I made an AI tool to run my job search, and it helped me get my dream role
When I turned to AI to help with my job search, I was five months into it and wasn't getting the traction that I thought I would get. I felt like I had done everything, which obviously was not the case. When you're in a moment like this, you can feel stuck and be blinded to the possibilities.
So, I went to AI and said, "I don't know what to do. I'm an exec in tech, and here's my résumé. I'm applying to these jobs, and I'm not having a lot of success."
It was able to walk me back from the edge and say, essentially, "Look, you're at this level, and your average job search time should be ABC, and you're only this far in. So, first, calm down."
It sounds silly, but it was really helpful to hear. Then it went on to say, "Now, let's talk about some things. I'm hearing what you did do, but here are some things that maybe you could do that I'm not hearing."
A research partner
Some of its suggestions were unexpected. One was to make a cake for someone, because it was a company that appreciates bold moves. I don't know if that was really good advice, but it did come up with that.
It would also suggest how to tailor a message to a particular person. Or, for example, to use email, not LinkedIn, because they're not active on LinkedIn — those sorts of tidbits.
One of the taglines I've developed from my experience is that one way to think about AI is not as a tool but as the world's best expert in whatever you need help with. The more you leverage AI through that lens, the more you get out of it.
I used it to create what's called a panel of experts. Now, you've got AI playing multiple roles at once. It can slice and dice and give you different views and a synthesized opinion.
Another example is downloading the profile information for the person you're going to interview with. You can have AI assume the role of the interviewer and do a mock interview, and you can do it live with your voice, and then get feedback on how you performed.
It also started calling out things like applying to incremental CEO roles. It recommended doing more cold outreach, which I hadn't leaned into too much. It helped me figure out a plan that worked for me and language that worked for me to do that, and it gave me concrete steps.
'You're missing it'
The way that I ended up at Pearl is interesting. When I saw the job description, I passed it up because, on paper, it's different from anything I'd done before. Now it's laughable, because I'm in it, and everybody's connecting my passion and my past with the role.
Maybe a week later, I saw the posting again and thought, "Why am I saying 'no' to myself? Let me just drop this thing into CareerBuddy GPT and see what it says.
I didn't think that I was qualified, but I said, "Give me your objective assessment." It came back and said, "Hey, you're missing it. Your résumé doesn't speak to it, but here's how your experience aligns."
It encouraged me to apply. So, then I did the network outreach, and I had a connection, which helped open the door. One thing led to the next. But what got me to apply was leveraging AI to the extent of not only answering, but also truly advising. I say trust, but verify.
It told me to do something different than what I thought was right. I can represent me, what I am, and what I'm not. AI can look between the lines and challenge and question.
When I was interviewing with our CEO, he asked me, toward the end of the interview, what my dream job was. I got about 15 to 20 seconds into stumbling around, and I said, "Look, I'm just going to be honest with you. I don't know how to spin this to make it sound good, because the honest answer is this: This job is my dream job."
No more throwing darts
After I started using AI, my job search still took a bit of time — maybe another five months or so. But I went from feeling like I was just throwing darts to where it felt much more targeted and precise. And, I'd gone from essentially getting no response to finding the right opportunities, having conversations, and it was a matter of finding the right fit. That can take time.
We're in a moment when people and companies are about to be left behind, and I want to help that not be the case. The opportunity to go to a company that really gets it, is going after this full force, and wants to rewire with AI — that sounds like the hardest role of my career, but also the most fun and the most relevant thing I could be doing for this moment.
So, not only did I stumble into the job, but I stumbled into my dream job.
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