Top Engineering Jobs in Chicago, IL

Build and optimize automated release engineering systems, including CI/CD pipelines, build and deployment tooling, and AWS cloud infrastructure. Ensure software delivery quality, security, compliance, and reliability. Lead complex projects, participate in on-call support, mentor teammates, and promote technical excellence. The role uses Go, Java/Kotlin, TypeScript, GitHub Actions, PostgreSQL, DynamoDB, Backstage, AWS, and AI development tools.

The GTM Engineer will automate sales workflows using tools, build integrations, design a win/loss analysis program, and collaborate with sales teams to leverage AI insights.

As a Senior Principal Engineer, you'll define and drive the technical strategy for customer experience platforms, lead architectural decisions, and mentor engineering teams to enhance customer and agent experiences.

Design, build, deploy, and maintain resilient, scalable production systems for Toast’s retail customers. The role sets long-term technical architecture and strategy, communicates technical direction, mentors senior engineers, improves engineering productivity, diagnoses performance issues, and drives initiatives amid ambiguity. Engineers collaborate directly with retail customers, visit stores, understand operational workflows, and use AI tools to improve development velocity and quality.

Design, scope, and implement scalable backend and platform solutions for a reservations and waitlist product. Improve performance and usability, collaborate with Product and Design, identify high-impact opportunities, and contribute across the stack including APIs and front-end integration.

Design, build, deploy, and maintain resilient, scalable software for Toast Delivery Services. Develop real-time delivery tracking, driver matching, pricing, refunds, and payment-related systems. Solve distributed-systems and scaling challenges, integrate with partner APIs, uphold production reliability, promote strong engineering practices, and mentor teammates.

Lead the ToastNow engineering team in delivering high-quality native mobile experiences for restaurant operators. Drive planning, execution, cross-functional collaboration, backlog development, production quality, monitoring, and issue resolution. Hire, mentor, and develop engineers while fostering diverse, high-performing teams. Champion AI tools and practices to improve development speed, quality, and team velocity.

Lead architecture and technical execution for Toast’s Payroll and Team Management products. Own authentication, authorization, and organizational hierarchy across a multi-tenant SaaS platform. Drive high-scale, full-stack initiatives, modern agentic development practices, integrations, technical strategy, quality standards, deployment practices, and cross-functional collaboration. Mentor engineers across teams and leverage AI tools and LLM integration to improve software development velocity and quality.

Lead design, build, deployment, and operation of highly resilient, high-throughput configuration and publishing systems. Define long-term architecture and strategy, mentor senior engineers, diagnose and fix performance bottlenecks, and leverage AI tools to improve engineering productivity and platform capabilities.

Design and implement Kotlin backend services and end-to-end systems for Toast POS device management. Lead technical designs, estimations, performance optimization, cross-team collaboration, and software quality practices including modern testing and observability. Mentor peers and drive product roadmap alignment with product, hardware, and QA stakeholders.