Outbound Squad
This sales podcast is for B2B reps and sales teams who want to turn complete strangers into paying customers. Join me (you can call me JBay) as I interview sales experts, leaders, and top-performing reps to learn the stories, secrets, and skills of the world’s most successful sales professionals.
Episodes
April 30, 2026 • 164 mins
Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts):
https://masterclass.outboundsquad.com/
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Outbound isn't dead, but it's broken. Reply rates are below 2%. Connect rates are below 4%. The irony? The tools designed to make outbound easier have made it exponentially harder.
But the top 25% of reps are booking 4.3x more meetings than everyone else. This course teaches you...
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Mark as Played
April 29, 2026 • 18 mins
Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts):
https://masterclass.outboundsquad.com/
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"I'm not interested."
"We already have a solution."
"Send me an email."
Sound familiar? Objections aren't rejections. They're signals that you haven't earned trust yet. Most reps freeze or fumble. You won't after this.
In 15 minutes, you'll master a repeatable framework for tur...
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Mark as Played
April 28, 2026 • 25 mins
Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts):
https://masterclass.outboundsquad.com/
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Less than 4% of cold calls get answered. And when they do, most reps fumble the first 30 seconds. This mini course will fix that.
In 23 minutes, you'll learn the exact cold call framework that's helped thousands of reps go from dreading the phone to booking meetings consistently...
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Mark as Played
April 21, 2026 • 13 mins
Get free access to the full course + companion workbook:
https://masterclass.outboundsquad.com/
91% of buyers believe salespeople don't understand what they do, what they care about, or what their company does. That's not a cold email or cold calling problem. That's a messaging problem.
In this episode, I break down the exact messaging framework we use with every Outbound Squad client to fix this.
You'll learn:
1) Why "pitchi...
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Mark as Played
April 14, 2026 • 57 mins
Jason was a guest on the recent webinar hosted by ZoomInfo. In this episode, Jason and Michael George from ZoomInfo reveal a proven framework that can triple your cold call conversions. Tune in to learn the strategies, mindset, and data-backed tactics that turn hesitant prospects into eager buyers.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
April 7, 2026 • 47 mins
In this episode, Jason and Kyle Vamvouris from SalesThread break down how AI is revolutionizing sales strategies and why RevOps as we know it might soon vanish. Tune in for bold insights and actionable tactics to stay ahead in the future of sales.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
March 31, 2026 • 56 mins
Jason was a guest on the recent webinar hosted by ZoomInfo. In this episode, Jason and Calvin Flax break down the Outbound Equation and reveal how to win high-quality meetings in a slower market through smarter outreach, stronger offers, and genuine buyer connection.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
March 24, 2026 • 76 mins
In this episode, Jason, Clara Johnson, and Nate Vogel dive into a high-energy sales enablement masterclass, unpacking how to build world-class programs that drive performance at scale using data, coaching, and customer-focused frameworks.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
March 17, 2026 • 57 mins
In this episode, Jason and Rippling’s Senior SDR Director, Bert Brokaw, talk about what it really takes to crush the Director of SDR role, from leading managers and aligning with executives to building a high-performing outbound culture. Tune in to learn how top leaders grow strategic SDR teams that consistently deliver results.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
March 10, 2026 • 8 mins
In this episode, Jason talks about why sales leaders must partner with enablement to drive real culture change and shares three lessons from top teams—becoming a trusted advisor, sharing the stage with reps, and prioritizing manager enablement over rep-only training.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
March 3, 2026 • 4 mins
In this episode, Jason breaks down why AI isn’t replacing SDRs anytime soon, sharing real hiring data from leading AI companies and explaining why human reps who learn to leverage AI will outperform, not be replaced by it.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
February 24, 2026 • 55 mins
Jason was a guest on the Outbound Kitchen - Sales Podcast hosted by Elric Legloire to share tactical cold-calling frameworks—using permission-based openers, problem-focused language, and compelling offers to boost connect rates, spark real interest, and book meetings that actually show up.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
February 17, 2026 • 59 mins
In this episode, Aaron Rissler shares his journey from IC to VP of Sales at Buyer's Edge Platform, revealing the lessons, strategies, and leadership insights he’s learned along the way to build high-performing teams, navigate corporate politics, and level up at every stage of a sales career.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
February 10, 2026 • 60 mins
This episode is the audio from our recent webinar on The Outbound Equation. Jason walks through a proven methodology for securing high-quality meetings in 2026 by reinforcing fundamentals like offers that deliver real value, world-class execution on phone, email, and social, and the critical role of leadership in creating predictable outbound pipeline.
Check out more free content and get coaching at https://outboundsquad...
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Mark as Played
February 3, 2026 • 60 mins
In this episode, Bryan Evans shares his journey from rep to VP of Sales at Neo4j and the leadership habits that help sales teams execute, forecast accurately, and win bigger deals.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
January 27, 2026 • 50 mins
In this episode, Jason Bay sits down with Rippling’s VP of Sales Enablement, Jonas Master to explore how effective sales training, paired with clear priorities, measurement, and reinforcement, drives real behavior change and consistent performance gains.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
January 20, 2026 • 10 mins
In this episode, Jason Bay and Clara Johnson share how sales leaders can build a culture of AE self-sourcing by weaving prospecting into weekly rhythms and leading from the front.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
January 13, 2026 • 9 mins
In this episode, Jason and Clara shared how SDRs can improve cold call qualification to boost pipeline conversion and set AEs up for success.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
January 6, 2026 • 5 mins
In this episode, Jason warns about the dangers of over-relying on AI and shares tips for leveraging it effectively in sales.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
December 30, 2025 • 60 mins
This episode is the audio from our recent webinar on the state of outbound. Sean Dwyer of ZoomInfo joined us to share what’s changing, what’s working, and how the best teams are adapting their outbound motion in 2026.
Check out more free content and get coaching at https://outboundsquad.com.
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Mark as Played
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