Behind the Brand®

Jeff Adamson [00:00:08]  Welcome to Behind the Brand presented by Neo. We take an inside look at the leaders behind today's most influential brands. I'm your host, Jeff Adamson. As co-founder of Neo Financial and SkipTheDishes, I'm fascinated by what it takes to build great companies. On this podcast, we'll learn from leaders that are reimagining, transforming, and innovating in the financial and retail industries across Canada. Let's get going!

I am excited to introduce Ashley Graf, Head of North America Marketing at Squarespace. After graduating magna cum laude from New York University, Ashley kicked off an impressive career in sports and entertainment marketing, working with clients across various industries including sports partnerships with the NFL, NBA, LPGA, and MLB.

Now at Squarespace, Ashley leads the marketing strategy for North America. Founded in a dorm room in 2003, Squarespace has evolved into a cutting-edge platform that empowers millions of individuals and businesses to build a brand and create an impactful online presence. With a team of over 1,400 and offices in multiple countries, Squarespace is at the forefront of website building and ecommerce.

Welcome to the show, Ashley!

Ashley Graf [00:01:15] Thank you, it's great to be here.

Jeff [00:01:17] I wanna start off talking about the awesome Super Bowl ad that Squarespace ran. So tell me about the Adam Driver spot.

Ashley [00:01:24] Our geniuses on the creative team led by David Lee. You know, these things come together kind of as a brainchild of our creative team, oftentimes in you know, talent that they want to work with. So there was a lot of passion for working with Adam.

As I’m told, Adam had an interest in doing something funny. So I think the spot is really clever, you know, the singularity of illustrating the point that Squarespace is a website that makes websites. So I think he was the perfect person to kind of hammer home this point that you know, we are a website builder tool that can help create all these websites across the greater web.

But I think the genius of it too was the selection of talent and how well he was able to hit this funny side. And I thought it was brilliant in the scope of the Super Bowl, right? So many spots. This one was particularly unique because it stood out from the whole landscape of spots out there. So I think in terms of brand recall, its ability to stand out, talent selection, it was one of our, one of our best years for sure.

This is, I think, our ninth year doing Super Bowl spots.

Jeff [00:02:31] It's simple, it's funny, and it's definitely like on character for Adam. Before we get into Squarespace specifically, I do want to talk a little bit about your journey to Squarespace. Take us back to how you got to Squarespace in the role that you're in today.

Ashley [00:02:47] My career kind of started in sports marketing. Interestingly enough, I, growing up was always kind of fascinated by sports as a way to bring people together and seeing all of the, you know, tens of thousands of people in the stadium rallying around one thing was fascinating. And then starting to make that connection that like, “Oh, this, like, brands are spending, there's a lot of spend happening in these places off the field”, right?

So that was around the time that these sports marketing programs were popping up. You know, some big schools had them, like Michigan. But NYU had one. I [thought] “What cooler place to be able to go and go study sports marketing than New York,” where you have all the leagues headed, headed up. You have ESPN offices. So to really learn sports business in a place like New York, was incredible.

But what that started to translate to over time as my career got past college, I was working first at an agency called Group M, [a] big media company or media agency that worked with a ton of blue chip brands, but across all of their sports and entertainment investments.

So then you start to see behind the curtain on how these brands are thinking about sports marketing and how they're really connecting. You know, they're spending X million on Fox Sports, and then they have this talent deal over here, and then they're creating this content around sports and they're pulling the talent into the content and they're weaving this whole thing together.

But all told they're spending, you know, tens of millions in sports marketing. But I really was like, wow, that's just as powerful as being at the league itself or being at the team itself. So I really started to become fascinated in the brand marketing side of how these investments come together and what the strategy is.

So that's what started to inform, I guess, or guide my decision to move into more brand focused roles. Ultimately, you know, landed at some places like Time Warner Cable, where, you know, I was working with sports programmers and sports sponsorships, and then ultimately, right before Squarespace, spent about five and a half years at an airline in the US called JetBlue, focused on our advertising, our brand marketing strategy. Part of that used sports entertainment, of course.

