AI and the Bottom Line, How Canva Turns Freemium into Conversions with Canva's CCO

You came in to build a different part of the business in a lot of ways. Like you're— you got brought in to build the enterprise. It's a big hurdle when you have a PLG motion and then you start to go into the enterprise. What did it look like day one?

Yeah, so I think the first things first is, and most of you probably know this if you've been knocking around in the SaaS world for a while, we all know it's a lot easier to go from PLG to SLG then to go from SLG to PLG, that is a very hard motion to backchannel. And so green flags for us were we had a lot of data, we had a lot of good product usage data. We weren't using it necessarily in the ways that looked like you could get a sales-led motion going, but we knew what we needed to do to get there. I think the other big green flag was we were building an enterprise product, so we had an intentionality to building something that was really right for enterprises as opposed to just having this self-serve product and thinking we could charge more and jam it into an enterprise. That was not our mindset at all. We wanted to give value first and get value second. Red flags? We hadn't done it before. We had a culture that thought touchless. We had a culture that like really leaned heavily on organic network-driven adoption. And so we had to think about like, what is organic network-led adoption inside of an enterprise?

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Hey everybody, my name is John Gleason. I'm the founder and managing partner at Success Venture Partners. The significance of that fund is that the LPs are some of the best CCOs in the world, 130 CCOs. So if there's one thing I love talking to and talking about and talking with, it's great CCOs. So let me introduce you all to my friend Rob Ji Lee Ho. There we go. Did we get that right? Nailed it.

There.

There we go. All right. So Rob is the Chief Customer Officer at Canva, where he oversees not only customer success, but Canva's entire sales and go-to-market functions. Rob brings over 20 years of industry experience leading and executing global marketing and sales initiatives. Before Canva, Rob was at HubSpot, where he was also the Chief Customer Officer. Before that, he was the Chief Marketing Officer at DocuSign, and prior to that, he spent 10 years at Adobe, where he's leading their go-to-market teams for their digital media business and was responsible for $7 billion worth of revenue. Truly one of the most accomplished and sharpest leaders I know in go-to-market. Everybody, let's welcome Rob. Here we go.

You're a pretty good hype man, John. That's good. Thank you.

Hype you up.

Yeah, that's good. You're gassing me right up.

Game on. All right, so, Rob, I got to ask, because you've got a pretty big title, Chief Customer Officer. But when we were prepping, It's more than just, you know, the customer side of things. It's in the entire go-to-market motion. What's your remit? What does it look like?

Yeah, I think it's an evolution that's going on in our industry, which is there are groups of people who care the most about a customer, and you organize those teams into a single organization. Some places call it go-to-market, some people call it the customer org. And some people describe the leader of that group as the Chief Customer Officer, really for no other reason other than to give a title that attaches to the most important entity in any business's radar, which is the customer. And I think just by title, it forces you back to focus on the customer. So it's a, it's a big, big to-do about a title that just really is focusing you on customers, which is like, it's so obvious, right?

Like ultimately all of us exist. We, we were building our companies to serve customers and somewhere in the mix we forgot about that capital C thing, the customer, right?

Yeah. Yeah. And I think we, we always used to sort of have these like very commercial sounding titles to do the same thing and it just disconnected the work from who you're serving. And so that's why Canva did it. That's why HubSpot does it that way. And that's why many companies have changed their titling to a chief customer officer or customer. Oftentimes it's like purely customer success, but in Canva it's customer success and it's sales and it's operations and things focused on the customer.

I love it. I love it. All right. So you've held the top go-to-market position though, at Adobe, at DocuSign, at HubSpot, now Canva. I often tell people, you know, when you're building a career, think of your career maybe as like if you're a venture capitalist, right? And unlike me, I get to make a whole bunch of mistakes. I only need one to work out. You're quite the picker. You picked 4 amazing companies. So just like, talk me through that, like, picking process. How'd that process come to be? You know, how did you know that, that this was the next one? Yeah.

