When to Write a Cover Letter (and When to Skip)
Write one when: the role is senior, the application is competitive, you're changing careers, you're applying to a small company where the founder reads the inbox, or the posting explicitly asks.
Skip when: the ATS gives you a text box and no upload slot, the role is high-volume entry-level, or you cannot write something genuinely specific. A generic cover letter hurts more than none.
The 4-Paragraph Structure
- Hook — one specific reason you're writing (product, mission, or a decision they made)
- Proof — one paragraph of your most relevant win, with numbers
- Fit — one paragraph mapping your background to the JD
- CTA — a clear ask, contact details, and a date you'll follow up
Half a page, always
Cover letters are read once, quickly. 3-4 paragraphs, 250-350 words. Longer than that loses the reader — and the callback.
Opening Lines That Actually Work
Skip "I am writing to apply for the [Role] position at [Company]." The recruiter knows. Every second in a cover letter is expensive — burn none of them on filler.
- Reference a specific product decision: "Your decision to sunset [feature] last quarter took nerve, and it's exactly the culture I want to build in."
- Reference a specific outcome you can mirror: "I ran the ProductHunt playbook that got Loom to #1. I saw yours hit #4 last week — I can help you close that gap."
- Reference a specific person: "[Founder]'s essay on [topic] shaped how I think about [thing]. I want to work in a company where that lens is the norm."
Closing With a Clear Ask
Ambiguous closes get archived. "I'd love to discuss further" is a wish, not a request. Replace it with a specific next step and a specific date.
- "I'll follow up next Tuesday if I haven't heard back — happy to answer anything in the meantime."
- "Would a 15-minute call the week of [date] work to walk through my [artifact]?"
- "I'm around this week and next — happy to fit your calendar."
Mistakes That Kill Cover Letters
- "To whom it may concern" — find the recruiter's name on LinkedIn
- Reusing the same letter with company names swapped — recruiters can smell it
- Explaining your resume — the recruiter already has the resume
- Starting every paragraph with "I" — vary the opener
- More than one page — always