Top Remote Principal Software Engineer Jobs in Chicago, IL

Leads architecture and development of scalable Node.js SaaS applications and data products. Responsibilities include designing systems, translating stakeholder needs into technical backlogs, writing user stories, coordinating architecture decisions, supporting product planning, improving business processes, and mentoring engineers. The role also incorporates AI-assisted development, code review agents, LLM APIs, agentic workflows, and generative AI tools.

Lead technical strategy and architecture for Azure Storage geo-replication, data protection, failover orchestration, and business continuity. Drive cross-team delivery, operational excellence, telemetry, automation, AI-assisted operations, and represent the team in executive and customer engagements.

Designs, develops, and leads scalable healthcare software solutions involving transaction processing, interoperability standards, integrations, and data platforms. Provides hands-on engineering, architectural leadership, quality ownership, risk management, technical mentorship, and cross-functional collaboration. The role requires building high-performance cloud-based SaaS solutions using microservices and serverless architectures, while guiding engineering strategy and ensuring secure, reliable delivery.

Founding engineer responsible for architecting and building core product systems, writing scalable Python backend code, designing and maintaining AI/ML infrastructure, instituting best development practices (testing, CI/CD), collaborating on product roadmap, and mentoring future engineers.

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 and build of production-ready cloud and AI systems, prioritize security and reliability, ship solutions quickly using modern engineering practices, collaborate with cross-functional teams, mentor engineers, drive customer adoption, and deliver reusable assets and end-to-end complex deliveries.

Design, develop, and maintain a native IBM i connectivity agent for Redwood RunMyJobs. Responsibilities include job submission and monitoring, spool and queue handling, CL/RPG invocation, security integration, API connectivity, troubleshooting, performance and reliability improvements, architecture, code reviews, testing, documentation, and collaboration with product and engineering teams. The role also requires validating AI-assisted solutions against authoritative IBM i documentation.

Build and maintain a Java-based connectivity agent integrating Redwood RunMyJobs with IBM z/OS. Responsibilities include JES, TSO, SMF, USS, security, cryptography, custom protocols, C/JNI integration, concurrency, troubleshooting, performance, architecture, testing, documentation, and collaboration. The role requires deep mainframe systems expertise, strong Java and C skills, DevOps experience, and sound judgment when using AI-assisted engineering tools.

Lead architecture and engineering for Microsoft’s enterprise Insider Risk platform. Build scalable, secure, privacy-conscious systems supporting risk modeling, behavioral analytics, detections, monitoring, investigations, workflows, and case orchestration. Partner with security, legal, HR, privacy, data science, and business teams to address complex risk scenarios. Drive technical strategy, align cross-team delivery, mentor engineers, and uphold reliability, confidentiality, compliance, and responsible data-use standards.

Lead development and operation of a scalable Kubernetes-based cloud-native platform. Shape the engineering roadmap, deliver enterprise platform capabilities, establish best practices, mentor engineers, and collaborate across Agile teams. Build highly available and fault-tolerant production services using Kubernetes and cloud-native technologies, while applying expertise in Go, Python or Bash, networking, Linux, and CI/CD practices.

Leads enterprise-wide quality engineering and test automation architecture across Humana. Designs scalable frameworks for web, mobile, API, integration, and end-to-end testing; integrates automation with CI/CD and DevOps platforms; establishes governance, standards, traceability, and quality gates; and mentors engineering teams. The role also drives AI-enabled testing, including test generation, self-healing automation, defect prediction, and intelligent execution, while advising stakeholders on modernization and enterprise transformation.

Leads enterprise-wide quality engineering and automation strategy, designing scalable test frameworks, reusable automation platforms, CI/CD integrations, and AI-powered testing capabilities. Establishes standards, architectures, and best practices while supporting web, mobile, API, microservices, cloud-native, and distributed applications. Provides technical mentorship, partners with engineering and DevOps teams, improves testing effectiveness and reliability, and drives adoption of intelligent automation, predictive quality analytics, and continuous testing practices.

