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Rob Giglio is the Chief Customer Officer at Canva, where he oversees Canva’s sales and go-to-market functions. Rob brings to Canva over 20 years of industry experience leading and executing global marketing and sales initiatives.
Rob joins Canva from HubSpot, where he was also Chief Customer Officer, and before that, he was the Chief Marketing Officer at Docusign. Prior to Docusign, Rob spent over ten years at Adobe, leading the global sales and go-to-market teams for their Digital Media Business Unit and holding responsibility for over $7B in revenue.
Discussed in this Episode:
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Why B2B marketers should embrace the CPG tactic of “concept testing.”
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How to embrace segmentation by differentiating your solution.
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Loyalty as a necessary part of every customer journey.
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Why substance beats sizzle every time in sales and marketing.
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Leading a large, remote-first team.
If you missed GTM 129, check it out here: 6 Proven Tactics Driving B2B Growth
Highlights:
06:07 – 3 lessons from B2C to that B2B marketing needs to learn.
12:25 – What is concept testing and how can marketers use it in B2B.
19:38 – Selling a massive transition to enterprise customers.
35:14 – How DocuSign overcame major user experience challenges.
39:50 – How HubSpot addressed issues with remote leadership.
44:34 – The importance of in-person interaction.
55:56 – The power in simplicity.
Guest speaker links (Rob Giglio):
LinkedIn: https://www.linkedin.com/in/robgiglio/
Host speaker links (Scott Barker):
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/
Where to find GTMnow (GTMfund’s media brand):
Website: https://gtmnow.com/
LinkedIn: https://www.linkedin.com/company/gtmnow/
X: https://x.com/GTMnow_
YouTube: https://www.youtube.com/@GTM_now
The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/
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I don’t know how I didn’t start on Superhuman sooner. It was the most seamless onboarding experience – everything in my inbox synced within minutes. Superhuman works with your existing Gmail or Outlook accounts. New year, time to take back control – 2025 is the year of inbox zero. If anyone also wants to take back control of their inboxes and empower their teams to do so, check out Superhuman at superhuman.com/gtmnow“ – Scott Barker
The GTM Podcast
The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
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GTM 30 Episode Transcript
Rob Giglio:The more generic you become in your marketing, the harder it is to really land a point with these consumers.
Scott Barker: What is the biggest mistake you see people making in B2B marketing?
Rob Giglio: Calling it B2B marketing. What is B2B marketing really? Like, what even is that? Remember that it’s people that you’re really speaking to, even if you’re in B2B.
Scott Barker: What did you learn about how to sell transformation rather than just software?
Rob Giglio: the businesses that decided to embrace change really prospered. and the ones that were more reticent and apprehensive to change fell behind.
So the ones that were willing to be bold were like massively advantaged. I am not a fan of sizzle over substance. Substance wins every time. It might not win quick, but it will win the most.
It’s expensive to be wrong. So you better be thoughtful. As a revenue leader, you’re not really looking for the sale,
You’re really looking for loyalty.
Scott Barker: Hello and welcome back to the GTM podcast. As always, you’ve got Scott Barker here, but it’s certainly not about me. It’s all about the guest always. And this guest, you know, I feel like the time, but super, super excited, uh, for this guest. We tried to tee it up, uh, actually when he was formerly at HubSpot and then, he turned me down and I was all bummed.
But then, we made it happen. I am joined by Rob Giglio, welcome to the podcast, man.
Rob Giglio: Thank you. I’m glad to be here. I mean, it only took us almost a year to pull this off.
Scott Barker: We made it, we made it happen. Um, and super quickly. So I always like to give a quick bio for the, the listeners. So, uh, Rob is currently the chief customer officer at Canva. He oversees Canva’s sales and full go to market function and brings over 20 years of industry experience leading and executing global marketing and sales initiatives.
Actually joined Canva from HubSpot where he was also the chief customer officer. And before that he was the chief marketing officer at DocuSign. Prior to DocuSign, Rob spent over 10 years at Adobe, uh, leading the global sales and go to market teams for their whole digital media business. And, uh, was responsible for over 7 billion in revenue, which is a scary number of a scary bag to hold.
Then previous experience include GM and marketing roles at Gap, Williams Sonoma, Clorox, Procter Gamble. Um, just to, uh, career, man. It’s, it’s, those are like the logos when you think of B2B software, like what are the first logos that come to mind? It’s probably people would rattle off, you know, Adobe, DocuSign, So that’s super.
Rob Giglio: Thanks
Scott Barker: That you’ve been instrumental in scaling them.
And I want to kind of dive into each stage of, of your background and some of the lessons from these iconic companies. But, um, something that stood out to me right away, uh, was You know, you spent the beginning of your career in like retail marketing, and then you made this jump to, to software. And I was curious because me, I’ve always, a lot from B2C marketing.
Um, and it does feel like sometimes we’re just like three to five years behind a lot of the trends that are happening and in B2C. and I was curious what you kind of learned from marketing in the B2C realm and selling and go to market that you’ve taken, uh, with you into kind of the B2B and technology landscape.
Rob Giglio: Yeah, um, what a great question. there’s so many things, but probably the most important thing that I, I took away from, it was like 10 years in consumer marketing and sales between Procter Gamble and Clorox. Um, some of the most important things I learned there were that, uh, you really can’t afford to be wrong.
Like it’s, uh, it’s very costly because you have a giant manufacturing process and you have physical goods that are in motion and shipped all around onto grocery store shelves. It’s really expensive if you make a mistake. And let me give you a good example. Like if you develop a label for your product and that label isn’t very good.
It doesn’t communicate the product name. It doesn’t have any of the brand attributes. You don’t know what’s inside the bottle or inside the box. Uh, you’ve just gone through a whole process of. Printing and shipping something that, that is really not going to work well on the shelf. And there’s nothing you can do once it’s up there. Like you really made…
Scott Barker: Run to the store, buy them all. Like just start..
