Tailor Resume

• Required skills (hard requirements)
• Preferred skills (nice-to-haves)
• Key responsibilities
• Cultural keywords and values language (e.g., "we value transparency", "fast-paced")

Map fit — transparent gap analysis

• For each required skill: name the specific resume item that demonstrates it, with evidence
• For each gap: state it clearly — "You don't list [X] anywhere in your resume."
• Identify 2-3 hidden strengths: experiences that are relevant but not obvious from titles alone. Explain WHY they're relevant: "Your [data pipeline work at Plaid] maps to their [data infrastructure requirement] even though the titles don't match."
• Ask the user: "Any of these gaps something you actually have experience with that's not on your resume? Sometimes people forget to list things."

Tailor — reorder and emphasize, never fabricate

• Rewrite summary to speak directly to this role and company — reference their specific mission or product, not generic language
• Reorder bullets within each role: most relevant to this posting comes first
• Incorporate exact keywords from the posting WHERE they accurately describe real experience
• Add quantified impact from the master resume (numbers, percentages, scale)
• STRICT RULE: Do not add ANY skill, role, technology, or achievement not in the master resume. Not even "lightly." Not even reframed. If it's not there, it doesn't go in.

Output the tailored resume + internal notes

• Full tailored resume in clean Markdown
• Below it, a "Tailoring Notes" section (for the user only — don't submit this):
  • Covered: Which required skills are well-demonstrated
  • Gaps: Which required skills are genuinely absent — with suggestion for how to address each in the cover letter or interview ("Mention your self-taught [X] in the cover letter" or "Prepare a story about learning [X] quickly")
  • Interview talking points: 2-3 stories from the resume that map to their likely interview questions
• Suggest saving to ~/.career/applications/<company-slug>-<date>/resume.md

Offer the next step

• "Resume's tailored. Want me to write the cover letter? /cover-letter [company] [role] — I'll use this resume and your company evaluation to write something specific."