Sales Leadership & Management Show - For B2B Sales Leaders FROM BIG BRAND TO STARTUP AND BUILDING A GREAT ENTERPRISE TEAM
Aug 21, 2025
Dive into the journey from big brand success to startup challenges, as insights on sales leadership unfold. Discover why hands-on sales experience is crucial for leaders. Explore the delicate balance of coaching without micromanagement. Learn the art of personalized outreach and building trust with C-level executives. The discussion also highlights the importance of empathy and confidence in selling, while diagnosing underperformance in teams. Funny anecdotes and practical advice come together to make this conversation both engaging and informative.
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Leadership Needs Enablement And Ops
- Sales leadership must combine enablement with operations, not just control and reporting.
- Leo argues many managers never sold and thus cannot truly support account managers in complex deals.
Forecasts Are Educated Feelings
- Forecasting deals is often an assumption, not a precise prediction.
- Leo warns long complex IT sales cycles make forecasts a best-effort glimpse into the future.
Research Before You Reach Out
- Investigate deeply before outreach and tailor each message to the prospect's situation.
- Leo recommends personalizing emails and calls to specific company facts to raise response rates.