AI Product Evaluations Senior Analyst

Sidley Austin•Chicago, IL

2d•$98,300 - $135,200•Hybrid

About The Position

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.

Requirements

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
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

Nice To Haves

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

Responsibilities

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.