Top Remote Principal Software Engineer Jobs in Chicago, IL

Lead technical vision and cross-team architecture for large-scale, high-volume backend systems. Mentor senior engineers, solve scalability and infrastructure issues, set code and design standards, and partner with product and design to deliver secure, AI-enabled consumer healthcare solutions.

As a Principal Software Engineer for the AAP team at Toast, you will design scalable systems, develop technical strategies, mentor engineers, and enhance data-driven initiatives.

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.

The Principal Software Engineer will design and optimize backend applications/services, improve payment integration, and oversee code quality within AWS.

The role involves building and optimizing a machine learning and simulation platform, supporting MLOps, model deployment, and infrastructure modernization, while mentoring engineers.

Provide technical leadership for internal platforms and security automation supporting Upstart Bank. Lead architecture, design, and implementation of platform services, APIs, relational schemas, authentication and RBAC systems. Partner with risk, compliance, and operations stakeholders, mentor engineers, mitigate technical risks, and drive long-term platform strategy and engineering standards.

The Principal Software Engineer will define technical roadmaps, guide system architecture, mentor leaders, and drive product direction in Capital Supply operations.

Lead and mentor an engineering team building GovIntel and GovChannel product capabilities. Own technical direction, design and deliver scalable SaaS features, APIs, integrations, and platform reliability. Partner with Product, QA, Cloud Ops, and stakeholders to prioritize work, drive CI/CD and observability practices, lead reviews and incident response, and apply AI-assisted tools to improve development speed and quality.

The Principal Software Engineer leads a team to develop full-stack real-time applications, integrates machine learning models, and influences software architecture in cloud environments while supporting healthcare analytics.

Senior individual contributor who architects and builds IAA's Azure-based data platform (ingestion, transformation, semantic modeling, delivery). Designs and implements complex production data pipelines, supports BI and ML workloads, sets standards, mentors engineers, and partners with business and engineering leaders to enable analytics, forecasting, and AI.

Lead architecture and technical direction for Athena, a production-grade distributed system that validates, deduplicates, and routes enterprise vulnerability data. Drive transition from prototypes to maintainable systems with observability, SLOs, incident handling, and operational rigor. Partner across teams on domain ownership, hire and raise engineering standards, and design pipelines that extract clean signals from unstructured vulnerability reports.

Design and build autonomous accounting agents, implement a custom accounting ledger, integrate financial data providers, and ship daily features using TypeScript/Node/Svelte. Work rapidly in an early-stage startup, make product decisions, and engage in customer problem discovery.

Lead design and implementation of advanced systems features for Postgres, focusing on performance optimization and scalability. Mentor engineers and drive architectural direction for large-scale database systems.

Lead AI adoption initiatives and cultural transformation in engineering at Yahoo Mail, enhancing developer productivity through AI tools and practices.

Lead architecture and technical strategy across an infrastructure platform ecosystem. Drive hands-on architectural improvements to graph engine and backend services, reduce technical debt, establish standards, champion AI-first engineering practices, run architecture/code reviews and mentorship, and collaborate with product and leadership to ensure scalable, extensible systems.

The Principal Software Engineer will drive the technical roadmap for Panthey's hosting platform, architect core services, and provide technical leadership and mentoring to engineers. They will work on distributed systems, container orchestration, and AI-native engineering practices, ensuring platform reliability and performance.

Lead design and implementation of AI-enabled ITSM and lifecycle automation: integrate ServiceNow and enterprise platforms, build reusable AI-driven automation skills, automate incident/problem/change workflows, improve data flows and observability, and deliver dashboards and playbooks to accelerate end-of-life lifecycle execution and reduce manual effort.

Lead technical aspects of an engineering team, design and revamp systems, improve efficiency, mentor engineers, and contribute to product strategy.

Lead design, architecture, and hands-on implementation of scalable healthcare SaaS systems. Drive interoperability (HL7, FHIR, EDI), mentor engineers, liaise with stakeholders, manage technical risk, and ensure quality, performance, security, and innovation.

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.

Design, build, and improve Elasticsearch distributed-systems components for scalable, concurrent, and consistent indexing. Maintain cluster coordination for performance and resilience, push system scale limits, investigate performance and concurrency issues, support operations/support engineers, and lead projects involving multiple engineers from design through delivery.

The Principal Software Engineer at Snout will define architectural direction, build features across the stack, and enhance team effectiveness, ensuring quality and performance.

Lead reliability, availability, and resiliency strategies for large-scale systems, drive operational excellence, and provide technical mentorship across engineering teams.

The Principal Software Engineer provides technical leadership for enterprise applications focusing on ERP and core systems, resolving complex issues, and enhancing solutions while ensuring best practices in full-stack development.

Lead technical direction for major full‑stack product areas, architect scalable systems across frontend, backend, and data, build AI-powered features (LLMs/embeddings), drive large cross-team initiatives, establish engineering standards (reliability, testing, observability), remove systemic risks, and mentor engineers while partnering with product and design to deliver customer-focused outcomes.