Then what really led me specifically to Squarespace – obviously a really cool brand out there in the marketplace. Spending in places like the Super Bowl, you can't not notice that. We were the Knicks jersey patch sponsor for a number of years too. But Squarespace was a product that I used actually, I built my wedding website on it five years ago.

I think about this at other jobs I've had, but you know, at JetBlue where I was previously, I was a customer for years before I ever went to work there. I love the product. I love the service. I would always try to fly JetBlue when I could, over any other airline, and Squarespace was similar. I used the product once and I was like, “Oh man, it's so intuitive. The design is so good!”

It's like, what a cool way to, in the case of my wedding, like this is kind of the first touchpoint that people have. I can make people excited through my beautiful website that I could not have built, you know, easily on my own. So it gave me a way to like, you know, create this beautiful look and feel for this event that I was throwing.

So ultimately in, I think it was 2021, I had applied before to things at Squarespace and a recruiter reached out, I think like, many months later, and was like, “Hey, we have this role, this North America role, would you be interested?” And that's, you know, one of those moments where you're like, “Oh, a brand I love, you know, wants to talk to me!” So it was kind of really organic in that sense. Just becoming a customer first and then getting lucky enough to work here.

Jeff [00:06:36] Well, and that's the beauty of working in consumer brands too. And like, at Neo, we're a consumer brand, we do consumer banking, you know. And Canada has far less consumer brands than the US.

Like we import a ton of consumer brands. You know, like Uber, Lyft, Netflix. Most of the brands I think that Canadians interact with every single day are from outside of Canada, but there's something different about working for a company where you were actually a fan of the company and so you've used their product.

And nothing wrong with being a B2B SaaS or you know, a niche player in a very important industry, but you can't exactly go to your mom and tell them, “Hey, like use Salesforce.” You know, like it's, a little bit different.

Ashley [00:07:18] No, it's so true. It's cool to be at a product that everybody, I mean everybody can use.

You have hobbyists using a platform like Squarespace to write about their gaming strategy. All the way through to people who are selling literally anything. Selling the soap that they make, selling their yoga classes. So I think, you know, working for a consumer brand that can be accessed by anyone for so many different things is incredibly cool. Just to realize how wide your reach is and how many people you can help.

Jeff [00:07:59] I do wanna touch on your time at JetBlue because to me it would've been such an interesting experience going through being in charge of marketing at an airline during Covid. What was it like to be in the business of spending money to promote people to go and fly, at a time when you know the sky is falling and everyone's terrified of getting sick.

Ashley [00:08:21] It was a wild time, as you can imagine. You're trying to pull on past experiences or benchmarks to try to understand how something will go. The only comparable, I think, was 9/11 in the airline industry that kind of like [a] complete drop off in demand. So the experience I think was particularly challenging for our leaders, you know, the CEO and president of our company to simply just guide. We had the strong balance sheet, but to start to have revenue drop off to almost zero.

From a marketing standpoint, you're, you know, pretty quickly like, okay, we have to start to tamper down some channels really fast. Really fast! And then try to identify where the pockets of demand are.

And really for those first few months, there were very few pockets of demand. And what we were, what we were hoping, what we were trying to at least encourage through channels like, you know, email marketing, like really just using our organic channels to start to say to our customers, “Hey, plan those holiday trips”, like trying to get them to pre-book for later in the year.

Nobody knew how long anything was gonna last. In a brand marketing capacity at that time I was, I think, leading brand activations, like partnerships, cultural marketing, those types of things. So we were pitching some ideas to get out in the market and do something that would at least endear some brand goodwill.

At the time, everyone's looking at the front lines. Who's on the front lines? Who's out there? And it was the healthcare workers, right? I led like the biggest, the largest scale promotion of my career at the time, which was giving a hundred thousand trips to healthcare workers. So national promotion, like very scrappy, we worked with an agency in New York called FairShare, and they helped us put together this really cool piece of content that was like clips of, you remember the 7:00 PM clap that was going on around like near hospitals, around New York, people clapping for the healthcare workers.

It was like clips of footage like that and then JetBlue employees thanking their loved ones who were healthcare workers. So it was kinda like frontline speaking to frontline because our employees, they had to show up and fly empty planes every day. So the piece of content was really cool and getting Robin's green light, our CEO's green light to give away that much was pretty impactful.

