How John Ley Built Brex' Sales Enablement Playbook and Advice for Other Enablement Leaders

Cracking Outbound

How to lead enablement by fixing what’s actually slowing your team down.

In this episode, Todd Busler talks with John Ley, Sr. Director of GTM Strategy & Operations at Brex, about what it really means to make enablement a strategic lever from day one.

John shares how his time at Square and Brex shaped his thinking, why you need more than playbooks and role plays, and what happens when you build tight feedback loops with sales reps. He gets into how real throughput wins often come from collaborating with teams like finance and risk, not just product marketing or RevOps.

You’ll also hear how a practical onboarding framework, strong conviction in your ICP, and a move away from static training decks can unlock meaningful results.

In this episode, you’ll learn:

• How to structure enablement around actual rep pain
• Why discovery struggles often come back to use cases
• What it takes to build trust as a first enablement hire

Things to listen for:

(00:00) Introduction

(01:44) John Ley’s first priority in enablement at Brex

(04:26) Building a reliable foundation for sales data

(06:06) Removing friction across ops, finance, and risk

(07:33) Rethinking ICP ownership and common traps

(10:21) The Brex approach to early outbound plays

(13:10) A smarter four-part onboarding for new reps

(18:32) Modernizing competitive training with AI tools

(22:04) Advice for CROs hiring first enablement lead