Many sales leaders come from quota-carrying roles. Terry Falk started as a corporate lawyer.

Now VP of Software Sales at 8am, he oversees a team closing 400 new customers every month. He shares with Todd Busler how legal training shaped his approach to sales and why his time managing complex contracts helped him think clearly under pressure. He also breaks down the mistakes that slowed his early sales leadership, how he learned to build a pipeline without relying on inbound, and what running a high-velocity SMB motion looks like today.

Listen in for a refreshingly honest take on getting better by going through the fire.

In this episode, you’ll learn:

• How legal experience can sharpen sales communication
• What happens when inbound drops and you’re not ready
• How to lead teams closing hundreds of SMB deals per month

Things to listen for:

(00:00) Introduction

(01:36) What legal training taught him about enterprise sales

(04:49) Early sales leadership mistakes at a Series A startup

(08:31) How he structured a repeatable outbound pipeline

(13:46) Balancing selling and hiring in early-stage roles

(15:51) What changed when inbound suddenly dropped

(17:24) High-velocity SMB sales explained through a “closing call”

(19:59) Shark Tank-style outbound and why it wasn’t scalable

(26:18) Finding their ICP using win data, not personas

(29:40) Why outbound in SMB SaaS looks very different

(34:28) Reps chasing whales vs. reps targeting coral reefs

(40:34) Using AI for seller ops instead of seller strategy