How I Write Cover Letters Hiring Managers Actually Read

STARTUP JOB SEARCH STRATEGY
A COVER LETTER THAT DOESN’T SUCK.

This Thursday in the Early Accelerator, I was chatting with a highly talented startup Sales Director in our group Q&A session.

He raised his little yellow emoji hand in Zoom and asked a question I’ve heard a hundred times in the last few years.

Ohhh, the dreaded cover letter.

Always there teasing you with its lack of mandatory submission but clearly placed there for a reason.

Are you going to be penalized if you don’t submit one?

Are you going to be penalized if you do and say something wrong?

Do hiring managers actually read them?

Let’s debunk the cover letter myths once and for all so you can use them as a tool to land more interviews.

NETWORKING
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WHY DO COVER LETTERS EXIST?

As you’re preparing your application, you may be asking yourself…

“Why in the world do cover letters exist?”

“This is a tech startup, not a college application. Why am I writing an essay?”

The rationale is simple.

They are there so the team wastes less of their valuable time interviewing and more time building and selling.

In the early 20th century, job opportunities were hyper-local, so there weren’t hundreds of applicants per position.

With so few applicants, you could interview everyone to ensure you made the right hire - No cover letter required!

These days, hundreds, if not thousands, of applications are submitted for some jobs (this will likely get worse as AI job application shops grow and remote work continues to increase), so it’s impossible to interview every candidate.

In response to the increase in applicants, fields for resumes, cover letters, LinkedIn profiles, personal websites, and work samples were created as scaffolding to ensure only the most qualified candidates made it to the interview round.

More hoops for the job seekers to jump through = Less hoops for the hiring team to jump through.

Or… at least that’s the intent.

DO ALL COVER LETTERS GET READ?

Cover letters are there to help the recruiter and hiring managers, so they must all get read - Right?

Wrong.

I’ve spoken to many recruiters, and they all say something different.

Most will scan the cover letter.

Many will completely ignore them.

Speaking from my experience as a hiring manager, I can tell you that I always read the cover letter.

And the reason why is the reason I recommend you always always always attach a cover letter.

SHOULD I SUBMIT A COVER LETTER?

The short answer is Y-E-S.

But it’s not just because it shows you checked all the boxes.

I recommend every job seeker submit a cover letter in their application because it is one of the few ways to stand out in the application process.

As a hiring manager, I look to the cover letter to find what makes this candidate stand out.

Resumes are cold and uncaring.

You submit a piece of paper that tells the hiring manager everything you have accomplished in your career.

They’ll tell you if they want to work with you.

There’s no room for uniqueness, enthusiasm, or storytelling.

So, whenever you are given an opportunity to stand out by going above and beyond, I suggest you take it.

A cover letter is one of those opportunities.

SO WHAT DO I SAY?

Write Like You Speak.

Do not write like a Victorian-era novelist penning a letter to their lover.

“I am writing today to express my sincerest interest in your company.”

As a hiring manager, I immediately get the ick from sentences like that because I think, “If this is the way this person speaks, I am definitely not going to enjoy working with them.”

So instead, write like you speak.

A good rule of thumb is to read it out loud and ask yourself, “If I were handing my resume to this person face to face, are these the words I would say?”

If the answer is no, re-write it.

Eliminate jargon, eliminate acronyms, and write at a seventh-grade reading level.

Personalize The Messaging.

There are a few ways that a cover letter can hurt your application.

Including the wrong company name is a big no-no and often grounds for immediate rejection.

Additionally, if the letter is so generic that it could be (and likely is) mass-submitted to hundreds of companies, it can hurt you.

If I’m reading a cover letter and there are no distinguishing characteristics that show me that this letter is unique and from the heart, I will assume you’re applying to hundreds of companies in a spray-and-pray method and that you just want a job.

I don’t want someone who just wants a job.

I want someone who wants THIS job at THIS company.

A generic cover letter does not do that.

There are many ways to personalize the message:

• Reference people you know or have spoken to at the company by name (this is where networking outside of just the hiring manager and recruiter is invaluable)

• Reference recent news articles about or press releases by the company (this is a great place to congratulate a company on their recent fundraising round)

• Reference a podcast you listened to or YouTube video you watched where the founder, an executive, or an investor was interviewed.

