Build a Job Outreach Automation Tool !!!

Hey everyone!

I'm excited to share a recent project — Job Outreach Automation, a Python tool I built to solve a very real problem from my own job search: personalizing and sending job-application emails to a large list of recruiters, without it turning into either hours of manual repetitive work or a risky spam-triggering bulk blast.

This project pushed me to think beyond "just loop and send an email" — into rate limiting, idempotent design, and handling sensitive data safely in a public codebase.

🧩 Tech Stack

Language: Python 3 (standard library only — no external dependencies)

Email: smtplib, email.mime for SMTP sending with attachments

Data: CSV for contacts and send-log tracking

CLI: argparse for dry-run and limit flags

Auth: Gmail SMTP with App Password authentication

💡 Project Overview

The tool takes a CSV of contacts (name, email, title, company), personalizes an email template per recipient, attaches a resume, and sends it through Gmail's SMTP server — while staying safely under sending limits and never emailing the same person twice, even across multiple days of runs.

Core features:

➕ Personalized emails — dynamically fills in each recipient's name and company

📋 Resumable & idempotent — every send is logged to CSV, so re-running the script never double-emails anyone

⏱️ Rate-limited sending — configurable daily limit + randomized delay between sends

🧪 Dry-run mode — preview exactly what would be sent, before sending anything for real

📎 Auto-attachment — resume gets attached to every email automatically

⚙️ How It Works

python send_emails.py --dry-run --limit 5 # preview only, sends nothing

python send_emails.py --limit 2 # small real test

python send_emails.py # sends up to the daily limit

🔐 Handling Sensitive Data

Since this touches real credentials (a Gmail App Password) and real personal data (other people's names and emails), I split the repo into a public, safe-to-share layer and a private, gitignored layer:

config.example.py / contacts.example.csv — safe templates, committed to the repo

config.py / contacts.csv / sent_log.csv — the real, personal versions, excluded via .gitignore and never pushed

This felt like an important habit to build early — even a small personal script shouldn't leak credentials or other people's data just because it's "just a side project."

🎯 What I Learned

Designing for idempotency using a persistent log instead of in-memory state

Balancing automation vs. platform trust — every feature that makes a tool "more automated" also makes it look more bot-like to spam filters, so restraint is a design choice, not a limitation

Structuring a small CLI tool with dry-run as a first-class mode, not a bolted-on flag

This was a great reminder that the hardest part of automation tooling usually isn't the "happy path" — it's the constraints around it: rate limits, safe resumption, and protecting sensitive data, even in a small personal-use script.

🔗 GitHub Repository

👉 View the source code: https://github.com/tejasviurka/Job-Outreach-Automation