Rob Giglio: No.
Scott Barker: over things. Yeah.
Rob Giglio: So you have to be very thoughtful about the way you develop, um, products in general, but then every tweak that you make to the product, whether it’s changing the package or changing the label or changing the price, Changing the bottle or, you know, the bottle size, uh, those things are very expensive mistakes if you get it wrong.
And so I think maybe one of the lessons, there’s, there’s several, but one of the core lessons is you really better be thoughtful and analytical and right about the way you make changes to your product offering. And so that’s, I think it, it raises the bar. You better be pretty darn good and make sure it’s, it’s going to work.
Otherwise you. You really, uh, you cost the company a lot of money. So that’s part, that’s part one. Like, uh, that then ties into maybe part two, which is, um, use data. Like data is there, you can find it, you can test, you can run analysis, you can do a something as simple and non scientific as a focus group.
You can run a test market, um, but you better do some analysis to figure out what’s working and not working. And so that I think is, um, Really critical. I think a lot of times, and especially if you just jump over to B2B, a lot of times it’s like somebody thinks it’s a good idea and it’s like a gut kind of choice and you may be as likely to be wrong as you are to be right.
And so, um, sometimes what happens is you’re right the first time and so you think you’re genius. And then you do it again the second time, it doesn’t work. And you’re like, whoa, was I not a genius the first time or did I just get lucky? And so that I think is like, you know, in consumer packaged goods, you don’t get that kind of, um, one person’s idea just takes all the like air out of the room and goes, like you, you really analyze it and do it right.
And so data is, is number two. So number one, it’s expensive to be wrong. So you better be thoughtful. Number two, use a lot of data. And number three is in consumer packaged goods, you’re talking to individuals. And so you have to think very carefully about messaging to individuals, like a person. How do they think?
What motivates them? What, um, what words work? What images work? What colors work? Um, what, where will they be shopping and why? And, and so you, you develop a whole go to market, which includes your, your marketing and your sales and your post purchase support around thinking about individuals, not thinking about, um, anonymous.
And I think, you know, when you think about consumer over to business, a lot of times B2B marketing is challenged by just thinking that B2B is something that’s like, um, Amorphous. Uh, but it’s still people inside of businesses that buy and people inside of businesses that make decisions and people inside of businesses that use the product.
And so applying those three things, one, really expensive to be wrong. So try not to be wrong. Uh, number two, use a lot of data. And then number three, uh, remember that it’s people, it’s consumers, it’s buyers that you’re really speaking to, even if you’re in B2B.
Scott Barker: Yeah, that’s super interesting and a lot of great, great points there. I mean, I’ve never actually thought about, you know, how. You really do only get one shot. You’re launching a new product. You’re going to a certain packaging on that. There’s going to be a certain messaging and there is no way to change that.
And you know, it ties into your second point around if you are right. Or if you are wrong, you better have the data to back it all up of like why we thought this was the best decision. Um, and yeah, it’s really interesting in, In software, in B2B, you know, I think, you know, experimentation is very welcomed and it’s a necessary part of the, the job.
Um, but it’s, it is also expensive, you know, running a campaign and like. Completely shifting our pricing model just on, you know, maybe a few customers that gave us feedback and we do all these shifts. And then, know, we have the luxury of like, oh, that worked. That didn’t work. Let’s quickly like shift it back.
But the training and the enabling. It’s I think it’s. Still costly in B2B. It’s just not as in your face and like quantifiable as easily you know.
Rob Giglio: There’s tactic that’s really commonly used in consumer packaged goods. And I don’t think we do it like hardly at all in B2B. I think some people do it. I’ve, I’ve, I’ve had conversations with other marketers and product teams who do it, but maybe it’s not like widely executed and it’s called concept testing.
Yeah. And the basic premise of concept testing is you have this great idea for a product, or you have a great idea for like a tweak on a product. Like you’re going to develop a line extension on, uh, I don’t know, some, some product that you’re selling. Uh, and you basically create a fake version of that product and you create positioning around it and you get a price and maybe even you go so far as to You know, create a fake bottle of it or, or can of it or whatever, and you show it to your potential buyers and you test that concept against other things, like other things that are currently in the category.
And you’re looking for like product interest and, uh, like, does it resonate with the things that people are looking for in that category? And you look for like price sensitivity, like, would you buy it at this price? Yes or no? Do you feel like it’s a good value compared to this other one? And. That like, I’m giving you the whole range of things you might do when you do concept testing, but like, we don’t really, most of us don’t do that in software, especially in like B2B go to market.
We rarely do concept testing. And yet think of all the like products we’ve all brought to market where we kind of like, uh, invent our positioning and invent our messaging as we’re going. Maybe we look at what competition is doing and we try to use their words. And like, just think if you added that step in this process, how much better your outcomes could be.
You’d avoid a lot of mistakes and you’d optimize what works. And the second thing related to that, that I’d share with you is we also in, and now I’m talking software in particular, but in software, most of the time in categories, we as general managers, CEOs, CMOs, CROs, we always think of it as like, we need to win the whole market.
Like we will take a segment like SMB or enterprises, and we will say to ourselves, Oh, we’re going to launch this thing. And we’re going to win the market. We never think about carving up the market and would it be more profitable to carve up the market and win segments? And, and the, the way that plays out, like, I’ll give you an example is like, let’s use like beer, you drink beer,
Rob Giglio: Get a beer or six.
So, uh, I love beer because it’s like a really good category to think about. Like the category is a certain size globally. But if you actually start to divide up, you have craft beers, you have light beers, you have domestic beers, you have international beers, you have beers in cans.
Scott Barker: In there. Some messais.
Rob Giglio: Now, right? You’re touching on it.
And like almost no beer manufacturer says to themselves, I need to own the entire market of beer. Like it just seems inconceivable. And so what they do is they pay attention to like segments and segment needs and taste profiles and preferences. And they say to themselves, I’m going to carve this category into parts, and I’m going to own this part, or I’m going to own that part, and that’s a, like, we don’t do that in software at all.
