Side project feedback please and thank you: Automated Job Hunt Spreadsheet

From a product value perspective, this idea is extremely good. You are taking a manual behavior that everyone is already doing and automating it with the power of code, which is the classic value add of software. This tool would also make it very easy for folks to follow the advice in our job searching course about building and understanding your interview funnel.

The problem with this idea is that it's very complex despite technically being a solo-player app:

1. The technology is complicated - You need to ingest the data from Gmail (3rd party integrations are always hard due to regular API/SDK changes), process it with an LLM (which won't always get the interview stage right I'm sure as this is fuzzy data), and then convert everything into structured data (the schema is no joke either, and you'll probably need a lot of fields).
2. You need the UI to be good - You are competing with someone just manually organizing their emails into certain folders/tags, and the Gmail UI is honestly not too bad. You need to be a step function better to be able to attract users, which means that your UI really does need to be clean, smooth, and intuitive. The design bar is high as Sai mentioned.

In short, you will need to be both good and back-end and front-end for this to have a real chance at success. The bright side is that even if this side project doesn't get any real traction, I'm sure you'll learn a ton just building it.

As for an MVP, I'm having trouble scoping it down into something super-duper simple that also provides some modicum of user value. I'm thinking you need to set up the Gmail ingestion (obviously), and from there, just have the LLM parse out a company and a status enum field? From there, you show it in a table of some sort. That should be enough to share, and if you really grind at it, I think you can have something decently polished in 1 week?

I've actually talked with other Taro members who have had a similar idea and tried building it, but none of them succeeded due to the aforementioned high quality bar. That being said, you are a senior engineer already, so you'll have a better shot.

If you are able to pull this off, this will easily clear 10,000+ users and probably hit 100,000+ and maybe even 1 million+ as well. This is one of those side projects that can easily be turned into a legit tech startup if there's enough traction.

Good luck!

Yes, email scraping would be the stickiest point that'd keep me from using this app (not saying this to discourage you but to highlight the extreme trust issue involved here). (Also, while GMail is ubiquitous, people use other email services as well.)

When it comes to GMail though, you could try to use Google Apps Script that provides a native integration with GMail. But you'll likely still need to wrap this up in your app, which takes us back to the original problem.

The key finer point I want to make is this:

Regardless of the tech and trust solution, you're converting highly unstructured data to structured data and applying heuristics to predict the stage of any particular interview. The stakes are quite high—mis-prediction can mess up the interview pipeline for a given company very badly!

So, I recommend that you show a snapshot of the email(s) that you processed to infer the interview stage in the UI, and give the user an easy way to correct the prediction made by your system.

Also, I know this is quite ambitious already, but a neat extension would be some scraping basic facts about the company and culture and presenting it to the user—homework that savvy candidates do manually today and hopefully take notes on as part of their interview prep. It can become rather time-consuming.

I'll be curious to know how this pans out!

So fun development, the project got chosen to be worked on in a partnership with the University of Toronto’s Intro to Software Engineering class this Spring 2025. Any helpful resources on remote collaboration would be greatly appreciated!

I love this idea! Job seekers need all the help they can get, and a seamless tool to reflect on the job search process is valuable. Why I like this idea:

• You're taking an existing user behavior and making it much easier. You're not introducing a new user behavior, so the likelihood of adoption is much higher.
• You're integrating with (or planning to) Google Spreadsheets, which is where the majority of engineers already track their applications. This is better for you since it's less to build, and better for the user since they don't have to completely overhaul their workflow.
  • The main value you're providing is the core infra of trawling through my email and determining the next step.
• There's a clear "why now" -- I'm guessing you're sending the emails into an LLM to determine if the email indicates a rejection, phone interview, offer, etc? This would have been hard/impossible 3 years ago, but is very achievable now.

A few thoughts:

• Could you show a 5-10 second video/gif of the tool? That would help people understand the core value and get excited by it.
• One concern I'd have as a user is data protection. Is your tool going to read through all emails in my inbox? That would make me nervous. Or can I somehow indicate which emails are job related (e.g. only find emails that contain the list of companies in my spreadsheet). Probably worth having some messaging around that.
• What are your plans to get initial users? Perhaps a Reddit or LinkedIn post where you offer to do "personalized onboarding" with the user so they can actually get value from it.