12 Lessons Learned Marketing to a Squarespace Audience
I’ve been selling to the Squarespace audience since 2015 — long enough to watch markets rise and fall, competitors disappear, and “the next big thing” fade into nothing.
In that time, I’ve generated nearly $2M in sales from other people’s products, built profitable plugins through joint ventures, and learned the hard way what it takes to survive when others burn out.
Some of these lessons apply anywhere. Others only make sense if you’ve lived inside this ecosystem for years.
Here are 12 of them.
1. Choose Your Niche for the Long Game — Bet on Inevitable Demand
When I started freelancing, I was working on a mix of video, photography, social media, and web design projects. Squarespace kept showing up in the mix.
By 2015, I made the call to focus on it. Not just because I had experience with the platform — but because I was heavily into digital marketing at the time, and I saw something others didn't.
Squarespace didn't have the same marketing features and functionality as Shopify or WordPress. My prediction was simple:
As the Squarespace market grew, its users would want the same kinds of tools, features, and marketing capabilities they were getting on other platforms.
I banked on the inevitability of that demand — and I built around it.
The reality check: I was right about the demand, but wrong about the timing. It took three years for the market to catch up to where I thought it already was. I actually quit 18 months in when my site sat dormant for months. I only came back when I realized I had built an asset that needed continued development.
The niche you choose isn't just about what's hot right now — it's about where you can anticipate future demand and position yourself to meet it before it hits. But you also need the patience to wait for that demand to materialize.
2. Your First Win Doesn't Have to Be a "Product"
I wanted to launch Squarespace templates. I failed. I didn't have the design skills, technical chops, or quality to compete. I was also too early — the market wasn't quite ready.
So instead, I sold:
Squarespace Tweaks — bite-sized, productized fixes
A subscription for Squarespace project leads
Consulting
These weren't glamorous launches — but they sold. They gave me cash flow, an audience, and credibility. That foundation made it possible to launch scalable products later without starting from zero.
The marketing lesson: I treated my business like a sandbox during those lean years, which gave me the freedom to keep experimenting with low-risk offers. When templates didn't work, I could pivot to services without losing everything.
3. Build What Clients Already Pay For
When I finally succeeded with plugins, it wasn't because I guessed at market demand. My dev partner (found on Upwork) and I had a simple validation method: we only built what clients had already paid us to create 1:1.
The marketing insight: The hardest part of marketing isn't getting people to buy — it's knowing what to build. When you productize proven 1:1 solutions, half your marketing work is already done.
4. Slow Burn Beats Big Splash
The very first plugins that we launched — there was no big hoopla. I even got a warning in the Squarespace forum at the time that I couldn't promote. I think there probably wasn't even a sale the first couple of days, but as the awareness grew and as the demand grew, sales started to come in.
I approach every marketing project with the same three questions:
Who's already looking for this and where?
Who's bound to be looking for this in the future, and when specifically?
What do they need to see, feel, or believe to buy?
Anytime someone comes to me with a product idea or something to offer, the first place I go is: "OK, who's already looking?" Because if there's no one looking for it already, then you've got a Herculean task ahead of you. But if you can immediately find those places where people are looking and you can set up shop or set up a presence in those places, then you're on your way.
5. Lead with Their Priorities — They Don't Care About Your Process
Squarespace buyers are almost always solving an urgent problem — either for themselves or a client. They're not browsing for fun. They have a job to finish: a website to launch.
Here's what they care about: Will this get my website done faster? They don't care about your tools, your methodology, or how clever your solution is. They care about outcomes.
This urgency is what makes the audience different from other creative markets. They're not buying inspiration or education — they're buying solutions to immediate roadblocks.
6. Leverage Search — It's Your Biggest Advantage
This audience Googles everything. Early, specific answers compound. A single helpful post or video can rank for years and quietly sell for you while you sleep.
7. Find Them Where They Already Are
The best buyers found me through:
The Squarespace Forum
Referrals from other experts and affiliates
Blogs inside the ecosystem
Social media (more for reputation than direct sales)
Even in my biggest revenue spikes, these weren't random buyers — they were people I'd already reached through these channels. The trust was built before the sale happened.
That's why my smallest marketing action — starting an email list — turned into my biggest long-term payoff. It kept me in front of them so that when urgency hit, they already knew where to buy.
8. Free Help Builds Marketing Assets
During the years when I wasn't making much money, I maintained credibility by helping lots of people for free out in the open — primarily in the Squarespace Forum and through free content.
This wasn't charity. It was asset building. Every helpful answer increased my visibility when urgent buyers searched for solutions. One detailed forum post about fixing checkout issues in 2018 still drives plugin sales today.
9. Retarget, Don't Cold Chase
I've tested Google, Pinterest, and Facebook ads. Retargeting — showing ads to people who had already visited my site or seen my content — consistently beat cold outreach.
Warm traffic converts because they're already problem-aware. Cold traffic in this niche is mostly tire-kickers.
10. Show, Don't Sell
The best content I've ever made? Simple, over-the-shoulder screen shares where I walk through a fix or feature in real time. No cinematic editing. No overproduced marketing.
Just: "Here's the problem. Here's how to fix it."
The funny thing is, that style of content often kept selling long after I made it — because the problems it solved were evergreen. A 5-minute video I made in 2019 showing how to add custom fonts has generated more affiliate revenue than some of my "official" product launches.
11. Collaborate, Even With Competitors
Some of my best partnerships were affiliate deals with other Squarespace creators — and sometimes even coaching competitors. The ecosystem is small enough that trust transfers fast. If someone's audience trusts them, that trust rubs off on you.
12. Fill the Gaps Squarespace Won't
My original bet on this niche was that Squarespace users would eventually want the same marketing capabilities they saw on Shopify and WordPress. That's exactly how it played out.
Squarespace adds some features lightly and avoids others to keep the platform simple. Those gaps are durable opportunities. My most consistent sellers live right there. Permanent gaps are marketing gold.
If I were starting today
Week 1 – Show up where buyers already are
Join the Squarespace Forum + one active group. Answer 10+ questions in public. Start a tiny email list.
Week 2 – Turn help into assets
Record 2–3 short screen shares (3–6 min). Post them (YouTube → quick blog). Send one helpful email.
Week 3 – Productize one fix
Package your most-requested solution (scope, price, turnaround). Publish a lean service page and announce it to your list. Turn on simple retargeting.
The goal isn’t a viral launch – it’s becoming the person this audience trusts to remove roadblocks fast. Everything else stacks from there.
Have an offer for the Squarespace market (or want one)?
I’ll help you spot the gap, position it, and map the first three channels to get buyers.
Final Takeaways for Anyone Marketing to the Squarespace Audience
Anticipate demand before it hits. Start small, solve urgent problems, and let that fund your bigger plays. Build where people already search — and keep showing up. Partner with others who already have trust. Watch the gaps. They'll keep you in business.
Want to shortcut the learning curve? I've spent over a decade building and selling to the Squarespace audience — products, services, partnerships, and SEO plays that keep working year after year.