Like, we never think to ourselves, like, oh, I, I’m a, um, I don’t know, I’m a CRM, and so I’m going to, like, own this country, this industry segment or vertical, and then this company size. Or maybe even more importantly, they don’t say like, Oh, I’m going to be the CRM for these kinds of business users.
Scott Barker: Yeah.
Rob Giglio: They usually say like, you know, most of the time we cut it by like a little company or big company. And, um, it’s a good thing because you kind of, you’re shooting for the moon, but it’s a bad thing because then your positioning and messaging is pretty broad. It’s pretty generic. And the more generic you become in your marketing, the harder it is to really land a point, you know, with these consumers. So anyway, that’s, uh, concept testing.
We should do more of it. And then the other thing is we should think about the segments of our market and think about whether we’re trying to own the entire category or segments of the category.
Scott Barker: Yeah. I mean, I love the, the beer example really brings that to life, the segments. It’s like, you know, we want to be the beer that you go to when you’re watching a football game. We want to be the beer that when you go to your local sushi restaurant, you always want to order. When you go to the beach, we want to trigger that.
And those are huge markets within the realm of beer. Yeah. Yeah. You know, beer and they’re tied to feelings. They’re tied to emotions. They’re tied to like these triggers and habits that can become really, really powerful. Uh, I think that’s a great way to look at it in this of concept testing. I mean, I wish we had this podcast, you know, and a half years ago.
I remember at, At Outreach, we went into a new category and, you know, we did all the data and, and, uh, analysis and we talked to a few folks and we’re like, wow, we’re going to bring this new feature and it’s going to, we’re going to leapfrog this category because we’re, we’re genius and we know where everything’s going and we, and we’re going to just build this new thing that everything, everyone’s going to want and, you know, ultimately it was it worked.
Somewhat failed launch, but had we done this kind of concept testing where instead of going and putting all these engineering resources and, and go in deep and like building it and then going and selling it, like Why don’t we build wireframes, build like basic functionality to like three versions of what we think this category could look like and then go and bring those to, to customers and be like, which, which one would you want?
How much would you pay for each? Um, that would have certainly saved us a lot of,
Rob Giglio: Yeah, you’re not the one. I think we all do it. I’ve, I’ve, I’ve done it. Like it’s, it’s, yeah, we, you know, we move into tech and then it’s, it’s as though we just think we’re in some other place. Like, it’s like, Oh, all the rules of basic like business practice or basic marketing disciplines. We don’t know.
They don’t apply to us because we’re someplace we’re in some other category or some other industry. And yet, when you think about it, like it’s, Most of those basic marketing disciplines and practices were based on like core consumer psychology, which again, like if you really go to, if you’re a first principles person, you act first principles and you’d say, well, what is the first principle I’m resting on in this case?
And you, you’d probably do these things, but oftentimes we just get run in really fast and we skip them.
Scott Barker: Totally. All right. So then, you know, you successfully make this transition over to, to software and let’s start at, at Adobe 10 year run, which is like, I think like 50 years in, in software land. Like it’s, it’s very unheard of to have a 10 year run. I think there was four promotions in there. You end up as the SVP of worldwide go to market and sales for the media business.
Um, paint the picture, like how many people were on your team at that time? Um, was that where that big 7 billion number, uh, was? Um,
Rob Giglio: Yeah.
Scott Barker: picture of that time period a little bit for me.
Rob Giglio: Yeah. Um, well it was, uh, it was a time period when software was going through a lot of change where we were going from perpetual. Box software sold primarily through distributors to, um, a cloud based, um, subscription model. So that was a, that was a pretty significant transition. Um, that allowed us to get access to a lot more end users and customers.
Um, it allowed us to improve the product more rapidly, um, and give customers the best possible product more regularly. So that was a huge win. Lower entry point. Like it, it was inexpensive to like, uh, pay per month. And that was, I think a lot of customers really appreciated that. Um, yeah, it was, it was a pretty exciting time to be.
Um, with a lot of really smart people, um, thinking of go, you know, clever, modern go to market methodologies. So it was, yeah, I mean, I, I look back on it and, um, no doubt, like certainly a highlight of my career. The product itself, the go to market, the innovation, and maybe most importantly, the people, like, like the people that I got to work with there are like, were just fantastic.
And it’s interesting. I was at a dinner recently with a friend who was there at the same time. And he and I were listing out the number of C level officers who are in different companies around the industry, who all were at Adobe at about the same time. And, uh, I remember when I was young in my career, people used to talk about how Procter Gamble did a good job of creating executives.
And many executives came out of Procter Gamble and went on to run companies. And, you know, for a period of time, people thought about, um, General Electric. GE used to be the place where that happened. And I know we don’t, you know, I don’t know that people talk about that now. Like, oh, a lot of executives come from a certain place or it’s a good training ground.
Scott Barker: Mafia, the infamous, uh, PayPal
Rob Giglio: I mean that’s a group of very, very successful leaders well beyond what I’m describing. But, um, yeah, I look around and it was a really great time to be there and it was a lot of really great people and it still has some really great people, but it, it just sort of flourished.
A lot of great leaders came out of there at that time.
Scott Barker: that. I feel like that, so that time period was kind of when I was starting my career in this transition to the cloud. And I look back at that time. It was a really cool time to be scaling a business and in a sales or marketing function because
Rob Giglio: Totally.
Scott Barker: Selling true digital transformation. Like it wasn’t, Hey, here’s like an incremental improvement here and we’re going to make your efficiency a little bit better here.
And you were saying, Hey, take my hand, Mr. Customer. And we’re going to go on a journey that is actually going to transform almost your entire business. And like the. The respect, the honor and like the, how that felt, um, it was much more than just being a sales and marketer. And, um, it was a cool time period.
