Cold Email Outreach — Summer 2026 Internship

A fully automated cold email pipeline I built to reach small tech companies in the Frisco/Plano TX area for a paid summer 2026 internship. The whole thing runs locally, reads from a CSV, sends through Gmail, and handles follow-ups automatically.

---

How It Works

The pipeline has two versions. V1 targeted a broader list using generic contact emails. V2 was rebuilt from the ground up with named human contacts found through LinkedIn and company websites, a shorter and more personal email template, and the resume attached to every send.

Finding Contacts

For v1, most contacts were pattern-guessed from company domains (info@, careers@, hello@). The bounce rate on that batch was high enough to rethink the approach entirely.

For v2, every contact was researched via LLM. I looked up each company on LinkedIn, found the founder, CEO, CTO, or head of engineering, confirmed their name and role. Every address in v2 is tied to a real person, not a catch-all inbox.

Email Template

The emails are short on purpose. The format is:

1. Name, major, and school
2. One sentence about what the company does (specific to them, not generic)
3. One thing from my resume that actually overlaps with their work
4. A soft ask about a summer internship
5. Note that resume is attached

Follow-ups

When an initial email is sent, a follow-up date is automatically set for 3 days later. A scheduled task picks these up and sends the follow-up without any manual work. If a company responded, bounced, or had a wrong address, the follow-up is cancelled automatically.

---

Results

V1 batch (generic contacts)

• 41 emails sent
• 12 bounced, 1 wrong contact, 1 blocked, 1 location mismatch
• 26 delivered
• 28 follow-ups sent
• 0 useful responses
• Lesson: generic inboxes have high bounce rates and rarely reach a decision-maker

V2 batch (named human contacts)

• 20 emails sent to specific named people (founders, CEOs, engineers)
• 5 bounced
• 15 delivered
• 14 follow-ups sent
• 2 interviews, 2 offers received, both rescinded (better offers already in hand)

Combined

• 61 total emails sent across both batches
• 41 delivered
• 42 follow-ups sent
• 2 offers from 15 delivered v2 emails (13% offer rate)

---

File Structure

companies.json        hand-curated v1 company list with alignment keys
companies_v2.json     v2 company list with named contacts and per-company notes
tracker.csv           v1 contact email mapping
tracker_v2.csv        v2 contact email mapping (all named people)
generate.py           writes one personalized email per company to emails/
generate_v2.py        v2 email generator using the shorter humanized template
build_master.py       merges v1 data into master.csv
build_master_v2.py    merges v2 data into master_v2.csv
send_emails.py        sends initial emails and follow-ups via Gmail SMTP
master.csv            v1 working file (41 companies)
master_v2.csv         v2 working file (20 companies)
emails/               v1 personalized email files
emails_v2/            v2 personalized email files
Manil_Shangle_Resume.pdf  attached to every v2 send

---

Setup

Create a .env file in the project root (already in .gitignore):

GMAIL_APP_PASSWORD=your16charapppassword

Generate one at myaccount.google.com/apppasswords. Requires 2-Step Verification to be on.

---

Workflow

Step 1 — Generate emails

python3 generate.py        # v1
python3 generate_v2.py     # v2

Step 2 — Build master CSV

python3 build_master.py    # v1
python3 build_master_v2.py # v2

Step 3 — Dry run

python3 send_emails.py --dry-run
python3 send_emails.py --master master_v2.csv --dry-run

Step 4 — Send

python3 send_emails.py --attach Manil_Shangle_Resume.pdf
python3 send_emails.py --master master_v2.csv --attach Manil_Shangle_Resume.pdf

Step 5 — Follow-ups

Follow-ups go out automatically 3 days after each initial send via a scheduled task. To trigger manually:

python3 send_emails.py --followups
python3 send_emails.py --master master_v2.csv --followups

---

Useful Flags

Flag	What it does
--dry-run	Preview without sending
--only "Company"	Send to one company only
--limit N	Stop after N emails
--delay N	Seconds between sends (default: 15)
--test-to you@gmail.com	Send one email to yourself without marking it sent
--followups	Send follow-ups instead of initial emails
--attach path/to/file	Attach a file to every email
--master path/to/csv	Use a different master CSV (default: master.csv)