Use ChatGPT to Write Perfectly Tailored and Customized Job Application Cover Letters

Updated August 2nd, 2024.

Looking for a job? You’re going to need a resumé, and a cover letter. The resumé is up to you*. Until recently, the cover letter was up to you too, and because cover letters can be hard to write, most people used the same cover letter over and over. But now… now we have ChatGPT, which can help you write a customized cover letter, specifically created for a particular job. So let’s do it.

In this article, I’m going to use my own resumé, and I’m going use ChatGPT to help me write a cover letter tailored to getting a particular job at Apple. Then I’ll do it again, using ChatGPT to help me write a cover letter for a different particular job at Disney. The letters shouldn’t be the same, because the jobs aren’t the same, and that’s the whole point.


(Wondering how to type that accented é, in resumé? I have two articles for you. This one tells you how to type accented characters (and more) on a Mac. This one tells you how to do it on an iPhone.)


Job 1: Senior Manager, Training and Content Development at Apple

Here’s a job that sounds interesting: Senior Manager, Training and Content Development, in Austin, Texas. Let’s apply.

Senior Manager: Training and Content Development job posting
Apple job posting

Here’s part of the job description. You can click here to read the entire PDF.

Apple job description
The Apple job description

I want to create a customized cover letter to go with my resumé. I want the letter to connect items in my resumé with the job description’s requirements. If I only wanted to write one such letter I’d do it myself, but job searches don’t usually go that way. Usually, one applies to multiple jobs. So we’re going to need multiple letters, and they are all going to be different, and for that we can use a little help.

So we turn to ChatGPT.

Asking ChatGPT if it can write a cover letter. Me: If I upload my resumé as a PDF, and a job description as a PDF, can you write me a cover letter that matches my skills and experience to the job? ChatGPT: Of course. Upload the job description.
Asking ChatGPT if it can write a cover letter
I uploaded the job description as a PDF. Me: Here's the job description as a PDF. ChatGPT: I'll review the job description. Upload your resumé so I can compare them.
I uploaded the job description as a PDF
Now they have my resumé. Let's see what ChatGPT can do! Me: Here is my resumé as a PDF. ChatGPT: I will create a targeted cover letter for you.
Now they have my resumé. Let’s see what ChatGPT can do!
Here's the letter (animated GIF showing various parts of the letter).
Here’s the letter

This would be handier as a PDF or a Word document, so let’s ask for those.

Asking for a Word document, and a PDF. Me: Can you save the letter as a PDF and as a Word document? ChatGPT: here are links to a PDF and a Word document.
Asking for a Word document, and a PDF

After a little bit of clean-up in Word I ended up with this (click to enlarge):

The Apple job cover letter
The Apple job cover letter

As you can see, the letter matches five of the job responsibilities with my skills and experience, as found in my resumé. Nice.


Job 2: Technical Analyst, at Disney

Now let’s apply for a different job, and see what kind of letter ChatGPT makes for us. This job is a Technical Analyst position at Disney. Click to read the entire job description, or just get the basics below:

Beginning of the Disney Technical Analyst job description
Beginning of the Disney Technical Analyst job description
Asking ChatGPT to write a second letter, for a different job. Me: I'm going to upload a second job description. Please make a cover letter for this one also. ChatGPT: Upload the job description and I will make a tailored cover letter.
Asking ChatGPT to write a second letter, for a different job
Job description uploaded, waiting for the letter. Me: here is the job description as a PDF. ChatGPT: I will make a tailored cover letter for you now.
Job description uploaded, waiting for the letter

… and here’s the letter.

The Disney cover letter. Animated GIF rotating through the first few paragraphs.
The Disney cover letter

Note: See where it says “ChatGPT can make mistakes.”? Well it made one (actually three) in this letter. ChatGPT said I had “hands-on experience with AWS, Python, and SQL” but I don’t. That’s not in my resumé– ChatGPT simply made it up! So, I asked ChatGPT to take that part out and give me another version, and then I asked it to save it as a Word document. This is what I got (click for the full-size version):

Disney cover letter
The Disney cover letter

It’s a totally different letter than the one it wrote for the Apple job. Compare the bullet points from each:

Apple Letter

The key responsibilities of the Senior Manager role at Apple align perfectly with my expertise:

1. Content Strategy and Alignment: I have developed long-term content strategies that align with business objectives, enhancing user productivity.

2. Adult Learning Principles: I am well-versed in adult learning principles and best practices through my extensive training experience.

3. Content Management: I have managed content performance, continuously identifying areas for improvement. 4. Impact Measurement: I have implemented systems to measure the effectiveness of training programs, ensuringtangible improvements.

5. Leadership and Inclusivity: I have built and led effective teams, fostering a culture of accountability and continuous learning.

Disney Letter

My expertise aligns with the Technical Analyst role in several key ways:

1. Collaborative and Agile Environment: Experience working within multi-functional teams to support software in a collaborative and agile environment.


2. Operational Support and Incident Management: Skilled in triaging service alerts, managing incident responses, and ensuring system uptime and availability.

3. Technical Documentation and Automation: Proficient in creating operational documentation and developing automation solutions.


4. Data Analysis and Problem-Solving: Ability to analyze data sets and service metrics to proactively identify and resolve technical issues.

Quite different, and both quite good. ChatGPT did a good job of comparing my resumé with each job’s requirements, and created unique letters to support my applications. That’s a lot of help.

(No, I am not really applying for these jobs– I’m going to keep doing what I’ve been doing all these years. But… if I were looking for a change, I’d use ChatGPT to help me write customized, targeted cover letters like these. Try it yourself and see!)

One more thing: GOOD LUCK with your job search! Leave a message in the comments here if ChatGPT helps you.

* Actually, you could ask ChatGPT to help you with your resumé– try it!


More ChatGPT tutorials by Christian Boyce

Copyright 2008-2024 Christian Boyce. All rights reserved.

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Christian Boyce

Christian Boyce is a Mac and iPhone expert with over 30 years' experience in the field. His specialty is teaching people how to get more out of their Macs and iPhones using the software and apps already installed. He is the author of several books, a guest speaker for Mac and iPhone user groups worldwide, and a former rocket scientist. He splits time between homes in Santa Monica, California and Round Rock, Texas.

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