And, and I also think we’re about to go into another one of those eras with,
Rob Giglio: You’re
Scott Barker: know
Rob Giglio: right.
Scott Barker: Probably even a bigger fundamental shift than, than the move to the cloud and mobile and even. Arguably the advent of the internet. And think we’re going to, we’re getting back there where we’re now going to be trusted advisors to bring our customers into this new, new age, which is, is pretty cool.
So beyond the, the network at Adobe and. You know, these people that you’ve been able to grow your career alongside, uh, what would you say the biggest learnings in that time period were, and, and maybe I’ll frame it because I think we are going back to digital transformation. Like, what did you learn when you were talking to someone?
About the cloud. And they’re like, that sounds terrifying. And, you know, we’ve got these security risks and like, there’s just no way. And like, that’s happening again now with AI.
Rob Giglio: Yeah,
Scott Barker: what did you kind of learn about how to, to sell transformation rather than just software?
Rob Giglio: I think, and I’m not sure I’m going to be able to articulate it really well, so I feel a bit at a loss, uh, but let me try. I think in that period, um, it was a re grounding in how important it is to think about the customer journey, like what a customer has to go through from one, one starting place to another.
And when you think about doing transformation, and in particular, if you think about transforming a customer experience. You have to really focus on the customer or you can’t create a journey and you can’t, you know, evolve and experience. And so that was like a, it was like a great reminder of, it’s about individuals and people as opposed to like businesses.
Like a business doesn’t follow a customer journey. An individual follows a customer journey, and maybe the business might transform in ways that look like a journey, but they don’t do it in the same way that a buyer would do it. And, uh, and I think, like, for me, that was like a big part of what was going on in that decade or so, was thinking about customer journeys and orchestrating them and making them as efficient and easy as possible, making decisions, like, more transparent.
For buyers, um, and certainly like Adobe, when we were talking to customers, we were trying to help them with digital transformation and the tools that were available that we were selling were helping our end customers create journeys for their own customers. And so we had to be really good at it ourselves.
Otherwise we just couldn’t be believable. So that was great. That tested us. Um, yeah, I mean, again, I don’t feel like I articulated that super well, but that’s, that was what was going on in that time period.
Scott Barker: I think you articulated it, it very well. Um, and I, yeah, it’s about that time that, yeah, it forced you to think about the individual. Cause a lot of the conversations were like, it was like almost fear based. People were like, well, we’ve always done stuff on prem. You know, there’s all this security. Like my job could be on the line.
If I bring in this cloud, like C suite doesn’t want this cloud thing. I think that we need it. I think it’s the future. But like, I need you to with me as we, as we go. Cause there just felt like there was a lot of fear, um, you have to, you have to map out and make sure that they’re feeling heard and, um, those are all valid,
Rob Giglio: Well, maybe a, maybe another good learning in that, um, in that era was that it were, it was the businesses that decided to, to like try it and to like embrace change. That really prospered. Um, and the ones that were more reticent and apprehensive to change and like, don’t break my model, like really fell behind.
And so the ones that were willing to be bold were like massively advantaged. And so I think the same thing, like, like if you look at AI now, like companies are out there testing and learning and trying, being bold will definitely like on the other side of this curve. look back and realize that they were advantaged by the change, um, period.
Scott Barker: Absolutely. Yeah. And articulating that to your customers. I think in this age, it would be a perfect example now to, to point to that and look at all of the, the people that. Digitally transformed quicker and embrace the cloud quicker. They dominated whatever category or market they were in and they did in a quick, a quick way and same will happen with with AI.
Rob Giglio: Yeah.
Scott Barker: Okay, so you have this this great run. I imagine it was It was tough to make the decision in 2022 to move over to, to DocuSign. Um, you know, incredible company, they were going through incredible growth. Um, but yeah, what made you decide to do that, that jump? And maybe, uh, again, paint the picture a little bit at DocuSign of like, revenue range or team size, whatever you can
Rob Giglio: I think maybe the thing that made me most comfortable and like kind of the, the inflection point was I had a fantastic team at Adobe, like really like amazing team. Uh, and the leaders that I had working for me, We’re really ready for the next thing. And so at some level I was kind of in their way. And so I felt like I personally felt very comfortable leaving, knowing that the company was in really good hands with really great leaders. Um, and that is absolutely played out. That’s like, you know, some of them are still there leading big parts of Adobe’s business. Um, some of them have left and they’ve gone on to really big roles outside of Adobe.
And so I think, you know, that it’s always weird to leave, like it’s hard to leave places. Um, but sometimes it’s just time. Like sometimes it’s just like. You need another challenge. That’s like going to test you in new ways. I was really fortunate because the CEO and the COO at DocuSign were people that I’d known for a number of years.
The COO was somebody that I had gone to college with and we had stayed in touch for years and I was. was excited to have a chance to work with him, um, and they wanted a CMO who would lead growth, which was really the PLG motion, and lead marketing. And so for me that was like, perfect. Like I, I love marketing, I love PLG, like those, those were the perfect roles to go in and do, and um, and there was already a really good motion in place.
And so really it was about like, could I help improve it, um, as opposed to like change it. Like it didn’t need a lot of change, it was, it was pretty good. In terms of scope and scale, uh, there wasn’t that many people. I think like maybe, geez, I don’t even know, maybe a couple hundred, three hundred, something like that. Um, it always felt like the right number. How about that? Um, and, and there we really focused on instrumenting, a digital experience because we’re talking really PLG, like driving a lot of the, a lot of the volume there. And so kind of tuning the PLG motion. To optimize the experience, uh, was critical and most of it was like down funnel, it was less up funnel.
It was more like, what is the onboarding process? What is the trial to paid experience look like? What is the paid to like growth experience look like? And there was a really great team leading that. In fact, the person who, um, was leading it, who came, um, from Adobe to DocuSign is still there. Leading it.