So how did I know Canva was the right place to go? Yeah. So I do, I do a lot of mentoring to folks that are younger in their careers. And one of the things I describe is as you're managing your career, you are actually managing a portfolio of opportunities. You have a portfolio of options and you're, you're going to place a bet. 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. Do you believe in the product? Is a number one. Do you believe in the leadership team and the culture? That's number two. Unlike placing a bet where you're removed from what happens with the outcomes. The third one is, can you make a, can you make a difference? Like, is this a company where your unique set of skills are needed and you're actually adding some kind of incremental value as opposed to just taking up a job in a role that anybody could do? And so I've tried to avoid jobs where like anybody could just do it because it would be hard to really create a difference. And I've tried to find places where maybe my unique experiences or things that I've learned along the way can be helpful to the company. So Canva was really pretty straightforward. A massive customer scale with a product that people loved. A leadership team that had an amazing culture, one that I really aligned with, one that was definitely customer first. Like we talk about giving value first and getting value second. We talk about our two-step mission, which is we want to do as much good as we can in the world as possible. But the only way to do a lot of good is to, to get a lot of value. So we want to be big so we can do a lot of good. And so I just— that aligned really well with me. And when I got a— I actually got a text from one of the founders who I had met years before, and it was like the afternoon before Thanksgiving here in the US. Australia obviously doesn't, doesn't celebrate Thanksgiving. And he's like, hey, can we talk tomorrow? And I was like, well, it's Thanksgiving. But maybe my family would be okay with that. Let me— maybe early morning. He's like, oh, sorry, mate, early morning is middle of the night for us. So late afternoon on Thanksgiving, we chatted and, and the rest was history. At the time, Canva was like maybe 170 million monthly active users. We're at 230 million monthly active users now. So the company has come a long way in a very short period of time. Yeah, I'm getting a wow from the audience. That's a quarter of a billion people using the product every month.

Yeah.

So clap for me. It's an amazing product. So back to the idea that it's a great product. And I think the cool thing is a lot of companies think about vanity stats. You know, you could throw a chart like this up and you could think about it as a vanity stat. But we at Canva try really hard to make sure that when we say monthly active use, it's actually completing a design. So it's not just opening something and starting. It's opening something and finishing, feeling like they've completed it. It's been shared with someone, it's been downloaded, it's been saved, it's been copied. Something has happened with that design. It's been published. And then that qualifies as monthly active use. So these are not vanity stats as much as they're, um, north stars for us to stay focused.

And I love that. It's like really thinking through almost like the desired outcome sometimes. Like, yeah, the first click we measured it there, but it's actually like people are getting like that desired outcome when they sign up for Canva.

Yeah, that's the idea.

That's the idea. Okay. The numbers are like, oh my God, those are insane numbers. Everybody, I think, admires Canva for the product-led motion that you've all built. You know, if there was a poster, you know, best PLG-led company, Canva would be probably front and center. But you came in to build a different part of the business in a lot of ways. Like you're, you you got brought in to build the enterprise part of the business. So tell me about that, right? Sometimes it's a big hurdle when you have a PLG motion and then you start to go into the enterprise. What did it look like day one? What were some of the, the cool things, the green flags, I'd call them, and what were some of the red flags?

