How An AI Job Coach Landed Me A PayPal Offer

This story is based on a conversation with Amar Saurabh, a product manager in his 30s from San Mateo, California.

After spending five years in product management at major tech companies like Meta and TikTok, I was ready for a change. I enjoyed the fast-paced environment at TikTok, but I wanted to find a more established and stable company in the US. So, in April, I began my job search.

Amar Saurabh says building a custom GPT for his job search only took about an hour and a half. (Credit: Amar Saurabh)

The Challenge of a Modern Tech Job Hunt

The initial two months were slow. Despite sending out numerous applications, I only managed to secure two or three interviews. The process was tedious, especially when it came to personalizing outreach messages to recruiters on LinkedIn. It took a significant amount of time, and I wasn't seeing the results I wanted.

Why Standard ChatGPT Wasn't Enough

I turned to ChatGPT for help, hoping to speed up the process of drafting messages. However, I quickly ran into problems. The responses were often generic and not tailored to my specific background. Because I use ChatGPT for everything from recipes to workout plans, it seemed to get confused and would mix up contexts.

It constantly asked me to re-upload my résumé or provide details about my career history, which defeated the purpose of using it for efficiency. This frustration led me to an idea: what if I created a specialized AI assistant exclusively for my job search?

Building a Personal AI Job Coach in Under Two Hours

I decided to build a custom GPT. These specialized AI assistants are accessible through ChatGPT's platform. While a free tier is available, I opted for the paid subscription at $20 a month to upload more documents.

The process was surprisingly simple. I created a new custom GPT and named it "PM job search advisor." I then fed it my résumé, my LinkedIn profile, and detailed information about the projects I had worked on throughout my career. I also gave it the specific context that I was targeting a senior-level product management role. In total, it took me about an hour and a half to get it fully prepared.

Putting the Custom GPT to Work

Once my AI advisor was ready, I put it to work. I started by asking it to draft customized messages for recruiters. I could specify the format, whether it was a short 300-character LinkedIn request or a longer email. It could even help me identify the right people to contact for a specific role and find their email addresses.

When applying for jobs, I used it to refine my résumé, ensuring it aligned perfectly with each job description. It was also an invaluable tool for interview preparation. I would provide the job description and my interview date, and then ask questions like, "What aspects of my experience should I highlight?" and "What questions should I anticipate?" This saved me countless hours of trying to recall specific details from my past projects.

Of course, it wasn't perfect. Sometimes it would forget details, and I’d have to remind it of a previous conversation. It would apologize and correct itself, much like a human assistant would. Overall, though, it performed exceptionally well.

From Frustration to a Flood of Interviews

The impact was immediate. While the number of applications I sent remained the same, the response rate skyrocketed. Over the next two months, I landed seven interviews with top companies, including Reddit, Intuit, and PayPal.

My custom GPT helped me through the entire process with PayPal, from writing the initial outreach email to preparing for each interview round. When the offer finally came, I even used my AI coach to help me negotiate my salary.

I officially accepted the role of lead product manager at PayPal. If I ever find myself in the job market again, I would absolutely use this method. The benefits are clear, and the technology is only improving. My next goal is to develop my GPT to have agentic capabilities—meaning it could handle applying to jobs and answering initial questions on my behalf.