The Revenue Leadership Podcast with Kyle Norton

E41: Jessica Chiew of Canva on Building AI-Native GTM Org

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Aug 1, 2025

Jessica Chiew, Head of GTM Operations and Strategy at Canva, reveals how her team is spearheading AI adoption within a massive organization. She discusses the dual approach of centralized support and functional ownership while stressing the importance of a strong data foundation for AI success. Jessica shares insights into navigating build vs. buy decisions, optimizing AI workflows, and the pivotal role of leadership in driving adoption. She also emphasizes engaging sales leaders to create a supportive culture that embraces AI-driven efficiency.

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ANECDOTE

Creative Renewal in Sales Ops

Jessica Chiew describes her role in sales ops as creative and refreshing during the AI transformation period.
It has allowed her team to reinvent sales rather than recycle old solutions repeatedly.

ADVICE

Embed AI in Job Descriptions

Make AI adoption part of everyone's job description to ensure consistent progress.
Assign a dedicated GTM AI Lead to accelerate momentum and coordinate efforts.

INSIGHT

Data Ops Evolves with AI

Clay tables and AI enrichment shift data operations from heavy engineering to business-context-driven analysis.
This new profile up-levels data roles closer to business needs for maximum impact.

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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