Jobs at Tailscale

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.

Build and maintain production-grade dbt data models and end-to-end data pipelines. Collaborate with Finance, Engineering, Sales, and Product to deliver reliable reporting, analytics, and scalable solutions, reducing manual workflows and ensuring data accuracy.

Build and lead Tailscale's Strategic Sales organization targeting enterprises (10,000+ employees). Personally own and close complex, multi-stakeholder six- to eight-figure SaaS deals, recruit and coach 3–5 Strategic AEs, design outbound territory and playbooks, drive account planning, forecasting, pipeline generation, and cross-functional GTM alignment with Product and Engineering.

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.

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.

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, 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.