I think the governor was doing those nightly addresses or daily addresses, press conferences. So he picked it up and talked about it. So it just, it felt like being part of this moment, it endeared a lot of goodwill at the time and felt like, felt like the right thing to do. And it got a lot of people, at a time when people have very little to be excited or feel really positive about. It's so challenging to lead a big cross-functional project, but everyone felt really, really, like, wanted to do it, wanted to work together and do that.So our focus was really, you know, tampering down channels where we could, but really getting out in market with something that couldn't, you know, remind people that we were still there and that we were going to do what we could to support the frontline.

Jeff [00:11:22] No, it was amazing to see companies like JetBlue come together and try to figure out like, how do we be a force for good? How do we do the right thing during a time of pretty great uncertainty. One of the things that I find interesting is people who have a career in perhaps more traditional businesses making the transition to tech businesses.

And so perhaps having that huge disruption and that scrappiness was actually maybe a good crash course for getting into a tech startup, but this is your first tech startup that you've worked at, and what has that been like for you? Like what new muscles have you had to build? New skills to learn? So that you can succeed in a completely different industry and even, I would imagine, a completely different culture too?

Ashley [00:12:07] Man, I think the biggest challenge in transitioning to a completely different industry was having to learn the business, frankly. Nothing totally prepares you for tech, especially coming from airline, like they’re such different, specific industries speaking their own languages.

But I think the biggest muscle that I developed in previous roles that has certainly helped me at Squarespace [is] that ability to be flexible and nimble and to be constantly watching your business. Airline was, things booked so close-in, it depended on your region, your routes and things like that. But you're every day like trying to book in, you’re trying to fill up your plane.

To me that really long-term forecasting and planning, that didn't help you so much at an airline. So here, being able to really like, dig in and figure out how to adjust things kind of down to the minute and shift plans close-in like that is something that felt innate to me. So it didn't ruffle me at all. It actually feels like a really good opportunity to constantly be making sure you're doing your best work, really know[ing] what's going on in the business all the time. And then like getting out your toolbox to make sure you're addressing the shifts in demand that you're seeing or the shifts in channel performance that you're seeing. Airline was a great crash course for those types of things that ended up being very helpful in tech.

Jeff [00:13:31] Agility is so much more of a virtue now, I think, than it was perhaps a few years ago. You do hear a lot about being able to adapt really quick. Resilience is also commonly thrown around as well.

I wanna go back to the very beginning and I'd love to hear, you know, what's the origin story of Squarespace? Like I remember coming across Squarespace probably like many people, where you're just like, I wanna build a website. And then you go to Google and you start looking up, and Squarespace always struck me as the most beautiful. Of the kind of websites that build websites. I love that you guys own that now. Like it just seemed to me that Squarespace was always the most aesthetically pleasing to the eye, functional.

How did you guys get to here? How did you start? Cause now you're, you're publicly traded, so take us way back.

Ashley [00:14:17] To many years before I ever even got here. So I can tell Anthony's story a bit. Anthony is our founder and CEO. Like incredible, you know, 20 years later, almost 20 years later, he's navigated us through 20 years of just incredible growth.

So Anthony, University of Maryland College student, a similar situation to many people today, right? Surfing around, trying to figure out the right way to, I think he was trying to build a blog, recognized that there was nothing as aesthetically pleasing on the market as he wanted. So decided to build it himself and then started to realize that there was an opportunity there, there was a gap in the market.

And then interestingly, kind of bootstrapped the company himself, for years. I think it was like almost four years. Where it was kind of just him engineer by trade, like he was the engineer, he was the marketer, he was the customer support person. Singular [laughs]. And then it started to take off at some point. I think he, you know, started to figure out the right, couple of channels to invest in to start to, I mean, you said it yourself, like you went to Google to, you know, look for a website builder, right?

So I think he was really, Investing primarily like Google AdWords for many years. And then, you know, demand starts to take off at a certain point, right? And you start to like kind of hit that tipping point in awareness. The big a-ha or unlock moment is when he started investing in podcasts.

