“Empathetic, but firm” – Sales Leadership principles from one of the best CROs in tech

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Cracking Outbound

Champify

26 episodes

4 days ago

If you think outbound is dead, you’re either lying or you’re bad at it. Quotas keep rising, your people are grinding, and the pipeline isn’t growing. It’s an equation that drives you mad. While everyone wants more opportunities, only a few know how to build an outbound culture that delivers. I’m Todd Busler, former VP of Sales, now co-founder of Champify, and I’ve spent my career sharpening how to build a company pipeline that’s self-sufficient. On this show, I’m talking to sales leaders who have cracked the outbound code. They’ve built an outbound culture beyond their SDRs and scaled repeatable systems that drive real pipeline without relying on hacks. We’ll break down the winning plays, processes, and frameworks behind growing that outbound muscle to help you get results faster. No fluff. No hacks. Real strategies from real people who have done it so you can stop guessing and start opening.

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Business

“Empathetic, but firm” – Sales Leadership principles from one of the best CROs in tech

Cracking Outbound

43 minutes

4 months ago

“Empathetic, but firm” – Sales Leadership principles from one of the best CROs in tech

Ryan Heinig, Chief Revenue Officer at 2X, shares his journey from leading top B2B SaaS companies like Qlik and AppDynamics to shaping outbound strategies at a growing tech-enabled services firm. He reveals how he successfully scaled outbound efforts by focusing on repeatable systems, strong leadership, and a balance of empathy and accountability.

In this episode, Ryan discusses how shifting from SaaS to services changed his approach to sales, why sales reps must master discovery and qualification, and how to create a culture of high expectations while fostering autonomy.

In this episode, you’ll learn:

The secret to building a sustainable outbound system
How to coach your team through real-time sales moments
Why being empathetic but firm is crucial for sales leadership

Things to listen for:

(00:00) Introduction

(02:14) Evaluating the opportunity at 2X

(04:46) Selling tech-enabled services vs SaaS

(06:39) Hiring for curiosity and coachability

(08:38) Balancing high expectations with empathy

(14:03) Scaling outbound from AE to CRO

(17:19) Maintaining PG culture across sales segments

(19:25) Leading indicators for outbound success

(23:29) Using AI to enhance research and outreach

(28:27) Overcoming consistency challenges in outbound

(35:31) Defining sales stages that align with buyer’s journey

(40:04) Playing the long game in sales