He’s a superstar. Uh, I don’t know if I’m supposed to say names, but I’ll say Neil Reina. He’s an amazing guy.
Scott Barker: Some Yeah.
Rob Giglio: That was great. And DocuSign wasn’t a huge company. It was, I think at the time, a couple billion in revenue. Um, but a lot of customers and it, and it, I was there at the time when COVID hit and the business inflected in a huge way, you And it inflected at the low end, you know, suddenly all these online transactions were accelerating.
And that was, that was nothing that, you know, we did, we were ready for it. We were ready to catch it. But, you know, that was more of a, an impact from the external environment.
Scott Barker: Yeah. Sometimes you get, you get lucky if you’re, you’re, you’re in the right place at the right time. Do the work.
Rob Giglio: What’s the expression? You’re better to be lucky than good.
Scott Barker: Yeah, exactly.
Rob Giglio: That might be, that might be the, uh, that might be the, my tagline of my career.
Scott Barker: You and me, both my friend, I think anyone who’s had any sort of success in their life, if they don’t attribute luck to some of it, they’re, they’re full of shit Um, but, so I love that first year, you know, I think the best leaders that I’ve, I’ve worked with and I’ve kind of been coached is, you know, your job is to kind of yourself out of a role, you know, set, you make your people so good and give them enough responsibilities that eventually you look around and you’re like, They don’t need me anymore.
It’s time for the next thing. So that’s a great way to end a, an incredible run. Um, okay. Uh, DocuSign. So obviously PLG since, since then has exploded and everyone’s tried to more or less copy what, what DocuSign has, has done and the success that they saw. Um, do you have an example of one of these little tweaks or experiments that you ran that you’re like, Oh, this is just like a small thing here that ended up Driving incredible results.
Rob Giglio: Yeah. Um, and I’ll just say generically, this is something that, um, you know, That we worked on. Uh, and I won’t give any, I don’t want to like share a lot of like the stats, but I can share the like basic customer experience. And I don’t think it’s, again, now it’s like, you look back, you got to remember, I left Adobe in 2020, basically end of 2019.
That was almost five years ago. And then I left, um, I left DocuSign in 2022. That’s like three years ago. So in this world. Like literally a year that goes by, everything changes. So it’s like, I’m sharing these stories and, you know, some of this is like what we might call in SAAS land, ancient history. So keep in mind, this is old, but I think some of the, the basic underlying, uh, premises are really poignant.
And the one thing that was a massive, um, change for us was we just stopped putting things in the way of customers who were trying to complete a task. So that’s the generic statement. Like, take things out of the way of people who are trying to do things. In the old days, when we were, I ran an e commerce site for William Sonoma and I ran e commerce for Gap.
In the old days, we used to talk about as page views, like if you could remove the number of clicks it took to go from like intent to action in an e commerce experience, that was a win. Like it was a massive win. And that was like a way that people thought about building web experiences to try to like optimize conversion, like just take pages out. You got to remember also in like 1999 and 2000, pages took a long time to render. So if you had people clicking through pages, it was not just like troublesome, it was slow. And so you just like philosophically remove them. But that same basic premise played out in, at Adobe, at DocuSign and HubSpot, plays out at Canva.
But there was an experience where we started looking at what things we were asking customers to share with us before we just let them complete the task they wanted. And in most cases, it was like a customer coming in and wanting to send a document for a signature. And the amount of hurdles we put in front of customers for them to go from, I want to send a document for signature to I’ve just sent it was mind blowing, like mind blowing.
It was like so many steps, so many fields to enter. Uh, we would send them a, like basically a, like a, a factor authentication process. We’d send them through CAPTCHA. Like, it was like, we made it impossible and that’s not a great user experience. And so that was like, what, like. To answer your question, that was probably one of the most profound.
The other thing we noticed, and this is on the other side of it, the other thing we noticed is if you wanted to stop your subscription with DocuSign, for instance, it was literally a single click of a button. Now, I think you might argue like, well, that’s a good customer experience. Maybe it is, or maybe it’s not.
I think what we weren’t doing is we were letting people just sort of cancel a subscription and go away really quickly, but we weren’t really reminding them Like what that entailed, like, Oh, we’re actually, if you just cancel this. We’re going to like potentially lose access to some of your documents. And, you know, you’ve already set up like this whole signing experience and now that’s going to go away.
And so like, maybe there’s something else you might want to do, but you might want to like downgrade. Maybe you don’t want to be on the like most expensive version. You want to go to a lower price version. And, and I think that like sort of two tails of like, it’s impossible to get in and it’s easy to get out.
Um, a really smart intern, like looked at that experience for us at one time and was like, I find this really bizarre how hard it is to, to do the first action and how easy it is to do the last action and this intern who was very young and like had a very clear mind pointed it out to us and we were like, Oh, great point.
Scott Barker: Yeah.
Rob Giglio: So anyway, there, that’s a lesson
Scott Barker: Yeah. I mean, and that’s super, just an actionable exercise that you can do almost every quarter is just like walk through. your self serve flow and see if there is any barriers that you can remove, you
Rob Giglio: Big time.
Scott Barker: Technology with, you know, all these different things you can do now.
Um, can we make it more frictionless? And I think that the second, like, of course you want to be able to easily, subscriptions and things, but there is a limit when there’s value, especially something so valuable like DocuSign. I think if, If I went to cancel my DocuSign subscription and they just popped up and said, like, Hey, do you have your mortgage agreement saved anywhere else?
I’d be like, oh
Rob Giglio: Right. Bingo.
Scott Barker: Probably a lot of documents that I just
Rob Giglio: Bingo.
Scott Barker: Is going to have. Let’s keep this live a bit.
Rob Giglio: You got it. You got it. I mean, again, it’s sort of like in a podcast, you can ask this question and I can give you the answer. And like on the one end, you can be like, Whoa, that’s super insightful. And the other, it’s like, no shit, like, it’s like some of this stuff is so basic, but I think oftentimes, not unlike some of the stuff we were talking about in consumer packaged goods, we just sometimes all forget about the basic.
