Episode Details

Justin sits down with Jessica Chiew, Global Head of GTM Strategy and Operations at Canva, to unpack what it really takes to evolve from a beloved PLG product into a full-fledged enterprise sales machine without breaking what made it great.

Jessica shares how Canva navigates the complexity of multiple handoffs across a PLG-to-SLG journey, why time to value is everyone's job (not just CS), and how she's thinking about marrying product usage data, CRM structure, and conversational intelligence into something actually actionable. 

Plus, both Justin and Jessica geek out on the AI and vibe coding moment we're all living through and why it changes everything for revenue teams.

Chapters

[00:00] Intro & Jessica's Path to Canva Justin welcomes Jessica and she traces her journey from Melbourne to San Francisco, through Asana, and into Canva's B2B buildout.

[02:57] Who Owns Onboarding and Time to Value? Jessica breaks down Canva's take on ownership across PLG and enterprise motions — and why success in the first hundred days is a team sport, not a CS problem.

[05:57] Moving Upmarket: What Changes (and What Doesn't) From solo users with credit cards to C-suite transformations with change management — how Canva's onboarding approach shifts dramatically as deal size grows.

[09:40] Using PLG Signals in an Enterprise World The Asana flashback: how rich end-user data and human relationship context can finally live in the same place, and what that unlocks for enterprise sellers.

[11:47] The Tech Stack Behind the Motion CRM alone isn't enough. Jessica walks through how Canva combines structured CRM data, product usage signals, and a full conversational intelligence database to build a real picture of account health.

[14:00] AI, Agents, and the Vibe Coding Moment Justin shares his own revelation using AI agents for GTM workflows, and Jessica drops that she recently vibe coded a weekly forecast interface. Neither of them is going back.

[16:21] What's Ahead for Canva GTM in 2026 Canva Create in LA, platform updates Jessica can't fully share yet, and the team's focus on becoming the gold standard for enterprise go-to-market.