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 05:14 Rick's Career Journey 07:50 From Sales Leader to CRO: The Biggest Shift 10:49 Why Curiosity Makes You a Better Leader 16:23 Building a Leadership Team That Learns and Experiments 17:54 Evaluating Leadership Beyond Revenue 22:50 Rick's Book Recommendation: The 7 Habits of Highly Effective People 24:53 Where to Find Rick Smolen Try ShipHero: shiphero.com
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