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

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 Werley

Episode 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 & Insights

• AI-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.ai

• https://www.linkedin.com/in/stevenwerley/

• https://www.stevenwerley.com/

• https://www.instagram.com/stevewerley/?hl=en

• Charity: 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!