Outbound Squad

Episod

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  Founding AE at 30 Minutes To President’s Club, Alex Murphy 03.08.2026 1j 21min

  In this episode, Jason and Alex Murphy from 30 Minutes to President's Club, talk about cold calling without the telemarketer feel, the offering mindset that keeps your self-worth out of the outcome, and his 3-question discovery checklist for first calls. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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  CRO of Orum on AI, cold calling, and the future of SaaS 27.07.2026 1j 12min

  In this episode, Jason and John Eitel from Orum, talk about why top sales teams admit they haven't cracked AI, how to centralize AI through RevOps without hurting rep productivity, why skill still beats tool stack, and the pipegen mix by segment that holds up from high velocity to enterprise. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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  Scaling Rippling’s 400+ BDR org with Ashley Kelly 20.07.2026 1j 6min

  In this episode, Jason and Ashley Kelly from Rippling, talk about how Rippling scaled from 40 to 400 BDRs in under four years, the "go and see" value that runs from Parker on down, and the SDR-to-CRO program that keeps reps around. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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  From rep to manager to leading global enablement at Shopify with Siobhan Sweeney 13.07.2026 1j

  In this episode, Jason and Siobhan Sweeney, formerly of Shopify, talk about her journey from door-to-door sales rep in New York City to first-time sales leader, why she made the jump into enablement, how Shopify built a world-class enablement org, and her take on executive presence, managing up, and coaching reps. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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  Too Good To Ignore 06.07.2026 44min

  In this episode, Jason guests on The Revenue Insiders to talk about Outbound Squad's Too Good To Ignore outbound methodology and its three pillars (disqualify, offer, provoke), the trigger, tension, trust messaging model that works across cold call, email, and social, and what it actually takes to build pipeline in 2026. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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  Tito Bohrt on building a world-class sales development org 29.06.2026 50min

  In this episode, Jason and Tito Bohrt from AltiSales, talk about his 4-part framework for building and diagnosing sales orgs, what's working in cold calling right now, and whether the SDR function is about to get replaced. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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  Motive CRO on moving up-market and leading an org of 3,000+ 22.06.2026 56min

  In this episode, Jason and Adam Block from Motive, talk about why they made the move up market, how they protected the mid-market and SMB business that was already working, how they rewired the culture for outbound, and the talent and metrics that matter when you're leading a 3,000-plus revenue org. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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  World-class enablement, AE self-sourcing, and onboarding 15.06.2026 54min

  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.⁠
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  From rep at ADP to CRO at Houzz with Tara Di-Cristo-Schmitt 08.06.2026 1j 8min

  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.⁠
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  Scaling unconventional outbound with Sr Dir of Sales Development at Rippling 01.06.2026 59min

  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.⁠
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  “Our BDR booked 7 meetings yesterday” with Paul Salamanca 25.05.2026 57min

  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.⁠
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  Leading teams at Google, Apple, Amazon, Gong, Yelp, and more 19.05.2026 1j 6min

  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.⁠
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  Armand Farrokh on building an outbound machine + creative ways to build pipeline 12.05.2026 1j 4min

  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.⁠
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  State of Outbound (Guest appearance on Mike Weinberg's podcast) 05.05.2026 55min

  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.
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  Outbound Masterclass: The ultimate guide to building qualified pipeline in 2026 (Full Course) 30.04.2026 2j 44min

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

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

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

  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
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  Mastering the Framework that Triples Cold Call Conversions 14.04.2026 57min

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

  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.⁠