Why do so many sales leaders fail before they even get started?

In this episode, Jarod Greene chats with Kelley Hippler, CRO at Briefly, about why people-centered leadership is the key to building sales teams that last.

Kelley explains how CROs fall into the trap of managing up, missing what their team really needs. She talks about the pressure leaders feel from day one and how it pulls them away from trust-building and coaching. Her mission is simple: leadership should clear the path, not block it. That starts with getting real feedback, removing friction, and making space for reps to succeed on their own terms.

In this episode, you’ll learn:

1. Why top ICs often flop as managers – The best sellers don’t always make the best leaders.
2. How to spot leadership red flags early – Lack of trust, poor coaching, and misaligned priorities are just the start.
3. What people-first leadership looks like – Focus on enablement, not activity metrics, and keep the spotlight on your team.

Things to listen for: 

(00:00) Introduction

(00:41) The real reason CRO tenure is shrinking

(01:09) What people-centered leadership means

(02:11) Why new leaders obsess over managing up

(03:58) Advice for aspiring managers in sales

(05:11) How to remove friction for your team

(05:50) The mistake top reps make as managers