30 Minutes to President's Club | No-Nonsense Sales #524 - Outbound Prospecting Masterclass: Everything You Need to Book Meetings in 2026
Nov 18, 2025
Jason Bay, CEO of Outbound Squad and expert in sales training, shares groundbreaking insights into outbound prospecting. He explains how to prioritize leads using the Martini-Glass Pipeline and craft compelling buyer-centered messages through the Messaging Matrix. Jason reveals the KISS Sequencing System, a strategy for multi-channel outreach that boosts replies by over 20%. He also discusses effective cold calling techniques and how to leverage AI with his 10-80-10 Rule to enhance productivity while maintaining a human touch.
AI Snips
Chapters
Transcript
Episode notes
Prioritize Fewer, Higher-Relevance Accounts
- Narrow your outbound pipeline and focus deeply on the accounts most likely to engage.
- Use a 'martini-glass' shape: fewer deals but higher account relevance and depth.
Hierarchy Of Relevance Beats Quantity
- Relevance hierarchy should guide segmentation: persona, industry, company, individual.
- The list is the strategy; better lists beat more touches.
E-Commerce Client Reprioritized Personas
- An e-commerce client found marketing leaders were best champions, not IT.
- They focused outreach on outdoor brands with mall presence and raised win rates.