The Transaction | Solving the Go-To-Market Skills Crisis in B2B Sales with Chris Orlob, CEO of pclub

Solving the Go-To-Market Skills Crisis in B2B Sales with Chris Orlob, CEO of pclub - Ep 64

August 28, 2025 / 50:52/S2 E64

B2B sellers and sales leaders find themselves in the midst of an unprecedented Go-To-Market skills crisis at a time when budgets are shrinking and selling is getting harder.
Joining the show once again is the inimitable Chris Orlob, CEO at pclub.io, the #1 Skill Transformation Platform for Revenue Teams. Chris joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into where the current sales skills crisis came from, what sales leaders can do to help improve their sales reps’ skill capacity, and why sales reps should start with getting a concrete understanding of a proper discovery process.
Plus, Chris discusses why B2B sales leaders should implement a skill transformation loop into how they train their sales teams.
Also, Craig addresses an elephant in the room, Matt bemoans the illegality of ‘hacking darts’ in Foster City, and Sam the Producer laughs at Craig.

Critical Takeaways

Investing only in Sales Process is not enough to help sellers hit their targets, because process only covers what to do. Whereas, Skill capacity doesn't stop at what to do. Skill capacity is what to do, why to do it, and how to do it so that you're building judgment. This way, reps can have audible-ready, rich business conversations that create value for both buyers and customers.
When training sales reps on new skills, it’s best to make sure they master one skill before they move on to learning another. This builds skill depth, rather than very shallow skill breadth. Without ensuring competency in one skill before moving on, all you achieve is motion without accomplishment.
The first, foundational skill that reps should train on is sales discovery. Having a strong grasp on discovery will help sales reps build stronger additional skillsets. It’s harder to build the other sales skills without having a solid understanding of sales discovery.
As companies’ go-to-market motions become increasingly complex, if they don’t address the low skill capacity of their sales team, they incur a growing ‘skill deficit’, which if left unchecked will lead to catastrophic results down the line.

Chapters

00:00 - Episode Preview

02:21 - Introducing Chris Orlob, CEO of pclub.io

03:33 - An Instructive B2B Sales Story: How to Interact with Procurement Leaders

08:06 - Craig & The Case of The Bloody-Eyed Business Meeting

12:19 - The State of the B2B Sales Skills Crisis in Go-To-Market Today

25:40 - Discovery is the Fundamental Sales Skills Reps Need to Learn

33:24 - How B2B Companies Should be Approaching Discovery and the Buying Process in Today's Market

44:25 - Why B2B Sales Leaders Need to Implement a Skill Transformation Loop Into Their Teams' Training

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Epic Quotes

“We are in an era of a Go-To-Market skills crisis.” - Chris Orlob
“Reps and sellers are drowning in technology, but starving for skills and skill capacity.” - Chris Orlob
“AI is not the solution to the skill gap.” - Craig Rosenberg
“If they can't build a case for me of how they're going to solve my problem, I don't really want to buy it.” - Matt Amundson

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