Top 5 Jobs in Financial Services That Are Most at Risk from AI in Chicago - And How to Adapt

Chicago's financial services sector is already using AI to discover research, automate tasks, and personalize client strategies - trends documented by Chicago Partners' 2025 overview - while national analyses from J.P. Morgan show AI is driving rapid task churn and reshaping jobs even as it creates new roles; the net effect for Illinois: faster automation of routine back‑office and middle‑office tasks and growing demand for workers who can apply AI to workflows.

The practical takeaway is concrete: reskilling into AI‑aware roles matters now, and programs like Nucamp's Nucamp AI Essentials for Work (15‑week) bootcamp teach prompt writing, tool use, and on‑the‑job AI skills employers want; read the industry context in Chicago Partners' analysis of AI in Chicago financial services and the labor outlook in J.P. Morgan's report on AI and jobs.

"With limited resources, small business can automate routine tasks with AI, allowing employees to focus on higher-value activities." - Triangle Business Journal

Selection of the top five at‑risk financial‑services jobs in Chicago used a triangulated, evidence‑based approach: first, occupational exposure frameworks (the Frey & Osborne-style risk scoring used in the California automation analysis) were paired with ACS‑style microdata to identify occupations with high routine‑task shares and large Illinois employment counts; second, national automation benchmarks - like the finding that roughly 30% of U.S. jobs could be fully automated by 2030 and that 60% will experience major task changes - helped set thresholds for “at‑risk” roles (U.S. job automation statistics and projections); third, evidence on where financial firms are actually deploying AI informed sectoral plausibility checks so positions heavily used for clearing, reconciliation, teller transactions, basic reporting, or loan processing were prioritized (Congressional Research Service report on AI and ML adoption in financial services).

The method emphasizes task‑level exposure over job titles alone and mirrors the rigorous, reproducible linkage of risk scores to ACS microdata shown in the California report, so the “so what” is clear: roles dominated by routine, rules‑based tasks in Illinois financial firms are flagged now so targeted reskilling pathways can be deployed before automation reassigns those tasks elsewhere (California automation risks for Latinos methodology example).

Clearing and settlement clerks at the Options Clearing Corporation (OCC) - a Chicago‑based, systemically important clearing house - face immediate exposure as OCC's Renaissance Initiative replaces ENCORE with the cloud‑native Ovation platform and reengineers clearing, settlement, and risk workflows during a single conversion cycle; Ovation's planned 2025 launch (with external testing through 2025) brings APIs, self‑service reporting, proactive settlement‑cycle monitoring, and streamlined nightly margin calculations that reduce repetitive reconciliation and data‑pull work (OCC clearing risk and data changes, Ovation transformation details from OCC).

OCC's earlier low‑code and RPA efforts - which cut manual evidence compilation from weeks to days and automated nearly two hours/day of routine tasks - show how automation shifts headcount away from rule‑driven work; analysts can already pull needed data in roughly 30 seconds, a speed bump that makes traditional clerk tasks vulnerable to automation (Built In Chicago coverage of OCC modernization initiatives).

The practical "so what": expect fewer manual reconciliations and more demand for skills in API interaction, exception handling, and automated‑process oversight.

“We stand in the middle of every trade.” - Steve Felix, Director of Process Automation, OCC

Middle‑office trade‑support and reconciliation analysts at DRW in Chicago handle the everyday plumbing of markets - trade capture, detailed reconciliations, P&L calculation, exception resolution, and reporting across futures, options, FX, and commodities - work the Operations Analyst posting lists as hybrid, West Loop‑based, and paying $90,000–$135,000; the role explicitly demands Excel plus SQL, Python, and VBA and expects candidates with 2+ years in detail‑oriented market roles, making scriptable workflows and reporting automation a core on‑the‑job skill (DRW Operations Analyst job listing on Built In Chicago with role details and qualifications).

DRW's public careers page shows the firm is hiring heavily in technology and data roles, so middle‑office analysts who can build or oversee analytical tooling and API‑driven reconciliations will stay valuable, while those who can't may find routine capture and reconciliation tasks increasingly embedded in firm tooling (DRW careers and job listings showing technology and data openings).

So what: mastering one scripting language (Python or SQL) plus robust Excel practices is the clearest short‑term hedge for a Chicago analyst wanting to shift from manual reconciliation to automated oversight and exception handling.

Alliant's Chicago‑headquartered, digital‑first model has largely moved routine teller transactions into online channels and a centralized Member Care Center, a shift that makes traditional retail‑bank teller work highly exposed to automation; the credit union reports customer‑service operations efficiency improvements (4.4% → 39,000 more successful member interactions) and says minutes returned to members totaled 1.5 million as part of a broader digital push (Alliant member experience and call-center efficiency data).

