… it’s a tribute.

Over nearly two decades of working as a copywriter, I can’t count how many times people have said to me “I hate writing about myself.” That statement was usually followed by an offer to give me money to write their bio or cover letter. 

Now a lot of folks are turning to AI tools like ChatGPT to write their cover letters. All you have to do is plug the job posting into our little AI buddy’s window and it churns out a cover letter that would, ideally, appeal to a recruiter hiring for that job. 

Seems like a great idea… until everyone starts doing the same thing. In fact, I saw a post the other day on LinkedIn where a recruiter was lamenting about all the ChatGPT-generated cover letters they had been receiving. 

How could they tell? 

If you’ve ever used ChatGPT to write something, you’ve probably noticed it uses gratuitous adjectives and recycled phrasing. It’s almost like a student who just found Thesaurus.com and is using it to stuff an essay with superfluous words to achieve the required word count. 

The recruiter in question was getting a lot of similar cover letters because everyone was entering the same prompt and not doing much to edit the results. 

I’m not here to crap on AI or ChatGPT. I think it can be a great jumping off point by providing a template for something you’re writing or ideas you can use and edit to make your own. It has tons of additional uses… if you can ignore the prospect of robots one day becoming sentient and killing us all, or at the very least, stealing all the fun jobs.

Anyway, back to the point of this post. I’m back in the freelance copywriting game now and I’ve been digging in the crates for my greatest writing hits and resumes, and I came across one of my best cover letters. It was the one that landed me an interview and subsequently one of the best jobs I’ve ever had from a creative standpoint: copywriter/producer at Indie88 – Toronto’s indie alternative radio station. Mind you, this was during the glory days of 2015 when ChatGPT was just a twinkle in some tech nerd’s eye.

When applying for creative jobs, your cover letter is your chance to show them what you’ve got. For this cover letter, I tapped into my experience working in other radio jobs as well as my stint as copywriter at a start-up that can only be described as Green Groupon. Remember when Groupon had those wild daily emails? Of course people loved the deals, but their creative email copywriting also got a lot of attention. So I wrote the cover letter in the style of a daily deal email. 

Without further ado, here’s the cover letter I sent to Central Ontario Broadcasting (Indie88 Toronto) with my application for the role of copywriter/producer. 

Dear Hiring Team,

Ever hire someone who’d been talked up higher than Tom Cruise scaling a Dubai hotel only to discover a YouTube comment section troll would have been more accurate? You won’t get burned like that again with today’s job application: For the small price of an annual salary and competitive benefits package, you get a passionate, creative, versatile and experienced copywriter who promises never to write a boring piece of copy again!

After graduating with honours from the Communication Studies program at the prestigious University of Windsor, Jessica Grajczyk had nepotism to thank for her first gig in Top 40 radio. A few years later she decided to expand her skills and soak up as much knowledge as she could in the world of copywriting.

Now, she’s turning her attention back to radio, and why not? Who could resist the allure of rebuilding their rad collection of promotional glassware, t-shirts from straight-to-DVD movies, GCs for the city’s finest gastropubs and sweet, sweet memories? 

As she embarks on this next adventure in her career, Jessica hopes to marry her extensive and varied copywriting experience with her deep roots in radio as the newest member of the creative team at Central Ontario Broadcasting.

If you’re looking for a writer with the wit of Tina Fey and Bill Hader’s lovechild, the work ethic of a start-up CEO with a coke problem, and an obsessive compulsion to edit until there’s one perfect word left, you should hire Jessica Grajczyk.

—

Indie88 ended up hiring me to brainstorm and write some of the most ridiculous creative copy of my life and broadcast it to millions of people for about 2.5 years. I had no radio copywriting experience. They took a big chance on me*. 

In short, you should put some stank on your cover letter when you’re applying for creative jobs. Don’t lean too heavily into ChatGPT, or at least get creative with your prompts (for example, you can ask it to write something for you “in the style of” something else to make it a bit more interesting.) ChatGPT can give you some inspiration, but don’t forget to inject your own personality and writing style into whatever it spits out. 

*I will include the caveat that I applied for this job from a place of privilege that I recognize. I am a CIS, hetero white woman. My parents paid for my university degree. My stepdad – a radio legend in his own right – got me my first entry-level radio gig. These other factors definitely helped get my foot in the door.