Listen now on Spotify, YouTube, and Apple.
Today, we’re diving into the secrets of scaling outbound with Zach Rego, CRO of Triple Whale, who’s done it twice.
Why listen to Zach?
He’s the master chef behind Triple Whale’s growth, joining as Head of Sales and now CRO.
Built a team from scratch and hit 10,000+ customers in just 3 years.
In today’s recipe, we talk about:
How to go from founder-led sales to a scalable team,
The real secrets behind outbound that works,
Scaling fast with 20 high-performing reps.
Some takeaways:
The Hidden Patterns of Sales Scaling:
The most fascinating part about Triple Whale's growth story isn't what everyone talks about – it's the counterintuitive moves they made that accelerated their success.
The Inbound-to-Outbound Trigger Point
Two specific metrics signaled the perfect moment to build outbound:
When ASP (Average Selling Price) growth flatlined
When churn patterns revealed that self-selected customers weren't the best fit1
The Anti-Attribution Philosophy
Rather than obsessing over lead source attribution, they focused on total revenue generation. This counterintuitive approach reduced internal friction and encouraged true collaboration between SDRs and AEs.
The Compensation Evolution Secret
They intentionally overpaid sales reps in the early months, telling them explicitly: "You're going to make a ton of money the next six months... but that's not your OTE for Q4 and Q1." This radical transparency led to high team retention despite later compensation adjustments.
The Target Account Paradox
Instead of measuring SDRs on demo volume for enterprise accounts, they shifted to pipeline generation. The insight: two well-qualified enterprise opportunities could generate enough pipeline for quota achievement, even with lower close rates.
Connect with Zach:
Chapters
00:00 Intro
00:41 Building the Initial Sales Team
07:24 Building the Outbound Motion
09:26 Hiring Strategies and Team Dynamics
19:12 Compensation Plans and Pipeline Management
24:25 Evolution of the Team
25:08 Challenges in Transitioning to Outbound
25:56 Maintaining Brand Integrity
27:08 Scaling and Personalization
30:07 Leveraging Partnerships for Growth
32:50 Headcount Planning and Hiring Strategies
38:51 Reflections and Lessons Learned
Share this post