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Joe Simpson joins Warren Kucker to discuss We Are the Picks and Axes — Selling the Infrastructure That Makes AI Actually Work. Key takeaways include Sales Evolution in enterprise environments and AI's integration into Enterprise Sales strategies.

EP. 7 41 min February 11, 2026 Recorded February 11, 2026

We Are the Picks and Axes — Selling the Infrastructure That Makes AI Actually Work

with Joe Simpson

"Total BS. The cream is gonna rise to the crop — it's not about the LLM, it's what you do with it."

About This Episode

Joe Simpson discusses navigating enterprise sales through an IPO, private equity acquisition, leadership transitions, and product evolution toward AI-ready data infrastructure at Alteryx. The conversation covers positioning, buy vs. build decisions, and changing buying behaviors.

About the Guest

Joe Simpson

Director of Enterprise Sales at Alteryx with 11 years at the company, leading field Account Executives across the West Coast. Has navigated the company through an IPO, private equity acquisition, leadership transitions, and product evolution toward AI-ready data infrastructure.

Key Takeaways

  • Sales Evolution in enterprise environments
  • AI's integration into Enterprise Sales strategies
  • Buy vs. build decision scenarios
  • Changing buying behaviors among enterprises
  • Impact of AI on job roles and responsibilities

Chapters

00:00 Evolution of Enterprise Sales
06:01 Positioning and Sales Process
11:32 Challenges in Selling AI
17:55 AI Tools in Sales Leadership
24:27 Buy vs. Build Scenario and Sales Conversation
31:31 Competition and Sales Process Challenges
Account ExecutivesSales ManagersRevenue OperationsVPs of SalesCRO