Outbound Squad

World-class enablement, AE self-sourcing, and onboarding 15.06.2026 54мин

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 08.06.2026 1ч 8мин

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 01.06.2026 59мин

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 25.05.2026 57мин

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 19.05.2026 1ч 6мин

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 12.05.2026 1ч 4мин

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) 05.05.2026 55мин

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) 30.04.2026 2ч 44мин

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 everyone else. This course teaches you exactly what they do differently. The Outbound Masterclass is a free, 3-hour course covering the complete methodology we've used to train 20,000+ reps at companies like Shopify, Gong, Zoom, Rippling, and iHeartMedia. Here's what's inside: 1) Disqualify and avoid wasting hours pursuing bad-fit accounts 2) Leverage AI as your personal assistant to eliminate most busywork 3) Control the Conversation with prospects on cold calls and secure the meeting 4) Own the inbox with best practices from 85M+ cold emails we studied with Gong 5) Handle nearly any objection prospects throw at you 6) Build offers prospective buyers feel stupid for ignoring This is the live premiere of the Outbound Masterclass. It's also available on-demand at the link below. Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts): https://masterclass.outboundsquad.com/ 💡 ABOUT OUTBOUND SQUAD We help B2B sales teams build pipeline through outbound. We've trained 20,000+ reps at 250+ companies. Our average client increases qualified pipeline by 22.3% within 90 days. 👋 CONNECT WITH ME LinkedIn: https://www.linkedin.com/in/jasondbay/ Website: https://outboundsquad.com Podcast: https://open.spotify.com/show/3M48nC6r29rITjQ1wFccdN

In 15 minutes, I'll help you handle any objection prospects throw at you (Mini Course) 29.04.2026 18мин

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 master a repeatable framework for turning "not interested" into "tell me more." Here's what we cover: 1) The psychology behind why prospects object (and why it's actually a good sign) 2) A universal framework for responding to ANY objection without sounding scripted 3) The 5 most common cold call objections and exactly what to say for each one Real examples and role-plays you can practice today This is a live session from the Outbound Masterclass launch series. The full course is free and covers 15 modules on the complete outbound methodology. Get free access to the full Outbound Masterclass course + companion workbook: https://masterclass.outboundsquad.com/ The workbook includes the objection handling playbook, word-for-word responses to the top 5 objections, and AI prompts for practicing in real-time. 💡 ABOUT OUTBOUND SQUAD We help B2B sales teams build pipeline through outbound. We've trained 20,000+ reps at 250+ companies including Shopify, Gong, Zoom, Rippling, and iHeartMedia. 👋 CONNECT WITH ME LinkedIn: https://www.linkedin.com/in/jasondbay/ Website: https://outboundsquad.com Podcast: https://open.spotify.com/show/3M48nC6r29rITjQ1wFccdN

Cold Calling: Give me 23 minutes and I'll eliminate your fear of the phones (Mini Course) 28.04.2026 25мин

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 phone to booking meetings consistently. Here's what we cover: 1) The 3-step cold call framework that triples meeting booked rates 2) Creative openers that reduce hang-ups and capture the prospect's attention 3) Engaging questions that anchor to pain and get the prospect to show up This is a live session from the Outbound Masterclass launch series. The full course is free and covers 15 modules on cold calling, cold email, messaging, objection handling, and more. Get free access to the full Outbound Masterclass course + companion workbook: https://masterclass.outboundsquad.com/ The workbook includes the complete cold call talk track template, AI prompts for building personalized openers, and frameworks you can implement the same day. 💡 ABOUT OUTBOUND SQUAD We help B2B sales teams build pipeline through outbound. We've trained 20,000+ reps at 250+ companies including Shopify, Gong, Zoom, Rippling, and iHeartMedia. 👋 CONNECT WITH ME LinkedIn: https://www.linkedin.com/in/jasondbay/ Website: https://outboundsquad.com Podcast: https://open.spotify.com/show/3M48nC6r29rITjQ1wFccdN

Messaging: Why prospects ignore your cold emails and cold calls (and how to fix it) 21.04.2026 13мин

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 "pitching" in cold emails reduces reply rates by up to 57% 2) The "push" vs. "pull" method and why most reps do it backwards 3) The 4 components of messaging that resonates: Priorities, Current Solutions, Problems, and Aspirations This is one module from the Outbound Masterclass, a free 15-module course covering the full methodology we've used to train 20,000+ reps at companies like Shopify, Gong, Zoom, Rippling, and more. Get free access to the full course + companion workbook: https://masterclass.outboundsquad.com/ The companion workbook includes every framework, template, and AI prompt from the course so you can implement what you learn immediately. 💡 ABOUT OUTBOUND SQUAD We help B2B sales teams build pipeline through outbound. We've trained 20,000+ reps at 250+ companies including Shopify, Gong, Zoom, Rippling, and iHeartMedia. 👋 CONNECT WITH ME LinkedIn: https://www.linkedin.com/in/jasondbay/ Website: https://outboundsquad.com Podcast: https://open.spotify.com/show/3M48nC6r29rITjQ1wFccdN

Mastering the Framework that Triples Cold Call Conversions 14.04.2026 57мин

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.⁠

AI in sales masterclass & why RevOps will disappear with Kyle Vamvouris 07.04.2026 47мин

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.⁠

The Outbound Equation: How to Secure High Quality Meetings 31.03.2026 56мин

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.⁠

Sales enablement masterclass with Nate Vogel 24.03.2026 1ч 16мин

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.⁠

How to crush the Director of SDR role with Rippling’s Sr SDR Director 17.03.2026 57мин

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.⁠

Not partnering with sales enablement? Big mistake 10.03.2026 8мин

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.

Here’s PROOF that AI isn’t replacing SDRs anytime soon 03.03.2026 4мин

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.⁠

How to Cold Call for Higher Connect Rates, Better Conversations, and Meetings That Actually Show Up 24.02.2026 55мин

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.⁠

From IC to SVP of Sales with Aaron Rissler 17.02.2026 59мин

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.⁠