After two decades in the SaaS and technology trenches, closing multimillion-dollar enterprise deals and building teams across the Americas and Europe, Claudio B. Landsberg distills his career into one simple truth: every great deal, every turning point, and every leadership lesson started with a question.
 
This book brings together 70 real questions Claudio has been asked throughout his journey—50 from clients and executives (from CEOs to CIOs and Procurement Directors) and 20 from sales professionals he has coached and led. Each question is presented exactly as it was asked—complete with the role, company size, and industry context—followed by a direct, experience-based answer forged in the real world of SaaS and enterprise sales.
 
Far from theory or motivational fluff, this is a field manual for anyone selling or leading in technology.

You’ll hear the conversations behind real boardrooms, cold calls, and coaching sessions—from skeptical CFOs to ambitious SDRs—and learn how to navigate each with confidence, empathy, and strategic precision.
 
Inside, you’ll discover:
How to turn objections into opportunity and curiosity into trust.
How to answer the unspoken questions C-levels really mean to ask.
How to coach teams through doubt, burnout, and complexity.
How to think like a true partner, not a vendor.
 
Written with honesty, warmth, and wisdom, Ask Me, I’ve Been There is a book about selling—but even more, it’s a book about listening. Because the best salespeople don’t just pitch; they understand.
 
For Jesus, my Savior — and for Daniela, Theo, and Thor, the best answers in my life.