Is your team still stuck in the old way of territory planning?

In this episode of V5, Jarod Greene is joined by Andrew Berger, VP of Revenue at Capchase, to challenge a long-standing sales tradition.

Andrew argues that quarterly and annual planning sessions waste more time than they’re worth. With countless hours spent on formatting, presenting, and guessing what will matter months from now, he believes the ROI just isn’t there. Instead, he’s pushing for a new approach that’s faster, more flexible, and powered by AI. By connecting systems and prompting smarter analysis, reps can spend less time preparing and more time selling.

In this episode, you’ll learn:

1. Why traditional planning slows teams down – Reps spend hours building plans that are outdated by the time they’re presented, creating more motion than momentum.
2. How AI can support better decisions – With connected systems and smart prompts, teams can surface relevant insights without digging through scattered data.
3. Where sales leaders can shift their focus – Moving away from rigid planning cycles opens up time to test, learn, and act on what’s actually working in the field.

Things to listen for:

(00:00) Introduction

(00:24) Territory planning is broken

(01:11) AI changes sales strategy

(02:08) Presentations waste time

(03:01) Smarter account planning

(04:31) Speed over structure

(05:29) Building with new tools