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

Feb 11, 2026

41 minutes

The conversation delves into the evolution of enterprise sales, the journey within Alteryx, the impact of AI on sales objections, challenges in selling AI, and the use of AI tools in sales leadership. It explores the changing landscape of enterprise sales, the role of AI in reshaping sales processes, and the challenges faced in selling AI solutions. Additionally, it highlights the use of AI tools in sales leadership and the complexities of implementing AI in sales strategies. The conversation covers the topics of building internal processes and GPTs, the buy vs. build scenario and sales conversation, changing buying behavior and approval process, competition and sales process challenges, and the impact of AI on job roles. Takeaways Sales Evolution AI in Enterprise Sales Buy vs. build scenario Changing buying behavior Impact of AI on job roles 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

Guests:

Joe Simpson

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Episode Summary

What happens when AI reshapes the market around you — but the core problem you solve hasn't changed in a decade?

Joe Simpson is the Director of Enterprise Sales at Alteryx, leading field AEs across the West Coast. He's been at the company for 11 years — through an IPO, a private equity acquisition, six bosses in 12 months, and an entire product evolution from "get analysts out of Excel" to "AI-ready data infrastructure."

In this episode, we dig into what it's like selling the picks and axes in an AI gold rush — when you're not an AI tool, but the thing that makes AI tools actually work.

We cover: → Why the Excel hell problem still exists in enterprise — and why AI made it worse, not better → The IT power shift: why business users are losing buying authority to security and governance teams → How Joe's team built custom GPTs for account research, persona prep, and pipeline reviews — without buying new software → The tire kicker problem: enterprise buyers with AI mandates but no idea where to spend → Why more approvers in the buying process signals something deeper about enterprise risk perception

Joe's take on AI replacing sales jobs: "Total BS. The cream is gonna rise to the crop — it's not about the LLM, it's what you do with it."