What’s worth knowing in the Squarespace world.
For designers, developers, and people building businesses around Squarespace.
What Most Designers Don’t Know About Squarespace Enterprise (But Should)
Beautiful templates? Check.
Easy drag-and-drop editor? Check.
Perfect for small business sites? Sure.
But here’s what almost nobody tells you:
Squarespace has an enterprise platform—and it’s a complete game-changer for clients with bigger needs.
And odds are, you have clients who could (and should) be using it.
This isn’t just a fancier billing plan. This is Squarespace with multi-site management, granular permissions, SSO, enterprise-level security, and scalable systems built for teams, departments, and high-stakes workflows.
If you work with larger organizations, municipalities, schools, or growing brands—this is your primer.
1) Most Designers Still Think Squarespace Is “Just” for Small Sites
That assumption is costing you money.
Yes, Squarespace is fantastic for solopreneurs and small businesses. But that same simplicity and elegance scales. With Squarespace Enterprise, organizations can:
Manage multiple sites from a single dashboard
Control who can edit what (down to pages or sections)
Launch trial sites that never expire
Use Single Sign-On (SSO) with Google, Okta, Microsoft, etc.
Get private onboarding, SEO guidance, design consulting, and a dedicated account manager
This is infrastructure. It’s built for the clients who “outgrew” basic website builders—without dragging them into plugin chaos and server maintenance.
2) Granular Permissions = Less Chaos, More Control
If you’ve ever delivered a site for a school district, city government, or national nonprofit, you know the pain:
Every department wants its own space
Everyone wants a login
No one wants anything to break
With Enterprise, you set role-based access per site (and tightly scoped areas), so Comms can publish news, HR can manage job posts, Facilities can update alerts—without touching design or global settings.
Result: content moves faster, brand stays intact.
Quick mental picture: Snow emergency hits. Comms toggles an alert banner site-wide in seconds—no “hey, can you jump in real quick?” text to you at 7:12 a.m.
3) SSO: Secure Content Without Custom Development
Staff intranet pages. Partner portals. Members-only downloads.
With SSO-protected sites and pages, your client uses the identity system they already trust—no brittle plugin stack, no custom auth build.
Result: friction down, security up.
4) Enterprise = Consistency at Scale
Franchise with 30 locations? University with 18 departments? Nonprofit with recurring campaigns?
Reuse design blueprints
Clone starter templates instantly
Govern everything from one account
You’re not “building another site.” You’re deploying a system—fast, consistent, on brand.
5) Real Support for Real Teams
When it’s mission-critical, waiting in a general support queue won’t cut it. Enterprise includes:
A dedicated account manager
Private training for client teams
Design audits and SEO help
Your clients don’t just get a website—they get a repeatable way to launch initiatives without calling you for every tiny change.
6) Who This Is Perfect For
Not every client needs Enterprise. But these do:
Agencies managing 5+ Squarespace sites
Nonprofits with multiple programs or chapters
Municipalities & school districts with accessibility, governance, and compliance needs
Multi-brand or multi-location companies rolling out product or campaign sites
Any team that’s hit the ceiling of a basic plan and needs security, speed, and control
7) The Two-Minute Fit Test
If a client checks 3+ of these, bring up Enterprise:
Multiple editors need access with guardrails
Department-specific areas or lots of microsites
Staff/partner content that should live behind SSO
Strict brand consistency requirements
Low tolerance for server, plugin, or update headaches
Pressure to launch campaigns fast without dev in the loop
8) “But Our RFP Says WordPress/Drupal…”
Cool. Talk operating model, not logos:
Governance: role-based publishing without risk
Speed: campaign sites in days, not sprints
Reliability: security and uptime handled by the platform
Total cost: less maintenance, fewer emergencies, more shipping
When decision-makers hear “fewer points of failure” and “faster to market,” they listen.
9) You Might Be Sitting on an Opportunity
The next time a client asks for a redesign—or says “managing our sites is a mess”—don’t auto-default to WordPress. Don’t assume Squarespace is off the table.
