Top Tech Jobs & Startup Jobs in Chicago, IL

Supports the evolution and administration of the enterprise Salesforce CRM platform. Responsibilities include gathering and documenting requirements, creating JIRA user stories and process flows, coordinating user acceptance testing, managing defects, supporting rollouts and training, assisting users with production issues, maintaining documentation, and helping prioritize enhancements against the strategic roadmap.

Supports franchise finance lending by underwriting credit requests, analyzing borrower financial statements, preparing credit summaries, monitoring covenants and risk ratings, and managing portfolio reviews. The role also assists with loan documentation, due diligence, closings, prospecting, syndicated loan negotiations, borrower relationships, and regulatory compliance. Strong financial modeling, risk management, analytical, communication, and relationship-building skills are required.

Conduct independent validation of bank-wide statistical, econometric, mathematical, AI, machine learning, and qualitative models. Assess conceptual soundness, implementation accuracy, data integrity, governance, and performance through back testing, sensitivity analysis, scenario analysis, and benchmarking. Prepare validation reports, manage findings, support model governance and regulatory exams, collaborate with stakeholders, and improve validation processes through automation.

Leads the lending application support team and owns day-to-day operations, Level 3 troubleshooting, system tuning, configuration, testing, defect management, implementations, acquisitions, and conversions. Supports process improvement, data mapping, reconciliation, change management, and product roadmaps. Provides leadership, mentoring, training, and best-practice development while coordinating with business stakeholders, technology teams, vendors, and consultants.

Lead Wintrust’s Model Risk Management team and supervise validation experts assessing bank-wide AI, machine learning, statistical, econometric, mathematical, and qualitative models. Perform model validation, including Python programming; manage the enterprise validation framework and model inventory; monitor AI trends and regulations; produce model risk reports; collaborate with business teams; facilitate regulatory examinations and audits; and lead model governance sessions.

The Senior IT Project Manager leads project initiation, planning, execution, and closure while ensuring technology governance and integration across business units, managing moderate to high complexity projects with a focus on financials and efficiency.

Develops new public-sector banking relationships through direct outreach, conferences, community activities, referrals, and collaboration with relationship managers. Supports RFP responses, client and prospect management, customer service, and public funds portfolio projects. Requires government-sector treasury management sales experience, strong communication and relationship-building skills, business development success, and moderate conference travel.

Support Trust Officer with daily trust account administration including account openings/closures, cash movements, correspondence, research and client inquiries. Maintain electronic and paper account documentation, monitor accounts, prepare spreadsheets and presentations, and perform basic accounting and banking tasks while adhering to regulatory and confidentiality standards.

Processes and balances customer financial transactions, operates a teller drawer in the lobby or drive-up, identifies cross-selling opportunities, recognizes and reports potential fraud, follows banking and regulatory procedures, and may open or close the bank or participate in community events. The role requires customer service, cash-handling accuracy, flexible shift availability, and occasional travel between branches.

Generate mortgage business through outbound calls to prospective and existing borrowers. Analyze customers’ financial needs, research mortgage guidelines, structure and present loan options, assist with applications, collect documentation, monitor loan status, and coordinate with internal teams, vendors, and customers through processing, underwriting, and closing. The role requires strong communication, financial analysis, organization, sales aptitude, computer skills, and compliance with NMLS requirements.