Sales Enablement Strategy: Why Preparation Is the New Differentiator

A modern sales enablement strategy isn’t about more activity - it’s about better preparation. In this episode of B2B Sales Trends, we explore why preparation has become the true differentiator in B2B selling and enterprise sales strategy.

In this conversation, host Harry Kendlbacher sits down with Gena Dakos, a seasoned sales enablement leader, to unpack how high-quality outreach, customer empathy, and thoughtful preparation help sellers stand out in a noisy, AI-driven market. From executive discovery to enterprise-scale deals, this episode reframes enablement as confidence, clarity, and credibility - not just training.
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You’ll learn:
Why preparation beats volume in modern B2B sales
How sales enablement strategy builds confidence with executives
What customer empathy really means in enterprise selling
How AI supports preparation without replacing human judgment

⏱️ Timestamps
00:00 – Why preparation is the new sales differentiator
04:45 – High-quality outreach vs volume in B2B selling
08:55 – Customer empathy as a core sales enablement strategy
13:40 – Preparing for executive discovery conversations
18:50 – Enterprise sales strategy and multi-stakeholder deals
24:10 – Enablement, confidence, and long-term performance

💡 Key Takeaways
Sales enablement strategy succeeds when it prioritizes preparation over activity
Buyers are informed - sellers must add insight, not ask generic questions
Customer empathy is built through research, not scripts
Executive conversations demand clarity, relevance, and conviction
Enablement works best when it builds confidence, not compliance

👤 About the Guest
Gena Dakos is a Sales Enablement Leader specializing in revenue enablement and enterprise sales strategy. With experience at Stripe, Rippling, FIS, and Gartner, Gena is known for building high-performing teams by deeply understanding sellers and designing the structure, preparation, and support they need to succeed in complex B2B environments.
Connect with Gena on LinkedIn:   / gena-dakos-3a12ab5b  
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🔗 Explore more at https://www.globalperformancegroup.com/