Top Tech Jobs & Startup Jobs in Chicago, IL

Manages and grows small-business banking relationships, including loans, deposits, treasury services, cross-selling, prospecting, credit documentation, and portfolio development. The role owns customer experience, achieves lending and deposit goals, supports referrals and community events, and evaluates client needs while adhering to credit, risk, banking policy, and CRA requirements.

Lead development and execution of WLF's strategic plan through market research, data analysis, initiative and product management, cross-functional collaboration, KPI creation, and regular reporting to executive leadership to drive growth and process improvements.

Processes customer banking transactions including deposits, withdrawals, check cashing, and loan payments while accurately balancing a teller drawer. Provides lobby and drive-up service, identifies cross-selling opportunities, recognizes and reports potential fraud, follows banking and regulatory procedures, and may open or close the branch and participate in community events.

Leads enterprise application security across applications, APIs, and SaaS platforms. Responsibilities include threat modeling, security architecture reviews, manual code reviews, Checkmarx-based SAST and SCA, DAST, API security, CI/CD integration, vulnerability remediation, AI-assisted SDLC workflows, incident response support, developer coaching, and risk reporting. The role requires secure coding expertise, knowledge of application security standards, and experience with regulated financial services.

Provides primary application support for core banking and lending systems, troubleshooting APIs and microservices, managing testing and defect resolution, and supporting upgrades, conversions, acquisitions, and data migrations. The role analyzes system interdependencies, coordinates with business, technology, and vendor stakeholders, and delivers tier-one application troubleshooting. Requires 24x7x365 support availability, lending or IT experience, analytical problem-solving, testing documentation, communication skills, and the ability to work under pressure.

Designs, deploys, manages, and optimizes Microsoft Azure infrastructure and PaaS services. Responsibilities include Infrastructure as Code with Terraform and Bicep, Azure DevOps automation, security and governance, monitoring, troubleshooting, production support, disaster recovery, and resiliency planning. Partners with technical teams on cloud modernization, provides senior-level guidance, and mentors cloud and Microsoft 365 staff.

Manage daily cash positions for correspondent bank accounts across Wintrust, including Federal Reserve borrowing and fund sales. Monitor collateral pledged for customer deposits, coordinate securities and loan pledging with the FHLB and Federal Reserve, assist with security settlements, manage correspondent bank access, and support Treasury projects. The role requires strong time management, financial or accounting knowledge, and the ability to work effectively in a fast-paced environment.

Acts as a strategic talent development advisor to business leaders by analyzing performance and training needs, designing learning experiences, leading talent development programs, facilitating training, coaching junior colleagues, and evaluating solutions for measurable business impact.

Supports private client bankers, portfolio managers, investment advisors, and trust administrators with administrative, analytical, research, reporting, presentation, document preparation, and client-facing tasks. Maintains client confidentiality while analyzing financial information and assisting with client meetings. This is a paid, 12-week summer internship for students entering their junior or senior year.

Paid 12-week commercial banking internship focused on credit analysis, commercial loan approval, financial statement spreading, financial ratio interpretation, collateral analysis, and underwriting credit approval presentations. Interns work with commercial banking teams, participate in professional development and community activities, and gain experience across commercial and industrial, commercial real estate, and specialty lending groups.