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Outbound Squad

Outbound Squad

Outbound Squad 422 Episodes Jun 15, 2026

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

World-class enablement, AE self-sourcing, and onboarding Jun 15, 2026 3240 In this episode, Jason and Mitch Thomas from Brooksource, talk about how to position enablement as a true sales partner, the plays their nearly 200 AEs use to self-source pipeline without an SDR team, and the in-person cohort onboarding that gets new reps ramped fast. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
From rep at ADP to CRO at Houzz with Tara Di-Cristo-Schmitt Jun 8, 2026 4099 In this episode, Jason and Tara Di-Cristo-Schmitt from Houzz talk about her journey from rep at ADP to CRO, what she learned about authentic leadership and transparency at HubSpot, how she prioritized her first 90 days as a first-time CRO, and her weekly rhythm for managing hundreds of reps. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
Scaling unconventional outbound with Sr Dir of Sales Development at Rippling Jun 1, 2026 3553 In this episode, Jason and Ken Amar from Rippling, talk about how he booked meetings at a 41% rate as an SDR, the custom landing pages and groundswell calls Rippling uses to break into accounts, high-value gifting and in-person plays that actually scale, and where he thinks the SDR role is headed next. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.
“Our BDR booked 7 meetings yesterday” with Paul Salamanca May 25, 2026 3465 In this episode, Jason and Paul Salamanca from Cymon AI, talk about how his BDR booked 7 meetings in a single day, the outbound motion two BDRs use to generate 30 to 40 meetings a month, his AI maturity model for sales orgs, and the coaching layer that ties it all together. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
Leading teams at Google, Apple, Amazon, Gong, Yelp, and more May 19, 2026 3995 In this episode, Jason and Miram Ebrahim from Nomix Group, talk about creative plays that land meetings, nailing your first 90 days in a new leadership role, and giving fearless feedback. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
Armand Farrokh on building an outbound machine + creative ways to build pipeline May 12, 2026 3867 In this episode, Jason and Armand Farrokh from 30 Minutes to President's Club talk about turning around an SDR team fast, the frameworks every outbound rep needs, and creative pipeline plays beyond cold calls and emails. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
State of Outbound (Guest appearance on Mike Weinberg's podcast) May 5, 2026 3316 Jason was a guest on The Sales Management. Simplified. Podcast hosted by Mike Weinberg. In this episode, they talked about why outbound is harder than ever, what broke the classic SDR–AE model, and Jason’s Too Good To Ignore outbound methodology. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.
Outbound Masterclass: The ultimate guide to building qualified pipeline in 2026 (Full Course) Apr 30, 2026 9881 Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts): https://masterclass.outboundsquad.com/ --- 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 eve
In 15 minutes, I'll help you handle any objection prospects throw at you (Mini Course) Apr 29, 2026 1096 Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts): https://masterclass.outboundsquad.com/ --- "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 ma
Cold Calling: Give me 23 minutes and I'll eliminate your fear of the phones (Mini Course) Apr 28, 2026 1553 Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts): https://masterclass.outboundsquad.com/ --- 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 pho
Messaging: Why prospects ignore your cold emails and cold calls (and how to fix it) Apr 21, 2026 834 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 th
Mastering the Framework that Triples Cold Call Conversions Apr 14, 2026 3428 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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