v1.3.03 loop iterations

Cover Letter Writer

Most cover letters are either generic form letters or rambling autobiographies. Both go straight in the bin. The Cover Letter Writer produces 300-word letters that reference the actual job posting, lead with a specific result, and answer the one question that decides whether you get the interview.

What this skill does

The reason most cover letters fail is that they're about the applicant, not the job. "I'm passionate about marketing and have always admired your company" is about the applicant. "Your posting says you need someone to rebuild content from scratch — here's exactly when I did that and the numbers it produced" is about the job. The first one gets filed. The second one gets the interview. The skill enforces the difference with hard rules: reference specific job requirements, include at least one quantified result, mention the company by name with real context, and never repeat the CV in prose form.

The structure is four paragraphs, under 350 words. Opening: a hook that earns the second paragraph — a specific connection, a product insight, or a direct result match. Generic openings like "I am writing to express my interest" get cut on first pass; they waste the most valuable real estate in the letter. Body paragraph one: the strongest match between the job's biggest requirement and a quantified achievement you've already delivered. Body paragraph two: a second match, or a value-add that isn't in the posting but would matter to the team. Closing: genuine reason for this specific company, a clear next-step request, and out.

The skill is opinionated about industry tone. A startup letter reads differently from a Fortune 500 letter. A creative agency rewards personality. A finance role rewards precision. A nonprofit rewards genuine mission alignment, not mercenary language. The same achievements get framed differently for each — not the substance, the register. If the user pastes a posting and a CV, the skill picks which two achievements to lead with based on what the posting actually emphasises, not what the candidate is proudest of.

It also handles the awkward situations head-on rather than hoping the hiring manager won't notice. Career change gets a single confident sentence about the through-line. Employment gap gets brief, specific framing. Overqualified candidates get a genuine reason for why the role is appealing despite the apparent step down. None of these get apologised for. They get named, addressed, and moved past — in the letter, not in your head.

When this triggers

·You're applying for a role and the posting is specific enough to write to
·You've been sending the same template to every job and the response rate is zero
·You're a career changer and need the letter to do work the CV can't
·You have a referral or specific connection to the company and want to use it properly
·You're overqualified or underqualified and the hiring manager will wonder why you're applying

Example

Trigger

User pastes a Head of Content job posting and says: 'I've been a senior content writer for 6 years. Grew organic from 12K to 180K monthly at [previous company]. Want this role.'

Output

Hi [hiring manager name], Your posting mentions you need someone to rebuild content operations from scratch — moving from sporadic posts to a consistent editorial machine. I did exactly that at [previous company], inheriting a two-person team and a backlog of abandoned drafts. Within 14 months we'd grown organic traffic from 12K to 180K monthly, while cutting publishing costs by 31%. Beyond the volume work, I bring a technical SEO background most content leaders lack. The 180K number isn't just more posts — it's also a content audit that consolidated 40% of our existing library to stop self-cannibalisation. The audit pattern is transferable to [their company]'s situation, where [specific observation from their site]. I've been a [their product] user since [year], and the [specific feature/post] convinced me to switch from [competitor]. Heading content for the company whose product I already advocate for is the version of this role that makes sense for me. Happy to walk through the editorial systems I'd build in week one. [Name] 287 words.

Get this skill + 9 more

Included in the The Freelancer Stack — win clients, deliver work, get paid. Save $100+ vs buying individually.

Get The Freelancer Stack — $99

What you get

139-line SKILL.md, ready to drop into ~/.claude/skills/
Tested through 3 Karpathy-loop iterations (versions v1.0.0 → v1.3.0)
Triggers automatically when relevant — no command to remember
Lifetime updates as the skill is refined further