Job Search ยท Reflections

I Treated My Job Search Like a Product to Build

And then I rebuilt the product four times.

Job SearchAI ToolsBuildingAutomationReflections

I graduated into a difficult market. Not just difficult in the "hiring is slow" way. I was an early career person trying to move from software engineering into a product role. Two years of prior experience. Competing with people who had been PMs for five years. The conditions were already stacked a certain way and I knew it.

So I made a decision pretty early on: I was not going to out-apply everyone. I was going to out-think it. What happened next was honestly one of the most chaotic, interesting, frustrating, and skill-building periods of my life. And I want to write it down.

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First: The Problem I Was Actually Solving

Job applications are time consuming. That part is obvious. But the real problem is not just volume. It is that everything requires the same amount of effort even when it should not.

Writing a cover letter. Researching a company. Finding the right person to reach out to. Following up. Keeping track of who you talked to. Every single task eats your day and most of it is just process, not thinking.

And then AI came along and made it faster for everyone. Which sounds great. Until you realize that if you are using Claude to write your cover letter and the next 500 applicants are also using Claude to write their cover letter, you are not standing out. You are just doing the same thing faster.

That is the problem I kept coming back to. Not just "how do I do this faster" but "how do I do something that other people are not doing."

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The First Thing I Built: A Resume Customizer on Lovable

Resume Customizer

Built with Lovable

Scrapped

Upload a resume, paste a job description, get customized bullet points back.

Lesson: The bottleneck was not the formatting. It was the research and the personalization.

What I learned from building it was more valuable than the app itself. I learned how to think about what the actual bottleneck is before I start building. And that became the seed of everything that came after.

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Then I Found Clay

I started using Clay on the free plan. You can only export 100 people maximum so I had to be very strategic about who I was pulling and what filters I was using. This alone taught me something real: when you have limited resources you get very good at defining your criteria precisely.

I also used Clay to generate personalized LinkedIn messages. And then I stopped, because I noticed something. Everyone was doing the same thing. The messages felt generated. Recruiters and founders could tell. The personalization was surface level because it was all coming from the same type of prompt. That was a pattern I kept running into. Every time AI made something easier for me, it also made it easier for everyone else. The tool was not the advantage. How I used it was.

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The App That Taught Me the Most

Research-First Cover Letter Tool

Built with Lovable + Anthropic API

Actually proud of this one

Upload resume and JD. Research the company. Save context you care about. Generate a cover letter that actually includes what you found interesting.

Lesson: Less like AI writing for you. More like AI helping you write better.

How the flow worked

1Upload resume and job description
2Research tab: find what actually interests you about the company
3Save specific points โ€” culture, AI products they're building, mission
4Filter research down to what's relevant to your profile
5Add your own notes before generating
6All context โ†’ Claude โ†’ cover letter that sounds like you

Did it save me time? Honestly, not that much at first. But it taught me how to think about user flows. How to use AI not as a replacement but as a layer. How to build something that respected the human judgment that should still be in the process. That ended up mattering a lot when I was talking to hiring managers about how I think about product.

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The Automation Era

At some point I went deep on automation and it got kind of wild.

n8n
Scraped job boards, pulled listings into Google Sheets, scored resume against JDs, flagged high-scoring ones by morning
OpenClaw
Searched Google, Indeed, and other boards simultaneously. Sent top listings every morning on WhatsApp. Folder per job, cover letter pre-drafted
Clay + Claude
Connected as a connector into the workflow for personalization at scale
And then I had a moment where I looked at all of this and thought: wait. I am spending more time building the pipeline than using it. The automation becomes the project and the actual goal gets a little blurry.

What it did teach me though: how to think in systems. How to chain tools together. How to build something that runs without you watching it. Those are real skills and I use them constantly now.

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The Cold Email Problem

Sending cold emails is also a time consuming task. When you are emailing three people at the same company for the same role the emails are almost identical. So I built a Google Sheet with columns for name, company, title, subject line, and body. The body column used Excel formula syntax to pull the person's name and company into a template dynamically.

The setup

Google Sheet: name, company, title, subject, body columns
Body column uses formula syntax to pull name + company into template dynamically
Different sheets for different role types
n8n grabs resume from Drive + pulls sheet + batch sends
What took an hour now takes a few minutes

I also tried Phantombuster for LinkedIn connection requests. Fourteen day free trial. It was reaching people I never would have found manually and the acceptance rate was around 10 to 20 percent. The subscription is expensive though. If you are doing very targeted outreach it can be worth it.

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The Personalized Website Move

This one was a little unhinged but I loved it.

When there was a role I really cared about, especially at a startup, I would build a quick personal website using Lovable specifically for that role and sometimes for that specific person I was reaching out to.

The process

Give Claude my resume and the job description
Claude generates a Lovable prompt
Lovable builds the site using my saved design screenshot as a style reference
Always came out in the same visual style
Not just "here is my resume." Here is a thing I made for you specifically.
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What the Whole Thing Actually Taught Me

1

Token awareness is a real skill

When you are running automations and pipelines all day you hit your API limits faster than you expect. Being mindful about what goes into a prompt makes the output better anyway.

2

Personalization beats volume every time

The cold emails that got responses were not the ones from the batch sends. Two genuinely personal emails a day beat twenty templated ones.

3

Building things is a better portfolio than describing things

Every project I built during the search became something I could talk about โ€” not in a "here is a thing I did" way but in a "here is how I think" way.

4

The tool is never the advantage

Claude, Clay, n8n, Lovable, Phantombuster โ€” all available to everyone. The advantage is knowing when to use which one, how to combine them, and when to stop automating and do something human instead.

5

Speed is a learnable skill

I built things in a day that I would have said would take me a week six months ago. Not because I got smarter but because I got better at scoping, prompting, and knowing what done looks like.

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The Honest Part

Not everything worked. Some of the automation was honestly busywork dressed up as productivity. There were weeks where I was building workflows instead of having conversations, and conversations are what actually move a job search forward.

The search took longer than I wanted. It was hard in ways that were personal and not just logistical.

But I came out of it with skills I genuinely did not have before. Technical skills, yes. But more than that: the ability to look at a messy, overwhelming process and ask "what is actually broken here" and then go build something for it. That, I think, is the thing worth writing down.

SD

Sukriti Dubey

Cornell MEng ยท Software Engineering, Product, and Data ยท Bay Area