3 Cold Email Hacks to Make Sure Your Pitch Gets a Response

April 7, 2017

Image credit: Gemma Evans via Unsplash

Cold email is a wonderful way to get more freelance clients… when done right. If you don’t quite know what you’re doing, it’s an exercise in futility, on par with arguing on the internet.

But it can feel that way even when you know what you’re doing. Sending 10, 20 great pitches every week (or every day), and getting little to nothing in response is torture. And you deserve better.

​I speak from experience: the very first big cold email campaign I ran (for a client) was a dismal failure. We did everything correctly, and got a whopping 2% response rate and zero sales for our trouble.

Since that failed campaign. I learned a lot. I learned from a true Pitch Master — my friend Lisa Baker. I devoured every resource that I could find on the topic. And I sent a fair share of prospecting emails and project pitches.

​Today’s post is not about how to write a cold email pitch. If you want to learn about that, go read this article where I break it down.

Instead, I wanted to build on that advice, and give you a much better chance to succeed. Because here’s the thing: even if your pitch game is downright godlike, it can ​still ​be freaking hard to get responses from potential clients.

​So you don’t feel like a desert island maroon shipping out messages in empty rum bottles, I’m going to share 3 tricks I picked up and successfully used to get clients to read my pitches and reply to them — sometimes within minutes.

Sometimes, cold email feels exactly as isolating as this. Minus the scenery

I mean, that’s what you’re supposed to do on a desert island, right?

They are dead simple, take minutes to implement, and will get you results as soon as you do. I do hope you give these a try. We’ll start with the obvious one…

1. These cold email subject lines have brain hooks. Use them

“What’s the best cold email subject line to use?”​ was one of the first questions I got following my article about pitching. And for good reason, because I glossed over it in the post itself. D’oh!

On the bright side, I’ll fix the situation in this article

Your email subject line is the second most important thing your potential client sees when they look at your pitch. Make it something vague or overly pushy, and they will ignore you — as they should.

But make it short, to the point, and specific to what you want to do — and it will leap off the screen and grab people by the eyeballs.

That’s why I always get the subject line out of the way first, by following a template — because you don’t want to overthink something so important and so easy to screw up.

Here’s a list of my favorite subject line templates for a cold email pitch:

  1. [Name], I want to help you [service you’re trying to provide] for [Website / company]

E.g. “Dave, I want to help you create pitch decks for Awesome Startup Inc.”

  1. [Service you’re trying to provide] for [Website / company]

E.g. “Creating incredible case studies for fencelikeinigomontoya.com”

  1. [main benefit / big, bold promise for the client’s website or company]

“Getting artisanalbutter.com on the 1st page of Google” — a bold promise that’s well-aligned with what your client wants is the perfect way to attract attention.

  1. If you’re subscribed to the client’s newsletter, just reply to their most recent email

“Re: [their own subject line]”

  1. [something quirky enough to get them to open] — not a template, but a really great way to get someone’s attention.

E.g. “I want to pay homage to your beard” (This comes from a real pitch I did ages ago. I knew the intended recipient had a luxurious beard, and I was consumed with envy.)

Note: when you’re pitching for a specific project, or contacting someone whose job is to sift through lots of pitches every day, it’s better to stop being cute, and use a straightforward subject line. Like this one:

“freelance pitch: [whatever the project they want is]”

E.g. “freelance pitch: 3 blog post topics for pugsindistress.com”

2. Track your cold email pitches with sneaky and insanely useful email plug-ins

Do you want to stop feeling like you just wasted hours of your life sending emails nobody would ever open, much less reply to? I know that feeling well (it’s shite). But it’s fairly easy to cure, or at least to ease significantly.

All you need to do is this: track your goddamn cold email! Always.

That way, even if you don’t get a single response, you will know who opened it, and who clicked on your link (if you had any). Then you can figure out whom to contact again with a follow up email — that we’ll discuss later.

It’s tough for me to recommend the best software for this task. I use Bananatag, because that’s the first-ever plug-in I discovered. And once I have something that works, I use it religiously in spite of better alternatives, until the software doesn’t exist anymore, the world burns, or I die of old age. Whichever comes first.

To give you more than one option, I did some research in preparation for this post. And wouldn’t you know it, every damn Gmail plug-in on earth now comes with built-in email tracking. Where was all this when I was starting out?

Anyway, here’s top 2 email plug-ins for tracking your freelance pitches:

1. Streak. This plug-in has a free plan that covers 200 emails per month. It works like a CRM, helping you sort all of your leads by separating them into categories. It also turns your Gmail inbox into a colorful mess while doing so:

Here's how Streak helps you manage cold email

It’s like a toddler ate some crayons and barfed right in your inbox (click the image for full size)

Streak looks insanely robust, with a ton of great features. I don’t use it myself, but my friend Lisa gave it her stamp of approval. She uses Streak to run massive affiliate promotions, pitch people on one of her billion side projects, and presumably she even digs the colorful bullshit. Go figure.

2. Bananatag. It’s the one I have been using for 2+ years now. It’s got a free plan for 5 tracked emails a day, which works out to 50 fewer emails than Streak gives you. It’s not a lot, but if you only send 2-3 highly personal cold emails per day, you don’t need more.

If you want to use Bananatag for pitching freelance clients, it works best as a Gmail plugin. Alternatively, you can set it up to work with any desktop email client like Outlook or Thunderbird.

