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Cover letters are supposed to help you shine, but most of them blur together into the same polite, forgettable paragraphs.
The intention is good (“I want them to notice me!”), but the execution… not so much. So, here’s a simple, honest guide to writing a cover letter that actually works, especially if you’re applying to Checkly.
Spoiler: shorter is better. And authenticity in this AI era is better than perfect polished perfection.
Hi, I’m Kaylie, Director of People at Checkly. I’ve read a lot of cover letters, and I want to help you write one that actually works.
What most cover letters end up being
If you only knew how many times I’ve read the same sentence, slightly reworded, by hundreds of candidates…
- A list of everything the job post mentions, with “I am excited about…” pasted in front.
- Obviously AI-generated text that sounds nice but says absolutely nothing.
- Claims about experience that don’t match the CV or LinkedIn profile at all.
None of this helps. It doesn’t tell us who you are or why you care about the role. And honestly? You’re wasting your own time writing something that isn’t going to move the needle.
Which brings me to…
What makes your cover letter stand out
Cover letters are totally optional at Checkly. But when they’re good, they can make your application stand out in a sea of hundreds.
Here’s what a great cover letter looks like:
1. Keep it concise and specific
When we publish a new role, we get hundreds of applications, sometimes over a thousand! We read through every single one, but that also means that we don’t have time for essays. A sharp, 3-paragraph cover letter beats a 1.5-page essay every time.
2. Tell us why you want this role
Not why you want a job. Not why you want “a new challenge.”
Why this role? What part of it sparks something for you? We want to hire people who choose us on purpose. If something about the company or role lights you up, say it.
3. Share a real example
Give us a story: a small, concrete example from your experience that shows you can do something this role needs.
Not a list of traits. Not “I am a great communicator.”
Something like: “In my last role, I rebuilt our onboarding flow from scratch and cut ramp-up time by 40%. I’d love to bring this kind of structured thinking to Checkly as you scale.”
That one example gives us far more than three paragraphs of adjectives ever could.
4. Write like a human
Drop the overly formal tone. We’re a friendly, direct, international team. It’s okay to sound like yourself.
5. Check your facts
We compare what you write with what’s on your CV or LinkedIn. Make sure they align. If your cover letter mentions 10 years of Go experience but your CV lists one year of Java… we notice.
Why this matters
A good cover letter isn’t about being poetic or impressive. It’s about helping us understand two simple things:
- Why you want to work here, and
- Why you think you can be great at this role.
That’s it.
If you can answer those clearly and briefly, you’re already way ahead of most applicants.
Extra: If you want real inspiration, check out the exact cover letter I submitted with my application.