Jeff [00:15:45] That's true. I do remember that. Yeah, that Squarespace kind of was all over podcasts.

Ashley [00:15:49] Yeah, like dominated podcasts. And still to this day, I mean we, that is a very significant part of our marketing strategy still. We find, you know, those are very qualified audiences, right. But it's also, it's part of our legacy at this point too.

But he started, I think, it was ‘This Week in Tech’. He placed one ad on ‘This Week in Tech’ and then saw a kind of takeoff. So now, I mean, we advertise and I think hundreds of podcasts across like so many different sectors, but it continues to grow from there. And then, I think nine years ago, then he started to invest, or we all started to invest in Super Bowl. So like you see how the scale rises, but there are certain things like podcasts that will continue to be a very successful tool for us.

But I think, talk about other turning points for a company. 2020, I mean, the whole web builder category, everything shifted online, right? Entrepreneurism took off, but like really reframed how people thought about being an entrepreneur and having a side business or a side hustle.

So that was another huge moment of growth for Squarespace too, with being able to kind of harness that moment and be this platform to really help these people reframing their businesses or taking advantage of the moment and starting their business for the first time, being the platform to help them do that.

Jeff [00:17:05] To me, I just, what I love about Squarespace is the fact that like when you remove the friction from doing something, you unlock so many new possibilities and categories. Like even for example, like when you think of Stripe, making it super easy to process payments online, all of a sudden a whole new category can explode.

Like 99% of the people when Anthony was starting up wouldn't have had the technical capabilities to build their own website. And now with companies like Squarespace, but Squarespace specifically, you've just made it so that so many more people can showcase themselves, their company, their service, anything they want online and that to me is just so transformational.

Ashley [00:17:47] It was! People don't even know what coding was really 20 years ago. So to be able to create a website where you don't have to do any coding, you know, we have tons of templates available, the process is so intuitive. Squarespace and others, we're not solely responsible, but we are one of the, one of the big ones that broke the category open, right?

So I think that's pretty impactful. And now people can, I mean, there's so many other tools. One of the cool parts of our growth or transformation in the past however many years was that not only could people create a website, now you can create a business, like you can sell, like you can your whole livelihood can be on a Squarespace site, right? So to go from, you can create your blog, you can create your, you know, hobbyist site to, okay, you're a photographer who wants to create their portfolio on Squarespace. So like, you see how it evolves, you're creating your website for your wedding, but now there's just been an explosion in people who are selling online and we've met that moment by continuing to evolve our product.

So in 2021, we'd been adding commerce products, but 2021 was really, 2020-21 was the moment that we really brought to market our real brand shift as well towards Squarespace as this tool to sell anything. And by that I mean, of course everyone thinks of physical products, physical goods, and that's certainly an enormous piece of our business.

But what the past few years brought as well was this new understanding in the many different ways that you can sell online, be that your time, you know, we have an appointment feature. Be that your content, so for, you know, think of all of the yoga studios and businesses in the wellness space that shifted to putting their content behind a paywall.

We have all these products and features that allow you to not only sell physical goods, but sell your content, sell your time. And I think that’s just another interesting way that Squarespace continued to evolve, to meet the moment and to help entrepreneurs be the most successful version of themselves.

Jeff [00:20:04] Okay, so Ashley, my background – kind of came up through food delivery, did a food delivery startup called SkipTheDishes, and one thing I was always paranoid about was commoditization. Listen, if I want to get food, I'm gonna open up my phone and I've got Skip, Uber, DoorDash. And up in Canada we're very proud of our kind of successful tech startup company called Shopify.

When it comes to competition, how should people be thinking of Squarespace relative to WordPress, Wix, Shopify, Webflow?

Ashley [00:20:36] It's a fair question. We have plenty of competitors, but I do think we assume a very distinct place in the market. We started very differently than Shopify. Shopify came out of the gate as an e-commerce platform.

We have a long history as a website builder, so I think that just how our trajectory started carved out a natural path for Squarespace. But we also, to your point earlier, being crafted to be very much design-forward, design-first. To be aesthetically pleasing, like that helps guide your audience, right?

