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Inside Monday.com's AI Pivot: Roy Mann on Three Waves, Agent Talent, and the Hardest Calls
Episode 229th April 2026 • The AI Revolution Show • Alex Theuma / Shift AI
00:00:00 00:33:48

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Roy Mann is the co-CEO of Monday.com, a company that's generated over $1 billion in revenue and serves 250,000 paying customers across 200+ industries. Roy shares the bold strategic pivots Monday.com is making to survive the AI platform shift. We explore why they're now letting AI agents buy seats on their platform, how they've fundamentally changed their company vision from "managing work" to "doing work," and the critical difference between adding AI features versus building AI-native products.

In this episode, we explore:

(02:09) Monday.com's unusual approach to broad market positioning

(05:41) The surprising challenges of rebranding to Monday.com

(09:33) How two co-CEOs make decisions when they disagree

(12:15) Roy's honest take on February's market crash and stock drop

(14:10) Why the per-seat SaaS model faces an existential threat

(16:13) AI agents are now signing up for Monday seats

(18:01) Roy's three waves of AI and his coding epiphany

(21:11) The mindset shift from managing work to doing work

(23:32) Build AI-native or add AI? Roy's take on the debate

(26:38) The hardest decision Roy can't delegate to anyone else

(29:37) Roy's advice for scared SaaS founders: go deep on technology

(32:05) The question investors should ask but never do

Links mentioned:

Roy Mann's LinkedIn: https://www.linkedin.com/in/manroy/

Monday.com: https://monday.com/

The AI Revolution Show is the intelligence podcast for B2B software founders navigating the platform shift, the founders building through it, and the founders already on the other side. Hosted by Alex Theuma, founder of SaaStock. Subscribe so you don't miss the next episode.

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