Yeah, so I think the first things first is, and most of you probably know this if you've been knocking around in the SaaS world for a while, We all know it's a lot easier to go from PLG to SLG than to go from SLG to PLG. That is a very hard motion to backchannel. I worked on that side of the business back when I was at Adobe, and I can tell you it's really hard to go from like a mindset of enterprise only down into a touchless PLG motion. It's way easier to go PLG upmarket. And the reason I say that is In a PLG motion, when you have a well-instrumented product and a decent amount of customer love and product engagement, you're getting signals every day. And so green flags for us were we had a lot of data, we had a lot of good product usage data. We weren't using it necessarily in the ways that looked like you could get a sales-led motion going, but we knew what we needed to do to get there. It was literally all about the data and its use. So that was one of the biggest green flags. I think the other big green flag was we were building an enterprise product. So we had an intentionality to building something that was really right for enterprises as opposed to just having this self-serve product and thinking we could charge more and jam it into an enterprise. That was not our mindset at all. We wanted to give value first and get value second. Red flags. We hadn't done it before. We had a culture that thought touchless. We had a culture that like really leaned heavily on organic network-driven adoption. And so we had to think about like, what is organic network-led adoption inside of an enterprise? And although I think Canva does a great job at PLG and we've done a good job transitioning early phases to SLG, there are a million and one great examples in the world that do it really, really well and arguably in many vectors better than Canva does. And we try to spend a lot of time watching what others do and we try to search and reapply. That's like the highest form of flattery.

Yeah, of course. And like, Canva's got a really special culture. So I imagine like, you know, introducing this new part of the business wasn't something that the founders took lightly. So like, what was the journey they went on? You know, were they, you know, fully fleshed out with where they thought PLG could take them? Was it the next frontier of scale? Like, what was their process when they came to you and they're like, yo, Rob, we got a job for you here?

Well, it was— it started with the company's mission is to empower the world to design. So if you're going to empower the world to design, you have to be where the world is designing. And largely that's inside of businesses, that's inside of companies, organizations, higher ed, places where applications, in particular SaaS applications, are largely controlled by some sort of administrative process. So think CIO, CTO, admin. And so to get into those kind of environments, we had to, we had to think differently. And so it started first with the founders saying, that's a place we want to help people design and create and communicate. And then the next step was, let's figure out how to go do that. The thing that was really I think as anybody who's a founder in here, the thing that really mattered a lot was like, don't have two different cultures. Don't build an enterprise culture over here with like all the downsides of what we think of as enterprise culture. Like there's a lot of like, you know, sort of like deal-making, finger-pistoling kind of vibe that we did not want to have. That's not our culture. We were, you know, we were really interested in like trying to take complex things and make them easy. And we were interested in helping businesses express themselves and communicate and scale. And we felt like we could do that with an enterprise motion if we did it in the context of Canva's culture.

Right. 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.

There weren't a lot. There was a couple. And they were frustrated because they knew what they wanted to do. And yet, you know, the product wasn't there, the motion wasn't there. We, we weren't really like putting the right signals in place. And one of the expressions is data drives signals and then signals drive actions. And so the data was living passively. We weren't grabbing it and sending signals to AEs, and those signals didn't have a set of steps or actions that live behind them. And so now, as an example, we gather together network effect inside of a business. We look at like multiple use and collaboration inside of an organization, and then we send a certain amount of touchless signals, email, in-product, maybe ABM. We might do retargeting. And then eventually that sequence is ready for some sort of outbound motion. But it's not a totally cold outbound motion. We're going outbound into an enterprise that's already using Canva. And so we think data drives these signals. These signals make us prepared to create actions, and then we have to have the right actions. And the process of how you do that matters as much as the skill. And so we started talking about, well, what would be the sales process we would follow? And one of the first things that everybody thinks about is like, will this be a Challenger sale or will you use MedPic or will you use Winning by design, SPICE. And I think those questions matter and the answers to those questions matter. And for the record, we did pick winning by design. We are using SPICE. We have a little bit of a Canva flair on it, and that process and methodology matters a lot. But actually what matters underneath that is the skill of our team, our customer success team being great communicators and having a playbook that's tied to those signals we're getting. And the AEs and our BDRs working in collaboration to have the right level of skill to carry good conversations. And the one thing that we all miss, everybody knows this, is are we super clear on the problem we're solving for our customers? And we anchor ourselves on that like daily. And so, yeah, process matters a lot. But if you don't have the skill to have a good customer conversation that feels genuine, that actually is empathetic around the problems they're trying to solve, like game over. You'll have a hard time. You really will have a hard time growing your, your sales momentum. Yeah.

