Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technology vision, strategy, and execution for Wintrust’s Wealth Management business. Partner with executive leadership to align technology roadmaps, budgets, resources, vendors, projects, and operational activities with business priorities. Oversee platforms, applications, governance, security, regulatory compliance, risk assessments, disaster recovery, incident management, and continuous control monitoring. Drive digital transformation, automation, analytics, and AI innovation while managing initiatives from intake through delivery.

Supervise branch teller operations, ensure compliance with banking policies and dual-control procedures, resolve operational and customer issues, operate a teller drawer, support exceptional service, identify cross-selling opportunities, and coordinate staff duties. The role also involves maintaining branch security, communicating procedure updates, participating in community events, and potentially traveling between branches.

The Senior Employee Relations Specialist manages employee relations for bank entities, including complaints, investigations, policy interpretation, disciplinary actions, conflict resolution, and employment-law compliance. The role advises supervisors, analyzes employee and ER trends, supports restructures and terminations, manages engagement surveys and action planning, partners with centers of excellence, and promotes consistent application of workplace policies.

The Assistant Vice President of Treasury supports liquidity, cash forecasting, collateral optimization, stress testing, capital management, and balance sheet oversight. Responsibilities include preparing accurate Treasury financial reports, advising business lines on budgeting and forecasting, and producing materials for ALCO and Capital Management Committee meetings. The role requires advanced bank financial analysis, regulatory capital knowledge, strong reporting accuracy, and at least five years of experience in treasury, ALM, FP&A, or related corporate finance.

Build and retain customer relationships by identifying financial needs, recommending banking products, referring customers to mortgage and wealth management partners, operating a teller drawer, opening and maintaining accounts, assisting with digital banking products, identifying fraud risks, supporting branch opening and closing, and participating in community and bank events.

Build and retain customer relationships by identifying financial needs, recommending banking products, opening and maintaining accounts, operating a teller drawer, supporting digital banking, identifying fraud risks, and referring customers to mortgage and wealth management specialists. The role also supports branch opening and closing and community events. Bilingual Spanish proficiency is required.

Oversee the allowance for credit losses and CECL estimation process, including data validation, reconciliations, model assumptions, variance analysis, waterfall reviews, management reporting, auditor and regulator reporting, and SEC disclosures. Lead ACL working groups, document procedures, support internal stakeholders and consultants, train team members, and supervise use of ACL software solutions.

Analyze structured and unstructured banking data to identify insights, risks, and opportunities. Partner with engineering, product, risk, compliance, and operations teams to develop governed data assets and use cases. Support unstructured data enablement, text analytics, data quality, lineage, critical data elements, and regulatory controls. Translate complex business needs into defensible data solutions across AML/KYC, fraud, reporting, customer experience, and operational efficiency.

Direct investment operations for institutional, intermediary, and sub-advisory accounts. Oversee operational coverage, reconciliations, settlements, portfolio accounting, pricing, corporate actions, reporting, client account maintenance, and data quality. Support GIPS-compliant performance reporting and risk analytics, resolve custodial discrepancies, maintain procedures, coordinate deadlines, cross-train staff, and drive operational improvements. The role serves as an escalation point for operational issues and requires extensive investment management operations experience.

Supports the evolution and administration of Wintrust’s enterprise Salesforce platform. Responsibilities include gathering requirements, creating JIRA user stories and process documentation, conducting user acceptance testing, reporting defects, supporting rollouts and training, assisting end users, prioritizing enhancements, maintaining product documentation, and identifying opportunities to leverage Salesforce capabilities. The role partners with business stakeholders, IT, product teams, and learning partners across the organization.