Three paragraphs, 250 to 300 words, opens with a specific hook from the JD, names two relevant outcomes from your CV, closes with a clear ask. Skip the 'I am writing to apply' opener.
Paragraph one: the hook. Name something specific from the JD or company that you're reacting to. 'Saw the JD specifies experience scaling payment infrastructure past $1B annual GMV, which is exactly the work I led at Stripe from 2022 to 2024' beats 'I am writing to apply for the senior engineer position'.
Paragraph two: two outcomes from the CV that map to the role. One sentence each. Quote the metric. Don't restate the CV; pick the two most relevant bullets and expand them with one line of context (the problem you were solving, the constraint you worked around).
Paragraph three: the ask. 'Happy to walk through the Stripe rewrite in detail, or share the design doc on request. Available for a 30-minute call any morning next week'. End with your name, no signature block needed for digital submission.
Strong openers name a specific thing. 'Saw the JD specifies X, which is exactly the work I led at Y'. 'Read the engineering blog post about Z last week and noticed the team is building W'. 'Reaching out because the JD's section on V is rare and matches the work I shipped at U'.
Weak openers paraphrase the JD back at the reader. 'I am writing to apply for the Senior Engineer position at Acme'. 'I believe I would be an excellent fit for your team'. They burn the most valuable sentence in the letter.
250 to 300 words, three paragraphs. Longer and the hiring manager skims. Shorter and you can't fit the hook, the two outcomes, and the ask.
Yes if you can find them. LinkedIn the hiring manager or team lead and address by name. If you can't, 'Hiring team at Acme' is fine. Avoid 'To Whom It May Concern' and 'Dear Sir/Madam'.
No. Pick two bullets from the CV and expand them with one line of context each. The cover letter's job is to explain why those two bullets matter for this specific role.
For mid-career and above, yes. The signal-to-noise of well-written cover letters is high enough that hiring managers read them when they exist. For entry-level and tech-heavy roles where the CV does the work, a strong CV alone can be sufficient.
To draft, yes. To send unedited, no. AI drafts read like AI drafts: over-flowery, vague, generic. Use the draft as a structure; rewrite each sentence in your voice with the specifics only you know.
Pick the CV, paste the JD, Claude drafts a starting point.
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