Branding, Resumes

This Wacky Cover Letter Scored Me My Dream Job

If there’s one way to make a recruiter yawn, it’s submitting a dry, dull cover letter that’s essentially a reworked version of your resume. Your cover letter shouldn’t just be a list of your skills and experience — it’s an opportunity to highlight who you are as a person, and what makes you different from all of the other candidates who are vying for the same position as you. You want to strike the right balance between professional, passionate, and creative. But what does that actually look like on paper?

Kaitlin Westbrook, a content writer and digital marketer at, seems to have struck just the right balance. Rather than a traditional cover letter, she applied for her current position with a cover letter formatted to look like a “clickbait” article, sensational headline and all. While we can’t guarantee this is the right approach for every job opening out there, it certainly was for Westbrook — not long after she submitted her cover letter, she scored her dream job.

We reached out to Westbrook to hear her take on why she thinks her approach worked so well, what she learned from it, and what advice she has for other job seekers trying to catch the attention of recruiters and hiring managers.

Kaitlin Westbrook CL (3)

Glassdoor: Can you tell us a little bit about your background?

Kaitlin Westbrook: I do content writing and marketing at Vecteezy, an online tech startup that provides resources for graphic designers and other creatives. When I applied for my position with Vecteezy, I wasn’t in the best place. I was doing contract work as a customer service representative, and because it was contract work, I knew it wasn’t going to last forever. I was ready to pursue something that utilized my strengths in a way my current job didn’t.

Long story short, I was applying for a lot of things that didn’t seem to pan out. Meanwhile, my contract was about to end soon, and I was worrying about rent and bills and where my future paychecks would come from. Then, an illustrator friend posted a Vecteezy position on Facebook. I knew right away I wanted it, but I wasn’t sure what the best plan of action would be.

Glassdoor: How did you come up with the idea for a “clickbait” cover letter?

Kaitlin Westbrook: Like any younger sibling, I called up my older sister to ask for advice. She’s an art director, so she’s always asking, “How can you do this more creatively?” So, we started discussing my cover letter, brainstorming different ideas on how to make it stand out. I wanted a writing job, so we broke it down; write a cover letter that advertises writing. Instead of a typical cover letter, I wrote clickbait on why the company should hire me. Once I wrote it, I submitted it and hoped I hadn’t made a mistake.

Glassdoor: Submitting a cover letter like this is definitely a leap of faith. Why do you think it worked so well?

Kaitlin Westbrook: I was applying for a senior level position with only some copywriting experience under my belt. So, while I really wasn’t qualified for a senior level position, I think the company saw I really wanted to work for them and that I was willing to hustle. 

With that in mind, they were able to offer me a content writing position that also involved marketing. I honestly think they appreciated seeing someone with drive.

Glassdoor: I also saw that you pointed out a grammatical error in your cover letter — that’s pretty gutsy!

Kaitlin Westbrook: The job listing required me to point out a grammatical error and include my favorite food in the cover letter. (I would never correct someone’s job listing otherwise!) 

I really tried to go above and beyond, and I think that showed.

Glassdoor: What advice would you give to job seekers looking to spice up their cover letters? 

Kaitlin Westbrook: This experience taught me professional risks can be worth it. Employers want professionalism and creativity, so it’s certainly a balancing act, but I would definitely try it again. I would encourage job-seekers to consider how they can be professional and still take risks, whether it’s in the cover letter, the resume, or something else. The right place will appreciate the creativity.


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