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

Cracking Outbound

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