Top Remote Principal Software Engineer Jobs in Chicago, IL

Design, develop, and operate highly scalable and resilient Azure VM Scale Set cloud services. Own features from architecture through deployment and operations, solve distributed-systems challenges at hyperscale, and drive reliability, security, performance, disaster recovery, testing, monitoring, automation, and engineering best practices. Collaborate across teams to deliver platform capabilities and customer outcomes.

Design, build, test, deploy, and operate scalable, secure Azure networking software and automation tools. Act as DRI, monitor production, troubleshoot incidents, run root-cause analysis, and drive reliability, performance, and cost improvements. Collaborate with PMs and architects, participate in design/code reviews, mentor engineers, and champion security, privacy, and compliance.

Lead hardware strategy, performance architecture, and benchmarking for large-scale Microsoft 365 and AI workloads. Investigate performance, scalability, and efficiency across compute, GPU, memory, storage, networking, and accelerators. Partner with Azure and platform teams, build AI-assisted performance engineering tools, and influence cross-organizational architecture and infrastructure decisions.

Provides technical leadership for Azure SQL databases supporting a highly available Azure service. Responsibilities include database performance tuning, reliability and capacity planning, schema changes, data migrations, observability, incident response, root cause analysis, operational automation, and technical strategy. The role partners with software engineers, SREs, and architects to improve scalability, durability, cost efficiency, and long-term service reliability across teams.

Design, build, and operate AI-powered automation, CI/CD systems, distributed services, developer tooling, and code-intelligence platforms. Own significant capabilities from architecture through production, improve engineering workflows using measurable evaluations, scale reliable automation and delivery systems, and operate secure multitenant services. Lead technical reviews, define reliability practices, integrate platforms through APIs and MCP, mentor engineers, and drive ambiguous technical problems to dependable production outcomes.

Build product features and improve technology platforms supporting claims processing and payment. Collaborate with subject matter experts, operations, and technology teams to design solutions that improve member experiences, operational efficiency, and provider relationships. The role requires individual technical contribution, ownership, comfort with ambiguity, and the ability to work across a broad technology stack in a fast-paced startup environment.

Design and operate large-scale, AI-native cloud infrastructure (especially Kubernetes/AKS). Improve service quality, automate incident prevention/remediation, accelerate engineering productivity, and integrate AI tools into development workflows.

Leads and contributes hands-on to development of an AI engineering platform for semiconductor testing. Designs agent tooling, RAG systems, cloud and air-gapped inference infrastructure, Kubernetes platforms, reusable AI patterns, and agent-facing UIs. Sets technical direction, selects hardware and inference stacks, manages production systems, resolves cross-team architecture decisions, and guides a small engineering team. Requires strong distributed systems, software development, leadership, communication, and LLM/agent tooling expertise.

Own the networking architecture and roadmap for AKS Flex and Unbounded, enabling secure, reliable, high-performance Kubernetes connectivity across sites, clouds, edge environments, and on-premises infrastructure. Design overlay and underlay networks, routing, encrypted tunnels, eBPF dataplanes, and distributed systems for high-latency and partitioned environments. Integrate InfiniBand and RDMA for AI workloads, lead cross-team architecture efforts, improve global fleet performance and reliability, and participate in production operations and on-call rotations.

Lead architecture and hands-on development of Azure Kubernetes Service capabilities for AI workloads. Design secure, reliable, scalable distributed systems; coordinate engineering teams; define testing and deployment strategies; improve observability and operational readiness; investigate production issues; and mentor engineers while advancing engineering practices.

Lead architecture and development for AKS Flex, scaling etcd and Kubernetes control planes for distributed node fleets. Design remote-node provisioning, lifecycle automation, Kubernetes-native APIs, secure bootstrap, upgrades, and reliability systems across Azure, on-premises, edge, and other clouds. Drive performance testing, production operations, open-source collaboration, technical strategy, cross-team alignment, and mentorship while solving distributed-systems, storage, security, and scalability challenges.

Leads development of distributed AI infrastructure for large-scale reinforcement learning and LLM post-training. Designs scalable, resilient systems; optimizes model, hardware, and inference performance; improves developer tooling and engineering practices; mentors engineers; and supports production services through reliability engineering, incident response, telemetry, and on-call operations.

