Ace the Cover Letter

And Get More Interviews

Applying to jobs online is depressing.

The odds? Abysmal. Apply-to-interview rates sit at <10% for most roles. And don't get me started on Big Tech—<1%.

You're practically sending your resume into a black hole. If you're going to play this game, you better up your odds.

Enter the cover letter—a field often marked 'optional,' but make no mistake, it's your secret weapon.

When Should You Use a Cover Letter

As I’ve said often, applying online is usually not worth your time. So then why am I talking about cover letters?

There are two major scenarios a cover letter makes sense:

1. For a company that you are networking to get a reference, and you want to stand out.

2. For companies that you don’t have time to network into but still want to apply to. You’re willing to put in 45 minutes for a cover letter and resume, but not 5-6 hours getting a reference.

In my experience, there are plenty of jobs you don’t care enough about to get a reference for. But they are level and comp fits.

These are great candidates for the cover letter.

Maybe the company isn’t your cup of tea. Or the product isn’t. But if the level and pay are a fit, these are great candidates to consider a cover letter.

Getting into the process with these companies helps finesse your interview skills, help you understand your market value, and, who knows… maybe they’ll end up a fit!

I can speak from experience: this is what happened with me when I joined thredUP in 2014!

The razor to apply is: how long have you been in the market? If you’ve been in the market a while, get your cover letter game going.

Not every company is going to read your cover letter. So it’s sometimes wasted work. But in aggregate over many companies, it has an impact.

Sometimes enough to put you over the edge for that next job.

The Market Is Still Tough

Acing your cover letter is especially useful because getting interviews is hard these days.

The job market continues its tumult. The latest hit of bad news this week came from Carta, who reported that startups are shutting down at record numbers:

That’s pretty stunning to see. There were 6x more startup closures in Q3 of 2023 as Q1 of 2019.

That’s a lot of people losing their jobs. And the pain in the market is not over yet. All these people losing jobs continue to push up the supply of workers.

Meanwhile, the demand for PMs continues to rise very slowly.

Anecdotes from Fellow Readers

Many of you have reached out to me over recent months about your misery in getting interviews.

Here are three select messages from fellow readers:

Despite 5 years of PM experience, applying online has been a giant blackhole. I’ve gotten less than 5 interviews that past 3 months.

It doesn’t seem like anyone likes my resume. I’m trying to switch into PM from a background as a Tech Lead. It doesn’t seem anyone wants to take the chance.

After a 15 year career in PM, I didn’t think I’d be here looking for an IC job. But I just can’t get GPM/director-level interviews.

When these messages come in, I tend to help folks. And one of the newer techniques has been the cover letter.

In fact - I worked with these three folks, and a few more, in the last few weeks.

All three of those folks use them to get interviews. And many others have benefitted.

So let’s break down these market-tested strategies.

Today’s Piece

We’re not going to cover the basics you already know. If you follow the strategies of a few commonly read books, you will not stand out.

Instead, we’ll cover:

1. Dissecting Bad Cover Letters

2. When Should You Write a Cover Letter? (More Detail)

3. 3 Great Cover Letter Examples

4. The Cover Letter “Formula”

---

1. Dissecting 3 Cover Letters

Some of you may be thinking, “I already know how to write a great cover letter.”

But what if you wanted to write an amazing one? Let’s look at several great cover letters - and how they could be better.

Cover Letter Example 1 - Most Common Example

Subject: Why My Journey Leads to [Your Company]

Hello,

I began my career as a junior developer, soon realizing that I wanted more than just code—I wanted to shape experiences. Fast-forward 5 years: I’ve led a team at Company X to pivot from a failing model to a product with 500K daily active users.

If you’re looking for a PM who understands the tech stack and has experience in the same industry, we should talk.

Warm regards,

[Your Name]

(Phone Number)

Not bad huh?

Your competition is submitting lots of cover letters like this. I see them everyday at Apollo.

But there are some things this could do better.

1. Be more specific about the role: This cover letter does a great job relating to the company, but it doesn’t relate to the specific role at all. Most hiring managers have role-specific criteria they heuristically use to rule out candidates that aren’t a fit.

2. Clarify the product impact: The result “led a team at Company X to pivot from a failing model to a product with 500K daily active users” sounds like something that would’ve been a whole company initiative. So it’s totally unclear what this PM’s role was, and if they just have an inflated ego.

Cover Letter Example 2 - The Cold E-mail

Subject: Solving [Your Company’s Pain Point]

Hello,

Rather than listing my achievements, let’s focus on you.

You’re looking for a PM to increase user engagement. I’ve studied your product and have identified three strategies to boost active users by 20% in the next quarter. Interested?

Best,

[Your Name]

This is a perfect cold e-mail.

But maybe not the best cover letter.

Here’s why:

1. Cover letters are for learning more: This doesn’t really help you get to understand the candidate any better. It just catches their attention.

2. No proof, just claims: Over-claiming and exaggerating is one of the most dangerous traits to have as a PM. By just claiming you can increase engagement 20% doesn’t impress folks at the cover letter stage.

Cover Letter Example 3 - The List

3 Reasons Google Cloud Needs Me as Their GPM for Kubernetes

1️⃣: Innovation
Pioneered a Machine Learning algorithm that increased user retention by 30%.

2️⃣: Experience
12 years across startups and large corporations, managing teams and shipping products.

3️⃣: Results
Generated $50M in additional revenue across all products managed.

For these reasons and more, I'm your next GPM for Kubernetes. Let's discuss how I can bring these results to Google Cloud.

This is another one that seems impressive right?

But if you’re going to break through at Google, here’s what you’ll need to do to enhance it:

1. Go from Unrelated to Related Experiences: The innovation of a ML algorithm isn’t really relevent to Kubernetes. Mentioning things like autoscaling, statefulsets, and ingress controllers would be much more relevant.

2. Being Specific: The content is vague. Even the experience basically just says 12 years. Saying “across startups and large corporations, managing teams and shipping products” could be said about almost anyone - even non-PMs.

I hope this section has given you an illustration of the high bar you need for your cover letters. These are six of the most common mistakes I see in cover letters everyday.

If you want to use the cover letter to get that interview and stand out in the process, you’ll need to raise the bar.

Let’s get into how.