Top Remote Principal Engineer Jobs in Chicago, IL

Owns enterprise AI security assessment, architecture, and control programs. The role evaluates AI systems, vendors, platforms, and shadow AI; designs secure architectures, guardrails, identity models, sandboxes, gateways, and runtime controls; and develops detection and response capabilities for prompt injection, jailbreaks, data leakage, and tool misuse. The engineer partners with governance, identity, platform, engineering, and security operations teams, advises senior leaders, drives remediation, and mentors security professionals.

Provides technical leadership for real-time RF sensor software development, integration, testing, and validation. Designs high-performance C/C++ systems, integrates signal-processing algorithms, debugs distributed and multithreaded applications, and transitions MATLAB/Python prototypes into production software. The role includes technical mentoring, customer and government stakeholder engagement, proposal development, documentation, system demonstrations, visualization tools, and approximately 10% travel for integration and field-testing activities.

Owns company-critical, long-term technical problems across multiple teams and organizations. Defines technical strategy, architectures, roadmaps, and engineering standards for large-scale customer-facing systems. Remains hands-on in software development while driving AI adoption in products and engineering workflows. Partners with senior product, engineering, and executive leaders to resolve complex problems, improve reliability and performance, and shape Dropbox’s technical direction.

Build and own Arcadia’s internal developer platform across a large-scale data lakehouse and Kubernetes applications. Develop self-service APIs, templates, golden paths, CI/CD capabilities, observability, security controls, and reliability practices. Lead platform migrations, improve developer experience, manage stakeholder needs and costs, set technical direction, and coach senior engineers. The role requires hands-on software development alongside expertise in cloud infrastructure, Kubernetes, networking, infrastructure as code, SLOs, incident response, and platform product management.

Hands-on technical leader who designs, builds, and deploys production-grade AI automation and agentic workflows. Responsibilities include rapid prototyping, RAG and document-intelligence systems, API integrations, orchestration, monitoring, reusable AI assets, and mentoring a small engineering team to deliver frequent releases and measurable business impact.

Lead the architecture and development of a production Agentic SOC that uses LLM-based agents to investigate security signals, gather evidence, make defensible decisions, and support SOC analysts. Own agent behavior, tool use, evaluation, guardrails, tenant isolation, auditability, reliability, and autonomous decision-making. Collaborate with analysts, detection engineers, product, and engineering teams while providing technical leadership and mentoring. Build scalable backend systems using distributed workflows, queues, cloud infrastructure, and data stores.

Lead the architecture and technical direction of Forward Financing’s core fintech platform. Design scalable distributed backend systems, guide cross-team initiatives, establish engineering best practices, resolve incidents, and mentor engineers. The role owns the technical roadmap and architectural vision while partnering across teams to improve reliability, observability, code quality, and delivery. Ruby on Rails expertise is required, along with strong communication, influence, agile development experience, and a broad backend or full-stack perspective.

Lead GitLab’s company-wide strategy for autonomous, agentic software development workflows. Identify and validate AI opportunities across the SDLC, build prototypes and reference architectures, establish evaluation frameworks and safety controls, and drive internal adoption. Partner across Engineering, Product, Infrastructure, Security, Architecture, and Data and ML teams to scale reliable, observable, compliant agentic capabilities into customer-facing products. Mentor senior technical leaders and represent GitLab externally on AI-assisted development and productivity measurement.

Leads architecture and development of SailPoint’s large-scale, multi-tenant identity security SaaS platform. Translates business strategy into technical roadmaps, designs reliable microservices and infrastructure, drives modernization from monoliths to distributed systems, mentors engineers, reviews designs, delivers code, and communicates technology strategy to executives and stakeholders. The role also requires adoption and oversight of AI-assisted engineering tools and technologies.

Provides enterprise technical leadership for Identity and Access Management and AI-era identity security. Defines architectures, standards, governance, authentication, authorization, privileged access, machine identity, secrets, and agent security controls. Leads threat modeling, adaptive authentication, AI-driven detection, monitoring, and response capabilities. Partners with engineering, product, infrastructure, cyber defense, and architecture teams; mentors technical leaders; establishes reusable secure-by-default patterns; and influences executive stakeholders on identity risk, security strategy, and technology investments.

