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.

You're invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!

Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.

Tune into The Revenue Leadership Podcast with Kyle Norton every Wednesday. Kyle dives deep into the strategies and tactics that drive success for revenue leaders like Jason Lemkins of SaaStr, Stevie Case of Vanta, and Ron Gabrisko of Databricks.

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

SPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of Sales

Topline

SPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of Sales