And I think like that through line to the customer is like so key. I was telling you backstage, the coworking space where, where I work out of sometimes, Guy Kawasaki, the Guy Kawasaki, who's your chief product evangelist, also works out of there. And I said, Guy, like, what, what should I be asking Rob? And he's like, you know, I'm not entirely sure, but listen to this podcast with Melanie and, you know, they go deep on just the culture of Canva. And the thing that like really struck me was just like this incredible customer centricity that you've woven into, whether it's like a student sitting in some remote place anywhere in the world, right through to, you know, a chief designer at IDEO, maybe that customer is front and center. And I thought that was like really a special customer thought.

I mean, it really like ultimately the headline is it always comes down to customer value. The way we think about customer value is we follow a customer journey framework. I think most of us— this is not any big like, ooh, new thing. Most of us do this. But I think the difference between those that talk about it and those that do it well are the ones who do it well actually start to embed the tracing and tracking of a customer journey from the very first point of awareness all the way through some expression of loyalty. And you can follow the through line of this single customer experience. You're not looking at it as like, what was my traffic last week? You're actually looking at it at the customer. How, what, what stages and steps are the customer following to get themselves to some level of loyalty? And are we helping them or are they doing it on their own? And ultimately, if all we think about that matters for Canva is taking someone who's aware and interested in the product and leading them through to solving the problems that they're trying to accomplish, that they're trying to knock down, which might be scaling design, it might be telling a story, it might be doing something as simple as managing a social media account. If we can draw them through that experience and they're happy with the outcomes, then we've won. That's one customer that's moved through the customer journey effectively. And then now the question is, can we do that at scale and can we do it without throwing a whole bunch of bodies at it? And so can we instrument it with some digital experiences and some great trained rep experience? If we can do that, we're off to the races.

So, okay, so as you built that upmarket enterprise motion, there was a lot of culture there that you wanted to keep, but no doubt there was like things that you wanted to change in process. So what were like some of the tweaks that you made and what were some of the things that you kept?

Yeah, well, I mean, the nice thing is on the, on the enterprise side, there wasn't much that we had to not do. One thing I would say that we had to not do was organizationally. Many of you might work in organizations where you have a customer success team that's like the high-touch customer success team. And then oftentimes what happens is there's a marketing organization or a product organization that is doing customer touches to your online PLG customers. And what that creates is a huge separation between teams that are essentially trying to solve the same problem, which is how do I help an individual customer accomplish the task that they're trying to accomplish? And am I paying attention to some of the same signals? And so maybe one of the things that we like knocked down was we just decided there's a pool of people And they are in businesses and they are individuals and they are in teams, but they live inside of this common population. And that population are our users. They're our customers. And we shouldn't care whether or not they're paying us a lot of money or a little bit of money or no money at all. We should actually be thoughtful about, are we helping them solve their problems? And are we moving them through a journey with the use of our product? And if we do that really effectively, we're gonna get value later. They're gonna tell people about us, they're gonna move up a, a version and maybe move to a paid version. They're gonna invite somebody else in their team to use the product, and ultimately maybe they become a, a larger paying customer. And so we worry a lot less about how much money we're making from a customer. We worry a lot more about how much value are they getting out of the product. Now, our first intent, because we wanna be scaled, is Can we do that digitally? Can we do it in product? Can we do it through email? Can we do it with some other outreach methodology? Can we do it with AI? If we can, we do, right? If we can't, we try to batch them up. We try to pull them into groups of customers that have like problems, and we can use something like a webinar, or we can use a group email, or we can use a group Zoom session, and we can invite them to connect with a customer success rep with enough scale and enough customers that it's like financially viable because that's what your CFO is going to care about. Like, what is the per-touch cost? And we don't worry about the per-touch cost if you're thinking about scale every time.

