Outbound Kitchen - B2B Sales Podcast OK22: How to Cold Call for Higher Connect Rates, Better Conversations, and Meetings That Actually Show Up - with Jason Bay, CEO of Outbound Squad
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Jan 8, 2026 
Jason Bay, Founder and CEO of Outbound Squad, shares insights from his extensive experience training companies like Shopify and Zoom. He reveals that effective cold calling is still alive, despite the average call lasting only 80 seconds. Discover his compelling cold calling framework, emphasizing customer problems over product pitches, and techniques that can drastically improve meeting show rates. Bay stresses the importance of habit-building in sales and how top reps leverage customer language to enhance engagement.
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Cold Calling Is Harder But Still Works
- Cold calling isn't dead but it's much harder and less effective than two years ago.
- Top teams still reach 15-35% conversion by investing in enablement, data quality, and operations.
E‑Commerce Audits As An Outbound Offer
- One e-commerce client ran AI site audits and shared checkout load times during outreach to create immediate value.
- Another mystery-shopped competitors and used findings to open conversations with prospects.
Use Permission-Based, Relevant Openers
- Open with a permission-based, highly relevant opener that names a specific issue you found.
- Ask for a minute to explain why you called so you immediately earn attention and permission.