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AI Job Search: My $340K Headway Offer, Including a $20K Sign-On
I used AI throughout my software engineering job search: first to improve my resume, then to find roles that matched my preferences, and finally to fill out and submit applications. That process led to my Headway offer. The $340,000 compensation figure discussed in this video includes a $20,000 sign-on bonus; it is not a $340,000 base salary or a recurring sign-on payment.
I start with a resume template, draft my experience with AI, and ask two separate models to grade the resume. I feed their feedback into revisions. Then I give Codex my resume and preferences for compensation, location, and remote work. It builds a spreadsheet of matching roles and applies through company websites, leaving longer written questions for me to handle together later. I also point it toward sources such as the Y Combinator directory and Levels.fyi's internship pay page.
Transcript
0:00I'm a software engineer and I
0:01just got a job offer where
0:02I'd make over $340,000 per year
0:06and that includes an outstanding
0:08$20,000 sign on bonus Here's how
0:11I find these types of jobs
0:13Spoiler alert I use AI literally
0:16throughout the entire process So
0:18if you're a computer science
0:19student and you're trying to break
0:21into big tech and you're tired
0:23of sending out 100 200 even
0:26500 applications and not getting any
0:29response from the jobs of your
0:32dreams then stop and save this
0:36video Step one I use AI
0:37to grade my resume I start
0:40with an online resume template I
0:43fill in my experience usually
0:45using another AI tool and then
0:48I give my resume to two
0:50different AI models usually a model
0:53like Claude Opus and also a
0:56model like Google Gemini But it
0:58doesn't really matter which models
1:00I want to give it to
1:01at least two distinct AI models
1:04And I will say this simple
1:06prompt to these models I'll say
1:08grade this resume After it gives
1:11it a grade I give the
1:13feedback to the AI model and
1:15I keep fixing the resume with
1:17the feedback until I get at
1:19least A− from two different AI
1:22models Step two I use AI
1:25to find my roles I basically
1:27go to Codex drop in my
1:30resume and I tell it to
1:32find roles that I'm actually interested
1:34in I give it my preferences
1:36for compensation my preferences for my
1:39location whether or not they have
1:41to be remote friendly I give
1:43it everything I actually want to
1:46find in my next role Codex
1:48then autonomously creates a
1:49spreadsheet of all the jobs that
1:51fit my preferences and I then
1:54tell Codex to apply to all
1:56of them I say if they
1:57have a text box that says
1:59why do you want to work
2:00here then skip it for now
2:02We can do that together later
2:03But for right now apply for
2:06all the jobs I also might
2:08give Codex a little bit of
2:10direction I might drop in the
2:11Y combinator directory for
2:13startup jobs or I might drop
2:15in levels fyi internship page
2:18with the knowledge that if you're
2:20paying your software
2:21engineering interns $150 an hour then
2:24you're probably paying your senior
2:26level engineers just a little bit
2:28more Codex will open the
2:30applications on the company website
2:33fill in the applications and
2:35then submit it autonomously By
2:37doing this process I was able
2:39to get some of the best
2:41tech jobs of my dreams and
2:44I now have a software
2:46engineering job Good luck
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