The Outbound Overhaul That Cut Ramp Time in Half and grew pipeline 142% in 3 months with Kyle Asay

Cracking Outbound

Kyle Asay, VP of Global Growth Sales at LaunchDarkly, shares how he revamped the company’s outbound motion during his first few quarters. He outlines the territory planning shifts, structural changes, and leadership plays that helped drive a 142% increase in pipeline and cut the time to first sale nearly in half.

In this episode, Kyle describes how account segmentation set the foundation, what it took to get long-time reps to buy in, and why simple frameworks have helped his team outperform expectations. He also reflects on managing pressure, avoiding whiplash changes, and what it takes to build trust as a new leader.

In this episode, you’ll learn:

• How to transition from inbound to outbound at scale
• The core three metrics Kyle uses to manage performance
• Why territory planning is the key to faster ramp times

Things to listen for:

(00:00) Introduction

(03:20) Increasing pipeline 142% with outbound segmentation

(05:00) Territory planning mistakes and how to fix them

(07:50) Getting rep buy-in without causing cultural whiplash

(13:12) Leadership lessons from tough feedback and early missteps

(16:44) The three outcome metrics Kyle never stops measuring

(20:21) Reducing time to first sale through better account focus

(23:23) Tracking rep activity without micromanaging

(26:52) Turning a feature-led product into a platform story

(34:58) Advice on choosing the right sales org and opportunity

(36:33) Mastering internal locus of control in your sales career

(42:06) Staying grounded as a sales leader in high-pressure roles