AI is transforming go-to-market operations—and at Canva, it's not just a trend, it's a mandate.

In this episode, Jessica Chiew, Head of GTM Operations and Strategy at Canva, joins Kyle to break down how her team is leading AI adoption across a 5,000-person organization. She shares how Canva blends centralized support with functional ownership, why they created a dedicated GTM AI Lead role, and how they prioritize use cases that deliver real business impact. Jessica and Kyle also dig into the realities of build vs. buy decisions, how to avoid tool sprawl, and why every GTM leader needs to be hands-on with AI.

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Key chapters:

(00:00) - Jessica Chu's GTM AI Transformation Journey at Canva Begins

(02:48) - The Most Exciting Time in Ops: Creativity and Existential Dread

(04:30) - From Vendor Fatigue to AI Enthusiasm: Renewed Curiosity in Tooling

(06:59) - Early Days of AI Momentum at Canva

(09:30) - Making AI Transformation Everyone's Job

(11:45) - Defining the Role: GTM AI Lead and Workflow Innovation

(14:25) - The Changing Nature of Data Ops in AI-Powered Sales

(16:50) - How Canva Organizes AI Transformation: Central Council vs. Functional Innovation

(18:29) - Cutting Through the Noise: Where to Start with AI in GTM

(21:00) - Why Data Quality Is the Prerequisite for GTM AI Success

(24:30) - Vendor Sprints and the Realities of Building vs. Buying AI Solutions

(29:00) - Execution as the Only Moat: Staying Ahead in the Commoditization Wave

(35:10) - Limiting Surface Areas: The Case Against Point Solutions

(38:30) - Balancing Experimentation with Simplicity for Field Teams

(41:51) - Organizational Change: Iterative Improvements vs. Big AI Bets

(46:45) - Hands-On Leadership and the Decline of Middle Management