SPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of Sales | Rick Smolen, CRO @ ShipHero

When Rick Smolen stepped into the CRO role at ShipHero, he took on responsibility for the entire customer lifecycle, from marketing and partnerships to customer success and support.

With a background primarily in sales, he had to learn how to lead functions outside his expertise without needing to have all the answers.

In this episode, Rick joins Sam Jacobs to discuss the leadership lessons that came with that transition, from asking better questions to building trust with his team. He also explains how to learn from failure, navigate setbacks, and focus on what you can control as a leader.

Rick talks about:

- Why curiosity makes you a stronger cross-functional leader

- How to challenge your team without micromanaging

- Why experimentation requires accepting failure

- What leaders should focus on when business results fall short

- How to prioritize important work that rarely feels urgent

Chapters

00:00 Introduction to Rick Smolen and ShipHero

01:10 What ShipHero Does