How To Write A Cover Letter For Startup Jobs

How To Write A Cover Letter

To whom it may concern.

Dear sir or madam.

Dear hiring manager.

These common opening lines to cover letters all have one thing in common.

They’re terrible.

They sound like they were written by a poorly trained AI.

I’ve hired for dozens of roles throughout my career and the most common problem I’ve seen with candidates has nothing to do with their resume.

Their cover letters use outdated and incorrect advice. They all talk about why they are uniquely qualified for this position.

They’re the perfect fit.

The reality? Everyone’s cover letter sounds the exact same. No one stands out. No one is the perfect fit.

It’s an ocean of sameness.

Here’s the good news. I’m going to show you what a rock solid cover letter is for 2022 and beyond.

A good cover letter is just like conversion copywriting, except the person you’re trying to sell is your future employer.

We’ll start at the beginning.

Do I Need A Cover Letter?

Yes, you fool. It’s your chance to stand out.

It’s ok, I’ll show you how.

Keep reading.

How To Address A Cover Letter

Who should you address a cover letter to?

My answer: no one.

The reason is simple. The first line of your cover letter has only job.

It’s job is to move the reader to the second line.

That’s it.

So all those trite and outdated openers? Throw them in the trash.

Here’s how I would start my cover letter:

  • “Want to know how I grew revenue 20% every year for 5 years?”
  • “I’ve written an article that was on the front page of Hacker News, but that’s not why you should hire me.”
  • “Hiring me guarantees that you’ll hit your revenue number this year. Want to know why?”

What do all those have in common? They lead with interest. They make you want to read the next line.

If the point of the first line is to convince them to read the second line, then what’s the point of the second line?

You guesed it. It’s to convince them to read the third line.

And so on.

Ask yourself these questions to get started writing the opening to your cover letter:

  • What is something interesting and unique about you?
  • What’s your best story to tell at a party?
  • What’s a time you were awkward as f%$#?

Those questions will help drill down to the real you. Your answers, translated into an opening line of a cover letter, will differentiate you.

Want to know my awkward story? My first job out of college I was hired as an affiliate marketing manager.

Before my first day they invited me to the office for a happy hour.

I was drinking craft beer from their office keg and having a blast.

Someone walked up to me and introduced themselves. “Hi, I’m Jason” they said.

“Hey Jason, what do you do here?”

Suddenly, laughter. A girl next to me said “Oh my god I’m so glad I was here for that.”

“I’m the CEO”, Jason said “this is my company.”

I had just asked the CEO what he did here. And I hadn’t even officially started the job yet.

I love telling that story now, and it would make a great opening line for a cover letter.

So that’s how you open a cover letter. With a hook.

Now let’s talk about length.

How Long Should A Cover Letter Be?

The perfect cover letter is long enough to be interesting and tell a good story, but short enough to keep their attention.

You would be shocked how little time recruiters and hiring managers spend reading your cover letters and resumes.

You get seconds of their time. Not even minutes.

They’ll skim your information in less than 30 seconds to make a decision.

You’re one of hundreds of applicants.

But what about those AI tools that screen your resume and cover letter for keywords?

Look, I can’t speak for every single recruiting team out there. But the jobs I have personally hired for did not use any fancy AI tools.

I personally reviewed every single application myself.

And yes, I’d disqualify people in seconds.

So, how does this relate to your cover letter length?

Do you remember my awkward story when I asked the CEO what job he did?

That story was 132 words.

Your cover letter should be no longer than 150 words.

Did you know that LinkedIn limits the length of your posts to 700 characters? That’s a little over 130 words.

Treat your cover letter like some broetry you read on LinkedIn.

Keep it short, to the point, and above all: interesting.

How To End A Cover Letter

We’ve covered how to begin a cover letter and how long it should be.

Now it’s time to talk about the end.

But wait, what about the middle?

That’s on you. champ. I can’t tell you how to describe yourself in an interesting way. And even if I could, you shouldn’t listen to me.

Write from the heart. Tell your best story. Act like you’re talking to your best friend.

Hell, call up your best friend and ask them to tell their favorite story about you.

Then come back and learn how to end a cover letter.

Ready? Here we go.

End your cover letter like a normal human being.

For the love of god, don’t end it with “I’d love to discuss this opportunity with you further and I look forward to your call.”

Puke emoji.

Here’s how I’d end my cover letter

“Talk soon, Nick. 555-555-55555”

That’s it.

If you’ve done your job correctly and written a reasonably unique and interesting story about yourself, then your cover letter did it’s job.

Everyone who applies for a job wants to get it. They want to discuss the opportunity further.

Saying that does nothing to make you stand out.

So the best way to end a cover letter is by saying nothing at all. Let your story speak for itself.

And leave your phone number. They might just call you.

Want to learn how to write amazing cover letters?

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