The Crash Guide to

Sending Better
Cover Letters

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By the end of this guide, you’ll be able to write and deliver the type of cover letter that gets shared around the office because it’s so good.

But before we get into how, let’s clarify something important. Your cover letter has only one purpose. Do you know what it is?

The purpose of a cover letter is…
to start a conversation.

Often, job seekers want to cram everything they want to say into their cover letter. But think of how overwhelming that is on the receiving end!

Have you ever gotten a text or DM from someone that was way too long? You get the idea. Don’t try to say everything with your cover letter. Just start the conversation.

Ready to dive in?

What’s in a great cover letter?

Hint: It’s not what you might think. Here’s a new way to look at cover letters, based on what works in the business world.
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In this day and age, your cover letter needs to do a few things well:
In short, for maximum results nowadays, think of your cover letter as a high-converting cold email.
to con•vert - verb

A marketing term that describes a person completing an intended action.

You, requesting access to Crash.
A hiring manager choosing to reach out to you after reading your resume.
cold e•mail - noun

An email (or tweet, DM, etc.) designed to succesfully start a conversation with a specific person you want to speak with.

The emails you get from spammers (bad example!).
A glassmaking texting you out of the blue to ask you on a date. Oo la la!
Let’s look at what all excellent cold reach-outs have in common:
tar•get rea•der - noun

The specific person intended to read something.

You, reading this. 😇
The specific hiring manager you're reaching out to.
   2.  They reach you in the right channel.
chan•nel - noun

The method or platform through which communication happens.

The Crash team reaching out to you here on the website, through Intercom live chat.
You sending someone a tweet, an Instagram DM, or an email.
Gary Vee sending you a text message.
   3.  They explain how they obtained your contact information, if it's not easily accessible.
   4.  They explain why they're reaching out to you, and why you should care.
   5.  They hit the key value propositions to convice you to learn more and reply.
val•ue prop•o•si•tion - noun

A promise of value to be delivered.

When you job hunt with Crash, you will enjoy it more.
You, to a hiring manager: "When you hire me, your boss will congratulate you on making a good hire."
   6.  They have a clear call to action (CTA) that makes it easy to take the next step.
call to action - noun

An instruction to take a particular action, usually a conversion action. Often abbreviated as CTA.

Create a Crash account today
You, to a hiring manager: Schedule a short phone interview with me [hyperlink to your scheduling tool of choice]
That’s pretty much it. Now let’s explore these elements of an awesome, professional cover letter that gets you in the door.

Building a better cover letter

To maximize your chances of getting a response and starting a conversation, your cover letter needs to make a solid argument for why you’re worth spending more than seven seconds learning about. We do this with a few steps:
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Step 1: Decide who to send your cover letter to

Writing anything like “dear sir or madam,” “dear hiring manager,” or “to whom it may concern” is hands-down the best way to sound just like everybody else. It‘s a great way of saying, “I care about this opportunity so much I did the same thing everyone else did and repeated it for every other company, too.” Yawn.

Think about asking for an interview like you’re asking for a date. It’s not about a date in general. It’s about a date with a specific, real, individual person.

A human is going to read your cover letter, and you’re better off being specific about which human.

The best person to send your cover letter to

Whenever possible, send your cover letter to the hiring manager for the role you’re interested in. Here’s how to find the hiring manager for a job.

If you can’t figure out exactly who to reach out to, get creative with titles and keywords. You can try:
It’s up to you to choose who to email. But the person you choose to email should make sense to email. If you’re interested in a customer service position, you probably shouldn’t reach out to the engineering manager. Instead, go for someone in the role or someone who heads that department up (like a customer success manager!).

In some early-stage startups, you can even reach out directly to the founders and get a response.

In fact, you should know there’s an advantage to reaching out to someone high up on the totem pole. Can you guess what it is?

If you reach out impressively and ask, “Are you the right person to talk about this?” (more on writing in Step 4) that person will often refer you to the exact hiring manager for the role. And that makes you look pretty good.

