How to Write Cold Email Pitches that Get You Hired

March 3, 2017
Photo credit: Yuriy Kovalev

(Image credit: Yuriy Kovalev via Unsplash)

A question landed in my inbox recently.

“Do you have tips for amazing proposals?”

And I do! An obnoxious smart-ass like yours truly has an opinion about everything. But here’s the thing: even if I told you right now how to write a persuasive proposal that seals the deal on a freelance job, my advice will do nothing for you.

That’s because a proposal is something your client sees at the very end, before you start on a project. At that point, it’s almost a triviality, because the client already knows they want to hire you.

I said as much in my response:

Oleg Starko: Answering your questions with a question since pretty much forever (click the image for full size)

So the real issue is: how do you get that far? How do you attract your client’s attention, and stoke their interest enough so they want an actual proposal?

To do that, you want to write a great cold email pitch. And that’s what this week’s post is all about.

When you’re finished reading it, you will walk away with a proven process to write two kinds of pitches:

  • A prospecting email… with brain hooks
  • A competent, confident project pitch

But first, let’s address what the hell I am talking about. What’s this “two kinds of pitches” nonsense?

“The ‘two kinds of pitches’ nonsense”

When you reach out to a potential client, there are two possible contexts:

  1. You want to offer them a specific service, have a good idea about their needs — but don’t know for certain if they are open to hiring a freelancer. A situation like that calls for a prospecting email, which serves as a conversation starter.
  2. You know they are looking for freelancers. Maybe you saw a project posting somewhere, or someone else referred you — or maybe you have a magical fortune-telling wombat that points you to good prospects (and if so, would you get me one of those?) If that’s the case, you can send a project pitch.

Both are similar, but different in several key ways. Now, let’s dig deeper and talk about how to write the damn things, shall we?

The prospecting email: your nuclear-powered icebreaker

By WofratzOwn work, CC BY-SA 2.5, Link

If you’ve never heard of nuclear-powered icebreakers, they are a Russian thing.

Those are huge fucking ships designed to navigate through ice-covered waters of the Arctic and Antarctic. Nobody but Russia builds these, because Russia is insane. But hey, thanks to that, I can hijack this term and make a bad analogy!

When you cold email a potential client, you will inevitably stir up all sorts of questions, concerns, and barriers in their mind. Things like:

“Who the hell are you?”

“Do I need this? What’s in it for me?”

“Do you understand my goals?”

“What if you suck?”

“Can we talk about this?”

Before they even considers hiring you for a freelance job, you will want to bust through those concerns right then and there — in your prospecting email. You want to forget about getting hired, and focus on getting the client’s attention and building trust first.

Now, before I get any more Zen master on you, let’s dissect an actual cold email pitch — and see how a prospecting email actually looks.

Here’s one of mine from forever ago:

This one got a response within 5 minutes (click the image for full size)

The first thing you’ll notice is, this is not the most well-thought out prospecting email ever. For starters, it has at least one typo. It’s also a little over-saturated with jargon (23-year-old Oleg thought he was very clever).

But it does a few key things right. So much so, that the client not only replied in 5 minutes, but also told me later:

“I answered your initial cold email — something I have never done in three years of business — is because of the custom effort you put into it.”

So let’s talk about what’s going on with this email script! We can break it down into four main components.

1. Make a relevant connection

“I came across your interview at [Website] recently…”

As your first step, you want to explain to the client why you’re reaching out. How do you know about their business? You want to convey the impression that this isn’t just a copy-and-paste cold email.

Even if the connection is flimsy, like in my case, it still works. And the more specific you get, the better — you’ll notice that I included an explicit reference to what exactly the client was talking about in the interview:

“…and read that you said how difficult it was [Who talks like that? Damn you, Past Oleg! – Oleg] for an “software-as-a-service” B2B-oriented company to gain traction and virality.”

Making a connection is critical, if you want to separate your prospecting email from dozens, if not hundreds, of other pitches that never bother with being personal.

2. Introduce yourself (very briefly)

“I have been working as a freelance writer for 4 years, specializing in B2B and B2C online content marketing.” [GAH, so much jargon. Double damn you, Past Oleg! – Oleg]

Next, let the client know who you are — but be quick about it.

Now, I didn’t handle that part very gracefully. I didn’t say, “I’m Oleg” or anything like that. I immediately started with a reference to my expertise. That’s great, but I should have managed to pack both my name and my credentials in the same sentence.

3. Address the “What’s in it for me?” question

“I’d like to help you saturate your blog with solid articles and suggest a few ideas on how [Company Name] could gain more brand exposure.