Like we continue to build for an entrepreneur that is, you know, concerned with having a very professional, very aesthetically pleasing product. So that's helped us continue to naturally find the right audiences for us. And I think as we have evolved, being able to then add products and services into our suite with that lens in mind.

You know we acquired, Unfold, our suite of social media products. We have a link-in-bio competitor called BioSite. So bringing all these things into the folds that are within this kind of look and feel and aesthetic that still feels very, Squarespace has continued to help us, I think, grow while keeping design first and feeling very distinct from our competition and what we bring to the market.

So now we can say we are this really beautiful, aesthetically pleasing, all-in-one platform that can help you build your website, that can help you sell, that can help you market your brand, that can help you grow your audience. So yes, we'll continue to have lots of competitors, be they in our core product like websites or in commerce or now I mean, you see this proliferation in creator tools. There are so many different tools that help content creators develop their content, house their content. But again, being this all-in-one platform that makes you look professional and beautiful, right out of the gate is our distinction.

Jeff [00:24:31] What about in terms of like, who your end customer is? Because when I think of Squarespace, I often think of that solo entrepreneur, but there's also, you know, you've seen Shopify Plus kind of going after enterprise. Squarespace just has so much flexibility to do so many different things. Like how do you prevent yourself becoming, trying to be everything for everyone versus kind of the best for a specific type of customer?

Ashley [00:24:55] Our target still remains relatively focused though, like I don't think that that has changed in the sense that a majority of our customers are solopreneurs, micro-small businesses. As more and more people, as more and more individuals sell and find ways to monetize their expertise, we are continuing to remain focused on that kind of persona and how we can help them continue to be, or start to be successful selling.

It's just there's a broader spectrum of entry points than ever, right? I mean so many people start selling these days through social media platforms, but then they ultimately need to house their business through a website. So being able to be like the right entry point at the right time for those solopreneurs and micro-small businesses will continue to be our focus.

Jeff [00:25:48] Tons of people find that space very, very challenging though. What do you think has been key to Squarespace's success in that solopreneur market?

You know, and I'm just thinking even in my past experience, like we worked with tens of thousands of individual restaurant owners and it's just, it's super challenging to scale it because, you know, it's just very fragmented. But you guys have done it quite successfully and like, what do you think has contributed to you guys being able to gain such a huge amount of market share in that space?

Ashley [00:26:22] Again, credit to the design and by design here, I also mean like product design. The focus on that and the focus on kind of being the customer, knowing what they want. Because we're very tapped into our customer community, what they're asking for, what their pain points are, continuing to evolve the product with that in mind.

We have also a very strong community of, we call them circle members. They're pro users who use the product, they use the product for their clients. So they're a really engaged audience of people that we continue to learn. So I think that continued focus on product design and really understanding the customer's needs helps us continue to be a top choice for [a] wide array of solopreneurs and micro-small businesses, and just simply the fact that they can not only build a website easily on Squarespace, but continue to scale their business easily on Squarespace, right? I think one thing that we hear often from a lot of our customers is that they've not only been able to publish their first site, but keep growing it year after year, new business lines, new product features. So I think the product is built for these people to continue to grow on Squarespace.

Jeff [00:27:39] I think about the history of Squarespace and I just think about Anthony starting up in 2003, what the web would've looked like back then. And then you've got the absolute explosion of mobile. I mean it, this has been happening for, for quite a while, but social selling, kind of explosion of social media platforms. Now, TikTok is taking over.

Where do you see e-commerce going? Like, and again, like, without getting too specific into forward-looking statements here, but just in your opinion, like what's the next disruption that's gonna occur in e-commerce or in web commerce in general?

Ashley [00:28:14]I think we need to start to see this multimodal selling continue to play out. There is certainly a dramatic increase in selling through social platforms, live shopping, but I think that at the end of the day, people want to have some level of ownership that you can't necessarily get in your, if you're selling through Instagram for example, or selling through TikTok. So when I think about the future of e-commerce, I don't know that I have a great answer for you in terms of like five and ten years.

But I think that some of these things, some of these trends that we're seeing in selling through social platforms, like that is only a great launchpad for people to gain a community, start to sell, and then ultimately start to come back to something that they grow themselves and have ownership of in the long term.