Step 2: Choose how you’ll send your cover letter

The best way to send your cover letter is the way that will make sure it’s received, opened, and read. Depending on lots of things (industry, recipient, timing, etc.) the exact answer to this question isn’t always the same. However, it’s best to use one of the following channels:
That’s right—you might end up sending your cover letter in a public tweet or private DM! It all depends on whether the person is active on that platform (LinkedIn/Twitter).

Unless your target recipient is super active on Twitter/LinkedIn, we highly recommend starting with an email. Here’s how to find someone’s work email address.

In that post, we explain how to verify the email address before reaching out. But, if you can’t be certain of someone’s exact email address, you have a couple options:

A. Use another platform

Is the person active on LinkedIn or Twitter? If not, are they active anywhere online? This can take some digging, but it’s well worth trying to find out. Google their name in quotes “like this” and dig through every result. Some Googling will take you a long way.

B. Trial and error (be careful)

It’s common to test sending an email to an address, and seeing if it reaches its destination. If you don’t get a “Mail Delivery Subsystem” error back within a day or so, it’s very safe to assume that your email went through. However, there’s a chance it went to spam or was accepted by a “catch-all” system.
catch-all - noun

A rule that tells an email server to accept all incoming mail, whether the email address exists or not.

If you email {anything} it will go through and route to the right person.
We recommend saving this as a last resort, after reaching out on other platforms, because it can cause your email address to get flagged as a spammer! So be very careful—don’t do it often.

Step 3: Write your subject line (or opening paragraph)

Pause reading—go scroll through your email inbox for a few seconds, and find the best subject lines. Why did you pick those? They’re probably very clear and descriptive, short and sweet, and relevant to you.

Step 4: Write the body of your cover letter

When you make a good first impression on the recruiter/hiring manager, you maximize your chances of winning the opportunity. When you come across like a human being, you win.

It can’t be like the other cover letters, though. It has to stand out.

And it can’t be wordy. If your cover letter is a giant wall of text, nobody will read it. Put yourself in the shoes of a hiring manager. Would you want to read this whole thing? It’s not even addressed to you:
What if, instead, your cover letter wasn’t identical to the others? What if it jumped out at the hiring manager, demanding to be read? Imagine if you were the director of marketing at Sketch, and you received this in your email:
It would catch your eye and get you interested pretty quickly.

Notice how this article isn’t titled “How to Write a Great Cover Letter in 2020”? Writing is only a small part of the picture. It’s the Digital Age! You can add visual media (like logos and screenshots) that communicate more quickly and more efficiently than your words will.

With that said, you still have to write. 😋

Here’s what you should include:

A. Admit how you got their contact information, if it’s not easily accessible.

This matters because it shows that you’re honest and resourceful.

A quick “I found your email on your website” or “I’m guessing your email address because I really want to speak with you” goes a long way towards establishing several kinds of trust with the other person.

B. Explain why you’re reaching out, in terms they care about.

When you hit the key value propositions to convince them to learn more and reply, you win.

C. Have a clear call to action (CTA) that makes it easy to take the next step.

Let them know what you want them to do!

Step 5: Proofread your cover letter. Twice!

Show you pay attention to the basic details. Make sure there aren't any typos or mix-ups of common homonyms. Your spell checker won’t catch those.

If you struggle with this for any reason, ask a friend or family member to proofread for you. In fact, that can be a good idea even if you’re really good at proofreading! It gets someone with “fresh eyes” looking at your work, which means they’re less likely to glance over an error.

Step 6: Send your cover letter at the right time

Heads up: right now may not be the best time to send your cover letter. I know you’re probably excited about the job. But ask yourself for just a second:

Would you rather wait to send it, and potentially get better results? Or send now and potentially miss your chance?

You see, when you take the time to read a guide like this, and put effort into your cover letter this way, it’s because you care about the results. (I hope.)

