I Used ChatGPT to Find Freelance Jobs. Here’s What Surprised Me

Job hunting has never felt more bizarre. Friends are getting interviewed by AI agents without realizing it until halfway through the call. And now, AI tools are helping candidates fight back.

Indeed recently launched an app inside ChatGPT, bringing job search directly into the chatbot interface. I’m a freelance journalist always hunting for contract work, so I had to try it. Here’s what actually happened.

Setting Up the Indeed App in ChatGPT

Getting started is pretty painless. You download the Indeed app from ChatGPT’s apps menu, then connect your existing Indeed profile. Once linked, it pulls in your saved preferences and resume details to personalize your search.

But before you connect anything, pause and check your privacy settings.

Head to Account, then Profile inside Indeed, and make sure your resume doesn’t include your home address, phone number, or email. According to an Indeed spokesperson, the integration doesn’t share your physical address, phone number, or login credentials with ChatGPT. Still, I’d personally opt out of the “Access my Indeed Profile” option just to be safe.

Also worth knowing: Indeed can access your past ChatGPT conversations through this connection. Read the terms and conditions carefully before completing setup. If you’re already cautious about what you share with AI chatbots, this is definitely a step where that caution pays off.

Once connected, you’ll see the Indeed icon inside ChatGPT. You can also call it up anytime by typing @Indeed in the chat box.

Conversational Job Searching Feels Surprisingly Natural

I kicked things off with a casual prompt. Something like “writing jobs in New York City that match my editorial and commercial experience.” No complicated filters, no dropdown menus. Just talking.

The results mirrored what you’d see on Indeed’s native platform. A scrollable list of job listings that expand into a larger window. Familiar enough that it didn’t feel jarring.

What I didn’t expect was the commentary underneath the listings. ChatGPT offered a breakdown of why specific roles matched my background, highlighted relevant market signals, and gave me a list of keywords to sharpen my search. That part was genuinely useful. It felt less like browsing a database and more like getting advice from someone who had actually read my resume.

Where It Gets Really Interesting

I kept chatting rather than just scanning listings. I asked follow-up questions, added more context about my interests, and the results shifted accordingly.

At one point, I asked it to narrow things down to reproductive health writing roles. It found jobs I wouldn’t have thought to search for directly. Plus, it reframed how I think about my own value as a candidate, which was something I could feed back into my resume and website copy.

The most useful moment? I asked, “Where would I fall short with this job?” It gave me a candid, specific answer. No sugarcoating, no hollow encouragement. Just honest insight about gaps I should prepare to address in an interview. That kind of directness is rare, and it’s exactly what job seekers need right now.

The One Frustrating Limitation

You can’t apply for jobs directly inside ChatGPT. Once you find something promising, you click through to Indeed to actually submit your application.

Honestly, that broke the flow a little. The whole appeal of having a single interface collapsed the moment I needed to switch platforms. But maybe that’s not really the point. Maybe ChatGPT is meant to be the smart front end of the search, and Indeed handles the official mechanics on the back end.

Should You Try It?

If you’re already using Indeed for job hunting, this integration adds real value. The conversational format surfaces insights you’d never get from typing keywords into a search bar. It’s not replacing LinkedIn or Indeed. It’s more like having a thoughtful coach walk alongside your search.

Could you find the same jobs by going straight to Indeed or Googling around? Probably. But the chatbox experience pushed my thinking in ways a traditional search wouldn’t have. For freelancers, contractors, or anyone trying to reframe how they pitch themselves, that extra layer of reflection is worth something.

The job market is rough right now. Any edge helps.