Checklists, Coaching, and Conversion: Sales Leadership Lessons from Wade Callison

Pillar Talk: Building Sales Leadership with Rick Smolen

Wade Callison, CRO of Files.com, shares his journey from product leadership to sales and reveals how technical domain expertise creates credibility that transforms selling relationships from transactional to consultative.
Curiosity, coachability, growth mindset, and self-awareness form Wade's core framework for identifying and developing sales talent.

Wade details creating a culture of continuous learning helps sales teams adapt and improve. In one example, Wade outlines the pre-call brief that models it's thinking on the pre-flight plan that pilots benefit from.

Currently focused on improving win rates at Files.com, Wade shares his strategic approach: rather than trying to fix everything at once, he's identified specific leverage points like establishing value before discussing price and strengthening champion enablement. This targeted methodology exemplifies the thoughtful, measured leadership style that has defined his career.
Whether you're an aspiring sales leader or looking to refine your coaching approach, Wade's insights offer practical guidance for transforming individual contributors into cohesive, high-performing teams. Connect with him on LinkedIn to continue the conversation and exchange ideas about sales leadership excellence.
Music by Ben Cina & Ayler Young

Chapters

1. Introduction to Sales Leadership Pillars (00:00:00)

2. Wade's Journey from Product to Sales (00:03:30)

3. Domain Expertise: The Foundation of Selling (00:09:16)

4. Key Skills for High-Performing Sales Teams (00:17:12)

5. The Pre-Call Brief: A Pilot's Approach (00:26:54)

6. Win Rate Strategy and Sales Plays (00:35:53)

7. Champion Enablement and Key Takeaways (00:44:02)