Scott Barker: Totally. I think I listen to podcasts just to remind myself of things. It’s kind of like, we’re not, you’re not gonna, this isn’t Elon Musk or people, you know,
Rob Giglio: Yeah.
Scott Barker: Future of the world. But like, I think we’re so caught up in our, our day to day. We’ve got a number, we’ve got our KPIs to hit, we’re hiring people.
And, sometimes just these reframing and hearing other stories are like, ah, right. We should do that exercise.
Rob Giglio: I agree with you. That’s what I like best about a lot of these kinds of podcasts yours in particular It’s just good grounding. It’s a good grounding on like, oh, yeah
It’s the basics. yeah, good
Scott Barker: Yeah. I have a, a tattoo that says just a series of remembering, and I think life and business is just that, you know, you learn these things in life and then you forget them and then you, life teaches you them again. And same with business, uh, sometimes that, uh, you just need to remember. Okay.
And then, so then you have the run and then you move over to HubSpot in 2022. I don’t know the exact metrics, but like from all and I know basics, like HubSpot was exploding during, you know, 2022 and as you join, I still think they are, I think they’re doing such a fantastic job.
Rob Giglio: Yep.
Scott Barker: Product wise, go to market, like, I’ve just been really impressed with HubSpot over the last, you know, call it five years.
Um, Is there anything during that HubSpot period you would do differently or something you, you, your team got wrong?
Rob Giglio: So I came on board and, um, we’re all remote. Everything is remote. Just, it was pretty close after COVID, like, we might have still been wearing masks on planes. I don’t remember, but it was something, some crazy, something like that.
And, uh, and it was a really big team. It was like 5, 000 people. It’s a really big organization. Um, early on, I, I don’t think I was like, Communicating is directly to both my leadership team and then the team underneath them about, like details of where we were going. In my mind, I knew where we were evolving to, and it was an evolution, not some big revolution.
It was a kind of steady improvement around managing the customer experience better. My leaders and I would talk about the transformation we were making and they were on board, but I don’t think I did a good job of like sort of sharing the vision, uh, deep enough in the organization. And so I think for a period of time, we just kept doing things the way we had always done them.
And that’s like as a leader in this environment where people aren’t all in the office and you’re not walking around constantly telling your story and like bringing people along on the journey. It’s easy to forget that if I’m not talking to somebody or they’re not seeing me on zoom, they might not know, like, where are we going?
What’s the, like, what’s the vision here? How are we going to evolve things? And we were in the process of going through pretty big evolution in the sales organization in particular around focusing on inputs and less, less focusing on outputs. And so we were focusing on like great, uh, deal creation. And we were focusing on like, how to progress deals effectively.
And then we were focusing on how do you close deals at really high rates? And yeah, certainly we cared about ARR and orders, but instead of obsessing just on like a one big pipeline number and one big closed one number, we pulled back and said, well, what does it take for each salesperson to be incredibly successful?
Well, it takes great creation. You better build a great pipeline. You better progress that pipeline pretty effectively, and then you better close it. And the same thing was true over on the customer success side. Like it wasn’t just about like how many, uh, quarter of the business reviews you had with customers post purchase.
That’s like almost like an output metric. It was like, well, what are you doing to understand how those customers are moving through their journey and engage with those customers along the way? Those are more inputs and, and less outputs. And like, I can describe it to you here and now, but I don’t think early on I, I did nearly enough to like share that deeply in the organization about the transformation we were making.
And so it happened, but it probably took longer than it should have.
Scott Barker: Yeah. I resonate with that for sure. I think it’s can be one of the hardest things. As a leader to like get the vision that feels so clear in your own head and, and push that out, you know, on a daily or weekly basis to the team, especially when you’re talking about thousands and thousands of people, um, that are working, working remote.
Um, that was one of the reasons like, you know, we’re, we’re a tiny team of six and I was like, we need an office. I, I need, because like, if I’m. I’m in my home office and sometimes I feel detached from reality. Sometimes I feel detached from that vision. If I feel that and I live, eat and breathe, and this is, this fund is my baby.
And it’s all I think about and eat, sleep and breathe. Like other people are feeling detached that way too. And like, just by being, and it doesn’t mean you have to always be in office, but that was the shortcut, at least for us. Cause we’re a small team and we have the luxury of doing it. getting people together, like made everything feel real.
And that vision was like how people carry themselves and hearing Paul or Sophie on their calls. And you it’s, it’s much easier. I don’t know.
Rob Giglio: yeah, I agree. I mean how often do we see on LinkedIn? Somebody goes to an event in person and like some part of their caption is something about it was great to be with people again I am energized by the interaction like it’s just human nature Like it’s it’s like it is what it is and I’m not doesn’t I’m not advocating for return to work kind of stuff That’s not that’s not what I’m saying.
But what I’m saying is the in person experience is a way better to communicate. It’s easy, easier to communicate vision, easier to communicate strategy, and you, you do it repeatedly. That was sort of, I think that was probably, um, historically maybe one of my strengths. Like I would walk around the office and, and just meet with people and teams and I would stay on message and talk about where we were going and what we were doing.
And it just allowed me to keep the team more focused. And I’ve had to learn new ways to do that digitally. I don’t think I’m nearly as good digitally as I was in person.
Scott Barker: Anyone’s as good.
Rob Giglio: Yeah.
Scott Barker: It’s, it’s one of those things that I’m not. I’m more in the in office camp than I ever have been. Um, and, but not to say everyone has to get an office, especially at a company the size of, you know, HubSpot or Canva. It just doesn’t make sense.
But I think there is times and periods whether you’re just starting. you have a really audacious, huge goal, or there’s a huge shift like AI, where I think you need to be very intentional with bringing people together. Because again, it’s about whether it’s a huge revenue goal, or it’s a huge you’re trying to accomplish, or a shift that shared vision becomes even more and more important.
