Rick Smolen, the Chief Revenue Officer of ShipHero, shares insights from his diverse career in finance and software sales. He discusses the challenges of stepping into the CRO role, managing the entire customer lifecycle, and leading teams in unfamiliar areas. Curiosity emerged as his strongest leadership tool, helping him navigate early mistakes. Rick emphasizes the importance of building a collaborative leadership team, embracing failure for growth, and prioritizing meaningful over urgent tasks in today’s fast-paced environment.
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volunteer_activism ADVICE
Let Go to Lead Successfully
Letting go and empowering your team is crucial for leadership growth.
Avoid doing tasks yourself to prevent burnout and enable team scalability.
insights INSIGHT
Curiosity Drives Cross-Functional Leadership
Curiosity is key when leading functions outside your expertise.
Being a thought partner and challenging ideas drives success beyond having all the answers.
volunteer_activism ADVICE
Set Clear Leadership Expectations
Set clear expectations with your team about your values and goals.
Focus on collective success and the prize, maintaining high standards.
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This book, first published in 1989, outlines seven habits that are designed to help individuals become more effective in their personal and professional lives. The habits are grouped into three categories: Private Victory (habits 1-3), Public Victory (habits 4-6), and Renewal (habit 7). The habits include being proactive, beginning with the end in mind, putting first things first, thinking win-win, seeking first to understand and then to be understood, synergizing, and sharpening the saw. Covey emphasizes the importance of personal integrity, effective time management, empathetic communication, and continuous self-improvement[2][5][4].
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
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