The Brutal Truth about Sales and Selling - We interview the world's best B2B Enterprise salespeople. The Brutal Truth about Sales and Selling - We interview the world's best B2B Enterprise salespeople.

WHAT IT TAKE TO BECOME AN A-PLAYER IN B2B SALES

Aug 26, 2026 · 42m

Summary

Amanda Machado, an enterprise IT sales veteran, shares strategies for differentiating commodity services by building trust and addressing client fears. She emphasizes honest cold calling, leveraging technical knowledge to create personal wins for CIOs, and embracing silence during negotiations. Machado also discusses how analyzing crushing losses drives improvement and why self-awareness is critical for long-term success.

Topics discussed

Introduction: Differentiating commodity services Amanda's background in telecom and insurance Challenging CIOs and changing business methods Overcoming cloud computing skepticism Building trust and managing client risk Personal branding and the sales relationship Cold calling strategies and honesty Using ransomware threats to earn meetings Customizable solutions and technical curiosity Early sales mistakes and lead quality myths Commodities vs. value when things break Helping IT pros demonstrate value to CEOs Learning from crushing losses vs. wins Handling rejection and the 'not now' objection Salary as a loan and quota as payment Competitive drive and personal motivations Financial struggles as a single mom Self-awareness and pre-call preparation The power of awkward silence in sales Building a network for client referrals Outward mindset and course promotion
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