When Rick Smolen stepped into the CRO role at ShipHero, he wasn’t just inheriting a sales team—he was taking on the entire customer lifecycle. From marketing to partnerships to customer success, Rick had to quickly learn how to lead teams in functions he’d never directly owned before. In this episode, he shares what that transition was really like, the mistakes he made early on, and how curiosity became his most powerful leadership tool.

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Key Moments:

(00:00) Introduction

(01:10) Overview of ShipHero and its services

(03:15) Rick's career Journey

(06:37) Challenges of transitioning to CRO

(09:36) Curiosity and leadership dynamics

(14:27) Building a leadership team and embracing failure

(18:12) Evaluating leadership success

(22:59) Key takeaways and book recommendations