Job Title: Strategic AI Advisor
Location: Chicago, IL
Duration: 3 months

Engagement overview

• Seeking an experienced consulting firm to conduct structured AI readiness assessments across four priority business functions. The purpose is to produce an accurate, function-level picture of each area’s preparedness to implement and sustain AI initiatives — covering the operational, process, data, and system factors that determine whether AI can deliver lasting value.
• This is not a high-level maturity survey or a benchmarking exercise. Client expects embedded assessment work: consultants inside each function, working directly with subject matter experts, process owners, and technical leads to produce findings that reflect how the function operates. The outputs feed directly into the AI Strategy team’s use case pipeline and inform the sequencing of Client’s AI transformation roadmap. Findings must be specific enough to drive investment and prioritization decisions, not general enough to apply to any financial institution.

Assessment framework

Each assessment covers five dimensions:

• Business strategy: Does the functional leadership have a clear view of where AI creates value in their area, are there defined priorities for the function
• Knowledge foundations: data quality, availability, and governance; whether the knowledge substrate — documented processes, accessible data, structured institutional knowledge — exists to support AI use cases in each function.
• Technical infrastructure: compute, storage, and integration readiness; whether current systems, data flows, and workflows can support AI use cases without significant re-architecture.
• Organization and culture: skills inventory, change readiness, and whether the function has the mindset and capacity to adopt and sustain AI-powered ways of working.
• AI applicability and ROI: where AI can deliver measurable value in each function’s specific context, and what the realistic return looks like relative to the effort required.

Deliverables

• Knowledge substrate map: a structured inventory of what data, process documentation, and institutional knowledge exists; what is well-documented and accessible; what is held primarily by individuals; and what is absent
• AI readiness gap analysis: a prioritized assessment of specific gaps across each of the five assessment dimensions above
• Prioritized roadmap: a practical plan that sequences remediation work from quick wins to larger-scale AI adoption; identifies what must change, who owns each item, and estimated timelines
• Use case opportunity inventory: the two to three highest-readiness AI applications within the function, each with a preliminary value thesis and ROI rationale

Key Skills Requirement

• Demonstrated 3+ years of experience conducting AI readiness assessments within financial services or market infrastructure organizations: clearing, custody, exchange, or equivalent
• Strong familiarity with the regulatory environment governing systemically important financial market utilities, including PFMI standards and model risk governance expectations
• Able to engage credibly with senior leaders in Financial Risk Management and Systems & Integration, where regulatory and operational credibility is non-negotiable
• Prior work must include assessment deliverables that were used to make actual investment or sequencing decisions