The practical evidence is stark: Alliant's new end‑to‑end digital mortgage and loan origination platform helped deliver a 158% year‑over‑year increase in direct lending and produced $145.7M in mortgage closings in June 2025 alone, showing how scaled digital channels can remove high‑volume, rule‑bound transactions from in‑person staff and redirect work into centralized mortgage operations and digital support teams (Alliant mortgage transformation details).

So what: retail staff in Illinois need to pivot from cash‑handling and routine form‑filling toward exception handling, digital onboarding and CRM/tool oversight - concrete, employer‑facing skills (basic API/CRM fluency, troubleshooting digital applications, and member‑experience coaching) that preserve career paths as teller roles compress or relocate to hubbed operations.

“It is an honor to be part of a team that has embraced transformational change. Our strong momentum will allow us to build upon the progress made unleashing new opportunities to wow our members and do good for the members, colleagues and communities we serve.” - Dan Bauer, Head of Residential Lending, Alliant Credit Union

Basic financial analysts and reporting accountants at firms such as Wipfli face concentrated exposure because their core tasks - repetitive journal entries, standardized management reports, and rule‑based reconciliations - are exactly what operational‑excellence programs and Industry 4.0 toolkits automate with RPA, intelligent document processing, and cloud analytics; Wipfli's guidance on digital transformation highlights how automation and data integration shift value toward oversight, analytics, and process redesign (Wipfli Industry 4.0 guidance on manufacturing transformation), and analysis of OPEX in financial services shows firms are using AI and automation to cut administrative burdens while demanding different skills from finance teams (operational excellence in financial services analysis).

So what: instead of running month‑end data pulls, Illinois reporting accountants who learn RPA/IDP oversight, SQL/Power Query, validation and exception‑handling, and basic model governance will move from production to control and advisory roles, preserving career value as routine report generation becomes embedded in firm tooling.

“Financial institutions are faced with immense margin pressure in today's environment, coupled with pressures surrounding competition, talent retention, attraction and, of course, regulation.” - Anna Kooi, financial services and financial institutions practice leader, Wipfli

Mortgage and consumer‑lending underwriters and processors who handle OppFi/OppLoans applications in Chicago and across Illinois face rising pressure as fintechs compress decision cycles: OppFi's public timeline of product moves - highlighted by a same‑day funding rollout and a Spring 2025 survey showing 1 in 5 consumers lack even a week of savings - means faster, data‑rich credit decisions are now operational priorities (OppFi press releases and news).

Those operational demands make routine document checks, income verification, and rule‑based pricing exactly the kinds of tasks that Intelligent Document Processing and model‑driven underwriting automate, cutting time‑to‑decision while surfacing exceptions for human review (AI commercial loan underwriting and intelligent document processing).

Firms that already underwrite at transaction speed show how machine learning can loop feedback into models for continuous improvement, so for Illinois underwriters the clear hedge is to shift from line‑by‑line processing to exception management, model governance, and vendor/API oversight - skills that preserve career value as routine approvals move into automated pipelines (Affirm underwriting approach and advantage).

So what: in Chicago markets, mastering exception workflows and explainability checks now protects roles more effectively than purely transactional underwriting skills.

“The company has a lot of advantages compared with payday loans, including the ability to build your credit score by making online payments. OppFi, the parent company of OppLoans, will also direct to other lenders if you can qualify for better options.” - MarketWatch, February 2024

Chicago‑area workers and employers should treat reskilling as a pragmatic defense: tap university credentials, short technical classes, and employer partnerships to move people from routine processing into exception‑handling, oversight, and AI‑enabled roles.

Local pathways already exist - UIUC's Gies Professional Credentials let workers stack 12‑credit graduate certificates in accounting or data analytics for applied business skills (UIUC Gies Professional Credentials (graduate certificates)), the University of Illinois Grainger/Discovery Partners initiatives are directing nearly $270 million toward AI research and workforce programs in Chicago that employers can partner with (Grainger: Building the AI Workforce (AI workforce initiatives)), and bootcamps that focus on workplace AI (for example, Nucamp's 15‑week AI Essentials for Work) teach prompt writing, tool use, and job‑based AI tasks employers want (Nucamp AI Essentials for Work registration).

For employers, the practical move is predictable: map the firm's routine tasks, link employees to short, stackable credentials, and use WIOA or continuing‑ed partnerships to lower cost and time‑to‑skill so Illinois teams can shift from production work to control, advisory, and exception‑management roles.

“AI education is not just about technical proficiency - it's about preparing a workforce that understands the ethical, societal, and economic implications of AI.” - Mahesh Viswanathan, Illinois Grainger College of Engineering