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Blissful Prospecting

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-pe...

Episodes

20 of 440 episodes

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 tha...

70:31Oct 19, 2026

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...

74:39Oct 12, 2026

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 ver...

77:32Oct 5, 2026

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 we...

73:12Sep 28, 2026

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...

54:54Sep 21, 2026

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 accountabilit...

77:26Sep 14, 2026

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 laye...

66:53Sep 7, 2026

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...

72:44Aug 31, 2026

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 cor...

71:16Aug 24, 2026

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...

66:57Aug 17, 2026

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 program...

66:06Aug 10, 2026

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 offer...

81:19Aug 3, 2026

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...

72:52Jul 27, 2026

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 s...

66:21Jul 20, 2026

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 firs...

60:57Jul 13, 2026

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 p...

44:05Jul 6, 2026

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...

50:36Jun 29, 2026

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 bu...

56:00Jun 22, 2026

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 nea...

54:00Jun 15, 2026

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...

68:19Jun 8, 2026