In today’s hyper-competitive markets, traditional sales playbooks are no longer enough. Customers are more informed, decision cycles are more complex, and winning deals requires more than just relationships or features. The Challenger methodology has redefined how high-performing sales teams engage with enterprise buyers — and this book takes it a step further.
 
Drawing from over two decades of experience leading SaaS expansion across the U.S., LATAM, and Europe, Claudio B. Landsberg breaks down the principles of teaching for differentiation, tailoring for resonance, and taking control of the sales conversation. With real-world enterprise case studies, actionable frameworks, and practical checklists, Challenge to Win is a hands-on guide to mastering the behaviors that consistently drive bigger deals, shorter cycles, and stronger customer loyalty.
Whether you’re a sales executive, enterprise account manager, or startup founder, this book gives you the strategies to build insight-driven conversations, lead with confidence, and win in complex, multi-stakeholder environments.
 
Key Takeaways:
Understand why Challengers consistently outperform other sales profiles.
Learn how to craft commercial insights that change customer thinking.
Apply proven frameworks to navigate C-level, legal, IT, and compliance stakeholders.
Build a Challenger playbook for SaaS and enterprise sales.
Lead and coach high-performing Challenger teams in global markets.
 
Challenge to Win is more than a methodology — it’s a roadmap to becoming indispensable to your customers and unstoppable in your market.