Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Develop and maintain Tailscale’s control plane, relay infrastructure, identity integrations, open-source client code, and backend services. Design, test, document, and operate scalable software with strong observability and security. Participate in incident response and customer escalations, improve system efficiency and stability, and collaborate asynchronously with engineers, designers, and product managers throughout the product lifecycle.

Leads and builds Tailscale’s global legal function, advising executives and cross-functional teams on corporate governance, product, privacy, data, security, intellectual property, employment, commercial, compliance, and international matters. Establishes legal strategy, processes, systems, and operating models; hires and develops the legal team; manages outside counsel; supports strategic transactions and partnerships; and translates complex legal and regulatory issues into practical business guidance.

Own and negotiate commercial agreements across customers, vendors, partners, marketplaces, technology, data protection, and confidentiality matters. Advise Sales and go-to-market teams on deal structure, risk, and contracting strategy. Build scalable templates, playbooks, approval processes, and self-service resources. Partner with Security, Privacy, Product, Engineering, Finance, and Operations on technology transactions, global matters, revenue considerations, and risk management. Improve contracting efficiency and support broader legal priorities.

Own and continuously improve onboarding and ongoing enablement programs for revenue team hires. Design scalable role-specific learning paths, manage program logistics and LMS content, partner with sales leaders and cross-functional stakeholders, track ramp and competency metrics, and iterate based on data and feedback. Pilot AI-driven learning tools while supporting skill development, product launches, process rollouts, certifications, and career progression in a remote-first environment.

Build and maintain production-grade dbt data models and pipelines across ingestion, transformation, and visualization. Develop reliable datasets supporting reporting, analysis, finance, revenue recognition, and company decision-making. Collaborate with Finance, Engineering, Sales, Product, and Marketing to understand data needs, improve manual workflows, validate data accuracy, and create scalable solutions using modern data tools.

Lead Tailscale’s Developer Relations Engineering team while remaining hands-on with integrations, prototypes, demos, open-source projects, workshops, tutorials, and technical content. Own the team roadmap, coach technical contributors, collaborate cross-functionally on launches and product feedback, and measure developer engagement, activation, adoption, and business impact. The role requires strong software engineering, developer advocacy, program management, communication, and experience working in public developer ecosystems.

Design, build, test, document, and optimize Tailscale’s client-side networking software. Develop connectivity features involving routing, VPNs, subnet routers, exit nodes, and NAT traversal; apply secure, scalable architectures; diagnose complex customer network issues; support escalations; collaborate across product and engineering teams; and contribute to open-source networking projects.

Source and engage technical and specialized talent across engineering, product, design, GTM, and G&A functions. Build targeted sourcing strategies, conduct talent research and market mapping, create personalized outreach, assess passive candidates, and develop inclusive pipelines. Collaborate with Talent Acquisition Partners and hiring teams, use sourcing data to evaluate pipeline effectiveness, and improve tools, workflows, automation, and AI-enabled practices.

Own full-cycle recruiting across Engineering, Product & Design, Go-to-Market, General & Administrative, or cross-functional portfolios. Develop sourcing and recruiting strategies, assess candidates, negotiate offers, advise hiring managers, use market intelligence and recruiting data, and improve hiring processes and candidate experience in a distributed technology environment.