Top Tech Jobs & Startup Jobs in Chicago, IL

Develop and maintain Tailscale's Windows client and contribute to cross-platform client and backend code. Build UI and platform integrations using WinUI/Windows native frameworks, write unit and integration tests, implement Windows platform features while preserving compatibility, and collaborate asynchronously across a distributed engineering team.

Provide Tier 2 technical support and escalations for Tailscale customers: troubleshoot complex networking and SSO issues, manage ticket SLAs, mentor Tier 1, collaborate with Product/Eng, and contribute to documentation and recurring friction elimination.

Work with product-minded engineers to turn AI-native prototypes (LLM gateways, agentic systems, proxies) into production-grade services: hardening, observability, security reviews, integrations with reference customers, and operational tooling to ensure reliability and maintainability.

Own frontend architecture and platform for a unified web console. Build identity-adjacent systems (auth, sessions, CORS/CSRF protections), shared infra and tooling, testing strategies, and enable other teams to ship reliable UIs. Collaborate across design, growth, and infrastructure; participate in on-call rotation.

Lead end-to-end product design for Tailscale's admin and DevOps workflows. Own discovery through delivery across GUI and CLI, collaborate closely with PMs and engineers, iterate from research and feedback, and ensure implementation quality for technically sophisticated B2B infra users.

Design, build, test, and operate backend control plane, platform, and identity services. Implement identity features (SSO, OAuth2, SAML, WebAuthn), SCIM sync, and scalable distributed systems. Own observability, incident response, on-call duties, and improve system stability, security, and efficiency while collaborating with product and design.

Design, build, test, and document core networking software features across client and backend services. Improve efficiency, scalability, and stability of networking systems, own running services (observability, incident response, support escalations), and bring a security-first mindset to design and implementation.

Lead and execute cross-functional strategic projects—pricing, international expansion, GTM infrastructure, AI adoption—perform deep data analysis, partner with RevOps, reduce rework, and deliver durable operational solutions from diagnosis through handoff.

Design, build, and maintain internal infrastructure and shared engineering services. Improve observability, CI/CD, and automation, operate cloud-managed services and VMs, participate in incident response, and collaborate with product and customer-facing teams to enable data-driven decisions and scalable systems.

Manage a small team of senior engineers to build AI-native prototypes and reference architectures. Translate customer signals into shippable POCs, set tooling and security practices for agent-generated code, hire and mentor engineers, collaborate cross-functionally with platform, security, and GTM, and drive strategy and planning for connectivity, identity, and AI infrastructure. Remote role with light travel (~10-15%).