AI Solutions Lead in Chicago, Illinois at Sidley Austin LLP

Summary:

The AI Solutions Lead will work directly with lawyers and business professionals teams to understand how they work, then build the prompts, instructions, and AI-powered workflows that make Claude Cowork and ChatGPT Custom GPTs genuinely useful in day-to-day legal practice.

This role is part prompt architect, part workflow designer, part trainer. The incumbent will craft sophisticated system prompts and multi-step workflows tailored to specific legal tasks contract review, research, drafting, matter summaries and configure Custom GPTs and Cowork automations that connect to the firms documents and data. In addition, the incumbent will coach users so they get the most from these tools independently.

Duties and Responsibilities:

• 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 firm-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 firm-wide 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.

Education and/or Experience:

Required:

• Bachelors degree in Business, Information Systems, Computer Science, Engineering, or a related field.
• A minimum of 2 years of relevant professional experience
• Experience with agile methodologies and familiarity with product management tools (e.g., Jira, Confluence, or similar).

Other Skills and Abilities:

The following will also be required of the successful candidate:

• Strong organizational skills
• Strong attention to detail
• Good judgment
• Strong interpersonal communication skills
• Strong analytical and problem-solving skills
• Able to work harmoniously and effectively with others
• Able to preserve confidentiality and exercise discretion
• Able to work under pressure
• Able to manage multiple projects with competing deadlines and priorities

#LI-HM1

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Applicants must be authorized to work in the United States without the need for employer sponsorship, now or in the future

The target salary range for this role is:

Salaries vary by location and are based on numerous factors, including, but not limited to, the relevant market, skills, experience, and education of the selected candidate. Our compensation package also includes bonus eligibility and a comprehensive benefits program. Benefits information can be found at Sidley.com/Benefits.

To perform this job successfully, an individual must be able to perform the Duties and Responsibilities above satisfactorily and meet the requirements. The requirements listed above are representative of the minimum knowledge, skill, and/or ability required. Reasonable accommodations will be made to enable individuals with disabilities to perform the essential functions of the job. If you need such an accommodation, please email sidleytalentacquisition@sidley.com (current employees should contact Human Resources).

Sidley Austin LLP is an Equal Opportunity Employer.