Top Tech Jobs & Startup Jobs in Chicago, IL

Own end-to-end sales compensation operations: process and audit monthly commissions, administer compensation platform configuration, build financial and scenario models, deliver recurring attainment and payout analytics, support quota and territory planning, resolve commission disputes, and drive systems automation and cross-functional integrations to improve scalability and data quality.

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.

Build and maintain core billing systems: integrate third-party billing platforms, implement metering/pricing/rating for subscriptions and usage-based models, ensure accurate usage tracking, observability, and high availability, automate reconciliation and reporting, collaborate with product/finance/support, lead incident response and provide technical leadership.

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.

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.

Build and ship internal AI enablement tools, workflows, and guardrails to help engineers use coding agents and LLMs safely and productively. Evaluate models and agents, partner with engineering teams, measure adoption and impact, and provide documentation, training, and hands-on support to increase engineering velocity and quality.

Design, build, test, and document client-side networking software for Tailscale's dataplane. Improve connectivity between clients, subnet routers, and exit nodes, optimize performance and reliability, resolve complex customer network escalations, collaborate with product and engineering, and engage with the open-source community.

Execute and QA campaign operations: build landing pages and emails, manage a 500,000+ newsletter, coordinate webinars, maintain marketing automation and CRM workflows, pull basic performance reports, and document repeatable processes to scale marketing execution.

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.

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.