Cold Client Outreach for Squarespace Designers
Everything you need to know to land your first client without knowing a single person.
Video
Timestamps
Slides from Video
Timestamps
0:00:43 — Introduces the topic: cold outreach for Squarespace designers (but applicable to anyone).
0:01:03 — Explains why outreach feels uncomfortable and why most people struggle with it.
0:02:03 — Highlights common fears: sounding spammy, being ignored, and waiting instead of taking action.
0:03:00 — Reframes outreach as helping people, not “cold pitching,” to make it feel more natural.
0:04:33 — Starts strategy: finding the right targets and understanding who you’re reaching out to.
0:05:25 — Introduces the “10-second screenshot test” to quickly identify website improvement opportunities.
0:10:24 — Explains how to find the right person to contact (not just generic emails).
0:18:30 — Breaks down how to write an effective, personalized outreach message vs. generic spam.
0:23:31 — Covers follow-ups: how often to do them and how to make them feel natural.
0:25:18 — Emphasizes “reaching out sideways” (networking for referrals, not just clients).
0:33:40 — Shares realistic outreach metrics (open rates, replies, conversions) and pipeline expectations.
0:40:23 — Wrap-up mindset: focus on starting real conversations, not closing everyone.
Why Most Outreach Fails
Cold outreach feels uncomfortable for most creatives, and that makes total sense. You were never taught how to do this. School taught you craft, not how to find clients.
There's also this fear that reaching out will come across as desperate or spammy. So you post, you wait, you hope the right person finds you.
The other thing people say is: I don't have time for this. And honestly, that feeling makes sense too.
Reframe:
You're not cold pitching, you're trying to help someone.
Think about it. There are small businesses out there right now with a website that's working against them. And you could fix that! That's actually a really human, generous thing to offer.
And if they don't respond? They're not rejecting you. They're just busy. They're in it. Life is happening. It's not about you.
At the end of the day, it's not a numbers game, it's a relevance game. 10 thoughtful, specific messages beat 500 generic ones every time. Cold outreach done right isn't pushy. It's just introducing yourself with intention.
Find the Right Targets
Before you write a single word, you need to know who you're even talking to. And this is actually the fun part. You're basically going hunting for opportunities people don't even know they're missing.
Two buckets: brands you already love whose site doesn't match their vibe, and businesses that are clearly doing well IRL but their online presence is letting them down.
The Screenshot Test
Pull up their site and within 10 seconds ask: do I already know what I'd fix? If yes, that's your lead. You already have something to say.
And don't just look at the design. Look at the whole picture.
What to Look For
No email signup? That's a conversation about building their list.
Bad or missing photography? Their site can't convert with iPhone photos from 2019. You can help them find a photographer or connect them with one.
No social presence or inconsistent posting? That's a retainer conversation right there.
Missing pages? No FAQ, no clear offer, no about page that actually says anything.
A great client isn't just someone who needs a new site. It's someone whose whole digital presence needs a person like you.
Where to Find Them
Google Maps and Yelp: local businesses with reviews but rough sites
Instagram: great product or vibe, bio link goes nowhere or to something embarrassing
Local directories, boutiques you walk past, farmers markets
Green Flags for a Ready-to-Buy Client
Actively posting but site looks abandoned
They're growing: new location, new product, press mention, but nothing has been updated
Do Your Homework
Before you reach out, spend 10 minutes actually looking at their world. Not an hour. Ten minutes. This isn't a research paper, it's just enough to sound like a human who paid attention.
What to Look At
Their website: look deeper than design. What are they selling? What's missing? What's confusing?
Their Instagram: what's their tone? Are they funny, earnest, aspirational? You want to match their energy when you write to them, not yours.
Recent activity: new launch, press hit, rebrand, new location? That's your opening. Timing a message around a moment in their business is gold.
Find the Right Person to Contact
This is where most outreach goes to die.
Not info@. Not the contact form. Not the CEO if it's a bigger company. You want the creative director, brand manager, or marketing lead. Whoever actually feels the pain of a bad website.
LinkedIn is your best friend here. So is the About page. So is just reading the Instagram comments to see who's replying as the brand.