Yeah, it's, you know, it's interesting you say that because I actually had a very similar conversation with John Hurstein, who's the CCO at Fox. Yeah, similar problem in that, you know, you could have the end user using Canva to help their kid with their homework and that person actually happens to be the chief customer officer at Big Company XYZ and is pulling you upmarket into that organization. And so the blanket statement is just like, treat all your customers like gold and really good things happen.

100%. Yeah. And I think, you know, a lot of us don't pause and actually like unpack the economics of our business models such that we do think about like, what is the real cost of letting a customer wallow versus what is the real cost of providing some level of support? And would you be willing to invest in building an infrastructure that provides the kind of scaled support and success experiences that customers really need? That's how we think about it. The one last thought that I'll throw out with you is we all do an amazing job of customer acquisition. This is an industry, SaaS in particular, we kick ass at orchestrated customer acquisition. Our lead funnels are dialed. We understand all of our funnels. We know the difference between top of funnel and lower funnel. We're great at it. That level of orchestration does not need to live in the presale environment. That orchestration actually is better served in the post-sale environment. Like, we should be better in the post-sale orchestration of customer experiences than we are in the front side, because most of us, if we're in a SaaS business, we have an install base and there's no way that the new customer acquisition in any given quarter is going to dwarf the current install base, all the values in the install base. So I just, I evangelize that with our team. I evangelize it with people that I talk to. I think it's, it's an overlooked discipline. The orchestrated post-sale, better than you are pre-sale.

And I love it because, yeah, we always talk about like Okay, what's the second order revenue if we give them a great experience? And what we forget about is like, what's the second order like loss that happens if we don't give them a great experience? And, and I think that is really hard to account for and we kind of just bury that deep somewhere and don't think about it. But man, it can really come back to bite you.

Yep.

All right. So we talked about a little bit about your process. This whole conversation was meant to be about AI. There's so many things I wanted to talk to you about.

Everybody's already talking about AI.

But what about I?

Every other session. We don't need that here.

But okay, so like, tell me some of the cool things that you're doing in your organization right now because you've got an AI-centric platform. No doubt you're doing a ton of amazing work.

We think about AI in like two forms. There's the AI that's in Canva that's available for customers to use. That gets a pretty significant portion of our attention, as you can imagine. Because we're trying to put experiences in the hands of our end users that allow them to scale imagery, ads creation. You know, I think we recently shared that we've had like 16 billion instances of AI usage, which I think ranks amongst the top AI use cases with some of the tippy-top performers in the AI space. So I think we're pretty good on the consumer side. So just like the way we try to make complex things simple, we are focusing for our own team to find complex workflows and complex experiences for our reps. And we're trying to stitch AI next to those to make them easier. And I think that's largely what everybody's trying to do. That's not unique to us. We have a mindset that's like, there are probably great tools in the world we should start with those tools and implement them in our own workflows as opposed to try to build them ourselves right now. And we're willing to try almost anything if it's a reasonable investment. And we're kind of finding our way. We're building rep to CS processes that are heavily underpinned with AI. We are using AI to like understand. So we're talking about these signals. You get data to give you signals. Signals guide actions. That framework is literally our AI philosophy. Great data underpins the models that we're putting in place and the experiences we're stitching on top. And so I think we're okay at it. I think we have a long way to go, which is nice when you're a private company. You can say statements like that. When you're a public company, if you say we have a long way to go, you're like hammered. But I'd say that Canva has a long way to go. We're going to focus first. On getting it right for our customers. Yeah. And then we're going to get it right for our own team and we're going to be thinking about ways to scale to make better experiences for our customers and make it easier for all of our reps to perform their tasks.

You know, I love that though, because it's, you know, it's almost that same humility that has made you such an amazing company from day one. It's like solve a small problem for a niche group, right? I think the initial goal was people in academic situations and do that really well and go from there and start small and make it big. And it's a pretty amazing journey you've been on. I admire it a lot. So, dude, thank you so much.

This was good. And thanks, everybody, for listening. Hopefully you got something out of that.

Yeah.

Thank you.

All right.

Have a great day.

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