Educate them. Show what Squarespace Enterprise makes possible. Be the first person to put it on their radar. That’s how you move from “web designer” to strategic partner.
Final Thought
There’s a version of Squarespace most people never see. Once you do, you start seeing possibilities everywhere.
If you want to:
Work with bigger clients
Pitch more ambitious projects
Build scalable systems that pay better and last longer
…stop treating Squarespace like “just a website builder.”
Squarespace Enterprise might be the most powerful tool your studio isn’t using yet.
Freelancer, Solopreneur, Founder, Entrepreneur — What’s the Difference?
(and why it matters if you want real freedom)
When I started freelancing, I thought all these titles were just marketing spin.
Freelancer. Solopreneur. Founder. Entrepreneur. Sure, they sounded different — but I assumed it all boiled down to the same thing: "I work for myself."
What I didn't see then is that each identity comes with its own patterns — and those patterns determine how you price, who you work with, the kind of opportunities you even notice, and how much freedom you actually have.
If you want to get off the client roller coaster, you first have to figure out where you are right now, and where you actually want to go.
The Freedom Spectrum
Think of it like a spectrum: Freelancer → Solopreneur → Founder → Entrepreneur. On the far left, you have the least leverage and the most dependency on your personal labor. On the far right, you have the most leverage and the least dependency on your time.
Your goal doesn't have to be "max leverage, no labor" — but you do need to know where you are and what each step toward the right would mean for your freedom.
Stage 1: Freelancer — Selling Time and Skills
Here you think "I do work for clients," and your freedom level is low because if you're not working, you're not earning.
Freelancers typically price based on effort like hours, days, or deliverables. They experience feast and famine cycles, say yes to whatever comes along, and find themselves being reactive instead of proactive. Freelancing can be great for getting paid quickly, but if you stay here without a plan, you're essentially an employee with multiple bosses and all the instability that comes with it.
The freedom check: How long could you step away before your income stopped?
Stage 2: Solopreneur — Owning the Business, Wearing All the Hats
Your mindset shifts to "I'm a business owner," and your freedom level becomes medium because you control more, but you're still the engine driving everything.
Here you move from "I work for clients" to "I run my own business." You start thinking about marketing, sales, and client experience, not just delivering the work. The big shift is taking a consultative approach where you see yourself as a business owner helping another business owner achieve an outcome.
Solopreneurs set processes instead of working ad hoc, build recognizable offers, and start choosing projects instead of accepting whatever shows up. The freedom check becomes: If you took a month off, would your business survive without a scramble when you got back?
Stage 3: Founder — Building Something Bigger Than Yourself
Now you think "I'm building an asset," and your freedom level is high because your income isn't fully tied to your labor.
A founder creates something that can operate without their constant involvement — a product, a platform, a team-run service. This is where you move from client work as the business to client work as one part of the business.
Founders develop documented systems, create assets that produce revenue without their daily labor, and build teams or partnerships where others own parts of the process. Your freedom check becomes: If you disappeared for 90 days, would revenue keep coming in?
Stage 4: Entrepreneur — Playing the Long Game
Your mindset becomes "I build value and turn it into more value," though your freedom level is variable depending on your focus and discipline.
An entrepreneur spots and captures opportunities, sometimes in their current business, sometimes in new ones. They think in terms of multiplying assets, not just operating them. This could mean starting, acquiring, selling, or investing in businesses.
Entrepreneurs focus on strategic partnerships and acquisitions, spread risk across multiple streams, and operate from vision rather than just daily needs. The ultimate freedom check: Do your assets generate more income than your living expenses?
How to Move Along the Spectrum
Most people don't jump straight from Freelancer to Entrepreneur. The common path involves moving from Freelancer to Solopreneur by shifting from "hired help" to consultative partner, setting up processes and choosing projects intentionally. Then you progress from Solopreneur to Founder by packaging what works into assets, hiring selectively, and reducing the need for you in every delivery. Finally, you move from Founder to Entrepreneur by decoupling income from operations and spotting scalable opportunities beyond your core business.
