How to customize your resume for any job with a custom GPT

It's surprisingly easy and saves a ton of time!

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I was on a walk with my friend Justin this morning when we started talking about jobs. He’s applying to a few at the moment, so naturally we were sharing stories about our recruiting experiences throughout college. It was a good time, and a pleasant walk down memory lane.

Back in college, I was very involved in a professional consulting club, and spent a ton of time during my freshman and sophomore years recruiting for different internships, jobs, and clubs. It was a twisting journey full of countless dead ends, failures, and funny lessons, but by the end I had finished recruiting earlier and was able to really enjoy my last two years at UCLA. (Highly recommend doing it this way, rather than the other way around)

Once a junior, I started sharing these lessons with my mentees in the consulting club, and eventually was inspired to start this blog to share them with even more people. I figured that all of the hard-earned recruiting lessons I’d learned were probably applicable to everyone who was looking for a job… so basically everyone. I’d write blogs here on Substack, post about them on LinkedIn, and then magically more people would start reading them.

And by far the most common question I’d get was “Dennis, how do I get a job/internship” or “Dennis, how do you write such funny LinkedIn posts” (just kidding, that rarely happened), to which I’d generally respond with this:

1. Getting an internship is super important to getting a full-time job after graduation, since you’re likely to get a full-time job offer if you did well in the internship

2. The more experience you have, the easier it’ll be to get more experience (since you’ve demonstrated your skills and abilities before)

3. Logically, the first internship will be the hardest to get

4. Therefore, apply to a shit ton of internships when starting out and try to get something, anything really. I started calling this the “spray and pray” strategy, since you’d be “spraying” your resume everywhere and “praying” it’d stick somewhere. I’ve written about my professional journey before, but long story short, I applied for 50 internships during my freshman year at UCLA (all at First Republic Bank, where I got one interview in Lending Services and ended up there the following summer), about 100 internships my sophomore year (and got significantly more offers, ~10), and only to a handful my junior year at top consulting firms. I ended up with an offer from BCG Seattle

Crucially, when spam-applying to all these summer internships, you’d ideally tailor your resume to highlight experiences most relevant to that job. And since resumes are usually read by an automated grading machine (a so-called “Applicant Tracking System”, or ATS) before ever being looked at by a recruiter, having a well-formatted resume full of target keywords that matched the job listing was vital to getting that first interview.

Back in my day (about 3 years ago), I had to do this all manually: I’d spend hours scouring job listings, changing verbs from “led” to “spearheaded” to “masterminded” (and etc.) depending on the particular listing, then applying to dozens of jobs with these custom resumes. As you can imagine, this would take forever.

But on this walk with Justin today, we discussed how it would probably be super easy to do this with AI. Of course. EVERYTHING WITH AI!!! (preferably with the word “agentic”)

Quickly, we hammered out the steps on how to do this:

1. Upload my resume, LinkedIn profile, this blog, and my travel blog to ChatGPT’s custom GPT maker

2. Give it extremely detailed instructions on what to do (tailor my resume, I have the exact wording below)

3. Create the GPT

4. Once created, simply give it the link to a job listing, and it’d automatically edit the bullet points for each of my experiences to best fit the provided listing

5. Celebrate

Sounds pretty doable. Fortunately, I wasn’t doing too much right when I got home, and figured that this project wouldn’t really take that long. Maybe 15-20 minutes to create the GPT and fine-tune it to output the correct stuff, and then I’d be pretty much set. Plus, I’d get a nice blog post out of it. (hello!)

So I did that, and it worked great. Check it out here!

Important notes and lessons learned from this mini-project, which are listed below in no particular order:

• The custom GPT can’t actually create the Word document or the PDF itself, only the text (despite saying that it could and then making me wait while it “generated” nothing). It can create the tailored bullet points, but I still had to input them into my resume template in Word. (For tips on this, check out my resume guide!)

• It took a bit of follow-up questions to fine-tune the output to what I was looking for, since the GPT creation interface didn’t seem to understand my simple directions to keep the section headers exactly the same. I’m used to using Perplexity for my projects, and that never hallucinates, so this experience kinda reminded me why I stick with my preferred AI tool lol. At the moment, however, you can only create these custom GPTs with ChatGPT easily

• Some job listings block AI crawlers, so for those, I couldn’t just give the GPT model the job listing link. For these, I simply copy-pasted the text of the job listing and that worked perfectly fine for creating the tailored bullet points

• It’s crazy how much time and mental energy this saved. Obviously, write your own initial bullet points to make sure they’re truthful and accurate, but once you have those the GPT can tailor them as needed. It’s crazy how many hours this would’ve saved me if this were around in 2022

Below is the exact text I used to customize the GPT:

Hey there! I’d like to create a custom GPT that tailors my resume to job descriptions with ATS-optimized formatting. Here are your instructions below, and I’ll also add some references for you to use. These are the current resume in PDF form, my LinkedIn account, and my personal and professional blogs. I’ve written a resume guide on my professional blog that I’d like you to reference as well.

(Resume attached)

LinkedIn: https://www.linkedin.com/in/dennis-gavrilenko/

Professional blog: https://www.interosity.co

Professional blog resume guide: https://www.interosity.co/p/resumes-101?r=tbrbl

Personal blog: https://www.adventurewithdennis.com/

ROLE: You are an expert resume writer, ATS optimization specialist, and recruiter.

TASK: When the user provides a job posting, analyze it and create a tailored resume.

PROCESS:

1. Analyze the job description for key skills, keywords, and qualifications

2. Reference the user’s uploaded resume and LinkedIn profile

3. Create a new resume version that:

   1. Highlights relevant experience matching the job requirements

   2. Incorporates high-impact keywords from the job description

   3. Maintains the user’s original formatting style and structure

   4. Ensures ATS compatibility (single-column, no tables, clear formatting)

   5. Uses action verbs and quantifiable results where applicable

4. Present the tailored resume in both PDF and Word format

CONSTRAINTS:

1. Only use truthful information from the provided documents

2. Maintain consistency with original experience and achievements

3. Flag any gaps between job requirements and background with [MISSING SKILL/EXPERIENCE]

4. Format should be ATS-friendly (avoid images, complex formatting, special characters)