Jobs at Tailscale

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.

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.

Conduct mixed-methods UX research, primarily usability and quality-validation testing, across the full study lifecycle. Recruit participants, scope studies, analyze results, communicate findings, and recommend improvements. Coach product designers and managers, build scalable research templates and workflows, maintain the research library and tool stack, manage participant panels and study logistics, and coordinate vendor procurement. Over time, assume ownership of research direction for product areas while supporting research operations and stakeholder enablement.

Conduct end-to-end UX research supporting product growth, including usability tests, surveys, interviews, experiments, and longitudinal studies. Analyze behavioral and quantitative data, identify adoption friction, define personas, and communicate actionable findings to Growth Product Managers and Designers. Partner with experimentation programs across acquisition, onboarding, activation, pricing, packaging, and billing while developing increasing ownership of the growth research agenda.

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.

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.

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.

Create technical, growth-focused educational content (tutorials, implementation guides, demos, comparisons) that drives discoverability and product adoption. Work with product, engineering, and marketing to build hands-on examples, optimize content for search and AI discovery, refresh existing assets, and measure impact against quarterly growth metrics.

Design and implement security and privacy improvements across Tailscales codebase. Audit features for vulnerabilities, perform threat modeling and security analysis, drive remediation, and spend at least half your time writing code to build security features, defenses, and tooling.

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.

Serve as the primary technical counterpart for channel partners, leading discovery, architecture, demos, and POCs. Enable partners with training, reference architectures, and playbooks; co-sell with AEs and Channel AMs; architect multi-party deals; provide product feedback; and drive partner-sourced revenue while maintaining high-trust technical relationships.

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.

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.