I know how powerful the feeling is to want to just click Send. It’s right there, you’re done, and you’re thrilled with your work. It’s great to want to complete the task!

But if you can control that urge, you can get better results. Before you actually send a cover letter this way, keep one thing in mind:

Jab, jab, jab…right hook!

You might have heard of this book on sales by Gary Vaynerchuk.

It’s about providing value and building trust before you make “the big ask.” The right hook. It’s about practicing delayed gratification (like the marshmallow experiment) because you want better results.

And it’s relevant to your cover letter. Your cover letter is a big ask, a right hook, pitching yourself to be hired for the job. Why you’re the best candidate, over whoever else.

So before you make the big ask—before you send your cover letter—you should have started building a bit of rapport, a relationship, with the person on the receiving end. In short, reading your cover letter should not be the first time they see your name.

I have to stress this again. 😂

Reading your cover letter should not be the first time they see your name.

If you really want the results from this job hunting process, do yourself a favor and start following department leaders at companies that interest you. Start engaging with them online—it’s too easy not to! And it yields such amazing results when you do finally throw your hat in the ring.

Here’s a simple way to engage someone:

Your job hunt outreach sequence

A great compliment is written as a “you statement” rather than an “I statement.”

Instead of, “I really loved your interview of Isaac Morehouse because I know the value of building a body of work, not just a nice-looking resume. I appreciate you and your content.“

Try,Your interview of Isaac Morehouse was particularly interesting—it reminded me the value and importance of building a body of work, not just a nice-looking resume. Thanks for producing excellent audio content.”
3. Within the next few days, send a new email/Tweet/DM asking them a good question about their company or body of work.

There are no shortcuts here. If you want results in your job hunt, Google them and their company, learn about them, digest what you find and question everything.

(Note: you can combine this with step #2 if time is of the essence, e.g. if applications close in three days or it’s a highly sought-after job.)
A great question is one you’ve genuinely tried to answer for yourself, but can’t. It’s founded in true curiosity, rather than fake intent to just put a question out there. If you struggle with this, shoot us (the Crash team) a quick email. We’ll help you out.
4. If they answer, thank them and feel free to keep engaging the conversation within reason.

You don’t need to have an all-out debate with them that ends in a dissertation—but if you have follow-up questions, now’s the time. Ideally, during the course of this conversation you’ll be able to bring up the topic of the job you’re interested in, or them hiring in general.

If they don’t answer, you’ll want to try this again a few more times—maybe on a different platform. If after a few questions they still won’t answer, move on to the final step of this outreach sequence.
5. Make the right hook! Deliver your cover letter! When it finally comes time to send this masterpiece off to its lucky recipient, make sure to do it at the right time. (Unless time is of the essence, in which case send it ASAP.)

If you can figure out the person’s general routine (check Tweets and other social activity times) and time zone, you can deliver your cover letter at the perfect time—early in the morning, late at night, you get it. Whatever time is likely to work best for them.

You can use an email scheduling tool like Boomerang for Gmail, or simply set a reminder for yourself on your calendar, reminders app, etc. Of course, don’t overthink this; just take a good guess and do it. The content is what ultimately matters.

Beyond cover letters:
The real secret to winning jobs and building a career you love

You’re so much more than that cover letter. You know that!
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On the job hunt, we tend to forget it that we’re more than our resumes and cover letters. We want to play by the rules, or we feel like we have to because that’s the only way there is. Like we’re risking our future if we try something else.

In reality, there’s only you, the value you can create for companies, and your ability to prove it. That’s all resumes and cover letters are meant to do, but they don’t do a great job of it.

There is so much more than just the old way to job hunt. There’s Crash, video pitches, job hunt campaigns, and more. 💁  When you’re willing to get creative, the sky’s the limit!

Next in this series:

Send video pitches.
Win interviews faster.

“The moment I saw him flipping off a trampoline, I knew I wanted to hire him.”

Nick Black, Founder & CEO, on LinkedIn