And that is what you can do through, you know, by owning your own business platform through a website where you're building it yourself and you're in control of your product, your audience and how you sell it.

Jeff [00:29:21] Even just think about social selling. Like if I see something on social media and I can't even recall a single person telling me that they've purchased something, you know, directly in a video that they were watching, and they could just seamlessly click on it, like a jacket they saw someone wearing in a YouTube video, and then it’s just like click, click check out. Like they may see what they like, but then they still go back to the website or they go to Google and then to the website to purchase it. Like buying things directly through social platforms, has that actually really even taken off yet?

Ashley [00:29:52] We looked at this a little bit, even in terms of a marketing play earlier this year with a program called Network. We're playing around and trying to learn more about it, but I can't tell you if from a meta standpoint, has online shopping through those platforms met the, you know, the growth thresholds that they've forecasted for it.

It's like it's going to have to come back to what the seller is trying to accomplish. And if people are successful selling through a program like TikTok, great. But I think the seller's going to continue to have a lot of control in the way that they want their product to come to market.

Jeff [00:30:27] Where does Amazon come into play? Because I think about, you're helping entrepreneurs build their own brand, sell directly from their own controlled platform. And then Amazon seems like it's the opposite. They're saying, “We're gonna aggregate all the traffic and we're gonna drive the most sales for you.” How does Squarespace think about Amazon?

Ashley [00:30:46] To be perfectly honest, it's not a big part of our day-to-day, especially not from a marketing standpoint, right? Like where I sit, it's not influencing our marketing decisions or our marketing roadmap in a big way. Etsy might even be like a better example, right?

Jeff [00:31:01] Yeah, good point.

Ashley [00:31:02] We want to enable them though, to be able to still sell through Etsy or other platforms like this. They can be driving traffic back to their side as well and selling through their own platform too. So I can't necessarily speak to how we think about Amazon, but we certainly want to enable our sellers to be able to sell through platforms like Etsy also.

Jeff [00:31:21] Yeah, it's almost as if you can make money by selling on Amazon, but you're not gonna really control your brand or your destiny, and so it's, it's kind of just like another revenue stream.

Last question I want to ask you is, you've worked for some amazing brands, you've had a ton of success in your career. I think a lot of people will be looking at you, Ashley, and saying like, “Okay, well how do I achieve the same level of success that you've had?” What would you give credit to your success to?

Is there any key things that jump out at you that you can say that, “Hey, this is kind of something that I've held onto or thought about” or advice that I was given that has helped you get to where you are?

Ashley [00:31:55] Moments in my career where I feel like I've had growth in a formidable way, right, like in a way that I really registered, it was because of maybe a couple of things. One, being around the right people that I could learn from, who invested in me too. Finding a mentor, finding people who are going to help you learn, who are going to be like, “It's this, not that,” has been critical. I also think that just trying to stay humble throughout your career and continue to have that learning mentality, take some calculated risks too.

Like moving from airline to tech like that was one of the hardest things I've ever done. But to be able to then a year later at Squarespace, be able to [be] like, “Wow, I have learned so much in the past year!” So those are the exciting moments. Where you’re like, “Okay, if I can continue to stay humble, keep learning, no matter what situation I'm in, like that will continue to unlock the next pathway to growth.”

Jeff [00:33:01] Yeah. I love how you said finding a mentor, not waiting for a mentor. Because I think, you know, if you want someone to come into your life and give you that guidance, you kind of need to go out and look for it.

Listen, super grateful for you coming on the podcast. Really appreciate you and everything that Squarespace is doing. Huge fan over here at Neo. Thank you so much.

Ashley [00:33:23] Thank you, Jeff. This was a blast.

Jeff [00:33:30] Thank you for tuning into Behind the Brand. If you enjoyed today's show, please subscribe and leave a review on your preferred podcast platform. If you’re interested in learning more about Neo Financial, visit us at neofinancial.com.

Behind the Brand is a production of Neo Financial and MediaLab YYC. Hosted by Jeff Adamson. Strategy, research, and production by Keegan Sharp, Alana Tefledzuk, and Kyle Marshall.