Top Tech Jobs & Startup Jobs in Chicago, IL

Leads software engineering projects and developers building cloud-based, full-stack solutions using distributed microservices. Designs service boundaries, APIs, reusable frameworks, and database integrations; establishes engineering standards; improves performance and reduces technical debt. The role requires technical leadership across Agile teams, collaboration with product managers and architects, mentoring engineers, and applying modern cloud, DevOps, testing, observability, and AI-assisted development practices.

Oversee end-to-end Level 2 functional and security certification workflows for payment partners, terminal vendors, and mobile application developers. Manage high-volume technical queries, coordinate cross-functional certification activities, engage external product providers, and drive projects through final approval. Apply expertise in EMV specifications, payment systems, and card security testing standards to ensure compliance with network requirements and streamlined certification timelines.

Designs, develops, tests, and supports enterprise integration solutions connecting applications, cloud services, data sources, and platforms. Leads complex integration initiatives, defines standards and reusable frameworks, partners with software, data, infrastructure, and architecture teams, and ensures interoperability, scalability, resilience, observability, and performance. The role also mentors engineers and advances Agile engineering practices.

Design, develop, and operate secure, scalable Java and Spring Boot microservices and REST APIs in cloud-native environments. Translate requirements into distributed technical solutions, guide engineers, conduct code reviews, and maintain development standards. Deploy applications using Azure or AWS, Docker, Kubernetes, and CI/CD pipelines. Implement testing, monitoring, security remediation, incident response, root cause analysis, performance tuning, and on-call support while using AI-assisted tools to improve engineering efficiency.

Lead SRE practices for highly available cloud-native platforms across AWS, Azure, and Kubernetes. Build observability, dashboards, alerting, infrastructure automation, CI/CD, GitOps, and self-healing capabilities. Lead incident response, root cause analysis, and remediation while improving reliability, scalability, and operational excellence. Partner with engineering, architecture, security, and platform teams, drive AI-enabled operations, and mentor engineers on SRE and cloud-native best practices.

Leads software engineering across architecture, design, prototyping, and delivery for pharmacy technology platforms. Provides mentorship, establishes development frameworks and best practices, collaborates with business and IT stakeholders, leverages approved AI developer tools, supports Agile/Scrum execution, improves performance and security, and leads production issue triage and root-cause analysis.

Associate Underwriters evaluate business operations, financial data, and industry trends to assess commercial insurance risks. They develop coverage and pricing solutions, collaborate with brokers, customers, and internal teams, and make decisions supporting profitable growth. The program provides structured training, mentorship, and hands-on experience in underwriting principles, risk assessment, coverage analysis, pricing, negotiation, and relationship management.

Provides consulting and auditing support to a dedicated client’s global health and safety team. Evaluates safety management systems, assesses risk, recommends improvements, develops action plans, and measures progress. Builds relationships with customer stakeholders across health and safety, operations, and engineering. Leads through mentoring and coaching while improving service delivery. The fully remote role requires approximately 75% travel to customer locations from February through October.

Participate in a structured underwriting development program while evaluating commercial business risks, financial information, industry trends, coverage needs, and pricing strategies. Partner with brokers, customers, and internal teams to create insurance solutions, make risk-selection decisions, and support profitable growth. Build underwriting, negotiation, communication, and relationship-management skills through formal training, mentorship, and hands-on experience.

Provide first-level support for trading applications, including user logins, account configurations, troubleshooting, production issue resolution, clearing support, vendor coordination, developer collaboration, and technical documentation. Support internal and external users through phone, email, and instant messaging while assisting with special projects and process improvements.

Lead the architecture and delivery of Salesforce Marketing Cloud and Data Cloud solutions for partner marketing. Design data models, knowledge graphs, identity resolution, batch and streaming pipelines, APIs, zero-copy integrations, and AI-enabled workflows. Establish orchestration, monitoring, CI/CD, governance, and reliability standards while mentoring engineers and partnering with marketing, data science, and Salesforce stakeholders.

Lead and scale Square’s Central Region field sales organization by managing Sales Managers and Territory Account Executives. Set regional strategy, optimize territories and go-to-market plans, drive pipeline and revenue performance, coach teams in the field, develop talent, and collaborate with Marketing, Sales Operations, Partnerships, and Product. Serve as a product expert and regional representative while building a high-performance, accountable sales culture.

Manages commercial banking portfolios for investor real estate clients, evaluating credit risk, underwriting complex financing arrangements, analyzing financial statements, reviewing loan documentation, and ensuring compliance. The role researches credit information, presents recommendations, supports process improvements, and collaborates with internal and external stakeholders. It requires commercial banking portfolio management experience, strong real estate lending and financial analysis skills, attention to detail, and the ability to work independently in a hybrid environment with up to 10% travel.

Lead strategy and roadmap for Adyen’s Issuing Servicing product, covering card and transaction auditability, program servicing, and dispute management. Drive platform-scale execution with Engineering, Design, Finance, Operations, Regulatory, and Compliance teams. Define customer-focused investments, success metrics, experimentation, and AI-forward product development for a highly automated global platform.

Manage employee benefits and wellness programs, including open enrollment, vendor implementations, M&A integrations, communications, and HRIS benefits technology. Govern enrollment platforms and carrier feeds, develop analytics dashboards, monitor regulatory changes, and support ERISA compliance activities such as Form 5500 preparation, plan reviews, and discrimination testing. Lead cross-functional initiatives and benefits vendor relationships.

Lead federal mergers and acquisitions tax engagements involving due diligence, transaction structuring, restructuring, insolvency, financial modeling, tax risk analysis, and regulatory matters. Manage major projects, improve processes, advise senior clients, develop business strategies, and mentor multidisciplinary teams. Build client relationships, apply U.S. federal income tax law, use complex data to provide insights, and represent the firm externally.

Leads consulting engagements focused on pricing, promotions, revenue management, and profitability optimization. Develops pricing strategies, analyzes market trends and customer profitability, oversees multiple projects, manages executive client relationships, drives business development, and mentors consulting teams. Uses pricing tools to evaluate performance, aligns promotional strategies with business objectives, and guides technological and business transformation initiatives.

Design and implement identity and access management strategies, manage user identities and access rights, develop federated identity and verification solutions, and apply encryption technologies. The role involves Azure Active Directory, CyberArk, RBAC, identity governance, cybersecurity enhancements, data analysis, client collaboration, and IT governance. It requires navigating complex situations while delivering secure solutions and maintaining professional standards.