AI Prompt Engineering Lead

Chicago, IL: Hybrid work from home: 2 days WFH, 3 days onsite in the loop

Summary:

The AI Prompt Engineering Lead will drive end-to-end AI solutions, for stakeholders throughout the professional services organization, working in departments across business departments with an initial focus on legal.

You'll partner with key business stakeholders to understand existing processes, workflows, etc., recommend AI solutions to automate existing business processes, and then deliver the solutions using tools like Claude Cowork and ChatGPT Custom GPTs.

Once the tools are delivered, you'll train the business users, and drive continuous optimization based on feedback from the business users.

What you'll be doing

· Design and maintain a library of complex, production-grade system prompts for Claude Cowork and ChatGPT Custom GPTs tailored to legal tasks: contract review, clause extraction, due diligence checklists, legal research summaries, and matter intake.

· Build multi-step prompt workflows that chain instructions, handle conditional logic, and produce structured outputs (tables, memos, checklists) formatted for attorney consumption.

· Configure and maintain Custom GPTs with specific instructions, knowledge file uploads (precedent packs, playbooks, style guides), and actions that connect to internal document stores and matter management systems.

· Set up and optimise Claude Cowork automations that route tasks, process uploaded documents, and deliver AI-assisted outputs within existing team workflows.

· Conduct deep-dive discovery sessions with practice groups to map current workflows, identify friction points, and translate attorney needs into precise AI task specifications.

· Run structured prompt testing and evaluation cycles — comparing outputs across model versions, prompt variants, and edge cases — to maintain quality and consistency standards.

· Deliver hands-on training sessions and workshops for attorneys and staff; build self-serve guides, prompt templates, and a prompt library they can adapt independently.

· Act as internal expert and escalation point for AI tool questions; troubleshoot underperforming prompts and continuously refine based on user feedback.

· Stay current on new capabilities in Claude, GPT-4o, and emerging models; proactively identify and prototype features (deep research, file analysis, voice, computer use) that add value for legal users.

· Maintain responsible AI usage guidelines; flag prompt patterns that risk hallucination, data leakage, or outputs unsuitable for client-facing use.

Skills we're seeking

· Bachelor's Degree, ideally in an IT, Data or Business related field

· 5+ years of professional experience in AI, IT or Product related roles

· 3+ years of experience in AI focused roles

· Must have strong experience with Prompt Engineering

· Must have strong experience with either Claude and/or ChatGPT

· Must have strong experience partnering with business stakeholders to understand business processes, workflows, etc. and subsequently recommending solutions, documenting specific requirements and managing the delivery of AI solutions

· Experience with Jira, Confluence or similar product management tools

Nice to haves

· Experience with Claude Cowork

· Experience building custom GPTs in ChatGPT

· Experience with Jira, Confluence or similar product management tools

· Experience building AI solutions for legal departments