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Jeremy Schwartz

Creating the Job You Want

Creative Ecosystem Manager AT Squarespace
Instagram: @jmsjmsjmsjms
BEST Treat: 10% off Squarespace


If BEST hosted a “How-To” Business TED Talk Extravaganza, I would hire Jeremy Schwartz as the keynote speaker. I could sell tickets at top cost, guaranteeing that each attendee would walk away more inspired, activated and smarter than when they walked in.

When I first met Jeremy he was a soon-to-be ex-lawyer with a 3-coffee-meetup-a-day schedule figuring out what career would really fulfill him. Cut to a few (many) years later at Squarespace where he sprouted an idea (Circle) and saw it through to fruition. Committing to his work in a genuine, honest, and thoughtful way.

This guy is someone you want on your team. Someone you want as your boss. The person who will give you the news you will use. In one of our heftier FOBs to date, Jeremy delivers valuable info -- what it takes to switch career paths, what to do when you have an idea (how you know you have an idea), what it’s really like working at Squarespace and why it matters.

Grab your matcha latte and get out there! - Alison

Let’s start from the beginning. You were a lawyer and then you “changed career paths” one might say. How did you do it? Leave nothing out.

Why’d I change career paths…? (1) I wasn’t that into lawyering and knew I was never going to be that into it, (2) I had a side hustle that gave me glimpses of worlds beyond midtown, and (3) I had a girlfriend (now wife!) who was not freaked out by the prospect of me giving up the career I had trained for.

As for how I did it….I decided to do the thing that business requires, and that lawyers work to avoid: I took a risk. More specifically, I took a low-paying, one-year gig at a finance firm in Sydney. This move amounted to a bet that a big step back in compensation/seniority/status would get me onto a totally new professional trajectory and payoff in the long run.

Sydney was great and the gig was so-so, and I decided that my next move would be to make my way into the tech scene that was starting to blow up in New York.

I spent the first few months that we were back home going to networking coffees and meetups and assuming that my value would be obvious, but it became clear pretty quickly that my fancy lawyer pedigree meant more or less nothing below 14th Street. At that point I realized that I had to do something more than be a well-trained former lawyer to make myself a viable hire. (Side note: My wife was working, we were living at my parents’ apartment, and I had savings from my time as a lawyer so I had the luxury and privilege of not making an income for at least a little while.)

I decided to partner with a developer to build a very basic (but sort of useful!) digital product and created a Squarespace website to promote it. The product got a tiny bit of traction but, more importantly, bringing it to market moved me out of the “Bored lawyer who wants to be in tech” column and into the “Business person who knows how to get stuff done” column.

One of my coffee circuit acquaintances was the then-COO of Squarespace. We’d meet every few months and I’d give him updates on what I was working on and he’d give me feedback and suggestions. At the end of one of these meetings he invited me to apply for a business role he was trying to fill. I’d had a great experience with Squarespace, thought I could learn a lot from the COO (I did!), and was really ready to have a job so I applied and got the job.

Having finagled a spot at a growth-stage company I then had to figure out how to be useful at a technology company when I’m not an engineer, designer, developer, customer support professional, ….


And now you are a Creative Ecosystem Manager. Explain.


Everyone knows Squarespace for our DIY website builder but the group that I head up, called Squarespace Circle, focuses on professionals who use Squarespace to build websites for their clients.

Think: A freelance graphic designer who develops logos and branding for small businesses … and builds the website that pulls everything together.

Or: A marketer who develops strategies and messaging for their clients … and builds the website where leads can be converted into customers.

My team works to inspire creative professionals to start building Squarespace websites for their clients, and provides support, resources, perks and benefits to help them improve their skills and grow their businesses.


landing page


I would say about 90% of the people I know use Squarespace. How do you and your colleagues wrap your head around creating and growing a brand that works for everyone?

Wouldn’t the web be a more beautiful place if 90% of websites really were on Squarespace?

Anyway, I’m going to pretend you asked two different questions...

  1. How do you create a product that works for everyone?

  2. How do you create a brand that resonates with everyone?

I think the answer to both questions is … maybe you can’t?

90% of people you know use Squarespace because we spent a lot of time (especially earlier in our history) focused on helping creatives showcase their work. That’s the use-case we thought the most about and we developed a brand that resonated with those customers.

We’ve obviously evolved beyond portfolio websites, but the belief that good design matters is still core to our product and brand: We think that everyone (lawyers, dry cleaners, and plumbers included) needs an online presence that’s impactful and stylish, and we try to build products and a brand that work for the subset of lawyers, dry cleaners, and plumbers who are open to that message.


Squarespace is a huge company —15 years old, almost 800 employees (!) with millions of websites created on the platform—but I still think of it as part of the “start-up culture.” Can you give me a glimpse behind the curtain?

Reading the paper over the past couple years has made it crystal clear that a start-up can have amazing perks and benefits and still be toxic and miserable place to work if the culture isn’t right…..

But, yes: Squarespace offers really nice benefits, lunch is catered, our company parties are great, and it’s nice to work in the West Village (and not in, say, midtown).  Beyond that, we make real and open-ended investments in fostering a workplace culture that’s comfortable and affirming to a wide range of people. I’m a white, cisgendered, straight, married white man so I inevitably experience the office differently from many of my colleagues, but my sense is that we’re on the right side of history when it comes to company culture.


Which company benefit is your favorite?