You don't need to know everything about them. You just need to know enough to make them feel seen.
The Vision Pitch
One approach that works really well and most people aren't doing: record a short video, under 2 minutes, absolute max 3, and send it with your outreach.
But it's not an audit. It's a vision pitch. You're not showing up to fix what's broken, you're showing up with ideas for where they could go.
The energy is: "I love what you're building and I keep thinking about what this could look like if..." That's exciting to receive. That's hard to ignore.
This works especially well as your second touchpoint. A reason to follow up that doesn't feel like nagging. First message plants the seed, the video makes them actually feel it.
Why video works when a message alone doesn't: they're not just reading about you, they're experiencing you. Your taste, your thinking, your personality, all in under 3 minutes.
That said, this is an option, not a requirement. A well-written message with that same energy works just as well. The method doesn't matter. The feeling does.
The Portfolio Problem
A lot of you are thinking: this all sounds great, but what if I don't have the work that would make a stranger say "yeah, they could totally do that."
This is the chicken and egg problem of being a new designer. And the vision pitch is actually one of the best ways out of it.
Here's the move: pitch them a spec project. Reach out and say something like: "I'd love to redesign your site. You don't have to publish it, you don't have to pay for it upfront. I just want to bring you along on the process and show you what's possible. If you love it, we can talk about how you can actually have it."
You're not doing free work. You're building a real portfolio piece with a real brand, and giving them a low-risk way to say yes.
You're not asking for a favor. You're offering one. That's a very different conversation.
Write the Message
You've found your person, done your homework, and you know what you want to say. Now you actually have to write the thing. This is where most people spiral.
They write and rewrite and second-guess and end up either never sending it or sending something so watered down it says nothing.
Here's the framework that cuts through that.
Open / Bridge / Ask
Start with something specific about them. Not "I love your brand." That's nothing. "I've been following you since you launched your candle line and the way you photograph your products are beautiful." That's something. They can feel the difference immediately.
The bridge is what you noticed plus how you can help. One or two sentences connecting their world to your skills.
The ask is one small, low-commitment next step.
What a Bad Email Looks Like
Hi! My name is Puno and I'm a Squarespace web designer with 3 years of experience helping small businesses grow their online presence. I came across your website and thought it could use some improvements. I'd love to hop on a call to discuss how I can help you reach your goals. Looking forward to hearing from you!
Sinceraly,
Puno
Why this doesn't work: it opens with the sender not the recipient, "could use some improvements" is vague and slightly insulting, "reach your goals" means nothing, it could've been sent to literally anyone, and there's no reason to reply.
What a Good Email Looks Like
Hi Clara,
I found Oat Bakery through a friend and honestly have been low-key obsessed with your packaging! The way your brand looks in real life and the way it shows up online feel like two different businesses though, and I think there’s so much potential!
I'm a Squarespace designer and I'd love to show you a few ideas. I’m sure you’re super busy, but we could do a quick call or happy to send over thoughts via email. See if it’s worth exploring?
Here's a little bit about me and my work: [link]
Cheers,
Puno
Why this works: it opens with something real and specific, the "two different businesses" line makes them feel seen without being mean, it's short and confident with no begging, there's one clear ask, and it gives them somewhere to go to check you out.
Include a Link to Yourself
People are going to look you up whether you tell them to or not. Make it easy. If they can't find you, they'll assume it's spam! Eep!
Totally get it if you don’t have a full portfolio or a social account that emulates all of your slashiness. A single page website, an Instagram account, a LinkedIn. Anything that shows a real human face is behind this message is enough.
Seriously, even if your Instagram hasn't been updated in months, don’t worry about it. It just needs to exist. It just needs to feel like you.
If you have nothing yet, start with LinkedIn. Warm photo, one clear sentence about what you do, add your ilovecreatives Squarespace Design Course certification (wink wink).
On Length and Subject Lines
Shorter than you think. 3 to 5 sentences for a DM, 6 to 8 for an email.
For subject lines, their name or brand name in the subject line helps. "Love Oat Bakery!" works great, but if true, more specific like “Long time customer, Love Oat Bakery!” is fun.
