Top Tech Jobs & Startup Jobs

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.

Develop Tailscale client and backend components with focus on iOS and Android. Implement cross-target shared code, unit and integration tests, support mobile VPN infrastructure, and maintain compatibility with recent and older platform versions while collaborating asynchronously on a distributed team.

Lead the dataplane product vision and roadmap to ensure secure, high-performance connectivity across clients, relays, routers, and connectors. Define customer-facing performance and reliability SLOs, drive regional capacity and relay operations, own operator UX (console and CLI), partner with engineering, GTM, and customers on production traffic commitments, and represent Tailscale externally to partners and enterprises.

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.