Top Tech Jobs & Startup Jobs in Chicago, IL

Designs, develops, and maintains automated testing solutions for customer-facing applications and web services. Builds UI, API, integration, performance, and functional tests; integrates automation into CI/CD pipelines; investigates defects; improves test coverage, software quality, security, and reliability; and collaborates with Agile development teams on code and test reviews.

Lead product management for a next-generation offer and loyalty platform. Own user experience, product requirements, roadmap prioritization, partner API integrations, performance metrics, analytics-driven iteration, feature launches, and cross-functional alignment across design, engineering, sales, support, and leadership.

Design and deploy AI agentic workflow frameworks, multi-agent orchestration platforms, LLM integration layers, retrieval systems, and evaluation pipelines. Integrate generative AI services to automate parsing, data mapping, and action triggers while building scalable backend architecture. Requires extensive software engineering experience with distributed systems, cloud platforms, JVM languages, containerization, microservices, asynchronous processing, and LLM orchestration.

The Product Manager will lead AI solution strategy and execution across the Clover ecosystem. Responsibilities include prioritizing AI workflow use cases, translating business processes into agentic experiences, defining metrics and roadmaps, building evaluation and confidence-scoring frameworks, implementing governance and audit workflows, prototyping prompts and agent systems, and partnering with vertical product managers. The role requires extensive product management experience, strong generative AI expertise, analytical execution skills, and hands-on technical prototyping capabilities.

Own the growth platform product strategy, enabling go-to-market teams and self-service workflows. Lead CDP implementation, experimentation infrastructure, A/B testing, event taxonomy, data governance, and growth technology vendor management. Drive cross-functional alignment across product teams, establish shared platform standards, and influence without direct authority. The role requires fluency in data pipelines, event schemas, webhooks, REST APIs, database architecture, and growth analytics and experimentation tools.

Design, build, and deploy production-grade Generative AI applications and multi-agent solutions. Develop RAG pipelines, integrate commercial and open-source LLMs, fine-tune models, and build scalable Python APIs. Optimize applications for performance, latency, cost, reliability, and scalability. Implement monitoring, containerization, CI/CD, and cloud deployments while collaborating with engineering, architecture, AI/ML, and product teams.

Senior Business Systems Analyst to define requirements for agent-facing servicing applications, design integrations/APIs with core banking systems, translate needs into user stories and acceptance criteria, improve agent workflows and productivity, and identify AI/ML opportunities for fraud detection, automation, and operational analytics. Supports testing, validation, and releases.

Develop and deploy Java Spring Boot microservices, REST APIs, automated tests, performance and chaos testing solutions. Manage EKS infrastructure, CI/CD workflows, monitoring, JVM and database optimization, and production support. Migrate TIBCO BW processes to Apache Camel and ActiveMQ Artemis, implementing resilient messaging and standardized exception handling. Maintain API documentation, testing records, and ServiceNow change-management tickets.

Design, develop, test, deploy, and support scalable Java and Spring Boot microservices. Build REST APIs, automated tests, Camel and Artemis messaging workflows, and resilient infrastructure on EKS. Collaborate on CI/CD, monitor production systems with Datadog, optimize performance, document APIs and testing outcomes, and manage ServiceNow deployment tickets. The role also involves migrating TIBCO BW processes to Apache Camel and supporting production installations across various U.S. locations.

Design and build scalable backend services and AI-powered applications using Node.js/TypeScript or Python. Develop AI agents, agentic workflows, LLM integrations, tool calling, evaluation frameworks, REST APIs, microservices, and event-driven services. Partner with Product and Business teams, provide architecture guidance and code reviews, lead an offshore engineering pod, and optimize backend and AI workloads for reliability and performance. The role is onsite in Rhode Island or Arizona.