You’d appear more professional to both partners and clients; also, good marketing content and strategic exposure will lead to increased visitor conversions and more revenue for the company. Sure, you’re already “playing with the big boys” like Marriot and Subway [You misspelled Marriott, you little shit! – Oleg], but there’s always plenty more potential for growth.”

There are two steps to this element. First, you explain what you’d like to do for the client — and then immediately follow up with what it will mean for them in tangible terms. If you just do the first step, the client is going to ask, “So what?” — and you risk losing their interest

Note: notice that I’m not pitching generic writing services here. You don’t want the client to think, “Hmmm, what do I need? Nah, I’ll decide later” — and forget about it. You want to do the same in your prospecting emails — be reasonably specific about the kind of service you want to provide.

4. Slow down and ask a question

“We can discuss the details whenever you want to, I just wanted to make sure if it’s something you’d be interested in.

If so, would it be OK if I sent you a few ideas on how I could help?”

Finally, even at the very end, a good prospecting email never screams, “OMG HIRE ME I’M SO AWESOME YOU WILL LITERALLY SHIT BRICKS THE MOMENT I DO A NANOSECOND OF BILLABLE WORK FOR YOU”

Let the client down gently. Ask them if they’d be interested, and then offer them something that’s hard to refuse. I mean, who would ever say no to free ideas?

After that, you can sign off and send out your prospecting email. Easy!

Note: this is a personal thing, but I like to let mine sit in “Drafts” overnight, or for a day. Then I give them a quick once-over in the morning, and hit Send.

And that’s how I write prospecting emails. Now, let’s talk about the project pitch — a slightly different beast.

The project pitch: your Gandalf moment

As we mentioned before, a project pitch is something you send in response to a specific opportunity: job posting, referral, prediction by your magical wombat (I still want one), etc.

The thing is, you’re not the only one.

Your project pitch finds your client at a dark time. They are wading through a sea of shitty pitches that aren’t remotely at the level they want. And then you appear on the horizon, ready to save the day. Just like a certain White Wizard:

Horse, badass beard, and magic staff are optional

You want your project pitch to cut through the mountain of bullshit your clients are definitely digging through. At a glance, it needs to show to the client, “Hey, I understand what you’re after — here’s how I can help.”

But a script is worth a thousand words of Oleg trying to explain something with way too many pop culture references. So let’s look at an actual project pitch — this time, from a true master.

Breaking down a cold email by a real-life Pitch Master

My friend Lisa is a veteran freelance writer and content marketer. She writes the best cold email pitches I have ever seen. Every time I compare one of her project pitches to mine, it’s not even funny — mine always look like I just tap-danced them on the keyboard.

For this post, I asked Lisa for permission to feature one of her project pitches — and she over-delivered, as always.

The email I’m about to show you got Lisa hired for a year-long retainer contract. And it’s glorious. There’s so much going on with it. So I’m going to stop gushing, and we’ll dig in.

This might just be the best cold email ever

For a full-sized version, with better formatting, click the image (opens in a new tab)

Right away, you’ll notice that Lisa’s project pitch follows the same structure as the prospecting email I described before.

1. Make a relevant connection

First, she mentions that a friend referred her:

“A friend just forwarded me your ProBlogger listing”

2. Introduce yourself

Then, Lisa introduces herself, managing to name-drop four big clients she has worked with before — and show that she’s familiar with the client’s brand.

“I’m a professional writer and blogger who’s written for national print magazines like Parenting and Pregnancy & Newborn as well as top parenting websites like and Red Tricycle (and by the way, congrats on winning RT’s Most Awesome Pinterest Board Award!).”

3. “What’s in it for me?”

When you’re writing a project pitch, “What’s in it for me?” becomes more like, “Prove you can help me with this.” Here, you can see that Lisa does something very few applicants for that job would have done. She doesn’t just tell the client how great she is — she shows them what kind of content she has in mind for their website:

“As a sample of the types of posts I’d write for you, here are a couple of ideas for your blog:”

That’s a powerful custom sample of Lisa’s work. It answers a big, hairy question the client definitely has: “Sure, her other work is good, but what if I don’t like her work for my site?” 

And then, Lisa does something else that most people would never bother with (that’s why they’re not Pitch Masters). She describes all the extra value she brings to the table… and backs it up with proof.

Just for fun, I’m going to go through Lisa’s cold email pitch, and count all the references to her formidable skills, experience, and personal enthusiasm that she’s dropped in there. (Is it just me, or is there a drinking game opportunity here?)

