Jobs at Tailscale

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.

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.

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, 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.

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.

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.

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.

Lead the dataplane product vision and roadmap covering WireGuard, DERP, subnet routers, exit nodes, relays, and app connectors. Define customer-facing performance and reliability SLOs, ownership of regional expansion, capacity, observability, operator tooling, and connectivity behavior across NATs, OSes, carriers, and enterprise networks. Partner with engineering, GTM, and customers to prioritize production traffic, regulated deployments, and enterprise integrations.

Develop and maintain Tailscale client and backend code with a focus on iOS and Android. Implement features in Swift/SwiftUI and Kotlin, write unit and integration tests, share cross-target code, support mobile VPN infrastructure and platform compatibility, and collaborate remotely with engineering teams.

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.