Cover Letter

The 3 Tiers

Always recommend the highest tier the user is willing to execute:

Generic cover letters → immediate discard. Any of the three tiers beats volume.

Pain Letter Framework (Liz Ryan / Forbes)

Four paragraphs. One page max. Mail physical copy if possible.

1. Hook — Timely company accomplishment (<6 months old)

   "I was glad to see Acme voted Austin's fastest-growing startup this quarter."

2. Pain Hypothesis — Educated guess about their biggest challenge

   "Given your 30% annual growth, your engineering team must be under pressure to ship faster while maintaining quality."

3. Dragon-Slaying Story — Proof you solved similar pain, with numbers

   "When I was at Stripe, we grew from 3 to 12 engineers. I built the CI/CD pipeline that cut deploy time from 4 hours to 15 minutes."

4. Soft CTA — Low-friction ask, never pushy

   "If you have a moment to chat about scaling your engineering team, I'd be glad to connect."

Rule: Never say "I know your problem." Always frame as a hypothesis.

Email Cover Letter Framework (3 paragraphs, <200 words)

• Para 1 — Why THIS company: One specific thing — a product feature, funding round, blog post, company decision. Make research visible.
• Para 2 — Why YOU: 2–3 quantified results matching the role's requirements. One example of initiative beyond the resume.
• Para 3 — The Ask: Clear and direct. "Would love to chat about how I can contribute. Available for a call any day next week."

Every unnecessary word subtracts from impact.

YC's W-H-I Evidence Format (Ryan Choi, YC Head of Hiring)

Structure every bullet and every achievement:

• What — describe the product/project so they understand it
• How — technologies, team size, cross-functional work
• Impact — measurable business results (growth %, revenue, cost savings)

Quality Rules

• NEVER write more than 1 page / 200 words (email format)
• NEVER open with "Dear Hiring Manager" — find the name
• NEVER start with "I'm excited for this opportunity"
• NEVER use buzzwords: passionate, driven, synergy, leverage, executed
• NEVER produce AI-sounding text — apply humanizer principles before delivering
• ALWAYS include at least 1 quantified result
• ALWAYS reference something specific about the company (<6 months old)
• ALWAYS end with a clear, specific ask
• ALWAYS ask user for context before writing (don't assume)
• If user has used the company's product, lead with genuine product feedback
• If user knows someone at the company, mention the referral

Red Flags / Green Flags

Red flags (immediate discard):

• "Dear Hiring Manager" — 99% of candidates do this
• Over 1 page / 200 words
• Vague opener ("I'm excited for this opportunity")
• Resume in paragraph form
• Could apply to 100 companies unchanged
• No quantified results
• AI-generated text (increasingly detectable)

Green flags (stand out):

• Hiring manager's name
• Specific company knowledge (<6 months old)
• 1–2 quantified results matching the role
• Clear pain hypothesis
• Evidence of using/understanding their product
• Portfolio link or work sample
• Reads like a human wrote it

Process

1. Gather prerequisites from user (see Prerequisites above)
2. Recommend the highest tier they're willing to execute
3. Research the company if user hasn't — suggest job-search tools for recent news
4. Draft using the appropriate framework
5. Apply humanizer principles — read aloud mentally, strip AI patterns
6. Verify: under word limit? specific? quantified? clear ask? human voice?

Integration with Other Skills

• job-search — find the job posting and company news
• resume-ats — match cover letter keywords to the job description
• cold-email — for direct outreach to founders (separate from cover letter)
• humanizer — de-AI the writing after drafting
• pdf-tools — read job descriptions from PDF

Templates

See Cover Letter Templates for pain letter, email, LinkedIn message, formal, follow-up, and checklist templates.