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In this episode, Jason Bay, Founder of Outbound Squad, breaks down the art and science of cold calling in 2025.

He shares data from training companies like Rippling, Shopify, and Zoom, revealing why the average cold call lasts just 80 seconds, and how top reps achieve 25%+ conversion rates while most struggle at 4.6%.

Jason walks through his complete cold calling framework: the permission-based opener, reverse pitch, money questions, and the tactics that drive 75-80% show rates. His candid breakdown of what separates average reps from top performers, backed by Gong data from 100K+ calls, provides a masterclass in modern cold calling.

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3 biggest takeaways:

- Lead with problems, not product: problem-based language gets 3x more meetings than product pitches

- The habit matters more than the outcome: build the weekly rhythm before optimizing the talk track

- Customer voice over product voice: steal language directly from sales calls and discovery conversations

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Who is Jason Bay?

Founder of Outbound Squad, cold calling trainer for companies like Rippling, Shopify, and Zoom

Connect with Jason:

- On LinkedIn: https://www.linkedin.com/in/jasondbay/

- Outbound Squad: https://outboundsquad.com

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Key stats from this episode:

- Average connect rate: 5.4% (top reps hit 13-15%+)

- Average conversion rate: 4.6% (top reps hit 20-35%)

- Average show rate: 56% (top reps hit 75-80%)

- Rippling sources 50% of pipeline from outbound cold calling

- Problem-based language: 16% success vs 5.5% for product pitches

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When you're ready

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Connect with me

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Chapters:

(00:00) Episode Overview

(01:13) Is Cold Calling Dead?

(01:57) Cold Calling Effectiveness and Statistics

(03:29) Challenges and Strategies in Cold Calling

(05:31) The Importance of Relevance and Offers

(08:12) Effective Cold Call Openers

(13:05) Reverse Pitch and Problem-Based Language

(18:28) Tailoring Cold Calls to Different Brands

(19:54) Leveraging Customer Language and Patterns

(24:52) Building a Weekly Rhythm for Outbound Success

(25:59) Creating a Coaching Culture

(27:03) Granular Coaching for BDRs

(28:15) Improving Call Metrics

(30:59) Data Accuracy and Provider Evaluation

(34:31) Top Reps and Their Techniques

(41:04) Incorporating AI in Sales Training

(46:34) Non-Negotiable Cold Calling Principles

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