Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as the primary technical counterpart for channel partners, leading discovery, architecture, demos, and POCs. Enable partners with training, reference architectures, and playbooks; co-sell with AEs and Channel AMs; architect multi-party deals; provide product feedback; and drive partner-sourced revenue while maintaining high-trust technical relationships.

Provide high-touch executive support to the VP of Engineering: manage complex calendars, meetings, travel, and communications; coordinate cross-functional initiatives and projects; prepare briefings and presentations; track decisions and action items; improve operational processes and systems; partner with CTO Chief of Staff and other leaders to drive organizational effectiveness in a distributed, fast-moving engineering organization.

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.

Lead resolution of high-severity post-sales escalations: investigate and reproduce complex networking and software issues, run customer calls, collect logs and evidence, create engineering-ready handoff packages, identify systemic patterns, and improve tooling and runbooks to raise Support's technical capability.

Partner with Account Executives to drive new commercial business by leading technical discovery, architecture design, demos and POCs. Guide complex deals, build scalable enablement and provide product/market feedback. Blend deep networking and security expertise with sales acumen to support quota attainment.

Lead the dataplane product vision and roadmap for Tailscale, owning connectivity features (WireGuard, relays, subnet routing, exit nodes, connectors), performance/reliability SLOs, regional relay capacity, operator tooling (console/CLI), and enterprise/regulatory deployments. Partner with engineering, GTM, and customers to drive production traffic commitments and improve connectivity across diverse NATs, OSes, carriers, and networks.

Join a remote Strategic Projects engineering team to turn AI-native prototypes into production-grade services. You will harden demos (LLM gateways, proxies, sandboxes), implement observability, error handling, and security practices, work with reference customers on integrations, and ensure agent-generated code meets production review and operational standards.

Own the end-to-end developer experience for embedding Tailscale into applications: define reference architectures, SDK and CLI roadmaps, golden paths, docs, examples, and onboarding. Partner with engineering, internal dogfood teams, GTM, and external partners to prioritize and ship developer-facing SDK, API, and CLI features that reduce friction from prototype to production.

Manage and mentor multiple small engineering pods building and operating the control plane. Provide technical leadership, drive cross-functional product outcomes, hire and grow engineers, oversee on-call and incident response, and ensure high-availability production services while fostering an inclusive, remote-friendly engineering culture.

Design, build, and operate Tailscale's global Funnel and DERP relay infrastructure. Improve networking features and dataplane in open-source client code, ensure scalability and reliability with SRE/DevOps practices, troubleshoot complex network issues, integrate observability and incident response, and collaborate across engineering and product teams with a security-first approach.