AI Becomes a Board Member and Thought Partner with Greg Shove, CEO at Section AI

This New Way

In this episode, Aydin sits down with Greg Shove, CEO of Section, to unpack how AI isn't just a productivity tool—it's a new cognitive layer for modern organizations. Greg shares how Section pivoted from executive education to AI enablement after a single eye-opening session with ChatGPT. He dives deep into what it really takes to embed AI into workflows, culture, and decision-making—and why “talking to AI” is now mandatory at his company. From building a company-wide second brain with Claude to simulating board meetings with GPT, Greg offers a masterclass in practical AI integration.

Timestamps:

1:35 – Greg’s background: from flameouts to $250M in exits

2:00 – Section’s pivot from exec ed to AI enablement

3:01 – The 6-month internal resistance to AI

4:50 – Why training isn’t enough: the real AI challenge is change management

6:07 – Why treating AI like regular software is a strategic mistake

8:26 – What successful AI deployments have in common

10:02 – Lessons from Shopify, Duolingo, and Fiverr on AI expectations

11:45 – The price of AI is too low—why that might change

14:03 – AI vs. analyst time: “an hour becomes a minute”

15:31 – Section’s 25% productivity gain with AI

18:58 – Measuring productivity impact without perfect data

21:24 – Clever metrics: output per headcount, OKRs, AI shoutouts

24:51 – Using Claude as a company “second brain”

26:11 – Greg’s AI desktop setup: Perplexity, GPT, Claude

27:43 – The Section Expert: maintaining company context for AI

29:27 – “Working with Greg” manual: how to humanize your AI input

31:00 – The difference between values and operating principles

34:42 – Roleplaying board members with AI before real board meetings

36:05 – Claude vs. ChatGPT vs. humans: who gave better board insights?

41:00 – AI for owner-operators: create your own board

42:26 – What Greg’s most excited about: how AI unlocks new opportunities

44:08 – Where to find Greg & Section + listener discount

Tools & Technologies Mentioned:

Claude (Anthropic): Used to build a company-wide second brain and simulate board member personas

GPT (OpenAI): Used as a daily thought partner and board advisor

Perplexity: A go-to AI for fast, accurate information lookups

Section Expert (Claude project): A centralized AI project workspace housing all of Section's key documents for brainstorming

ProfAI (Section’s product): An AI-powered coach designed to teach people how to use AI effectively

ChatGPT for Teams: Mentioned as a better, paid alternative to free-tier tools

Gemini Pro: Noted for its screen-sharing and future context-awareness potential

Copilot (Microsoft): One of several LLM tools tested during board simulations

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