Cover Letters

The very first thing that a prospective employer sees, when you apply for a job, is the cover letter.

There are a lot of mixed opinions out there about the role of cover letters. Some believe it's a big waste of time, that nobody reads them. Personally, I think it's a good opportunity to stand out, and to improve the odds of making it to the next step in the funnel.

I want to do something a bit different here. Instead of giving you a bunch of advice about what makes a good cover letter, I want to show you the cover letters I've written that have led to job offers. Each of these letters is exactly what I submitted, for companies that eventually made me a six-figure job offer.

I'll also be reviewing them, to discuss what I think I did well, and what I'd change if I was writing it today.

Let's get into it!

Khan Academy is a non-profit that creates online educational materials primarily for elementary and high school students.

Here's what I wrote:

Several years ago, I wanted to build my first web application. I had been doing light web development work (landing pages, contact forms) for a while, and wanted to see if I could build something more interactive.

I had a friend who was working as a tutor, teaching high-school math, and he wanted a way to quiz students online. I've always been passionate about education, and it seemed like an awesome project.

The MVP was very bare-bones, and it was held together with duct tape, but it worked. There was a simple auth system, students would complete quizzes, they would be graded and the results would be emailed to my friend.

The product only worked when you had a tutor available to guide you through the material, though. I wanted to build something that would help students who didn't have access to a tutor. I was exploring the idea of building it into a generalized product with built-in lessons when I discovered Khan Academy.

Khan Academy was almost exactly what I had wanted to build! I went through a few of the lessons, and was thoroughly impressed by the quality of the instructions (Sal Khan has such a talent for teaching) and the clean interface for the practice problems.

Ultimately I realized that I wouldn't be able to build anything that offered a better experience, and have since been building other web applications, but I never stopped being passionate about education, or wanting to build tools to help people learn.

I'd love to chat about why I think I'd be a great addition to the Khan Academy team :)

-Josh

And here's what I think today:

Video Summary

The first thing I notice about this cover letter is the tone. It's not written with the stuffy formal language that cover letters are typically written in, there's no “To whom it may concern”. Instead, it's written in a casual, conversational tone.

Now, part of this is that I was matching my tone to the organization. Khan Academy is a very casual sort of organization. We can see this right away from their homepage:

If I was applying to an investment bank, then it would be a good idea to “dress up” the language a bit, to make it more professional.

But, I also don't want to veer too far away from my personality! I am not a formal person. I don't own a single tie. And so if I was to try and apply in a super-formal way, it probably wouldn't seem genuine. And so even if I was applying to a fintech company, my letter would probably still be a bit more casual than others.

The next thing I notice about this letter is that it immediately jumps straight into a story, from the very first paragraph. I talk about how the first web app I built was an educational platform, how it wasn't very good, and how I discovered Khan Academy and was blown away.

There are two advantages to this story-based format.

The first is that it's more likely to capture the reader's attention. Again, imagine that you're the hiring manager with a stack of 400 applications. You're probably skimming these cover letters very quickly. But if you open a letter which is written in a different tone and has this unusual format, it might pull you out of autopilot, you might actually take the time to read it more thoroughly.

The second advantage is that it really shows that I've put effort into this. This letter was clearly written for Khan Academy specifically. If I was going to apply to Google or Microsoft or any other company, I wouldn't be able to copy/paste this letter and make a few tweaks. I would need to start from scratch.

Organizations want to hire people who are enthusiastic about their product and/or mission. And I think this letter does a good job showcasing that enthusiasm.

Of course, we won't be able to write a story like this for every job we apply to. It's particularly hard to tell an interesting story when it comes to agencies and service-based businesses, since they don't have a core product or mission. But for product companies, I think this is a good format.

Now in terms of things I would change if I was writing this letter today, there would be two things:

1. I talk a lot about why I want to work for Khan Academy, but I don't mention anything about why Khan Academy should want me to work for them. I don't highlight the skills or experiences I've had that would be beneficial for the organization!
2. The story is a bit too long. I would try and shorten it. The overall length is OK, but I would shorten the story and include a paragraph or two about my strengths.

Glitch is a collaborative coding app. It's similar to sites like CodeSandbox, but with an emphasis on community.

Here's what I wrote:

Hi Glitch!

My name’s Josh, and I’m a senior software developer. I currently work at Khan Academy, but I’m super interested in working at Glitch.

I’ve been building web things for almost as long as I can remember - I think my first website was a collection of my favorite GIFs when I was 11 or 12, back in the “Welcome to my homepage, it’s under construction, sign my guestbook” days. It was rudimentary, but then so was everything else; it did about as much as every other website.

Of course, things have changed a lot since then. I’ve had the luxury of adapting with the internet, but newcomers nowadays have a much steeper hill to climb. I work part-time at a local coding bootcamp, and it’s made me realize just how much stuff you need to know to be able to build something that fits in with today’s web.

I think this is a necessary trade-off, because while things are more complicated, the stuff we build is so much more powerful. But I love the idea of making it more approachable. I’m really excited about the work Glitch is doing to enable folks to learn how to build, from the ability to “View Source” across the stack, to the community aspects like being able to request help from others when stuck on a bug, to making source control simple and enabled by default.

I think I’d be a great candidate to help build the community site for a few reasons:

• I have strong technical skills with Javascript and React. Khan Academy is one of the oldest and largest production React applications, and I worked on a project to convert it to a modern single-page-app architecture. I’ve created and maintained several popular open-source React projects, such as a GUI project manager (Guppy) and an animation library (react-flip-move). I’ve spoken at several React conferences.

• I’m passionate about design and UX. I really like building whimsical, delightful experiences, and I believe that it’s a huge boost to productivity when you can work closely with design and leverage your own intuition. I do all the design work on my side projects, and it’s a ton of fun.

• I love building quirky, weird, experimental projects. For example, I’m currently working on an app that allows folks to create their own generative art. This gives me empathy for fellow tinkerers, and I’d derive a lot of satisfaction from knowing that my work at Glitch helps folks build similar things.


Looking forward to hearing from you,
-Josh

And here's what I think today:

DigitalOcean is an infrastructure company, a bit like Vercel. They're lower-level, allowing developers to lease virtual slices of servers, which they can use however they wish.

Here's what I wrote:

Hi there!

My name is Josh, and I’m a senior front-end developer. I currently work for Khan Academy, but I’m super interested in working for DigitalOcean.

I’ve been a DigitalOcean customer for many years, and I’ve really enjoyed how accessible it makes server provisioning and administration. As a mostly-front-end developer, DevOps is pretty far outside my wheelhouse, so it’s been tremendously useful for me! Empathy is so important for building great products, and I have a built-in empathy for enabling folks to build products they believe in without getting drowned by the complexities of cloud computing.

I think I’d be a great fit for the role for a few reasons:

• I have strong technical skills with Javascript, HTML and CSS. I’ve been building things for the web in one form or another for over a decade (back when layouts were done with HTML frames and tables), and I’ve kept up with the industry. For the past few years, I’ve worked primarily with React.js. I championed the switch from Backbone to React at a previous job, have made significant architectural changes with React at my current job, and have produced a lot of tools for the open-source community, like an animation package and a GUI project manager.
• I care about the details. I really like working closely with product and design to create amazing, polished user experiences, and will often go the extra mile to include whimsical touches. DigitalOcean’s “Love is what makes us great” value really resonates with me.
• I’m passionate about learning! I really liked that the job posting emphasized that DigitalOcean believes in a growth mindset. I’m excited by new challenges and the opportunity to develop further.


Looking forward to hearing from you,
-Josh

And here's what I think today: