C
Senior Prompt Engineer
Claire Dupont
Freelance · Senior · Chicago
About the role
We are a healthtech company building AI-assisted clinical documentation tools. We have a working product. We have paying customers. And we have a set of prompts that are costing us in hallucinated outputs, inconsistent formatting, and edge cases that embarrass us in demos. We have tried fixing this internally — it needs a specialist. We need a senior prompt engineer for a focused 8-week engagement. You will audit every prompt in production, rebuild the ones that are failing, set up automated regression tests, and hand over a system we can maintain without constant firefighting. The scope is defined. The budget is approved. We need someone who can start within two weeks.
Key Deliverables
List the expected deliverables for this project.
- Audit all production prompts and categorise by failure mode
- Rebuild failing prompts with documented design rationale
- Build a regression test suite (minimum 150 test cases) covering known edge cases
- Deliver a prompt maintenance guide for the internal team
- Present findings and recommendations in a structured final review
Requirements
Technical stack needed for this mission.
- 5+ years prompt engineering with LLM APIs in a shipped product
- Proven experience building prompt regression test suites — not manual testing
- Deep familiarity with structured output, few-shot design, and chain-of-thought patterns
- Experience in a regulated or high-stakes domain (healthcare, legal, or financial) strongly preferred
- Able to deliver clean documentation and handover materials
Contract Type
Fixed-price
Level
Senior
Budget Range
$12,000 – $22,000
Duration
1 – 3 months
AI Expertise
NLP & Prompt Engineering
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