Ask HN: Writing cover letters for tech jobs

I agree. I want the resume to be bullet lists but the cover letter to explain why they are a match.

I also see it as a filter on effort. If the applicant doesn’t care enough to make sure I know why they are a good fit, do they really care about the job?

In my experience, only checking off checkboxes rarely leads to the correct match.

Resume writer here that also writes cover letters for clients, converted to writing after 20 years in tech recruiting. Almost any time that a client asks for a cover letter, my response is "Here it is, and I hope you never have to use it".

If you're using a cover letter to apply for a job, it means you have no human inside the company that is advocating on your behalf. Your friend wouldn't ask you for a cover letter (in most cases) if he/she was going to refer you internally. So when you are required to use a cover letter, it usually means you're applying to a job 100% 'cold' as an outsider.

Unfortunately that may be the case sometimes. If a cover letter is required, there are a few key elements

1 - prove to the reader that you actually paid a bit of attention to the job requirement. I spent 20 years in recruiting, and generic cover letters that clearly weren't written for me ("Dear Esteemed Employer") never got my attention. I want to know what interested you in this opportunity, or briefly what you know about the company (could be lots of things).

2 - Talk a bit about what you're interested in from a work perspective. What kind of work do you want to be doing (and hopefully that is the work we're offering).

3 - Maybe check off a few boxes from the job spec. If they require a degree and n years with Python, a few sentences to check off those boxes will make it easy for the reader (often a recruiter or admin with little experience and limited knowledge of the domain) to say yes to you as a candidate.

Semi-formal tone. You can link to GitHub, but usually I link GitHub and LinkedIn on a resume.

This is great advice in the right context, but it's not a universal context. If it's a big tech company in SV, for example, or really any company > 100 people in a crowded and desirable industry to be in, cold emailing people isn't going to make a good impression. Or if it does yield a positive response from someone, that's either not going to be a good company to work for, or not a good person to use as a contact at that company. Pushiness for the sake of pushiness isn't a foolproof solution, in both careers and dating.

OTOH, in smaller and more close-knit communities of employers (for a completely random example, "architecture firms based in Des Moines", or "health-focused startups in SF"), where there's a relatively small group of smallish companies with a lot of cross-pollination between employees, this might be an effective strategy.

It probably feels better than dropping a resume in some online drop box, because you are personally taking action rather than sitting around and waiting for callbacks that are probably not going to call back, but just because something feels better doesn't mean it's more effective.

FWIW, I myself and plenty of other people I know have gotten really good jobs at big tech companies simply by making sure that any company of interest has a copy of one's resume in their vast database of resumes. It doesn't take any time at all to do that, so no time wasted, and it's one more way in which a potential employer can find it. Even it's just an additional 5% chance to get hired, that's a 5% chance that didn't exist before and doesn't cost time or money.

Ultimately the only advice I can give anyone is to consider all avenues. Nothing's a gigantic waste of time if you're unemployed or unhappy at your current job. If you know people at the company, great. If there's someplace you can send in a resume or even apply for a specific position, great. If you have a non-stalkery means of making contact with people at the company (maybe going to meet ups or relevant conferences or whatever), also great. None of these approaches are mutually exclusive and most complement one another.

I've been laughed at by HR at one startup where I mentioned I did it for every job whenever possible.

I usually use it to explain my background, and how it relates to the position.

However...I find myself not having to do it much anymore since usually it is the companies that are seeking me out, or I have referrals.

Full text below

"Your posting caught my eye because I've been a reader of How-To Geek for years. In fact, I discovered your site through the article you wrote about setting up a Raspberry Pi as an always-on downloading box. Thanks to that article, I've now got 3 Pis sitting around my apartment doing various jobs.

I'm currently a Technical Architect with doejo, a digital agency specializing in WordPress development and one of only 13 WordPress.com VIP partners worldwide. What that basically means is that we work on enterprise-scale WordPress. (See also a talk I gave at a local meetup detailing some important considerations for large WordPress sites https://www.youtube.com/watch?v=TB_e7yZ4MCM)

I wanted to reach out because the position that you and How-To Geek are in sounds like the position that Investor's Business Daily, one of our former clients, was in a couple years ago.

When we were brought on with IBD, they were deploying code to production late at night or on weekends because they were scared their deploys would break. There were pieces of the site that just plain didn't work. And there was technical debt all over the place that kept their developers from doing their jobs effectively.

I led the team that took WordPress and bent it to our will to produce one of the most custom digital publishing workflows I've ever seen. After migrating 100k+ pieces of legacy content and completing and documenting the new WordPress build, we handed it off to their internal development team and got to work on their DevOps situation. I helped their operations team architect and deploy staging environments so they didn't have to be scared of production deploys anymore. We helped them replace their out-of-date source control with Git and put in place processes that worked with them instead of processes they had to work around.

This whole re-launch and re-build resulted in a site that loaded 25% faster and brought in a ton more traffic. Couple that with the fact that they now trusted their developers and felt comfortable pushing changes to production in the middle of the day, and it was a win all around.

As far as tech stack, I exclusively use Nginx these days and I've never looked back. Javascript and jQuery are squarely in my wheelhouse. I know WordPress actions and filters like the back of my hand and I'm not afraid to use them or trace through someone else's use of them to get things back on track.

To sum up, I'm really impressed you've grown How-To Geek as far as you have while still deploying to production from your laptop. I think it's great that you see the challenges you have when it comes to infrastructure and technical debt. I'm excited by these challenges and look forward to taking them off your plate so you can get back to running and growing one of the best tech sites online today.

I would love to talk more about the position and answer any questions you may have for me.

(And yes, I won't pull punches when I see some particularly terrible code. I have a library of facepalm GIFs at the ready.)

Talk soon, Keanan"