Behind the CXO Title: Prioritizing What Matters Most with Will Cook

In this episode, we sit down with Will Cook, Chief of Staff at Skycrest Roof Co. Will shares his unique path from consulting to serving as an infantry officer in the U.S. Army before joining the CXO program. He reflects on his first year helping to launch Skycrest, where the role meant doing everything from marketing to operations while learning the business from the ground up. Will highlights the importance of humility, listening, and building relationships with founders and frontline teams, especially in a people-driven industry. He also discusses evaluating talent in fast-moving environments, practicing relentless prioritization, and leaning on the CXO peer network to navigate the inevitable highs and lows of growing a young company.


Key Takeaways:

• Learning the business from the ground up builds credibility, deepens relationships, and ensures leaders make informed decisions that create lasting value
• Relentless prioritization helps executives focus on the highest-impact initiatives, avoid distractions, and drive meaningful results in fast-moving environments
• People are at the center of every decision, and knowing your team’s strengths, weaknesses, and motivations is key to building trust and driving performance
• Steadiness through highs and lows is sustained by leaning on peers and mentors, creating a support system that strengthens resilience and perspective


Chapters:

• 00:00 - Introduction
• 07:56 - What Makes a Good CXO
• 12:05 - Building Relationships with Founders
• 14:36 - Advice for New Leaders
• 17:24 - Best Advice Ever Received


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You’ll also find other Bigger. Stronger. Faster. episodes, alongside our Microcap Moments and Everyday Heroes series—highlighting the people and stories that make the microcap space unique.


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