I’ve been actively looking for a new job for about nine months now, ever since I realized there was no way I could possibly succeed at the one I started in January of 2025. With the advent of AI technology, I’ve been making use of it to improve my resume, tailoring it quickly to each job description. 

I don’t just upload it as-is; I usually have to change a couple of things. But still, it’s faster than doing it myself, and that’s what AI is supposed to be for: improving efficiency of repetitive tasks. Revising a resume for each job posting is definitely a repetitive task. 

I generally use Claude to generate my resumes. I used to use Gemini, which is the AI I primarily use for day-to-day tasks, but Gemini had a nasty habit of inserting things from the job description into the resume without telling me — for example, if the job description said Smartsheet knowledge was required, Gemini would say I had that, even though I don’t and never mentioned it in the source file I gave it. Worse, though: Gemini has been having difficulty allowing me to download files. I tell it to output a file a certain way, and it does, but it hides the file behind some sort of unique-identifier tag instead of giving me a button I can use to download. I have yet to figure out how or why this is happening. 

So I switched to Claude, and I find that Claude does a lot better anyway. Its formatting is acceptable, if a little cramped, and the few times it’s added something to my resume that’s a stretch it informed me so I could remove it. (Actually, it offers to remove it itself but that would cost me more tokens and I can handle a quick deletion.) When I enable Thinking mode on Claude, it also will review the job description and tell me if it’s too much of a stretch — for example, if it requires electronic health records knowledge, I definitely don’t have that. It’ll still write me a resume if I ask it to, but usually I trust it and skip that job. 

Claude can be a little repetitive, though, when it responds. For several of the job descriptions I’ve fed it, there’s been a bit of a stretch, usually as it refers to the industry the job is in. I have no experience in manufacturing or aerospace, but my skills as a PM are transferable, and I can learn about manufacturing or aerospace (or whatever else). A PM is a PM is a PM, after all. But whenever there’s a stretch, Claude says “The honest gap is…”, which was interesting to read at first but the more applications I put in the less I like seeing it. 

I’m doing all of the resume creation processes in a single chat, so Claude remembers what I’ve done and is better at understanding what I want it to do. You’d think it would change the phrasing. But the honest gap (see what I did there?) between AI and humanity is that AI only has a set number of responses it can use. Even generative AI can only do so much. 

I’m not going to stop using AI for my resumes; after all, everyone else does too. But as a writer who tries to avoid repetition (except when I’m using it intentionally), it’s very obvious to me when AI is repeating itself. Maybe that doesn’t bother anyone else, but I personally don’t care for it.