Define technical direction for hyperscale Azure Storage components; architect, develop, test, and support highly scalable, secure, compliant, and highly available cloud services. Lead multiple engineering projects, improve reliability, scalability, performance, consistency, and observability, and apply AIOps for incident detection, root-cause analysis, and operational excellence.

Owns end-to-end production software, architectural decisions, and improvements to the engineering lifecycle. The principal engineer will expand AI-assisted development, make speed safe across reservations, payments, mobile, and international systems, and influence a growing team’s engineering practices. Success means enabling a fourteen-person team to ship with the effectiveness of a much larger organization.

Lead architecture and roadmap for Azure PostgreSQL systems; design and review scalable, maintainable database engine features (query processing, storage, transaction logging, recovery, versioning, IO, scale-out). Influence coding standards and run code reviews, write proof-of-concept or production code, contribute to open-source PostgreSQL/Linux, and participate in rotational on-call operations.

Lead the architecture and implementation of scalable cloud compute functionality across ARM64 and x86 platforms. Design hypervisor layers, cross-platform build pipelines, and performance optimization solutions while writing, reviewing, documenting, and testing production software. Coordinate globally to deliver compute features and resolve low-level software issues. Provide technical, organizational, and functional leadership to engineers.

Develop and operate production AI framework components, runtimes, benchmarking systems, performance tools, and integrations. Benchmark and optimize large language model training and inference across GPUs and Microsoft hardware, build automation and observability, investigate cross-stack performance and reliability issues, and deliver scalable platform improvements. Principal engineers additionally set technical direction, lead multi-team initiatives, define architectures, and mentor technical leaders.

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.

Principal frontend-focused software engineer responsible for leading frontend architecture, standards, tooling, accessibility, performance, testing, and deployment practices. The role delivers scalable customer-facing web applications, component libraries, and design systems using React or Angular. It includes cross-functional product collaboration, technical decision-making, mentoring, modernization initiatives, and occasional full-stack work. The position is remote, requires U.S. citizenship, Public Trust 6C eligibility, and approximately 0–10% business travel.

Lead enterprise AI architecture, strategy, and technical vision across products and business segments. Design and deploy scalable GenAI applications using LLMs, agent workflows, RAG, vector databases, NLP, and computer vision. Establish standards for AI security, monitoring, cost management, responsible AI, and documentation. Partner with product, data science, engineering, executives, customers, and vendors while mentoring teams and driving reusable AI platforms and services.

Lead as a customer‑embedded principal engineer to design, build, and ship production-grade solutions. Translate business needs into technical approaches, influence senior stakeholders, accelerate delivery in ambiguous environments, and transition work to FDE crews while driving long-term account impact.

Lead the technical vision, architecture, and roadmap for Pika’s web and multiplatform creative products. Design scalable user-facing systems, real-time collaboration, messaging, generative AI workflows, and cross-service observability. Partner with product and design leaders from ideation through launch, while driving architecture reviews, technical excellence, mentorship, and engineering strategy.

Leads the strategic direction of backend and full-stack engineering, architects scalable distributed systems and microservices, and drives modernization, reliability, security, and performance initiatives. Designs APIs, data architectures, pipelines, infrastructure, and observability practices; delivers customer-facing service improvements; establishes engineering standards; and mentors engineers. Collaborates across product and technical teams to make architecture and business trade-offs and lead large-scale initiatives from vision through production.

Design and build Seeq’s internal platform, including infrastructure, services, multi-tenant Kubernetes clusters, system interfaces, and secure deployment capabilities. Improve scalability, reliability, software delivery, and infrastructure cost and performance. Lead migrations, integrate security practices, architect distributed systems, collaborate cross-functionally, and mentor engineers while remaining hands-on at Staff or Principal scope.

Design and implement high-performance backend systems in Rust, optimize architectures, participate across the development lifecycle (debugging, testing, optimization), integrate third-party devices and data, incorporate AI tools, mentor senior engineers, and lead architectural and technical strategy across teams.