Outbound Squad

Outbound Squad

Business EN ↓ 425 episodes

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.

Author

Outbound Squad

Category

Business

Podcast website

outboundsquad.com

Latest episode

Jul 6, 2026

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Episodes

Sales Enablement Masterclass with VP of Sales Enablement at Rippling, Jonas Master 27.01.2026

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.⁠

A simple framework to get AEs self-sourcing pipeline 20.01.2026

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.⁠

Improving cold call qualification 13.01.2026

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.⁠

"AI doesn't have a point of view" (a warning) 06.01.2026

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.⁠⁠

[Playbook] State of Outbound: AI and what to expect in 2026 30.12.2025

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.⁠

“We increased pipeline by 170% this month!” 23.12.2025

In this episode, Jason and Clara Johnson break down how narrowing your outbound focus by industry, persona, and triggers led one team to a 170% increase in pipeline while driving higher response rates and bigger deals. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.

How to 3x your contact rates 16.12.2025

In this episode, Jason and Clara Johnson break down why reps need an omnichannel outbound strategy and show how using coordinated calls, emails, social touches, and AI-driven research can triple contact rates and unlock pipeline. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.

[Playbook] How two reps closed a $30M+ deal (the largest in company history) 09.12.2025

This episode is the audio from our webinar on sales mastery. We were joined by ⁠Rona Cohen and Ryan Smith at ZoomInfo to share how they closed the largest deal in company history ($30M+) and what it takes to get big opportunities across the finish line. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Dialers won’t fix your cold calling problem 02.12.2025

In this episode, Jason and Clara Johnson break down why autodialers hurt connect and conversion rates, and share smarter ways to fix your cold calling results, including opening with a concise buyer-focused reverse pitch. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Biggest mistake when re-engaging closed/lost opps 25.11.2025

In this episode, Jason and Clara Johnson share a simple framework for re-engaging closed lost opportunities by using time-based insights, past deal context, and tailored messaging to turn overlooked accounts into new pipeline. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Meet our new Head of Training, Clara Johnson! 18.11.2025

In this episode, Jason announces Clara Johnson as the new Head of Training in Outbound Squad, discussing how her previous experience as a successful sales leader will help them grow the company, create a formal outbound methodology, and produce better thought leadership content. They also discuss the future of outbound sales, the potential impact of AI, and the importance of adapting to new sales...

Negotiations Masterclass With Todd Caponi 11.11.2025

In this episode, Todd Caponi shares how to negotiate effectively in sales, covering the history of negotiation, common myths, the four levers of negotiating, and strategies to protect your contract value while driving deals forward. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

[Playbook] Steal this PipeGen framework: How we generated $70M+ in new pipeline every week 04.11.2025

This episode is the audio from our recent webinar on pipeline generation. Marcus Chan from Venli joined us to share how to build a repeatable pipeline generation framework to drive consistent and high-quality pipeline in 2025. Note: Audio issues occurred during the webinar recording. We apologize for sections where the audio is missing or unclear. Check out more free content and get coaching at ⁠⁠...

A masterclass on sales coaching with Mark Hunter 28.10.2025

In this episode, Mark Hunter shares how sales leaders can build a strong team culture and coach effectively by understanding what motivates each rep, leading by example, keeping energy high, and delivering focused, personalized coaching that drives lasting behavior change. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.

How to handle vet AEs who think they know it all 21.10.2025

In this episode of our new behind-the-scenes series with the Outbound Squad sales training team, Jason Bay and Clara Johnson share how sales leaders can get veteran reps prospecting again using data, AI prompts, and a “red-pen” approach to AI. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

A simple framework to get AEs self-sourcing pipeline 14.10.2025

In this episode of our new behind-the-scenes series with the Outbound Squad sales training team, 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.⁠

Improving cold call qualification 07.10.2025

In this episode, Jason and Clara Johnson kick off a new behind-the-scenes series with the Outbound Squad sales training team. They 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.⁠

[Playbook] Account Executives: Steal this framework to self-source 30%+ of your pipeline (without making hundreds of cold calls) 30.09.2025

This episode is the audio from our recent webinar on AE self-sourcing. Erika Fuchs from EliseAI, Rob Anderson from TitanX, and Darin Alpert from ZoomInfo joined us to share how top reps self-source pipeline to book more meetings and crush quota, without making hundreds of cold calls. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Cold Calling: Use this intro to book 3x more meetings 23.09.2025

In this episode, Jason shares some cold calling tips and examples that will help you outperform average reps by 3x. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.

Steal this cold calling framework to book 2-3x more meetings 16.09.2025

Jason joined The Chris Bussing Podcast [ Sell More | Live More ]⁠. In this episode, they talked about AI in outbound sales, the "Reason to Meet" strategy, key sales tools, standout messaging, and cold outreach tactics. Check out the show notes, more free content, and get coaching at ⁠https://outboundsquad.com

[Playbook] State of Cold Calling (from analyzing 1B cold calls) 09.09.2025

This episode is the audio from our recent webinar on cold calling. Colin Specter from Orum and Calvin Flax from ZoomInfo joined us to share what top reps do to land more meetings through the phone, based on insights from 1B cold calls completed using Orum. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

"AI doesn't have a point of view" (a warning) 02.09.2025

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.⁠

10 ways the best teams are booking meetings right now 26.08.2025

Jason⁠ was one of the speakers on ⁠Sell Better⁠'s webinar on cold outreach. In this episode, they shared simple-to-execute tactics the best teams use to land more meetings from calls, emails, and LinkedIn messages. Check out the show notes, more free content, and get coaching at ⁠https://outboundsquad.com

[Playbook] No, cold calling isn't dead (how to land a sh*t ton of meetings in 2025) 19.08.2025

This episode is the audio from our webinar on cold calling. ⁠Nick Cegelski⁠ from 30 Minutes to President's Club and ⁠Waseem Kaati⁠ from ⁠Shopify⁠ joined us to share how to increase cold calling conversion rates. Check out the show notes, more free content, and get coaching at ⁠https://outboundsquad.com

Why your outbound messaging doesn't land 12.08.2025

In this episode, ⁠Jason⁠ shares the levels of relevance in sales messaging and where you can use this to outbound and sell better. Check out the show notes, more free content, and get coaching at ⁠https://outboundsquad.com

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