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Outbound Squad

by Outbound Squad

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The Brutal Truth about Sales and Selling - We interview the world's best B2B Enterprise salespeople.

Latest episodes

Coaching & leading enterprise sales reps

October 19, 2026 · 1 hr 11 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…
Scott Leese on why personal brand is the only moat that’s left

October 12, 2026 · 1 hr 15 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…
Future of Saas, moats, pipegen, and more with Ryan Heaphy

October 5, 2026 · 1 hr 18 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…
Mental health and finding fulfillment in sales with Alex Kremer

September 28, 2026 · 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…
Second-line SDR leadership with Brandon Jackson

September 21, 2026 · 55 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…

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Lessons from a first-time sales manager

September 14, 2026 · 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…
Building an AI-native sales motion with Heath Barnett

September 7, 2026 · 1 hr 7 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…
Tackling new territories, multi-threading, and more with Krysten Conner

August 31, 2026 · 1 hr 13 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…
The Too Good To Ignore Outbound Methodology

August 24, 2026 · 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…
Meet Amanda Long, our newest Pipeline Consultant

August 17, 2026 · 1 hr 7 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…
VP of Revenue at Adroll on empathy, accountability, pipegen, and more

August 10, 2026 · 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…
Founding AE at 30 Minutes To President’s Club, Alex Murphy

August 3, 2026 · 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…

Full episode archive on Apple Podcasts →

About the show

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.