How I cold DM clients

Cold outreach gets a bad rap. 

I get it — unsolicited messages can be annoying at best and intrusive at worst. I can’t tell you how often I open LinkedIn to see notifications in my inbox, hoping it’s a cool opportunity…only to find yet another spammy message from someone trying to sell me something. 

Even with all the spam out there, I believe cold pitching can be a valuable strategy for freelancers. In fact, I still send cold DMs to get clients, even six years in. 

I thought it’d be easier to show not tell how to pitch yourself, so I’ve included actual messages I’ve sent on LinkedIn below. 

These are all cold DMs that I’ve received a positive response to. Not every message I send leads to landing the client (usually due to timing or rates) but if I had to guess, I probably have a 75% response rate. Which I’m pretty proud of! 

Alright, enough yapping. Let’s get into it: 

Cold DM #1: InMail Message 

I have LinkedIn Premium (don’t judge me) so I was able to send a message to this person without being connected.

I had followed this company for a while. And, as you can see in the message, I had actually interviewed for a full-time role there years ago. So I used that connection as part of my pitch. 

Response: Immediate interest! They liked my writing samples, asked for my rate, and were eager to get started. 

Did they become a client? Sadly, no. I’m not sure exactly what happened, but I know that they were in the middle of hiring a FT marketing person when this conversation happened. So I can only assume they no longer needed support once the new person was onboarded! 

Cold DM #2: Connection Request With Message 

While researching for an article I was writing, I stumbled upon this company’s blog. I knew that this company would be a fitting client for me based on the content I write, so I found the content marketing manager on LinkedIn and sent a connection request with a quick message. 

Response: Immediate interest! They asked for specific writing samples and then we moved the conversation over to email.

Did they become a client? Yes! They’re one of my current clients and they are so great to work with.

Cold DM #3: Reaching Out to Someone in My Network

I had previously connected with this person in a Slack group, and we ended up connecting on LinkedIn, too. Months later, I saw that they shared content from their company’s blog and I thought it seemed like a good opportunity to reach back out. 

Response: Positive! Liked my writing samples but they didn’t need additional support at that time. 

Did they become a client? No, and my contact eventually moved on from the company. I see this one as a “planting seeds” moment. You never know when someone is going to need a freelancer, and when they do, they’re going to look to the people in their network first.

Cold DM #4: Responding to a Post 

A person at this company posted about looking for freelancers for their new blog program and I immediately messaged them. 

Disclaimer: If you’ve been on LinkedIn lately, you know that anytime someone posts about looking for a freelancer, there are about 1,000 comments on the post within seconds. This interaction happened in 2022 when LinkedIn wasn’t as saturated, so I don’t know if I’d get a response in today’s landscape. But I still want to include it since it helped me land one of my biggest clients! 

Response: Immediate interest! Asked for me email and the process was a blur after that. 

Did they become a client? Yes! I’ve been working with this client since 2022 and they are one of my most stable and reliable gigs. 

My Tips for Sending Cold DMs

1. Take the curated approach: I think my response rate is high because I only reach out to companies that I think would be a really good fit. I don’t send a templated message to tons of people hoping to get a couple of responses. I take my time to find the right person, choose a few writing samples that are relevant to the company, and personalize the message.

2. Tailor your message: Include a note in your message that shows you are familiar with the company/industry/content. I also recommend sending samples that are tailored to that company vs. sending your portfolio link for them to sift through. 

3. Send it to the right person: As a marketing writer, this means I look for the content marketing manager or similar roles. If you’re a journalist, that means looking for the right editor to pitch. Or, maybe you offer graphic design. You’d probably want to reach out to a digital marketing manager or creative director.

4. Don’t be spammy: This should be an easy one to follow. Be respectful. Don’t send a DM if someone specifically says they don’t want to be messaged. This is the quickest way to annoy people and squash your chances of getting a response. 

5. Follow up: My rule of thumb is to follow up once, usually a week or so after the first message. If I still haven’t received a response after that then I move on. Again, don’t be spammy — sending too many follow ups will only annoy the person on the other end! 

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✍️ On a Personal Note

Here’s what I’m up to lately in life, work, and everything in between.

• Doing: Putting the final touches on our kitchen renovation (which has taken me and my husband nearly two years to complete since we did it ourselves 🫠)

• Planning: I’ve been really enjoying my work with my local small business client, so I’m working on creating a service to help more small local businesses stand out online 👀 Watch this space!

• Reading: Other freelance newsletters, like The Simple Freelancer. I want to give a shout out to Stephanie of The Simple Freelancer for including Rough Draft in her Freelance Writing Toolkit! The toolkit includes freelance opportunity newsletters, courses, newsletters, and resources that can help you easily get started with freelancing today. 

I’ll be back in your inboxes on March 4th 💌 In the meantime, let me know what you’re working on and how I can help!

Rough Draft is a bi-weekly newsletter where I share tips and musings on creating a freelance career from scratch. Subscribe here. You can also find me on LinkedIn, Twitter, Threads, or my website. 👋