How to Tailor Your Resume to a Job Posting

I used to pass on 99% of jobs because I didn't match the words. A hiring manager told me I was reading the words but not the need.

A guide from MyJobDaddy · Tyson McKay

For a long stretch of my career I read job descriptions the way you'd read a bouncer's list at a club door. I'd scan the requirements, find the two or three I didn't have, and quietly put myself back in line. I don't have half these skills. I've used the product they keep mentioning but not for twelve years. They want a certification I never bothered with. In those days I passed on something like 99% of the jobs I looked at, because it didn't seem like there was a match, and it felt almost rude to apply for something I so obviously wasn't.

Then I met a hiring manager who told me, pretty bluntly, that I was missing out on good opportunities. Not because I wasn't qualified. Because I was reading the words but not the need.

The twelve-year product that was five years old

Once I started actually reading job descriptions instead of grading myself against them, I noticed something that I'd been sliding right past. Over and over, companies were posting things like "must have 12 years experience using X product," and I knew for a fact that X product had been around for five years, sometimes less. Nobody on earth had twelve years on it. The people who built it didn't have twelve years on it.

So how could they want someone with that many years? Here's the part that took me too long to see. They don't. That number is silly, and everybody in the room knows it's silly. What they actually want is someone who has used similar products to solve the problems they are having right now, and "12 years with X" is just the clumsy way a requirement got written down by somebody who needed to fill a box on a form.

That's the whole trick, and it's the thing most people never do. You stop asking "do I have this exact thing" and start asking "why do they need a person who can do this." Why do they need twelve years on a product? Because they have a problem that product solves and they want someone who's solved it before, on anything. Why do they need that certification? Usually because someone once got burned by a hire who didn't know the basics, and the cert is the shorthand for "please know the basics." Once you read for the why, the wall of requirements turns into a short list of problems, and you almost always have more of the answers than the words let on.

Then I looked at my own resume the same way

When I changed how I read the job description I also had to change how I read my own resume, because my resume had the exact same disease. It listed what I'd done in my words, from my side of the desk, organized the way my career had happened to unfold. None of that is how the company is reading. They're reading with their problem in one hand and my resume in the other, trying to match them up, and I was making them do all the translating.

So I started listing the skills I'd developed, and I listed them in the same manner the company had. Their language, their priorities, their order. If they led with the product, I led with my experience on products like it and named the problems I'd solved with them. If they buried something I was strong at, I pulled it up where they'd see it. I wasn't inventing anything, I want to be clear about that, every line was true. I was translating it into the language of the job I wanted instead of the job I'd had.

This did take time. It's slower than firing off the same resume to forty postings. But I started to get more call backs, which is more than forty identical resumes had ever gotten me.

The last pick of the third pile

I recall one of those call backs in particular. They told me, and I'm not sure they meant it as flattery, that they had already interviewed twelve people, and I was the last person in their third pile. As in, they'd sorted the candidates into three stacks, and I was the worst of the worst stack. I thought that was pretty funny, mostly because the last pick of the third pile had just gotten in the door for an interview, which is the only thing a resume is ever for.

Then I did well in the interview. Too well, apparently. HR said I was too good and they thought I was gaming the system. The hiring manager was concerned I'd leave. And the third person in the room loved that I could answer granular technical questions without a computer in front of me, because those were the actual problems behind the twelve-year requirement, and I'd solved them before.

I got the job. My resume wasn't perfect. It was just good enough to get noticed, and then it was the thread I needed to pull on.

How to actually do it

If you want to do what I eventually learned to do, here's the shape of it, and you can do every bit of it with nothing but the posting and your current resume.

Read the job description twice. The first time, don't grade yourself. Just read it. The second time, for every requirement, write down the why next to it, what problem are they trying to solve by asking for this. "12 years on X" becomes "they need someone who's run X-type systems and can troubleshoot them." "Must have cert Y" becomes "they need someone who knows the fundamentals cold." Do that for the whole list and you'll end up with a page of problems instead of a page of gatekeeping.

Now go through your own history and find the places you solved those problems, on whatever tool, in whatever job, even the ones you'd stopped counting. Then rewrite your resume to lead with those, in their words, in their order. Mirror the posting's language. If they say "incident response," you say "incident response," not "handled outages." If they care most about the thing in their first paragraph, that's your first bullet. Cut the stuff that was important to you but isn't to them. Keep every single line true.

Do that, and stop passing on the 99%. Most of those postings were never asking for twelve years. They were asking for somebody who'd read the need.

What it looks like on the page

It's one thing to describe the method and another to watch it happen, so here's the same move on my own resume, today, not back in the third-pile days. This is the summary at the top of my resume, before and after I tailored it to a real posting for a VP of Cloud and SaaS Security. Every fact in the after was already in the before. Nothing got invented. Watch what got reordered and relabeled.

Look at the first three words. The before opens with "IT leader since 1996," which is true and is also how I'd describe myself at a dinner party. The after opens with "Cloud and SaaS security executive," which is the title they're hiring for. That's the whole move in one line, I stopped describing myself and started answering their question.

Then look at what got relabeled. The posting asks for "governance," "risk management," "security by design," and "continuous compliance," and not one of those phrases is in the before, even though I'd done every bit of that work. The after says "risk governance architectures," "embedding security-by-design," "continuous compliance automation," their words, for experience I already had. "Cybersecurity and HIPAA programs" became "cloud security programs, HIPAA compliance frameworks," because that's the vocabulary they're screening for. Same life, their language.

And notice what I kept. The line about framing decisions in operating and financial terms, and presenting risk to a board, was already good, so it stayed, just tightened. Tailoring isn't tearing the whole thing down, it's keeping what already lands and translating the parts that don't.

Where this stops being a grind

I did all of this by hand, one posting at a time, and it works, it's just slow, and when you're serious about a search you're not doing it once, you're doing it for every role worth chasing. That's the part MyJobDaddy takes off your plate. You upload the resume you already have and paste the job description, and it rewrites the resume to mirror that posting's own language and priorities, the translation I used to do at my kitchen table, and writes a cover letter for the same job. You see the before and after of your summary and first role free, before you pay anything. The truth in it still has to be yours. You just stop doing the translating one tab at a time.

Here's how I actually use it now. I still read through every job description myself, start to finish, so that I understand what their need is, that part I'm never handing off, it's the whole lesson of this piece. Then I run it through MyJobDaddy. On Elite it scores my fitness for the role and then it identifies the gaps, the places where what I've done and what they're asking for don't line up yet. That's when the fun begins, because I can talk through my lived experience, the stuff that never made it onto the page, and have it translated into the customized resume and cover letter. The reading is still mine. The digging and the translating got a lot faster.