Lead the architecture and development of high-throughput streaming infrastructure processing over one million messages per second with sub-second latency. Responsibilities include scaling real-time computation, improving caching, designing message deduplication, enabling zero-downtime deployments, delivering customer-focused projects, shaping the technical roadmap, and mentoring engineers.

The Principal Engineer will lead the design and delivery of core platform capabilities, focusing on scalable systems, AI application, and mentoring engineers while driving architectural decisions and improving operational systems.

Leads quality engineering activities for medical device and pharmaceutical products, including CAPA, complaint investigations, SCARs, quality metrics, post-market surveillance, change control, regulatory compliance, and continuous improvement. Coordinates cross-functional investigations with Engineering, Manufacturing, R&D, Commercial, and Field Service; evaluates product risks and trends; supports new product development, audits, and design controls; and serves as a quality subject matter expert while mentoring engineering teams.

Lead the design and production delivery of agentic AI systems, translating domain expertise into ontologies, tool contracts, evaluation frameworks, and reliable orchestration patterns. Own context management, guardrails, tracing, testing, and observability while setting technical direction for an engineering pod. Collaborate with engineers, subject matter experts, product leaders, security teams, executives, and clients. The role requires production experience with agent frameworks, multiple model families, cloud AI platforms, agentic development practices, and coding tools.

Drive technical marketing for Zero Trust Branch and Digital Experience solutions through customer proof-of-value pilots, architectural demos, networking lab design, troubleshooting, technical collateral, and field enablement. Serve as the technical bridge between field teams and engineering while validating solutions, supporting enterprise evaluations, and improving post-sales time-to-value. The role requires deep networking, packet analysis, cloud networking, monitoring, and customer-facing technical expertise.

Provide technical direction for GitLab Dedicated, a managed single-tenant SaaS platform. Lead architecture and transformation across resilience, failover, tenant orchestration, change management, automation, and platform integrations. Identify systemic reliability and scalability risks, establish reusable platform patterns, strengthen service ownership, and guide cross-team technical decisions. Mentor senior engineers and advance engineering excellence across the organization.

Partner with sales teams to win strategic data security opportunities. Present technical solutions, gather customer requirements, lead product evaluations, configure solutions, and design evaluation test plans. The role requires extensive pre-sales experience, security and networking expertise, data protection and web technology knowledge, and collaboration across matrixed go-to-market and partner teams.

Designs and develops internet-scale data processing, infrastructure management, and observability platforms across cloud and on-premises environments. Establishes engineering standards, resolves complex distributed architecture challenges, and provides technical leadership across the organization. The role requires experience with large-scale orchestration systems, internet protocols such as DNS, WHOIS, and RDAP, architectural trade-offs, and internet security technologies.

Serve as a global SME for Industrial Metaverse technologies (PLCs, IoT, cloud/edge, digital twins, AI, EMC/RED, cybersecurity). Lead standards work, develop test programs, perform and supervise complex testing, train staff, represent UL externally, and support clients and continuous improvement across regional or global labs.

Provides department-wide technical direction for k0rdent across Kubernetes, AI infrastructure, AI applications, and observability. Designs cross-cutting systems, establishes engineering standards, resolves architectural risks, mentors Staff and Principal engineers, and aligns product strategy with durable technical execution. The role also engages customers, partners, upstream communities, and industry forums while contributing code and prototypes to solve complex infrastructure problems.

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.

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.

Lead design, build, and deploy of large-scale data platforms for LLMs, RAG, and agentic AI systems. Hands-on coding, architecting fault-tolerant pipelines, establishing MLOps/DataOps best practices, mentoring engineers, and operationalizing research into production across Exabyte-scale distributed systems.

Lead the architectural evolution from monolithic applications to distributed systems. Define service boundaries, establish architectural standards, shape technical roadmaps, and ensure platform scalability, resilience, and maintainability. Collaborate across engineering teams, solve complex technical challenges, mentor engineers, and influence organizational direction through high-impact architectural decisions.

Develop low-level, high-performance instrumentation within CICS and z/OS using HLASM. Design production features for mission-critical mainframe environments, diagnose complex system behavior through dumps and traces, analyze performance bottlenecks, and collaborate with an experienced engineering team. The role requires deep z/OS and CICS internals expertise, systems programming knowledge, and proficiency with JCL, SDSF, and USS.