And never use "Collaboration Opportunity" or "Quick Question." or anything with “Quick”. Instant delete!
Email vs DM vs LinkedIn
Small local business: email or Instagram DM
Product brand with active social: Instagram DM first
Agency, studio, creative director: LinkedIn or email
Or all of the above, because why not?
Follow Up Without Being… Weird
Most people send one message, hear nothing, and assume it's a no. Silence is not a no. People are busy, distracted, your email landed on a bad day. It happens.
But we're also living in an era of absolutely unhinged inbox spam. So two touches max. Anything more and you're part of the problem.
Touch 1
Your original outreach. Warm, specific, short. Open / Bridge / Ask.
Touch 2
5 to 7 days later. Do not say "just following up." That phrase is dead. Give them something small and genuine, a new thought, a relevant idea, a one-line observation.
Something like: "Hey, was thinking about your site again and had one more idea I wanted to share. Happy to send it over if you're curious."
That's it. Light, warm, easy to respond to.
After that, let it go. You showed up twice with intention and that's enough.
Track Your Opens
Use MailTracker or Streak, both free Chrome extensions, to see if someone opened your email and how many times. If they opened it three times and never replied, they're interested but hesitant. That changes everything about your follow-up energy.
MailTracker: getmailtracker.com
Streak: streak.com
Note: native Gmail read receipts only work with Google Workspace accounts. If you have a personal @gmail.com, use one of these instead.
And if they say not right now? Put them in your tracker and check back in 3 months. "Not right now" is a maybe with a timeline, not a door closing.
Don't Just Chase Clients!
Reach Out Sideways Too
Not every outreach has to be to a potential client. Some of the best work comes from people who never hired you directly.
Reach out to studios, agencies, and solo designers too. They're not your competition. They're your referral network.
How it works: a bigger studio lands a client that's too small for their rate. They need someone they trust to hand it off to. That someone should be you.
You don't need to work for them to get work through them. You just need to be on their radar as someone reliable, easy to work with, and good at what you do.
One agency relationship can quietly become 60% of your referrals. Not because you pitched them every week, just because you showed up, did good work, and they knew your name when it mattered.
How to Reach Out Sideways
Same Open / Bridge / Ask framework, just different energy. Less "I can fix your website," more "I'd love to be someone you think of when you need support."
Offer something useful. Help updating a client's site, social posts during a busy season, overflow work. Creatives help creatives. Lead with that energy!
And if you're in the ilovecreatives discord, the network is already there. Just gotta say hiiiii.
Build a Simple System
Outreach without a system is just chaos with good intentions. You send a few emails, lose track of who you contacted, forget to follow up, and wonder why nothing is converting.
You don't need fancy software. A basic spreadsheet is great!
But if you love an app, I looooove Streak and/or Notion.
What to Track
Name and business
Where you found them
Date of first outreach
Platform used
Did they open it?
Date of follow up
Their response, even "no" or "not now" is data
Next action and date
Set a Weekly Goal
5 to 10 outreaches per week, one or two a day.
Every Few Weeks Ask Yourself
What's getting replies and what's not?
Am I reaching the right people?
Does my message actually sound like me?
Iterate.
The Math
Open rates: 20 to 30% is solid
Reply rates: 5 to 10% is realistic for beginners, 15%+ means your targeting is dialed
Conversion to paid: 1 to 3% from cold outreach is completely normal
100 outreaches = roughly 1 to 3 clients. That's not failure, that's the funnel.
At 5 to 10 a week you hit 100 in about 2 to 3 months. That's a real pipeline.
Zero replies doesn't mean you're bad at this. It means try adjusting your targeting or your message.
The only stat that is universally true is:
0 Outreach = 0% Conversion
One Last Thing
The goal of cold outreach isn't to close everyone. It's to start real conversations with people whose work you genuinely care about. You're don’t have to be a salesperson. You're an EXCITED creative who found someone worth reaching out to. People can feel that!
If you leave today and send one email, a real one, specific, to someone whose work actually excites you, that's a win. Pat pat, you did that.