401K matching and free lunch are both great, but the most meaningful perk by far has been parental leave. I took 18 weeks after our twins were born in January 2017 and consider that time and experience priceless. Seriously: I don’t think there’s any amount of money that I’d have accepted in lieu of that time off.

If I ran the world, everyone would have at least 18 weeks leave and everyone (birth parent and partner) would be required to take at least 12 of those weeks. Even if you have a generous leave policy there’s still pressure to get back to work and I think making that time a company policy and not an individual choice would improve things.


Okay, so you’re at Squarespace, killing it, and see an “opportunity in the market.” Besides chatting it up at the water cooler, what are some actionable steps you took to develop it?

Actually, at Squarespace we chat at the kombucha and cold brew taps….

I think there are two things you need to do to get momentum for a new idea and they should happen more or less simultaneously: Use data to make the argument and complement the data with insights and stories from actual customers. You’ve got to get on the phone and talk to people; and you’ve got to find new ways to think about the same facts.

By the way, when I say “data” I don’t necessarily mean you have to do heavy-duty statistical analyses on giant data sets; I just mean that you need to make your arguments based on a set of facts that you can cite and that others can verify.


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Okay, so the idea is developed. How did you get everyone else to sign on?

As I was trying to get colleagues and counterparts in the company to contribute/cooperate on “my” idea, I would do one of three things. (1) Make it worthwhile to help (i.e., find win/win situations). (2) Make it free to help (i.e., re-appropriate work they’d already been done). (3) Make it low cost to help (i.e., request teeny tiny tweaks to what they’re already doing).

There are obviously times when you need to simply insist that counterparts contribute or support your work and that requires some degree of formal authority, but if you take the time to understand your colleagues’ goals and motivations you can usually find a way to get some approximation of the help you want without resort to hierarchy.


And we’re live! CIRCLE has a heartbeat. Tell us why it matters in a few sentences.

Squarespace has done a good job of making it easy for anyone to make a website: Switching fonts, changing layouts, publishing blog posts, etc are all trivial. This raises the obvious question: Why would you need a professional to build a website on a DIY platform?

My answer is that Squarespace solves the “how” (how do I add a photo? How do I add a page?) and Circle members answer the deeper questions:  Which photo tells the right story, what layout will lead to conversions, how should you present yourself to visitors.

With the newly re-launched Circle website we tried to communicate what Circle is and the opportunity Squarespace website design represents for creatives by having members tell their stories. They’re pretty inspiring!


One thing we often run into when designing, now that Squarespace templates are so widely used, is Clients needing something more custom but that maintains the user-friendliness function. Is this that?

As a non-designer, I don’t usually deviate too far from the templates we provide as starting points, so the websites I create definitely read as “Squarespace.” The fact is that the more I deviate from the template, the worse my websites become. Basically, it’s hard for me to improve on the templates my colleagues have created.

On the other hand, people who have more creative vision can push their website projects way beyond and achieve really custom looking websites using native functionality.

What we also see is that at some point creatives bump up against the platforms’ guardrails, and that’s when they start using bits of CSS and Javascript here and there to do more advanced stuff. This is pretty straightforward tech-wise and really opens up the creative possibilities.




So it’s really taking Squarespace the TOOL and evolving it into Squarespace THE COMMUNITY?

Totally. Even among Squarespace customers who have had great experiences with our platform, “Squarespace subscriber” is rarely a core part of their identity. For the Circle community, though, Squarespace is an integral part of their day-to-day work and “Squarespace professional” is part of their professional identity. Not surprisingly, they’re keen to connect with and learn from each other online and IRL.


We get it that Squarespace is a great “eco-system” to grow ideas, but what are some tips for other 9-to-five-ers that are working to make ideas known in their own jobs?

If you’re looking to create change or start something new at your company, my advice is to spend your time identifying a real problem and solving it. By “real” I mean the problem you identify has be important to the organization as it currently exists (i.e., it can’t be your pet peeve and it probably shouldn’t be a plan for radical change).

This means you really need to understand your organization’s goals and how the whole machine works together to achieve those goals. This sort of understanding only comes from paying attention at all hands or QBRs, lurking in other teams’ Slack channels, grabbing coffees with colleagues and asking about their work, etc. Once you’ve got a mental model of how the org works, you can start finding the points of friction, the underutilised assets, or the extensions that will make the org more impactful.


When you get stuck, where do you ask for help?


And, colleagues. At this point, Squarespace is filled with experts in basically every discipline (technical, creative, finance, comms, etc) and I’m not afraid to ask questions or for help.


Sounds like a lot of work. And you did all this while having twin boys -- how do you balance a full personal life with maintaining excitement (and endurance) in your professional life?

Having a committed partner helps, as does having family very nearby, but aspects of my personal life have definitely fallen by the wayside. I used to have a pretty regular yoga practice, but I mostly haven’t exercised since the boys were born. On the other hand, taking care of two 25 pound toddlers is sort of like boot camp.


Now that you have successfully launched a brand within a brand, what’s next?

Transforming clever whiteboard drawings to the real world is where things get really hard.


Briefly describe who you are and what you do and why you like BEST:

I started as the boyfriend to a friend of BEST, but I’m happy to now officially be a first-degree FoB. I like BEST because they put their money where their #resistance mouth is by supporting organizations whose existence and mission are under threat. #stayBESTtogether is pretty awesome.


You made it! Here’s a treat from Jeremy—
10% off Squarespace with code Circle10


Learn more about what Jeremy and his team have created here.
We especially dig the navigation hover states ;) and the
Member Stories.
Email us when you’re ready to build your own!

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