It's hard to write the perfect  cover letter. In addition to the general awkwardness of figuring out what to say, there's the question of whether anyone is actually going to read it. In this day and age, it's hard to say whether an HR bot is simply going to scan your  resume and accept or reject you without any shred of human contact.

In other words, is the cover letter dead?

According to Jesse Hertzberg, former COO of Squarespace, it is most definitely not. After singling out one of the best cover letters he'd ever seen, he said, "Don't let anyone tell you cover letters are BS. They aren't. I'm hard pressed to review a CV without a cover letter, and if the cover letter doesn't engage me, it's as if there wasn't one."

The letter in question started out with:

"While reading the 15th February OregonLive article on the spin-up of Squarespace operations in Portland I was intrigued by the critical stance the COO took on potential office space. Then after scoffing at the "How to Apply" section of the job posting, I let it percolate for a few hours then decided what the f---. Here goes:"

Except that in the original version, the expletive wasn't bleeped out. It was there in all its glory, as were several others.

Hertzberg outlined several things that worked about the letter, but the most important three were these:

1. It was interesting

The cardinal sin of a cover letter is being boring. Yes, you want to be professional, but you also want the hiring manager's eyes to not glaze over.

No one's eyes glazed over reading this letter. It included gems like:

"You will not find a better fit for the particulars of this job, as you've defined them, certainly not in a Portland native. Why? Because I started out and grew-up with the darling of the Silicon Valley all through the dot.com era; I was fire-hardened through many years living & working in Manhattan and now am barrel-aging in Portlandia."

Don't be afraid to be creative--it's actually riskier to not take a chance. Or as Hertzberg put it, "Remember that I'm reading these all day long. You need to quickly convince me I should keep reading. You need to stand out."

2. It put attention on the company

Another common mistake is to simply regurgitate your resume. The purpose of a cover letter isn't just to talk about yourself. It's to link what you've done in the past with what you can do for this company, now.

This candidate had bullet points on how he could contribute, including some tongue-in-cheek ones:

  • "I will hook you up with the best Ashtanga instructor in Portland"
  • "I'm certified as an instructor in the discipline of Rational Process and Problem Resolution and will teach it to the customer support staff and leadership"
  • "I love MCM design, furniture and architecture and can consult on the PDX site-search (at least I can tell you if you are picking a dog and could do better)"
  • "I am one funny mother-f-----"

3. It was grammatically perfect

Despite the use of complex phrasing and vocabulary, this unconventional cover letter was error-free.

Always have someone else review both your cover letter and resume, especially because you've been looking at them so much you're more likely to miss something. Remember that they both need to reflect your professionalism, because your prospective employer only has them to go on.

Hertzberg summed it up like this: "Last, but not least, proofread the sh-- out of your letter ... If you can't pay attention to detail in your application, what kind of faith can I have in your day-to-day work?"

The full version of the cover letter can be found  here.