Day 10 of 28 · AI Job Hunt
Cover Letters That Actually Get Read
⏱ 5 min
📊 Beginner
Let's address the elephant in the room: do cover letters even matter?
The honest answer: it depends. Some hiring managers read every one. Others skip them entirely. But here's what's true across the board — a great cover letter never hurts, and a generic one actively hurts. The problem was always the time investment. Writing a genuinely good cover letter used to take 20-30 minutes.
With AI, it takes 3-5 minutes. That changes the math completely.
The structure hiring managers actually want to read.
What makes a cover letter get read
The cover letters that get read have three things in common:
1. They're specific to the company. Not "I'm excited to apply to your company" — but "I'm excited about [Company] because your recent expansion into enterprise suggests you need someone who can scale customer success operations."
2. They answer "why you, why here." Not your life story. Just two things: why you're great for this role, and why this company specifically appeals to you.
3. They're short. 150-250 words. Three paragraphs max. Nobody reads a full-page cover letter.
Knowledge Check
What's the ideal length for a cover letter?
B
150-250 words — three paragraphs that answer "why you, why here"
C
As long as possible to show thoroughness
D
A full page (400+ words)
Short and specific beats long and generic every time. Hiring managers are scanning, not reading novels. Three punchy paragraphs — a hook, your value, and a close — is all you need. AI can draft this in under 3 minutes.
Write a cover letter for a Customer Success Manager role at Notion. I have 4 years of CS experience at B2B SaaS companies, managed a $3M book of business with 95% retention, and I'm a personal Notion power user. Keep it under 200 words.
**Dear Hiring Team,**
I'm applying for the Customer Success Manager role at Notion — a product I've used daily for three years to manage everything from client portfolios to personal projects. That's not a line for a cover letter; it's genuinely how I organize my life.
In my current role, I manage a $3M book of business across 45 B2B accounts with a 95% retention rate. I've built QBR frameworks, driven expansion revenue, and reduced churn by identifying at-risk accounts before they escalate. The part I enjoy most is helping customers discover workflows they didn't know were possible — which is exactly what Notion does as a product.
I'm drawn to Notion specifically because I believe the best CS teams don't just support customers — they make customers love the product. I'd love to bring my SaaS CS experience and genuine product passion to help Notion's customers unlock more value.
I'd welcome the chance to discuss how I can contribute.
Best,
[Your name]
---
**Word count: 167**
**Why this works:**
- Opens with a genuine, specific connection to the product
- Includes concrete metrics ($3M, 95%, 45 accounts)
- Bridges personal passion with professional capability
- Under 200 words — respects the reader's time
↻ Replay conversation
The cover letter formula
Every strong cover letter follows this structure:
Paragraph 1 — The hook. Something specific about the company or role that caught your attention. Not flattery — a genuine insight. "Your recent launch of [feature] tells me you're investing heavily in [area] — and that's exactly where I've spent the last 4 years."
Paragraph 2 — Your value. Two to three sentences about what you bring. Include one metric. Connect your experience directly to what they need. This is the "why you" paragraph.
Paragraph 3 — The close. Why this company specifically. What excites you about the opportunity. A simple, confident close.
That's it. No fluff, no life story, no "I am writing to express my interest in the position of..."
Knowledge Check
What should the opening line of your cover letter do?
A
List your years of experience
B
Express general excitement about the company
C
Make a specific, genuine observation about the company or role that shows you've done your research
D
State your name and the position you're applying for
A specific opening earns the reader's attention. "Your recent expansion into enterprise" or "I've been a Notion user for 3 years" tells the hiring manager this isn't a mass-mailed letter. That 5 seconds of research (which AI does for you) separates you from 90% of applicants.
Batch-producing cover letters
Here's the workflow that lets you write personalized cover letters at scale:
Step 1: Feed AI your master document (background, skills, achievements).
Step 2: Paste the job description and company name.
Step 3: Prompt: "Write a 150-200 word cover letter for this role at [Company]. Use my background to create a specific, personalized letter. Open with something specific about the company. Include one metric from my experience. Keep the tone professional but human."
Step 4: Spend 60 seconds reading it. Tweak anything that doesn't sound like you.
With this workflow, you can produce 5-10 personalized cover letters per hour. Each one reads like you spent 30 minutes on it.
Final Check
What's the biggest mistake people make with AI-generated cover letters?
A
Including specific metrics
C
Sending them without reading them — AI occasionally gets details wrong or sounds too generic, and 60 seconds of review catches these issues
D
Using AI at all for cover letters
AI is your drafting partner, not your final editor. Always read the output before sending. Check that company details are accurate, metrics are correct, and the tone sounds like you — not like a robot. That 60-second review is the difference between "impressive" and "obviously AI-generated."
✉️
Day 10 Complete
"The best cover letter isn't the longest. It's the one that makes the hiring manager think: 'This person actually cares about THIS role at THIS company.'"
Tomorrow — Day 11
LinkedIn Profile Makeover
Tomorrow you'll transform your LinkedIn profile into a recruiter magnet with AI.