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

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 exits2:00 – Section’s pivot from exec ed to AI enablement3:01 – The 6-month internal resistance to AI4:50 – Why training isn’t enough: the real AI challenge is change management6:07 – Why treating AI like regular software is a strategic mistake8:26 – What successful AI deployments have in common10:02 – Lessons from Shopify, Duolingo, and Fiverr on AI expectations11:45 – The price of AI is too low—why that might change14:03 – AI vs. analyst time: “an hour becomes a minute”15:31 – Section’s 25% productivity gain with AI18:58 – Measuring productivity impact without perfect data21:24 – Clever metrics: output per headcount, OKRs, AI shoutouts24:51 – Using Claude as a company “second brain”26:11 – Greg’s AI desktop setup: Perplexity, GPT, Claude27:43 – The Section Expert: maintaining company context for AI29:27 – “Working with Greg” manual: how to humanize your AI input31:00 – The difference between values and operating principles34:42 – Roleplaying board members with AI before real board meetings36:05 – Claude vs. ChatGPT vs. humans: who gave better board insights?41:00 – AI for owner-operators: create your own board42:26 – What Greg’s most excited about: how AI unlocks new opportunities44:08 – Where to find Greg & Section + listener discountTools & Technologies Mentioned:Claude (Anthropic): Used to build a company-wide second brain and simulate board member personasGPT (OpenAI): Used as a daily thought partner and board advisorPerplexity: A go-to AI for fast, accurate information lookupsSection Expert (Claude project): A centralized AI project workspace housing all of Section's key documents for brainstormingProfAI (Section’s product): An AI-powered coach designed to teach people how to use AI effectivelyChatGPT for Teams: Mentioned as a better, paid alternative to free-tier toolsGemini Pro: Noted for its screen-sharing and future context-awareness potentialCopilot (Microsoft): One of several LLM tools tested during board simulationsSubscribe at⁠ thisnewway.com⁠ to get the step-by-step playbooks, tools, and workflows.