The GTM Playbook Big Brands Don’t Want You To See
October 16, 2025
Go-to-Market strategies often scale fast, but sustaining real customer value is where the challenge begins. In this episode, Jason Hemingway is joined by Rob Giglio, Chief Customer Officer at Canva, and Georg Ell, CEO at Phrase. They explore what it takes to build and execute global Go-to-Market strategies that don’t just launch well, but land with lasting impact.
Drawing from senior roles at Adobe, DocuSign, HubSpot, and Canva, Rob shares what he’s learned about meeting rising customer expectations, adapting to global complexity, and using technology to engage customers faster and more meaningfully. We explore how brands can maintain clarity, consistency, and relevance, even as their markets, teams, and product offerings evolve.
Go-to-Market strategies often scale fast, but sustaining real customer value is where the challenge begins. In this episode, Jason Hemingway is joined by Rob Giglio, Chief Customer Officer at Canva, and Georg Ell, CEO at Phrase. They explore what it takes to build and execute global Go-to-Market strategies that don’t just launch well, but land with lasting impact.
Drawing from senior roles at Adobe, DocuSign, HubSpot, and Canva, Rob shares what he’s learned about meeting rising customer expectations, adapting to global complexity, and using technology to engage customers faster and more meaningfully. We explore how brands can maintain clarity, consistency, and relevance, even as their markets, teams, and product offerings evolve.
He also reveals Canva’s guiding principle of “give value first, get value second” and discusses how a long-term mindset drives stronger partnerships, faster adoption, and more meaningful relationships with customers worldwide.
What You’ll Learn:
- How to transform complex go-to-market strategies into orchestrated customer experiences
- Why prioritizing customer value before revenue drives sustainable long-term growth
- How to leverage AI for customer insights while maintaining authentic human connections
- Why local presence and cultural understanding are crucial for global market expansion
- The importance of usage metrics as the north star for measuring customer success
- How to balance rapid growth with thoughtful customer-centric implementation
Rob Giglio is the Chief Customer Officer at Canva, bringing vast expertise in global go-to-market strategy and customer-led growth. With previous leadership roles at Adobe, DocuSign, and HubSpot, Rob has established himself as a leading voice in scaling software businesses across complex international markets. His experience spans both B2B and B2C sectors, beginning at Procter & Gamble, where he developed his foundational understanding of brand-consumer relationships.
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Highlights and YouTube Chapters:
- 00:00 Introduction
- 01:54 B2C Roots, B2B Impact
- 04:01 How AI Transformed GTM Data Access
- 06:56 Customer-Centric Simplicity
- 11:30 Overlooked in GTM? The Actual Customer
- 14:30 Scaling Global GTM via Resellers
- 20:04 Inbox Confession: Automate Everything?
- 22:22 GTM Misfire: When Incentives Go Rogue
- 28:04 The Real North Star
- 33:21 AI’s Role in Global GTM
- 36:47 Rob’s Final Principle
Episode Resources:
- Rob Giglio, Chief Customer Officer - Sales / Success at Canva
- Canva Website and LinkedIn
- Georg Ell, CEO at Phrase
- Jason Hemingway, CMO at Phrase
- Phrase Website