So getting people together can be at least a
Rob Giglio: Well, I’ll give you a good example. Um, we have, our, our headquarters is in Sydney for, for Canva and we have, um, offices there that are like alive. They are like vibrant. And I go down there, um, and I leave so excited about the work I’m doing and the product and like my coworkers, like in ways that like, I can’t remember in my career feeling that way.
Um, and it’s, I think largely because. Everybody’s together and excited about what we’re doing. The same thing is true. We have an office in London and we have an office in Austin. And when I go to those offices, we have these teams, we call them, we call them vibe teams. And it’s like a mix of human resources meets facilities meets, uh, I don’t even know, enablement, it’s like these sort of combo roles.
And these vibe teams are creating like the most exciting work environment and like getting people jacked up about working for Canva and I go to these places and I leave like I go to London. I was there a couple weeks ago and I was in Austin about a month ago. I leave like super enthusiastic. And when I sit in my home office that you see in the background, I don’t end my day nearly as enthusiastic.
Scott Barker: Yeah, it’s, I, I love that. I like the idea of a vibe team. That’s, that’s pretty, pretty
cool.
Rob Giglio: Maybe you’ll have our chief people officer on sometime. She’s doing some super innovative stuff.
Scott Barker: I’d love that. We’ll make it happen. All right. I got a couple more questions for you. Uh, but thanks for taking the time, man. This has been
Rob Giglio: Of course. Yeah, that’s fun. I feel like I’ve meandered around, so sorry for that.
Scott Barker: This is the place for meandering. This is perfect, but I want to go to a listener question and these last couple, we can kind of just and bang them through.
This is from a founder, early stage founder. Question is what is the biggest mistake you see people making in B2B marketing?
Rob Giglio: Calling it B2B marketing.
Scott Barker: There you go.
Rob Giglio: Yeah,
Scott Barker:Love how quick that was. And
Rob Giglio: Yeah.
Well, I mean, like what is B2B marketing really? Like, what is it? Like, what even is that? Like, I mean, if you broke it down, I’m being a bit of a smart ass here. So I apologize to whoever asked that question, but like, like you, you don’t invite a business to come to your event.
Like B2B marketing is oftentimes events, right? We do event marketing, experiential marketing. That’s your classic B2B. Uh, like you’re not inviting the entire company to come to your event. You’re inviting individuals to come to your event. Here’s another one. Uh, like one of the most, one of the hallmarks of B2B marketing is something called ABM, account based marketing. But like, are you really marketing to the account? Or are you marketing to people in the account? It’s brutal. I like, I, I like, I am a B2B marketer myself, but it’s like, I mean, I’m embarrassed to say that I’m a B2B marketer because it’s not a thing. Like you’re, we, we market to, we market to people. People are the ones who can like process information.
Soon we may be marketing to AI. Like I think they’re like, that’s coming, but that’s really like information transfer. We’re going to be doing information transfer to AI, not marketing to AI. Okay.
Scott Barker: That rabbit hole.
Rob Giglio: That’s spicy.
Scott Barker: Opened a door. We can’t go down. Uh, maybe another podcast, but. I’ve been thinking a lot about that, of even how we build products. Soon we’ll be building products for agents. We’re going to be marketing to agents. We’re going to be.
Rob Giglio: Yeah. Yeah. Yeah.
Scott Barker: But I like that. Just remember that it, you’re marketing to a human. Get
Rob Giglio: Yeah.
Scott Barker: Get fun.
Rob Giglio: Yeah,
Scott Barker: That’s, that’s the way to do it. Um, uh, all right. Final two questions. I keep these intentionally vague. Take them whichever way you want them. Um, what is one widely held belief that revenue leaders still believe to be true?
That you think is bullshit or no longer serving us.
Rob Giglio: sizzle over substance. I am, I am not a fan of sizzle over substance. uh, substance wins every time. It might not win quick, but it will win the most. And so, uh, a really splashy, cool campaign, uh, dropped at the Super Bowl might last a couple months, but it’s not going to sustain you if there’s not substance. And what I mean by substance is like the product value has to resonate for the user. Uh, and the message has to address pain points and needs and the value proposition has to be clear and easy to understand. And so that for revenue leaders, like substance really matters. Here’s another one. Um, if you’re a revenue leader, you might be a CRO.
And I think sometimes CROs, like, get lost in the, like, have a lot of sales reps, do a lot of stuff, have a lot of calls, send a lot of emails, pound people with outreach. No offense to the outreach, but outreach. And I mean, outreach in the generic sense, not the
brand. Um, but like substance is going to work.
Like if your customer has a pain that you can solve, if you can clearly articulate that, the solution, you’re going to get the, you’re going to get the window is going to open, the door is going to open and you can have a conversation and you can begin discussing like how your product can deliver impact.
So, so the thing that I think is bullshit is sizzle over substance. Most people don’t call it sizzle. Like they, they, no one’s willing to admit that they’re doing sizzle, but it is definitely sizzle.
Scott Barker: Yeah. I like it. What I’m almost hearing there is like the, the, so the sizzle is, yeah, you spend all your time, you know, on this beautiful, creative campaign. And you think that alone is going to be enough. Or you spend all this time doing a perfect sales process and you get this customer over the line that’s maybe not even a perfect customer for you.
And you’re forgetting that. You know, your job as a revenue leader is so far beyond just pipeline creation and, and getting to that close one. You have to be in line with product. You have to be in line with, you know, the entire customer journey, removing that friction. Like that is the,
Rob Giglio: Yeah. Maybe. Okay.
Scott Barker: Sexy part.
Rob Giglio: I love, I love where you’re going, Scott. That was actually, you teed me up into another like related thought, which is that like, ultimately as a revenue leader, whether you’re a marketer, your customer success, your sales, your product marketing, whatever, you’re not really looking for the sale.
