A few years ago a friend of mine invited me to a “closed door” after hours meeting at his house. It was a small gathering of 10 or 15 founders where folks could speak openly and candidly on any subject. I don’t think I’ll be violating that pact by saying that I briefly met Anthony Casalena who started Squarespace. I don’t remember much of this interaction except that I remember him talking about the Squarespace superbowl ad and how they had tried every possible marketing channel under the sun at Squarespace. He spoke of marketing as a core competency at the company, and I sort of flashed to various billboards and subway ads, and facebook ads, and whatever else and made a mental note in my head “Squarespace is good at marketing.” At the time I didn’t care much…I was a product-centric founder, i cared about engineering and design, and marketing was far from a craft I was a) familiar with and b) cared to be. Fast forward a few years, and I have become quite tuned to marketing as a discipline. I’m at a company that is circling around the cup on “product/market fit” and bringing great Marketing DNA into Wildcard has been a top priority of mine for the past few months. Even before we launched Wildcard 2.0, I kind of new that engagement was going to be solid from our beta, and I began to get serious about understanding what the right Head of Marketing fit was for us. As with any new discipline not represented within the team of a startup, it’s usually the founder’s job to go learn it when nobody at the company knows it. So I geared up to learn Marketing 101. I remember when we were an engineering culture in the earliest days, and I had to go “learn design” at least well enough to understand the craft and identify our leader in the field. Today design is a point of strength in our company, but it started as a weakness with me doing a bunch of research, buying a bunch of coffees, taking online HCI classes at Stanford, and getting the basics down before we could develop it into a strength under Khoi and Steve. With marketing, this learning process was actually much harder to pickup than design. I found our network didn’t reach as far into the marketing community as it did into design. I guess most of the engineers and founders we know have worked with great designers over the years, but the numbers got smaller when we’d ask our friends “do you know any great marketing leaders or teachers?” We got routed to plenty of agencies, and point solutions, and ex-agency folks, or young up and comers, but it took a while to really develop an understanding of the full marketing stack from performance to brand, and to really understand what we needed at this stage in Wildcard.
I hate the idea of paying recruiters 30% of a years salary to fill a key role. I know it’s a no-brainer sometimes, but building a team is a core strength of ours, and something about retaining recruiters just has always been hard for me to digest. We kept working to better understand the craft, and even built up competency on the “growth hacking” side of the marketing spectrum (not surprising that we got good-ish at the more technical part of the stack first given our dna), and over a few month period we got to a point where we could identify really what we were looking for in a Head of Marketing. With that clarity now under our belt, one of our board members strongly urged me to take meetings with recruiters. I did, and I wasn’t shy about my ask. I wanted someone who had seen the whole thing, from first marketer in, to iconic consumer brand known and loved by millions. I wanted them to have built a team, gained familiarity with the entire stack, and to be of the “startup cloth.” It could be the #2 at Kayak or Venmo or something on that scale, or the #1, but if I was going to pay that kind of money to make this hire, I wanted best in class, humble, roll up their sleeves ready and on the same level in their field as our other leaders are in Engineering, Design, Data Science, etc…To put it in the words of one of the recruiters, “there are like 5 of those people in New York City…you basically want a unicorn.”
As it turned out, we never ended up hiring a recruiter. Through a mutual friend, we started spending time with a super thoughtful, humble, and experienced person who happened to be a user and lover of Wildcard already. He was the first marketing hire and Head of Marketing at Squarespace from when they were Wildcard’s size and no marketing budget to hundreds of people, a super bowl ad and $45M in annual spend. People he worked with through more than four years at Squarespace spoke to his appreciation for product, his desire and ability to live at the intersection of product and marketing, and his overall wonderful contribution to their team and culture…especially in the early days of the company. I was a bit worried that coming from a now huge company like Squarespace, with a 15 person marketing team and running that kind of scaled effort that Wildcard might be too early for him, but as it turns out this is exactly the stage and moment in a company’s life that he had been looking for in his next chapter.
I’m so excited to have Matt Haggerty joining Wildcard as our first Head of Marketing. Design and Engineering have been our strengths for the past 2.5 years, and I can’t wait to turn marketing into Wildcard’s third super power with Matt’s help :)
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