How to rethink outbound by focusing on quality, efficiency, and what actually moves the needle.

In this episode, Todd Busler sits down with Andrew Berger, VP of Revenue at Capchase, to talk through how outbound has changed since the early days of cold calling with a phone book.

Andrew reflects on lessons from building Square’s outbound engine, how internal tools and third-party data powered real personalization, and why setting ROI thresholds shaped every decision. He shares the difference between selling to buyers new to financing and those already in the market, and how that distinction drives team structure and messaging.

It’s an inside look at how being in the trenches, testing constantly, and rallying around one clear metric are helping the team scale.

In this episode, you’ll learn:

• Why high-volume outbound no longer guarantees results
• How to use team structure to prioritize pipeline
• What it takes to build trust with executive teams through selling

Things to listen for:

(00:00) Introduction

(02:28) Breaking into tech through a Craigslist post

(04:14) Learning ROI through early sales experiments

(06:51) Personalization tactics that actually drove strong results

(09:10) Smart tools that streamlined outbound prospecting work

(12:45) Leading with investor-style accountability and returns

(15:40) Learning to manage with clear expectations

(19:37) Splitting playbooks by buyer type and readiness

(22:51) Messaging shifts based on market familiarity

(30:22) Rallying the team around one weekly metric