The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 810: AI and the Bottom Line, How Canva Turns Freemium into Conversions with Canva's CCO Rob Giglio

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Jul 10, 2025
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ADVICE

Strategic Career Betting

  • Evaluate career opportunities like investment bets based on product belief, leadership culture, and ability to add unique value.
  • Avoid roles where anyone can perform the tasks; seek where your skills make a difference.
INSIGHT

PLG to Enterprise Sales

  • Transitioning from PLG to enterprise sales is easier than moving the other way around.
  • Data and intentional enterprise product design enable this upward motion effectively.
ADVICE

Data-Driven Enterprise Sales

  • Use product data to send targeted signals that guide outreach actions in enterprise sales.
  • Equip teams with relevant skills and clear problem focus to enable genuine customer conversations.
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