The Transaction

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

20 snips
Aug 28, 2025
Chris Orlob, CEO of pclub.io and a B2B sales expert, dives into the pressing skills crisis facing sales teams today. He highlights the importance of mastering specific skills before moving on, advocating for a skill transformation loop in training. The conversation covers the shifting dynamics of B2B sales, emphasizing emotional intelligence and effective discovery techniques. With sales becoming increasingly competitive, Orlob stresses continuous learning as essential for success in this tech-driven landscape.
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INSIGHT

Skill Capacity Is The Missing Lever

  • Sales teams are drowning in tech but starving for real selling skill capacity.
  • Skill capacity equals what to do, why to do it, and how to build judgment in reps.
ANECDOTE

Apology Email Won The Deal

  • Chris lost a near-six-figure deal when procurement offered $40k against a ~$100k ask and he refused to concede.
  • After his SVP insisted, Chris wrote an apology email and the deal closed within days.
ANECDOTE

The Bloody Eyeball Play Worked

  • Craig presented with a burst blood vessel in his eye and candidly addressed it as the "elephant in the room."
  • Calling attention to the issue relaxed the room and he ultimately won the deal.
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