• Reference a newsletter that highlighted the company

• Speak about your personal story and personal mission and why the company’s mission is uniquely personal to you

• Connect specific examples from your highlight reel of experience that are particularly valuable to the company due to its current size, stage, or growth rate

There are too many ways to personalize the message for me to list them here.

Just please personalize the message or risk your submission being best-case neutral or, worst-case, a disqualifier.

Include Unique Value Props.

With all the layoffs, hiring freezes, company closures, and tighter funding, the startup hiring market is hyper-competitive.

But, if there’s one thing I’m seeing from the Early Accelerator members, it’s that creativity and value delivery win eyeballs.

I have seen people…

• Include a link to a personalized Loom video expressing their interest in working for the company and tying it to their personal journey and highlight reel of badass results.

• Include a link to a Notion page designed with elements from that company’s branding and highlighting why they’re a good fit for the position and how they would help the company in more detail than a resume can provide.

• Include a link to a video of them using the product and providing a product review.

• Include a link to a value deliverable (ex: a playbook, case study, spreadsheet, template, mock-up, customer interviews, etc.) they crafted using their prior experience and tailored specifically to what they know about the company’s needs.

You never know if someone is going to read your cover letter, but if they do, you want to make sure you leave an impression that has them saying, “Damn, I’ve never seen that before.”

As a hiring manager, when I see people do this (and it’s very very rare) it immediately demonstrates to me they’re not going to waste my time and (as long as their experience is relevant and their messaging is compelling) worth making it to the next round.

I’m also far more excited to interview these people than a candidate with a boring old resume.

Speak To Their Needs.

Most people will talk about their highlight reel but won’t relate it back to specific problems or opportunities facing their target company.

Speak not just about your experience but also about what it felt like inside the company when that was happening.

Share what it looks like and feels like when a certain problem arises or when a company is at a specific stage of its growth journey, then relate that back to your target company’s current state.

There’s a classic saying in sales that you want to, “Sell the destination, not the journey.”

That’s true in sharing your experience in the cover letter.

Share the pain of what it looked like before, the ecstasy of what it looked like after, and how you can help the company experience the ecstasy with far less (or better yet no) pain.

THAT SOUNDS LIKE A LOT OF WORK.

That may sound like a lot of work, but it’s only a lot of work if one of two things is true.

1. You’re not actually interested in the job or the company, so putting together a thoughtful piece of outreach is like getting a root canal without novocaine.

2. You’re mass applying to hundreds of jobs instead of thoughtfully applying an application strategy to a targeted set of ideal jobs and companies.

Also… yeah, it is more work than just submitting a resume, which is why most people don’t do it and why, if you do it right, it can make you stand out in the process!

We’re here to stand out and make the best impression.

Not do the least amount of work.

That being said, to make it take less time, I recommend using ChatGPT.

• Copy and paste the job description into the prompt.

• Attach the pdf of your resume (or copy and paste it into the prompt)

• Ask ChatGPT to craft a cover letter for your application to the job description copied above and your resume attached in the pdf.

• Edit the copy to be in your voice and to sound like you talk.

• Add personalization (you could also include this in your prompt).

• Add links to external deliverables (you could also include this in your prompt).

I’ll say it again - DO NOT USE THE FIRST OUTPUT FROM CHATGPT WITHOUT EDITING IT AND MAKING IT SOUND LIKE YOU.

Another way a cover letter can work against you is if it is clearly written by AI.

The hiring manager is going to think to themselves, “They couldn’t take the time to edit this a little bit so it doesn’t sound like a robot? Come on.“

The job search is not about easy - it’s about standing out.

It’s about clearly understanding the exact role and company you want to work for, doing everything possible to get the attention of the people who can influence the hiring decision, and making as compelling of a case to them as humanly possible.

If you don’t submit a cover letter, will your application still receive the same attention?

That’s possible.

Can you confidently say, “I did everything possible to land that job?”

Nope.

If you get rejected, will you be left wondering, “I wonder if things would have been different if I had just taken Kyle’s advice and used the cover letter as a way to differentiate myself from other candidates and clearly articulate who I am, what I’ve done, the value I will deliver for them, and my level of excitement about the opportunity?

Yes, you’ll wonder about that for the rest of your life.

So don’t wonder — just craft the letter in the way I’ve highlighted and win the job you’ve always wanted.

So… until next week.

Let’s become career champions together 🏆

Kyle

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