Top Tech Jobs & Startup Jobs in Chicago, IL

Partner with Account Executives to drive new commercial business by leading technical discovery, solution architecture, demos, and POCs. Guide complex deals, align technical and business objectives, provide product and GTM feedback, and build scalable enablement resources, demo environments, and solution blueprints for the SE team.

Drive product positioning, messaging, launches, and sales enablement for Tailscale. Conduct customer research, competitive analysis, and create collateral, demos, and enablement to generate pipeline and support revenue teams.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for weaknesses, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security, incident containment, and technical security analysis while collaborating with engineering teams in a distributed startup environment.

Provide Tier 1 technical support by resolving configuration and networking issues, managing a high-volume ticket queue, meeting response and resolution targets, maintaining strong customer satisfaction, troubleshooting across operating systems, and partnering with Customer Experience, Product, and Engineering teams to improve user outcomes.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Apply and evolve the visual identity, create reusable templates and design systems, collaborate cross-functionally, present concepts, incorporate feedback, and manage multiple projects while delivering polished, production-ready work.

Serve as a technical, customer-facing engineer for strategic enterprise customers: lead onboarding, provide hands-on configuration and troubleshooting, run QBRs, drive adoption and expansion, relay customer feedback to product/engineering, and produce technical documentation to enable self-service and long-term success.

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.

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.