That’s not what you’re looking for. You’re really looking for loyalty. Like the ultimate like end of journey. Is loyalty and loyalty is usually expressed. over time and it’s expressed with like, uh, levels of commitment, which might be like growth. Uh, and then it’s expressed with advocacy, which is, would this person like say they love your product?
Um, so I think like, that’s actually what gets in the way. Like, if you think that the, like, the end game is a single transaction, you might think Sizzle can get you there because I can close the deal. I can discount the product and I can get the deal. But if you think loyalty is the end game. Yeah, you still want to close the sale, but you’re really thinking like this thing’s got to last for a long time.
They’ve got to be successful from, you know, early on in their journey. They need to see what they can do with it. It needs to work for them. It needs to solve problems, make an impact, and then you’ll start to earn this bigger goal, which is loyalty.
Okay, there you go.
Scott Barker: like to add another stage to like most customer journeys where it’s like, becoming a, a customer is just a, Another stage in that journey. The, the true note style is like now they’re in the loyal customer bucket. And
Rob Giglio: We, we do that. we do that. So a little, so props to, props to the Canva crew. Our customer journey starts at lack of awareness. And goes all the way to loyalty. And we think about how do we draw people through this entire experience to get to loyalty and loyalty expressed as like time, like longevity, deep product use or growth, if you’re a business and then advocacy.
Scott Barker: Cool.
Rob Giglio: And that’s a canvas.
Scott Barker: Canva, ahead of the game. Everyone should steal that. I think that’s a great new kind
Rob Giglio: We would love for people to steal it. You can steal it.
Scott Barker: Yeah, awesome. All right. Final question and then I’ll let you go, my friend. Um, You know, you’re at Canva, nine months in the role. I call this the silver bullet question. we know there’s no silver bullets, but what is one tactic or strategy that’s actively working at Canva right now?
Rob Giglio: Simplicity is what works best. And what I mean by that is, um, kind of back to this sizzle of our substance. dilemma. Simplicity is about everything in the entire customer experience. It’s about how easy the product is to use, how easy it is to find features. Simplicity is about the marketing message.
What does this thing do? And what will it do for you? Um, simplicity is about, um, the entire customer journey. Make it simple to move from one place to another. Make it simple to add other users. Make it simple to, um, upgrade your contract. Actually, make it simple to cancel if it’s not working for you. Um, what I like about simple and the reason it’s so important to, I think, all businesses, not just us.
I mean, we’re using Canva, but like it’s simplicity is something that is a tactic that I’ve felt is like, It’s my, I think I would describe it as maybe my silver bullet over the years, because it can be measured. If it’s simple, you can figure out if it’s working or not. If it’s complicated, uh, good luck trying to figure out how to measure it, because you’re like, oh, it’s a little bit of this, and it’s a little of that, and it’s this thing over here, and next thing you know, you have no way to put metrics on it.
Um, simple could be described like any person can describe it. Like if you can’t describe what your product does, you’re in big trouble. Uh, if your webpage, if you land on the homepage of a product and you read that webpage and you have no idea what the hell the technology does, you failed, you’re not simple, so it could be described.
And then finally, when things are simple, they can be trained on. So from a sales methodology standpoint, if you’re going to have a sales methodology that you want to train all your reps on. If you don’t pick one that’s simple, that’s easy to understand and easy to remember, you’re in trouble. Like maybe like 5 percent of your team will actually become certified in your methodology, but the other 95 will be like fumbling through trying to figure out what, what’s the method we’re using and they’ll fail.
And so I think like up and down the go to market stack, simplicity is the key.
Scott Barker: I love it. I was actually just talking to Craig Rosenberg on another conversation we’re having about this exact topic we talked about, I’ll leave everyone with this quote from, uh, Vinnie Pazenzi. He’s a boxer and it was made fun. It was made famous by a recent movie called In the Blood. And reporter asked him, what’s the biggest lie you’ve ever been told?
And he goes, it’s not that simple. they go, why not? He’s like, no, that’s the biggest lie I was ever told. It’s simple. You know, you do the basics right. You know, you, you, you do all these things we were talking about. Remove friction, show up authentically. Like. You know, our job, we like to over engineer everything, but it can be simple.
And when, when it’s done simple, it’s done
Rob Giglio: Yeah. Well,
maybe the other thing is like, I don’t think simple is easy. I think that’s maybe another like, um, point. Simple is actually kind of hard. And you do, you do simple
Scott Barker: I
Rob Giglio: to, to, um, Well, you do, you do hard things to make it simple. Um, so that mainly, like, if you think about it, like, if you could figure out a way to take things that are hard and make them, um, Easier?
You’ve simplified things in ways that like someone couldn’t have done on their own. And that’s a, that’s a massive win.
Scott Barker: I agree. Couldn’t agree more. Yeah. It takes a lot of work to make things simple, but, um, anyway. the man. Thank you so much for taking
Rob Giglio: Thank you, Scott.
Scott Barker: Really enjoyed this conversation.
Rob Giglio: Yeah, me too.
Scott Barker: know, for our listeners, uh, I say it every week, but listening is just, you know, part of the game. Uh, execution is, is where it happens.
So hopefully we gave you some ideas, thoughts, tactics to take into your own business. And, uh, Rob, LinkedIn guy, X guy, hiring
Rob Giglio: I’m a LinkedIn guy.
Scott Barker: you want to shout out.
Rob Giglio: I’m a LinkedIn guy. We’re hiring a lot of salespeople, um, all over the world. So we would love to love to see people looking. Um, yeah, we’d love people to try Canva, use it, tell a friend, get loyal.
Scott Barker: We’re happy Canva, [01:00:00] Canva users. You can definitely put us in the loyal bucket if we’re not already.
Rob Giglio: Thank you, Scott.
Scott Barker: I love it. Thanks, man.
