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.
34 min
In this episode, Jason joins Meridith Elliott Powell on the Ask for Change podcast to talk about turning uncertainty into pipeline. They dig into why AI made inboxes harder to break through, using closed-won data to pick who to skip, how multichannel outreach triples contact rates, and prospecting your own clients for expansion. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 12 min
In this episode, Jason and Todd Caponi from Sales Melon, talk about why AI is just the latest chapter in a story sales has seen many times before. They dig into why more buyer information never replaced the seller, mapping buyer behavior onto your current sales stages, celebrating lost deals to sharpen qualification, and the five core jobs of a first-time CRO. Check out more free content and get help with outbound at https://outboundsquad.com/.
1 hr 40 min
In this episode, Jason, Joey Gilkey, and Rob Anderson from TitanX, talk about why outbound is moving from the volume era to the precision era. They dig into why fewer reps and more activity rarely hit the number, calculating cost per conversation and per meeting, how parallel dialing drags down connect and conversion rates, and the account dossiers TitanX's reps used at the event. Check out more free content and get help with outbound at https://outboundsquad.com.
The newest 50 of 443 episodes
34 min
In this episode, Jason joins Meridith Elliott Powell on the Ask for Change podcast to talk about turning uncertainty into pipeline. They dig into why AI made inboxes harder to break through, using closed-won data to pick who to skip, how multichannel outreach triples contact rates, and prospecting your own clients for expansion. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 12 min
In this episode, Jason and Todd Caponi from Sales Melon, talk about why AI is just the latest chapter in a story sales has seen many times before. They dig into why more buyer information never replaced the seller, mapping buyer behavior onto your current sales stages, celebrating lost deals to sharpen qualification, and the five core jobs of a first-time CRO. Check out more free content and get help with outbound at https://outboundsquad.com/.
1 hr 40 min
In this episode, Jason, Joey Gilkey, and Rob Anderson from TitanX, talk about why outbound is moving from the volume era to the precision era. They dig into why fewer reps and more activity rarely hit the number, calculating cost per conversation and per meeting, how parallel dialing drags down connect and conversion rates, and the account dossiers TitanX's reps used at the event. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 10 min
In this episode, Jason and Chris Farwell from Octave, talk about how to coach and lead enterprise reps who may already be better sellers than their managers. They dig into finding the problems buyers actually need to fix, translating technical pain into margin and cash flow, knowing when to coach reps and when to just tell them, and turning customer relationships into warm intros. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 14 min
In this episode, Jason and Scott Leese from Scott Leese Consulting, talk about building a career and income that don't depend on any one job. They dig into why personal brand might be the last career moat, when to start earning outside your W2, his 10-a-day plan for growing your network, and how he builds his calendar around family time. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 17 min
In this episode, Jason and Ryan Heaphy from Fractal Software, talk about what it takes to build a repeatable sales motion in early-stage vertical SaaS. They dig into why the VP of Sales hire usually flops, what a world-class sales playbook actually includes, reverse-engineering quota from pipeline, and what cold calling looks like in vertical SaaS. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 13 min
In this episode, Jason and Alex Kremer from Alluviance, talk about why 70% of sales pros are struggling with their mental health, the two wells analogy and the hungry ghost trap, rewiring where your motivation comes from, and selling from presence, not pressure. Check out more free content and get help with outbound at https://outboundsquad.com.
54 min
In this episode, Jason and Brandon Jackson, formerly of Common Room and now at Ping Identity, talk about his four-pillar CPAD framework for SDR leadership, why dial counts aren't the real measure of a good day, aligning SDR with marketing and sales at once, and where AI belongs in the SDR workflow, and where it doesn't. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 17 min
In this episode, Jason and Matt Rogers from Neo4j, talk about breaking into a cold enterprise territory in person, the monthly accountability one-on-one to run with every rep, the hero move that traps first-time leaders, and using AI to scale coaching without watching every call. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 6 min
In this episode, Jason and Heath Barnett, formerly of Mixmax, talk about why PLG and product-led sales aren't the same thing, the three layers of a real ICP, account scoring with sub-scores that stack, and why AI investment flops without rep skill investment. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 12 min
In this episode, Jason and Krysten Conner, sales coach at krystenconner.com, talk about the where-we-win report every new AE should run, the ship jumper move and other warm-path openers, ghost-writing a referral email your champion will send, and running EMT discovery on outbound-led calls. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 11 min
In this episode, Jason, Clara Johnson, and Amanda Long from Outbound Squad, talk about why outbound needs its own methodology, the three core parts of Too Good To Ignore, how to scale it across your team, and practical plays your reps can use to book more meetings. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 6 min
In this episode, Jason and Amanda Long from Outbound Squad, talk about the daily practice ritual that took her to the top of the leaderboard, how she made it impossible for her manager not to promote her, and how to nail your first front-line leadership role. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 6 min
In this episode, Jason and Mark Haas from AdRoll, talk about why the top rep is often the worst first-time manager, his journey from programmer to rep to VP, and how he runs his day-to-day leading revenue. Check out more free content and get help with outbound at https://outboundsquad.com.
1 hr 21 min
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.
1 hr 12 min
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.
1 hr 6 min
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.
1 hr 0 min
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.
44 min
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.
50 min
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.
56 min
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.
54 min
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.
1 hr 8 min
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.
59 min
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.
57 min
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.
1 hr 6 min
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.
1 hr 4 min
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.
55 min
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.
2 hr 44 min
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://outboundsquad.com/podcast/
18 min
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://outboundsquad.com/podcast/
25 min
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://outboundsquad.com/podcast/
13 min
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://outboundsquad.com/podcast/
57 min
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.
47 min
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.
56 min
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.
1 hr 16 min
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.
57 min
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.
8 min
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.
4 min
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.
55 min
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.
59 min
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.
1 hr 0 min
This episode is the audio from our recent webinar on The Outbound Equation. Jason walks through a proven methodology for securing high-quality meetings in 2026 by reinforcing fundamentals like offers that deliver real value, world-class execution on phone, email, and social, and the critical role of leadership in creating predictable outbound pipeline. Check out more free content and get coaching at https://outboundsquad.com.
1 hr 0 min
In this episode, Bryan Evans shares his journey from rep to VP of Sales at Neo4j and the leadership habits that help sales teams execute, forecast accurately, and win bigger deals. Check out more free content and get coaching at https://outboundsquad.com.
50 min
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.
10 min
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.
9 min
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.
5 min
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.
1 hr 0 min
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.
13 min
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.
13 min
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.
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