Shows / 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
- Outbound Squad
AI: History is repeating itself with Todd Caponi
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…
- Outbound Squad
Outbound: The precision era is here with TitanX
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…
- Outbound Squad
Coaching & leading enterprise sales reps
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…
- Outbound Squad
Scott Leese on why personal brand is the only moat that’s left
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…
- Outbound Squad
Future of Saas, moats, pipegen, and more with Ryan Heaphy
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…
- Outbound Squad
Mental health and finding fulfillment in sales with Alex Kremer
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…
- Outbound Squad
Second-line SDR leadership with Brandon Jackson
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…
- Outbound Squad
Lessons from a first-time sales manager
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…
- Outbound Squad
Building an AI-native sales motion with Heath Barnett
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…
- Outbound Squad
Tackling new territories, multi-threading, and more with Krysten Conner
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…
- Outbound Squad
The Too Good To Ignore Outbound Methodology
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…
- Outbound Squad
Meet Amanda Long, our newest Pipeline Consultant
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…
- Outbound Squad
VP of Revenue at AdRoll on empathy, accountability, pipegen, and more
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…
- Outbound Squad
Founding AE at 30 Minutes To President’s Club, Alex Murphy
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…
- Outbound Squad
CRO of Orum on AI, cold calling, and the future of SaaS
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…
- Outbound Squad
Scaling Rippling’s 400+ BDR org with Ashley Kelly
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…
- Outbound Squad
From rep to manager to leading global enablement at Shopify with Siobhan Sweeney
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…
- Outbound Squad
Too Good To Ignore
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…
- Outbound Squad
Tito Bohrt on building a world-class sales development org
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…
- Outbound Squad
Motive CRO on moving up-market and leading an org of 3,000+
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…
- Outbound Squad
World-class enablement, AE self-sourcing, and onboarding
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…
- Outbound Squad
From rep at ADP to CRO at Houzz with Tara Di-Cristo-Schmitt
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…
- Outbound Squad
Scaling unconventional outbound with Sr Dir of Sales Development at Rippling
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…
- Outbound Squad
“Our BDR booked 7 meetings yesterday” with Paul Salamanca
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…
- Outbound Squad
Leading teams at Google, Apple, Amazon, Gong, Yelp, and more
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…
- Outbound Squad
Armand Farrokh on building an outbound machine + creative ways to build pipeline
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…
- Outbound Squad
State of Outbound (Guest appearance on Mike Weinberg's podcast)
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…
- Outbound Squad
Outbound Masterclass: The ultimate guide to building qualified pipeline in 2026 (Full Course)
Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts): https://masterclass.outboundsquad.com/ ---…
- Outbound Squad
In 15 minutes, I'll help you handle any objection prospects throw at you (Mini Course)
Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts): https://masterclass.outboundsquad.com/ --- "I'm…
- Outbound Squad
Cold Calling: Give me 23 minutes and I'll eliminate your fear of the phones (Mini Course)
Get free access to the full course + companion workbook (50+ pages of frameworks, templates, and AI prompts): https://masterclass.outboundsquad.com/ --- Less…
- Outbound Squad
Messaging: Why prospects ignore your cold emails and cold calls (and how to fix it)
Get free access to the full course + companion workbook: https://masterclass.outboundsquad.com/ 91% of buyers believe salespeople don't understand what they…
- Outbound Squad
Mastering the Framework that Triples Cold Call Conversions
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…
- Outbound Squad
AI in sales masterclass & why RevOps will disappear with Kyle Vamvouris
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…
- Outbound Squad
The Outbound Equation: How to Secure High Quality Meetings
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…
- Outbound Squad
Sales enablement masterclass with Nate Vogel
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…
- Outbound Squad
How to crush the Director of SDR role with Rippling’s Sr SDR Director
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…
- Outbound Squad
Not partnering with sales enablement? Big mistake
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…
- Outbound Squad
Here’s PROOF that AI isn’t replacing SDRs anytime soon
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…
- Outbound Squad
How to Cold Call for Higher Connect Rates, Better Conversations, and Meetings That Actually Show Up
Jason was a guest on the Outbound Kitchen - Sales Podcast hosted by Elric Legloire to share tactical cold-calling frameworks—using permission-based openers…
- Outbound Squad
From IC to SVP of Sales with Aaron Rissler
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…
- Outbound Squad
The Outbound Equation: A proven methodology to secure high-quality meetings in 2026
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…
- Outbound Squad
From Rep To Sales Exec with Bryan Evans, VP of Sales at Neo4j
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…
- Outbound Squad
Sales Enablement Masterclass with VP of Sales Enablement at Rippling, Jonas Master
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…
- Outbound Squad
A simple framework to get AEs self-sourcing pipeline
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…
- Outbound Squad
Improving cold call qualification
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…
- Outbound Squad
"AI doesn't have a point of view" (a warning)
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…
- Outbound Squad
[Playbook] State of Outbound: AI and what to expect in 2026
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…
- Outbound Squad
“We increased pipeline by 170% this month!”
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…
- Outbound Squad
How to 3x your contact rates
In this episode, Jason and Clara Johnson break down why reps need an omnichannel outbound strategy and show how using coordinated calls, emails, social…
- Outbound Squad
[Playbook] How two reps closed a $30M+ deal (the largest in company history)
This episode is the audio from our webinar on sales mastery. We were joined by Rona Cohen and Ryan Smith at ZoomInfo to share how they closed the largest deal…
- Outbound Squad
Dialers won’t fix your cold calling problem
In this episode, Jason and Clara Johnson break down why autodialers hurt connect and conversion rates, and share smarter ways to fix your cold calling results…
- Outbound Squad
Biggest mistake when re-engaging closed/lost opps
In this episode, Jason and Clara Johnson share a simple framework for re-engaging closed lost opportunities by using time-based insights, past deal context…
- Outbound Squad
Meet our new Head of Training, Clara Johnson!
In this episode, Jason announces Clara Johnson as the new Head of Training in Outbound Squad, discussing how her previous experience as a successful sales…
- Outbound Squad
Negotiations Masterclass With Todd Caponi
In this episode, Todd Caponi shares how to negotiate effectively in sales, covering the history of negotiation, common myths, the four levers of negotiating…
- Outbound Squad
[Playbook] Steal this PipeGen framework: How we generated $70M+ in new pipeline every week
This episode is the audio from our recent webinar on pipeline generation. Marcus Chan from Venli joined us to share how to build a repeatable pipeline…
- Outbound Squad
A masterclass on sales coaching with Mark Hunter
In this episode, Mark Hunter shares how sales leaders can build a strong team culture and coach effectively by understanding what motivates each rep, leading…
- Outbound Squad
How to handle vet AEs who think they know it all
In this episode of our new behind-the-scenes series with the Outbound Squad sales training team, Jason Bay and Clara Johnson share how sales leaders can get…
- Outbound Squad
A simple framework to get AEs self-sourcing pipeline
In this episode of our new behind-the-scenes series with the Outbound Squad sales training team, Jason Bay and Clara Johnson share how sales leaders can build…
- Outbound Squad
Improving cold call qualification
In this episode, Jason and Clara Johnson kick off a new behind-the-scenes series with the Outbound Squad sales training team. They shared how SDRs can improve…
- Outbound Squad
[Playbook] Account Executives: Steal this framework to self-source 30%+ of your pipeline (without making hundreds of cold calls)
This episode is the audio from our recent webinar on AE self-sourcing. Erika Fuchs from EliseAI, Rob Anderson from TitanX, and Darin Alpert from ZoomInfo…