Issue No. 30Week ending Sunday, July 26, 2026436 episodes · 1837 articles
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From Sales Rep to $4B GTM Leader: The Playbook for Building Sales Teams (w/ Sam Levy of NetSuite)

With Jim Milbery, Devin Mathews, Sam Levy · Sunday, July 26, 2026

This episode features Sam Levy, Head of Go-to-Market Strategy and Execution at NetSuite, discussing his career path from a college telemarketer to leading a $4 billion GTM organization. Sam and Devin Mathews explore the evolution of sales from hustle-driven early roles to data-centric leadership, the importance of strategic career moves and community, and Sam's prediction for the future of CEO roles.

Key takeaways

  • Sam Levy, who leads NetSuite's $4 billion Go-to-Market organization, makes a bold forecast: 90-95% of future CEOs will emerge from sales or marketing backgrounds. Read more →
  • Sam Levy, NetSuite's Head of Go-to-Market Strategy, argues that rapid revenue growth often "exposes the cracks" in a sales organization, making targets feel harder to hit even when the numbers are met. Read more →
  • Sam Levy, head of Go-to-Market Strategy at NetSuite, highlights the dilemma of high-performing “lone wolf” sales reps: their productivity might be tolerated if their disruptive behavior doesn't become a "cancer to the team" or impede broader scale. Read more →
  • Sam Levy, Head of Go-to-Market at NetSuite, saw his organization scale from $250 million to $4 billion by moving sales leadership beyond gut feeling, embracing data, and then AI. Read more →

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