Design, implement, and operate production-quality AI framework components, benchmark and optimize large model training and inference across GPUs and Microsoft hardware, build automation and observability, drive cross-team projects from definition to deployment, and provide technical leadership and mentorship for improvements in performance, reliability, and model onboarding velocity.

Build and improve Azure Kubernetes Service capabilities for Linux and Windows containers. Develop distributed cloud infrastructure, automation, observability tooling, and reliability improvements at global scale. Support AI-native infrastructure, including GPU orchestration, model deployment, inference, and platform operations. Accelerate engineering workflows, prevent production incidents, integrate AI tools, and contribute to Kubernetes and cloud-native platform innovation.

Lead technical direction for Elastic’s core billing platform across cloud providers. Design and operate scalable billing systems, data pipelines, APIs, and PostgreSQL architecture. Improve reliability, observability, incident response, deployment, and CI/CD practices. Partner with SRE, Cloud Infrastructure, Product, Design, and Finance teams, guide architecture and roadmap decisions, review technical work, mentor engineers, and participate in on-call rotations.

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.

Lead technical vision and architecture for AI frameworks, performance, benchmarking, and tooling. Drive cross-team alignment, mentor engineers, ship high-performance distributed software, and improve model onboarding, runtime performance, reliability, and Azure hardware efficiency.

Designs and develops secure, performant Copilot products and platform services across Windows, Mac, and mobile. Builds distributed AI and agent-driven systems capable of reasoning, planning, and executing tasks. Collaborates with infrastructure, platform, application engineering, and research teams to ship high-quality software. Champions AI-assisted development, coding-agent adoption, prompt design, tooling best practices, and human-in-the-loop systems.

Leads end-to-end design, development, quality, and integration of complex software solutions and cloud services. Provides technical leadership for enterprise-wide projects, manages engineering processes, risks, dependencies, and delivery priorities, and writes code across the software ecosystem. Collaborates with multidisciplinary teams to deliver measurable, user-centric technology solutions, primarily supporting healthcare caregivers.

Lead design and implementation of Azure full‑stack, scalable skilling platform features. Drive CI/CD, reliability, automation, and AI/LLM-enabled capabilities. Mentor engineers, enforce engineering best practices, coordinate cross-team dependencies, and improve test automation and observability for enterprise-scale services.

Lead the technical vision and architecture for scalable, secure, high-performance distributed systems. Provide engineering leadership, mentorship, and architectural guidance while driving reliability, automation, CI/CD, security, performance optimization, and technical strategy. Investigate emerging technologies, oversee complex problem-solving, establish engineering standards, and collaborate with product and business stakeholders to align technology roadmaps with organizational goals.

Principal Software Developer responsible for designing, developing, and scaling distributed, high-throughput software systems. The role delivers features, improves reliability, identifies bottlenecks, leads system migrations from monoliths to microservices, and works across the technology stack. Responsibilities include architectural design, cloud engineering, technical leadership, mentoring developers, communicating technical decisions, and using AI and automation tools to improve engineering outcomes.

Architects and leads qualification, performance validation, automation, reliability, and fleet-readiness efforts for next-generation Azure Storage infrastructure. Develops tooling, telemetry, and performance analysis frameworks while partnering across Storage, Compute, Networking, Platform Engineering, and hardware teams. Provides technical leadership through architecture, incident resolution, mentorship, and engineering best practices. The role is onsite three days weekly in Redmond, Washington.

The Senior Principal Product Architect leads the architecture of Workload Automation and DevOps solutions, focusing on automation technologies, hybrid cloud environments, and mentoring teams to modernize software engineering processes.

Build and operate production-quality AI framework, runtime, benchmarking, performance, automation, observability, and developer-tooling systems. Optimize large language model training and inference across GPUs and Microsoft hardware, diagnose cross-stack reliability and performance issues, and improve model onboarding, hardware utilization, Azure efficiency, and deployment speed. Senior engineers own major components and projects; Principal engineers define technical direction, architecture, and multi-release strategy while leading cross-team initiatives and mentoring technical leaders.