

Outbound Squad
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
Mentioned books

28 snips
Oct 14, 2025 • 11min
A simple framework to get AEs self-sourcing pipeline
Jason and Clara dive into the importance of AEs self-sourcing their own pipelines in response to industry changes. They discuss how embedding prospecting into weekly routines strengthens accountability, featuring daily huddles and activity updates. Leaders actively participating in prospecting sessions fosters a culture of engagement and commitment. Practical tips are shared on managing meeting loads while making training relevant and impactful. Overall, it’s about aligning leadership behaviors with the prospecting efforts of the team.

5 snips
Oct 7, 2025 • 10min
Improving cold call qualification
Discover how to elevate cold call strategies and boost conversion rates. Explore the importance of asking 'money questions' to pinpoint buyer criteria. Learn about multi-threading and engaging stakeholders early to identify economic buyers. Tactics to avoid empty meetings and ensure real pain is recognized are shared. Clara explains when to qualify prospects during calls and offers practical steps for integrating effective qualification questions into your sales process. Get ready to enhance your outreach skills!

25 snips
Sep 30, 2025 • 1h 2min
[Playbook] Account Executives: Steal this framework to self-source 30%+ of your pipeline (without making hundreds of cold calls)
Join Erika Fuchs, an Enterprise Account Executive at EliseAI, Rob Anderson, Chief Revenue Officer at TitanX, and Darin Alpert, Strategic Account Executive at ZoomInfo, as they dive into the art of self-sourcing. They reveal how top reps can book more meetings without endless cold calls. The trio discusses the evolution of prospecting, effective dialing techniques, and the importance of prioritizing outreach. Discover the psychology behind group emails to C-suite executives and the benefits of leveraging referrals to enhance pipeline efficiency.

14 snips
Sep 23, 2025 • 7min
Cold Calling: Use this intro to book 3x more meetings
Jason shares powerful cold calling strategies to help you triple your meeting bookings. He emphasizes the importance of speaking the buyer's language instead of using buzzwords. The discussion includes practical tips like using reverse pitches and incorporating company-specific details. Real-world examples demonstrate how to avoid typical solopreneur pitfalls and leverage social proof. This insightful guide is packed with actionable tactics that can significantly boost your sales performance!

20 snips
Sep 16, 2025 • 1h 23min
Steal this cold calling framework to book 2-3x more meetings
Chris Bussing, host of The Chris Bussing Podcast and founder of Tech Sales Accelerator, dives deep into the world of cold calling and outbound sales. He shares insights on leveraging AI tools to enhance sales efficiency and introduce the compelling 'Reason to Meet' strategy. Bussing emphasizes the importance of personalized messaging in outreach, practical tips for mastering cold calling techniques, and the value of effective networking. Listeners gain actionable strategies to transform their sales approach and book more meetings.

23 snips
Sep 9, 2025 • 1h 1min
[Playbook] State of Cold Calling (from analyzing 1B cold calls)
Colin Specter, Senior VP of Global Sales at Orum, and Calvin Flax, Business Development Manager at ZoomInfo, dive into the world of cold calling. They share insights from analyzing over one billion cold calls, revealing the secrets to increasing connect rates. Learn about the reverse pitch strategy that uncovers prospects' pain points and effective engagement techniques that prioritize authenticity. The duo also discusses overcoming common challenges and the excitement that comes from landing meetings, providing tactical advice for sales professionals.

6 snips
Sep 2, 2025 • 5min
"AI doesn't have a point of view" (a warning)
Discover the fine line between AI assistance and human creativity in sales. A warning highlights the risks of over-dependency on technology, stressing the importance of personal insight. Tips are shared on how to effectively integrate AI while maintaining a thoughtful, human touch in your approach. This conversation ignites the debate on preserving individuality in a tech-driven landscape.

14 snips
Aug 26, 2025 • 45min
10 ways the best teams are booking meetings right now
Join James Buckley, a sales strategy champion, Will Aiken, the founder of a video outreach platform, and Jed Mowerly, a prospecting expert, as they share actionable tactics for booking more meetings. They explore the importance of finding an authentic sales voice, leveraging AI tools for outreach, and mastering cold calling techniques. The trio debates segmentation versus personalization, emphasizing efficient targeting. With insights on building trust through effective communication, this discussion will elevate your sales approach.

13 snips
Aug 19, 2025 • 59min
[Playbook] No, cold calling isn't dead (how to land a sh*t ton of meetings in 2025)
Nick Cegelski, co-author of "Cold Calling Sucks, and That's Why It Works," and Waseem Kaati from Shopify discuss the resurgence of cold calling in sales. They reveal effective strategies like personalized openers and engaging tones to capture potential clients' interest. The conversation touches on overcoming common misconceptions, the importance of identifying pain points, and utilizing intent data for better outreach. Listeners will gain insights into structuring calls and improving conversion rates while dispelling the myth that cold calling is obsolete.

8 snips
Aug 12, 2025 • 8min
Why your outbound messaging doesn't land
Discover how to make your outbound messaging resonate with potential buyers. The discussion dives into the levels of relevance in sales messaging, highlighting the need for tailored content that speaks directly to buyer personas. Learn how AI tools can elevate your outreach efforts and improve engagement. Transform your sales strategy by applying these insightful techniques!