AI Product Evaluations Senior Analyst in Chicago, Illinois at Sidley Austin LLP

The AI Product Evaluations Senior Analyst, part of the Firm's Data & AI department, is responsible for supporting the evaluation, selection, and piloting of the Firm's legal-technology and AI products and related systems. The incumbent supports product evaluations end to end; conducting market research, assisting with vendor selection, and coordinating with information security, procurement, IT, and practice stakeholders. The Senior Analyst helps plan, administer, and analyze structured product evaluations and pilots, ensuring they are well-organized, criteria-driven, and clearly documented, while producing the analysis and reporting that inform selection and rollout decisions.

Duties and Responsibilities:

In coordination with the team's Product Management Manager and Leadership:

• Support the day-to-day administration of product evaluations, pilots, and proofs of concept across the Firm's legal-technology and AI portfolio.

• Conduct market research and landscape analysis to identify, compare, and shortlist candidate products, vendors, and capabilities.

• Assist with vendor selection, including preparing evaluation criteria, demo question banks, scorecards, and comparison summaries.

• Coordinate with information security, procurement, IT, and practice stakeholders to gather requirements, schedule reviews, and track dependencies through the evaluation lifecycle.

• Help plan and administer structured evaluations and pilots defining scope, timelines, participants, and success criteria in coordination with leadership.

• Collect, analyze, and synthesize evaluation inputs (participant feedback, usage data, KPIs) into clear findings and recommendations.

• Prepare evaluation summaries, stakeholder updates, and reporting to support selection, prioritization, and rollout decisions.

• Maintain organized documentation of evaluation processes, criteria, vendor materials, and decisions.

• Participate in project teams to support implementation, training, and change management for selected products.

• Identify opportunities to improve evaluation methods, templates, and repeatable processes.

• Contribute to the development and ongoing maintenance of standard evaluation documentation and related materials.

Education and/or Experience:

Required:

• Bachelor's degree from a four-year college or university

• A minimum of 5 years of experience in a law firm, corporate legal department, or professional services environment

• Proficiency in MS Excel, MS Word, and PowerPoint

• Demonstrated ability to manage multiple assignments with competing deadlines and priorities under minimal direct supervision

• Excellent written and verbal communication skills

Preferred:

• A minimum of 2 years of experience working with legal technology and/or AI tools (e.g., research tools, workflow or practice management systems, generative AI platforms)

• Experience supporting product or vendor evaluations, procurement, or information security review processes

• Demonstrated understanding of law firm structure and business practices, as well as practice-specific terminology

• Experience managing or coordinating projects from inception through planning, execution, and completion

• Familiarity with market and competitive research resources (e.g., analyst reports, vendor landscapes) and legal research tools

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 and stakeholder-management skills

• Strong analytical and problem-solving skills

• Ability to communicate technical concepts clearly to non-technical stakeholders

• 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

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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.

Sidley is an elite global law firm with a known reputation of deploying innovative strategies to achieve powerful results.