Jobs at Tailscale

Build and maintain core billing systems: integrate third-party billing platforms, implement metering/pricing/rating for subscriptions and usage, ensure accurate usage tracking, automate reconciliation and reporting, establish observability and incident response, and collaborate with product, finance, and support teams to deliver reliable billing features.

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.

Build and maintain Tailscale's native Windows client using C#, XAML, and WinUI/Windows App SDK. Implement platform integrations and UI components, ensure compatibility across Windows versions, write unit and integration tests with Microsoft Testing Platform v2 and xUnit, and contribute to cross-platform client and backend code (including Go). Collaborate asynchronously within a distributed team and iterate quickly in a startup environment.

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.

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.

Own the full sales cycle for new business: prospect, qualify, demo, and close deals with senior technical buyers. Source one-third of pipeline, manage forecast and CRM in Gong and Salesforce, attend and organize events, and support customers across time zones.

Manage and grow existing customer accounts through upsells and renewals. Identify new use cases, educate customers on product features, drive adoption, create mutual success plans, forecast revenue, and collaborate with Solutions Engineering, Customer Success, Support, Marketing, and Product. Own quota for upsells and renewals and participate in recorded customer meetings for training and quality.

Manage and grow existing customer accounts through upsells and renewals. Educate customers on Tailscale features, create success plans, maintain pipeline and accurate forecasting, collaborate with Sales Engineering, Customer Success, Support, Marketing, and Product, and participate in recorded customer meetings for training and quality improvement.

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/Engineering, and drive improvements to user experience while maintaining high CSAT.

Serve as Tier 2 escalation for technically complex SaaS support tickets. Troubleshoot networking/VPN issues, ACLs, subnet routing, SSO integrations, and Kubernetes basics. Maintain SLAs, high CSAT, mentor Tier 1, collaborate with Product/Eng to remove recurring friction, and contribute documentation and improvements.

Own the full new-business sales cycle: prospecting, handling inbound leads, demoing, negotiating and closing deals with senior technical buyers. Build and iterate sales playbooks, source pipeline, analyze market trends, attend local and industry events, support customers across time zones, and manage pipeline and forecasts in Gong and Salesforce.

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.

Work on an AI-native Strategic Projects team to turn prototypes (LLM gateways, proxies, sandboxes) into production-grade services. Focus on hardening, observability, security review, operational tooling, customer integrations, and closing long-tail bugs and failure modes to ensure reliability and maintainability.

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.

Own and grow mid-market customer accounts through outbound prospecting and inbound leads. Drive renewals, expansions, and net-new logo acquisition; forecast revenue; collaborate with marketing, product, solutions engineering, and customer success; record customer meetings for training and quality improvement.

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.

Build and maintain backend services for Tailscale's control plane and identity systems. Implement sign-on features (SSO, OAuth2, OIDC, SAML, WebAuthn), SCIM sync, and observable, secure, scalable services. Participate in design, testing, incident response, on-call rotation, and product decision-making alongside product and design teams.

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.

Lead and execute cross-functional strategic projects—pricing, international expansion, GTM infrastructure, AI adoption—perform deep data analysis, partner with RevOps, reduce rework, and deliver durable operational solutions from diagnosis through handoff.

Partner with Account Executives to drive Commercial new business by leading technical discovery, solution architecture, demos, and POCs; guide complex multi-stakeholder deals; provide product and GTM feedback; and build scalable enablement resources, demo environments, and solution blueprints for the SE team.