Why This Matters for Freedom
Freedom isn't just "working for yourself." Freedom is having assets that generate more income than your expenses, and the further you move along this spectrum, the more that becomes possible.
The biggest mistake is staying in one stage without realizing it's a stage.
Your Next Step
If you want to start stepping into bigger opportunities — the kind that require you to think and operate like a business owner, not just a service provider — you need to be in rooms where those opportunities live.
That’s why I curate the $10K Project List — weekly leads for high-value creative projects.
It’s the easiest way to start positioning yourself as a partner to other business owners, not just a pair of hands.
Why “Charge Your Worth” is Bad Pricing Advice
If you’ve been freelancing for a while, you’ve probably heard this one:
“You just need to charge what you’re worth.”
It sounds empowering. It makes you feel like you’re standing up for yourself.
But here’s the thing. It keeps you focused on you — your confidence, your insecurities, your self-esteem — instead of the real drivers of price.
If you want to get off the client roller coaster and build a business around assets that don’t depend on your time, you need a different way of looking at pricing.
Here’s what I teach the freelancers I work with 👇🏽
1. Pricing isn’t about you
“Charge your worth” turns pricing into a self-esteem exercise.
Clients aren’t buying you. They’re buying an outcome.
Your worth as a human being is infinite. The market value of your work? That’s entirely about the impact it creates for them.
When you see that clearly, pricing stops being about whether you “feel confident” and starts being about what the result is worth in their world. That’s a much more stable foundation to build on.
2. The ceiling on your price isn’t your skill — it’s the size of the budgets you’re around
If you only talk to people whose max spend is $2K, that’s all you’ll ever get offered — no matter how good you are.
High-value projects live in different rooms. The people in those rooms have different priorities, different timelines, and a different idea of what “reasonable” looks like.
I’ve seen freelancers go from $2K projects to $20K projects without changing their skillset — they just started showing up where $20K was the norm.
That’s the real “glass ceiling” in pricing, and it has nothing to do with your talent.
3. High-Budget Clients Aren’t Buying Your Time — They’re Buying Certainty
When you’re in the $10K–$50K project range, the client isn’t asking, “How many hours will this take you?”
That’s a small-budget question.
Big-budget clients are asking:
“Will this solve the problem?”
“Will this help us hit our goal?”
“Can you deliver without making it harder for us?”
They’re buying certainty — certainty that you understand the stakes, that you’ve thought through the risks, and that you can make the project happen without creating more problems than you solve.
Once they feel that from you, the hourly math disappears. If you keep pulling them back into an “hours × rate” conversation, you don’t raise their confidence — you lower it.
4. You’re not just the person doing the work — you’re a lever
When you price like a freelancer, you’re selling labor.
When you price like a business owner, you’re selling impact.
If your work helps a client generate $250K, charging $25K isn’t “expensive” — it’s a bargain.
I’ve talked to people who delivered projects in the $20K–$60K range that took the same effort as a $2K job. The difference wasn’t the workload — it was the scale of the result.
5. Bigger projects aren’t harder — they just require more trust
The leap from a $2.5K project to a $25K project is almost never about technical complexity. It’s about trust.
High-budget clients need to know:
You can handle the scope.
You’ll keep the project on track.
You won’t create new problems in the process.
That trust comes from how you show up, the process you lead them through, and the proof you can give that you’ve handled similar stakes before — or that you’ve thought far enough ahead to de-risk the project.
The real shift
When you stop trying to “charge your worth” and start charging based on value:
You stop negotiating against yourself.
You start having better conversations with better clients.
You start building a business that isn’t chained to your hours.
That’s how you get off the client roller coaster for good.
Want to see what those bigger projects actually look like?
Every week I curate a list of $10K+ web design and creative projects so you can see the kinds of opportunities where value-based pricing isn’t just possible — it’s expected.
It’s called the $10K Project List. When you start seeing these every week, you stop wondering if bigger budgets exist — you start figuring out which ones you want.
This was originally posted on the Freelance to Freedom newsletter by Omari Harebin.