But I’m an old curmudgeon trapped in a young person’s body, and I don’t use Gmail. Or a desktop client. Don’t judge. If you’re like me, you can still make use of Bananatag, like so:

  1. Sign up for a Bananatag account with your non-Gmail email address.
  2. Whenever you send a freelance pitch you want to track, append “btag.it” at the end. For example, “mr.bater@gmail.com.btag.it”
  3. Then you will get an email notification if someone reads it, or clicks the link inside. Easy!
These days I use it to cold email influencers, which also works surprisingly well

These days I use it to cold email influencers, which also works surprisingly well (click the image for full size)

According to Bananatag, the “btag.it” function is a legacy feature, and they might stop supporting it in the future. But it’s there for now, and I like it.

Note: in the next section of the post, we’ll talk about 2 other tools that have built-in email tracking — Boomerang and FollowUp.cc. Their free plans are very sparse, which is the main reason I’m not covering them here immediately. But they are useful for performing Hack #3, which is probably the most important one…

3. Follow up email, a.k.a. your shining beacon of hope

When you send out a freelance pitch, chances are that most clients won’t even notice your message immediately. Others will see it but ignore it. Still others will open it, read it, then decide to reply later — but forget (of course).

No matter what the problem is, there’s one cure: sending a follow up email. It makes the single biggest difference between cold email campaigns that just feel like you’re yelling into the abyss… versus the ones where you actually get through to your potential clients.

“Look back at me, damn you!” Picture: “Into the Abyss” by Sucilla Mooteeram. Art Society of Trinidad and Tobago

There are many, many ways to write a follow up email. As with anything that could be done in multiple ways, there are even more opportunities to fuck it up fiercely.

So I’m going to give you one script for a follow up email. Use it if you don’t hear back from the potential client after one week. Here it is:

Subject: Did you miss this? Fw: [your original subject line]

Hey [Name],

I wrote to you last week about [the topic of your pitch], and I was wondering if you saw it. I didn’t want this to get buried in your inbox, so I thought I’d follow up and ask.

You’ll find the original email just below. After you read it, hit “Reply” and let me know if this is something you’d be interested in?

Here’s the original email:

[your original email]

If you want to send your follow up emails manually, I recommend setting aside 30 minutes every week to do it. Alternatively, you can automate the process using tools like Boomerang or FollowUp.cc.

Full disclosure: I don’t like either of them much — at least for those freelancers who are just starting out. Boomerang lets you schedule 10 emails per month on its free plan, and FollowUp.cc doesn’t have one (as far as I know).

Still, they are better than nothing. And if you’re inexplicably allergic to manual follow-up, then Boomerang is a decent option for you. Lots of my technically minded friends use it (talking about you, Rocky!) and I have yet to hear even one complaint.

Here’s how Boomerang can manage follow up email for you:

  1. First, you’ll need to install the plug-in. Go to http://www.boomeranggmail.com and install it. You don’t need to sign up for anything, because it uses your Gmail account by default.
  2. Next time you write a follow up email, you will notice a few additional buttons:

(click the image for full size)

  1. By clicking the “Send Later” button, you’ll be able to schedule the email for whenever. I recommend waiting for a week after you’ve sent your initial cold email pitch.

Boomerang gives you a fair number of option for scheduling follow up emails (click the image for full size)

If you decide to use FollowUp.cc, you will notice that it works in a similar way to Boomerang. All you need to do is determine the time you get reminded about your follow up email, set a few conditions like canceling it if the client replies, and you’re set!

If you’re using a different email client, then you can set follow up reminders by using email commands:

Set to remind me about my follow up email in 7 days

In this example, I set FollowUp.cc to remind me about my follow up email in 7 days (click the image for full size)

You can get the full list of email commands for FollowUp.cc right here.

Do you have any favorite tools or tricks to help you with cold email?

If you do, I would love to hear about them!

In a few week’s time, I’m going to be running a freelance experiment on my blog: I will test several strategies for landing freelance clients (referrals, cold email, Upwork, etc.), setting aside 30 days for each. At the end, I will share the results with you.

So if you know about any other cold email hacks that I never mentioned in this article, leave a comment and let me know!


  • Reply Nadine Mandjoli Yaya April 7, 2017 at 5:06 pm

    Hi Oleg,

    Thanks so much for this boosting information! As you are yet to run the experiment on cold pitch success vs RFP, I will be interested in knowing what brings in more clients.

    • Reply Oleg Starko April 12, 2017 at 1:09 pm

      Hey Nadine, thank you for the comment! That’s exactly why I’m going to do this — so I can share with other subscribers. 🙂

      • Reply Nadine Mandjoli Yaya April 22, 2017 at 8:58 pm

        Thanks Oleg!

        It was just wonderful! As I was able to download some other templates, you are really building the giant in me!

        Thanks, once again!

        • Reply Oleg Starko May 8, 2017 at 12:18 pm

          Thank you for letting me know you were able to download the templates, Nadine. 🙂

  • Reply Rocky April 11, 2017 at 10:48 pm

    Ever have that moment where you go, “omg this post is brilliant! I can just share this instead!”
    These are one of those posts. Just brilliant!

    Also, I took a double take when I saw my name!

    • Reply Oleg Starko April 12, 2017 at 1:10 pm

      Did I steal your thunder, Rocky? 🙂 I dunno, you can probably write a post that’s just as good for your niche of indie devs. Pitching to game journos is its own kind of hell, I’m sure you could add a ton of value there.

      Thanks for the share, though, I really appreciate it!

    Leave a Reply