Upwork Proposal

Upwork Proposal Generator

Write a concise, winning Upwork proposal that directly addresses the client's needs. Clients skim proposals on mobile, between meetings - if it takes more than ~30 seconds to read, it's gone. Optimize every line for a fast skim.

Setup

Follow ../_shared/setup.md. Then Read the resume at primaryResumeSourceAbsolutePath for full context (identity, skills, experience, projects, research).

Step 1: Resolve the Input

The argument is either a proposal id (an integer, when launched from the JobPilot UI) or a raw job description (manual use). Detect which:

• Integer id → fetch the draft row and use its stored job details as the JD:

  curl -fsS -H "authorization: Bearer $JOBPILOT_API_TOKEN" "$JOBPILOT_API/api/upwork/proposals/$ARG"
  

  Use jobDescription as the posting, plus jobTitle / clientName / jobUrl for context. Remember the id - you will PATCH the result back to it in Step 7. (A draft launched from an Upwork search recommendation already has these fields filled and source:"search" - same flow, no extra work.)

• Anything else → treat the argument itself as the job description. There is no row yet; you will POST a new one in Step 7.

Step 2: Analyze the JD

Identify: what the client needs built/fixed, required tech and skills, scope and timeline clues, pain points/challenges, and any specific questions the client asks. Pull out one concrete detail unique to this posting - you'll reference it in the hook so the client can tell the proposal isn't a mass send.

Step 3: Select ONE Matching Case Study

Pick the SINGLE most relevant project from the resume - one that matches their problem, not just their tech stack. One specific, on-point case study beats five generic ones. Don't list everything. If a portfolio/GitHub/live link exists for it, keep that link ready.

Step 4: Write

Order it the way it gets read - them first, you second, never the reverse.

Hook (line 1, bolded): Open with a bold line that names their problem or goal in their words. Upwork renders **text** as bold - use it on this line so it stands out instantly. This is the single most important line; if it reads like "Hello, I'm excited to apply," the proposal is deleted. No "Hi" / "Dear client" / "I'm excited to apply" / "I came across your posting."

Case study (1–2 lines): One relevant project, stated specifically - what you built, the outcome with a real metric (users, perf gain, revenue), and a link if available. Tie it directly to what they need. Don't narrate your career; the client cares about their problem, not your journey.

Specific question (1 line): Ask ONE sharp question about their project that proves you read the posting and thought about it (scope, an edge case, a decision they'll need to make). This both shows engagement and opens a conversation.

CTA (1 line): End with a real next step - the specific question above, or a calendar link if the resume/profile provides one. Never end with a dead phrase like "Looking forward to hearing from you." Create the next step.

Step 5: Answer Screening Questions

If the posting has screening questions, answer each one short, direct, and specific. "How many years with React?" → "4 years, including [project]." Never write a 300-word essay for a one-line question - long answers read as AI padding.

Step 6: Apply Humanizer

Invoke the humanizer skill on the full text in embedded mode (final rewrite only).

Step 7: Persist to JobPilot

Save the result so it appears on the Upwork page. screeningAnswers is a JSON array of { "question", "answer" } objects (empty [] if the posting had none).

• Launched with an id → PATCH the existing draft (status stays draft):

  curl -fsS -H "authorization: Bearer $JOBPILOT_API_TOKEN" -X PATCH "$JOBPILOT_API/api/upwork/proposals/$ARG" \
    -H 'content-type: application/json' \
    -d '{ "proposalText": "...", "screeningAnswers": [] }'
  

• Launched with a raw job description → POST a new row:

  curl -fsS -H "authorization: Bearer $JOBPILOT_API_TOKEN" -X POST "$JOBPILOT_API/api/upwork/proposals" \
    -H 'content-type: application/json' \
    -d '{ "jobTitle": "...", "clientName": "...", "jobUrl": "...", "jobDescription": "...", "proposalText": "...", "screeningAnswers": [] }'
  

  jobTitle is required; derive it from the posting. Include clientName / jobUrl when the posting provides them.

Then print the proposal (and any screening answers, each labeled with its question) to the terminal so the user can paste it into Upwork.

Rules

1. Under 150 words for the body. Shorter wins on mobile. Brevity reads as confidence.
2. Them before you. Their problem leads; your background supports. Never open with 3 paragraphs about yourself.
3. No AI tells. No "Certainly, here is..." preambles, no robotic symmetry, no functional emoji bullets (✅ 📌 🔹 ☑) - those scream AI. If an emoji appears at all, at most one, used the way a person would.
4. No fluff - drop "passionate", "dedicated", "committed", "excited", "thrilled", "leverage", "utilize", "innovative", "cutting-edge", "seamless", "robust".
5. No generic openings ("I came across your job posting" / "I'm a senior developer with X years").
6. Be specific. Real project names, metrics, tech, and links from the resume - referencing their actual job, not a template.
7. One matched case study, not five. Relevance beats volume.
8. One CTA, and make it a real next step (a question or a calendar link).
9. Match tone. Casual posting → casual; formal → professional.
10. No fabrication. Only reference resume content. Don't invent metrics or links.
11. Don't mention freelance status (Top Rated, JSS) in body - it's already on the profile. Exception: if the posting explicitly asks.
12. First person as the candidate.

Output

Plain text proposal that pastes into Upwork's input. Use **bold** only on the line-1 hook (and sparingly on one key phrase if it genuinely helps a skim) - no markdown headers, no bullet lists in the body. Output screening-question answers separately, each labeled with its question.