management.Respecting Rapport: A masterclass in setter etiquette—why pushing for financial qualifications too early kills deals and how warmth and trust lead to conversions.Why Humans Still Matter: From building trust to reading nuance, Steven highlights the irreplaceable role of human connection in complex, high-value sales.Accessible AI Tips for Salespeople: From uploading transcripts into ChatGPT to roleplaying and getting real-time feedback, Steven reveals underused techniques for personal improvement.Connect with Steven Werley:Closable.aihttps://www.linkedin.com/in/stevenwerley/https://www.stevenwerley.com/https://www.instagram.com/stevewerley/?hl=enCharity: https://www.laughingatmynightmare.com/?srsltid=AfmBOopSlTrlRBEQaSyBQNQTafa8JNoAUC1eRzpqoUw3bBtCdhHDyXSD Connect with Frank Somma:https://www.franksomma.com/https://www.linkedin.com/in/fsomma/https://www.instagram.com/franksomma/Want to take your sales skills to the next level and thrive in the age of AI? Frank Somma is offering a special discount to our podcast listeners!Mention this podcast when you contact Frank and receive a 10% discount on your first coaching session, keynote, or workshop booking!

Quote: "There's just an invaluable skill set to being able to use AI to assist you—while still being an amazing salesperson, carrying real conversations without a robot on the other end." - Steven WerleyEpisode Summary In this insightful episode of "Selling in the Age of AI," Frank Somma welcomes Steven Werley, founder of Closable.ai and a former Army Ranger turned sales strategist. Steven shares how he helps sales teams and entrepreneurs transform inconsistent pipelines into high-performing revenue machines by integrating AI with human-centric sales leadership. From diagnosing weak points in the sales process to training AI for smarter follow-ups, Steven unveils how technology can make us better—not replace us.Key Topics & InsightsAI-Augmented Sales Coaching: Steven trains AI models to mirror his sales coaching style, dramatically reducing feedback loops by automatically reviewing sales calls and suggesting improvements.Boosting Show Rates with AI: By analyzing setter calls with AI, Steven identified friction points and rewrote scripts—resulting in a leap from a 35% to 80% show rate.Human in the Loop: Even with automation, Steven stresses the importance of human oversight to ensure authenticity and maintain trust.Reverse Prompting Framework: Steven breaks down a simple yet powerful method to train AI using best-in-class sales trainer methodologies—redefining how sales teams can level up with LLMs.Real-Time Pipeline Intelligence: AI is used to track deal velocity, identify where prospects drop off, and suggest tailored follow-ups, providing better forecasting and pipeline management.Respecting Rapport: A masterclass in setter etiquette—why pushing for financial qualifications too early kills deals and how warmth and trust lead to conversions.Why Humans Still Matter: From building trust to reading nuance, Steven highlights the irreplaceable role of human connection in complex, high-value sales.Accessible AI Tips for Salespeople: From uploading transcripts into ChatGPT to roleplaying and getting real-time feedback, Steven reveals underused techniques for personal improvement.Connect with Steven Werley:Closable.aihttps://www.linkedin.com/in/stevenwerley/https://www.stevenwerley.com/https://www.instagram.com/stevewerley/?hl=enCharity: https://www.laughingatmynightmare.com/?srsltid=AfmBOopSlTrlRBEQaSyBQNQTafa8JNoAUC1eRzpqoUw3bBtCdhHDyXSD Connect with Frank Somma:https://www.franksomma.com/https://www.linkedin.com/in/fsomma/https://www.instagram.com/franksomma/Want to take your sales skills to the next level and thrive in the age of AI? Frank Somma is offering a special discount to our podcast listeners!Mention this podcast when you contact Frank and receive a 10% discount on your first coaching session, keynote, or workshop booking!

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Selling in the Age of AI - Episode 23: Steven Werley

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Quote: "There's just an invaluable skill set to being able to use AI to assist you—while still being an amazing salesperson, carrying real conversations without a robot on the other end." - Steven WerleyEpisode Summary In this insightful episode of...

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