Here they are, with my emphasis:

  1. “I’m always following the latest trends on pregnancy, birth, and baby gear — all of which is great fodder for blog ideas.” [“Lisa has ALL the ideas!” is an actual thing I and other people say – Oleg]
  2. “This could be a recurring column for the blog;” / “This could also be a series of posts,” [Way to increase perceived value of her custom samples! – Oleg]
  3. “I’d also love to promote the [website] blog by interviewing product owners and designers (like I did in this post) and soliciting guest posts.”
  4. “I’m obsessed with social media and SEO, I’m a WordPress guru, and I know enough HTML/CSS and Photoshop to be dangerous.” [Not a fan of the word “guru”, but hey – Oleg]
  5. “Here’s a post from my blog that did well in social media:
  6. “I really wish [website] had existed five years ago, because I needed you then … I’d really love to help other moms find your site now. I’m pretty sure a lot of them need you as much as I did!”

Finally, Lisa also links to a few samples of her past work — but only the ones directly relevant to the project:

“Finally, I’m linking to several samples of my work.”

4. Slow down and ask a question

“I’d love to hear more about your content marketing needs and your strategy and vision for growing the blog. If you agree that we might be a good match, write me back. I look forward to talking with you!”

At the very end, Lisa just asks (but not out loud), “Do you agree we might be a good match?” — and asks the client to write back. Which she knows they will — because if I were the client and got this pitch, I’d be screaming, “Shut up and take my money!” 

And that’s how you write an amazing project pitch! Now, I’d love to hear from you…

What’s the BEST (or WORST) cold email advice you’ve ever received?

Leave a comment below and let me know!


  • Reply Nadine March 3, 2017 at 12:02 pm

    Hey Oleg,

    This was a nice one! You really make cool edible beans for everyone. Thanks for sharing your gifts with the world!
    I would like to have your view on someone changing career (starting newly, without a famous portfolio like Lisa).


    • Reply Oleg Starko March 3, 2017 at 11:54 pm

      Hey Nadine,

      Thank you for the comment!

      If you’re starting anew, I would say that the “Crystal Ball Technique” is your friend. 🙂

      There are actually all sorts of ways to get around lack of samples. I think I need to do a separate post just about those. 🙂 Would you like that?


      • Reply Nadine Mandjoli Yaya April 7, 2017 at 7:04 pm

        Hi Oleg,

        Sorry that, I never had any notice on the replies, hence never visited this. Thanks for referring me to them and you have amazingly changed my proposal response rate! I have gone through this and even still taking note, to make sure, I make you proud within weeks to come!

        Thanks once, again!

  • Reply Blossom March 6, 2017 at 4:03 pm

    Hey Oleg~

    Thanks for addressing this question.
    Say I already messed up in my pitching process and sent 100s already, but I want to try again. Should I use a different email? What should my subject line be?

    Could you also email me your response in case I don’t get notified of your response?

    • Reply Oleg Starko March 6, 2017 at 5:21 pm

      Hey Blossom,

      Thank you for the comment!

      By “messed up,” do you mean that you already sent 100s of pitches to people, but you want to try them again?

      If so, I would use the same email. In my experience, unless someone explicitly told you not to email them again, it’s not too late to make amends. So say you’ll pitch someone you have previously wrote to, and then respond with:

      “Didn’t you already write to us?”

      That’s a perfect opportunity to apologize (if needed) and tell them why this time they want to pay attention. And you can use tools like Streak or Bananatag to track your pitch, so you know when people have opened it. So even if they don’t respond, you will know if it’s worth following up, and what to write in your follow-up message.

      Now, as far as the subject lines, I always use the same several kinds:

      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.

      2. [Service you’re trying to provide] for [Website / company]
      E.g. “Creating incredible case studies for”

      2a. Another option is to make your subject line about the result or benefit you provide, like…
      “Getting [website] on the 1st page of Google” — this can sound a bit scammy if you do it wrong, so be careful.

      3. If I’m subscribed to a client’s newsletter, I would just reply to one of their emails, so it would be “Re: [their own subject line]”

      4. Sometimes I write something quirky that I know will get attention. Like this one I did once:
      “I want to pay homage to your beard” (I knew the CMO of the company had a big bushy beard)

      I hope this helps. 🙂 I’ll email it to you as well.

  • Reply Marni April 7, 2017 at 6:17 pm

    Is it just me or does anyone else find it impossible to read your inserted jpgs (such as your sample email prospect letter)? They’re always fuzzy and when I try magnifier it’s just bigger and still fuzzy?? I’m on a new PC laptop using IE 11 and Windows 10. Thanks!

    • Reply Oleg Starko April 8, 2017 at 8:19 pm

      Hey Marni, thank you for commenting! The jpg’s look absolutely fine to me. I will ask a few people to take a look and let you know. 🙂

    • Reply Oleg Starko April 10, 2017 at 10:42 am

      Hey Marni, I made it so if you click on the image, you get a larger-sized version to open in a new tab. Hopefully it should be legible for you. 🙂 Let me know if it helps!

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