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Rob Giglio

Rob Giglio

Chief Customer Officer at Canva, overseeing sales and go-to-market; previously CCO-level leader at HubSpot, DocuSign, and Adobe.

Sep 15, 2026

8:12
What kinds of data pieces tell you that you're doing a good job? Like, how do you know you're successful as CXO?
8:19
Yeah.
8:21
Well, and it's not just me and my org.
8:24
The whole company actually orients around usage metrics.
8:29
And I would say Canva's North Star, if you will, is monthly active use.
8:36
So we're really oriented around this customers, both paid and free, having success with Canva.
8:46
Because we know that if they have success with Canva, then good things happen.
11:25
I would actually love to start the AI conversations asking you, are there interesting ways that you're using AI as a leader in how you lead and how you approach your role?
63:18
Can you share one of those moments? What happened and what did you learn from it?
63:22
Yeah.
63:23
Well, why don't I share? Well, I'll share two.
63:25
Let me give you a small one that I think every single person can probably relate to.
63:30
And then I'll give you a little bit bigger one.
63:32
Great.
63:32
So the small one, which is like high in frequency, is when I used to commute, which was like every day for the majority of my career until like 2020, I would say almost every day or every other day I'd be driving home.

10 MINS LATER

73:40
But I'm curious, I asked folks, everyone who connected me, I said, what's the one question you want to ask Rob? And I mean, they all gave me different questions, but I think one that consistently came up is folks said you're ambitious you've got to like really senior c-suite roles what do you need to do if you want to become a ceo so i guess the question was twofold one do you want to be a ceo and two if you do what do you think you need to do in your own control to get there
6:33
How'd that process come to be? You know, how did you know that this was the next one? Yeah, so how did I know Canva was the right place to go?
6:40
Yeah, so...
6:43
I do a lot of mentoring to folks that are younger in their careers.
6:46
And one of the things I describe is as you're managing your career, you are actually managing a portfolio of opportunities.
6:54
You have a portfolio of options and you're going to place a bet.
6:58
And the way you'd place a bet on a career should be very similar to the way you'd place a bet on making an investment.
7:04
Do you believe in the product is a number one.

8 MINS LATER

14:41
So like, what did it all look like? Like, was there actually, was there any AEs there when you got there or did you have to like start that from the ground up? There were a couple.

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