Jobs at Tailscale

Lead and build a Commercial expansion sales team for existing customers (<750 employees). Coach AEs, drive pipeline generation, refine opportunity management, partner with marketing/product/SE, and travel to customers and industry events.

Design, build, test, and document Tailscale's client-side networking software. Enhance connectivity between clients, subnet routers, and exit nodes. Diagnose and resolve complex customer network escalations, optimize performance and reliability, collaborate with product and engineering, adopt security-centric designs, and engage with the open-source community.

Design and implement security controls across cloud, OS, Kubernetes, networks, and CI/CD. Audit infrastructure, perform threat modeling, remediate vulnerabilities, and write software for security features and defenses.

Design and implement security and privacy features across Tailscale's codebase. Audit features for vulnerabilities, perform threat modeling and security analysis, drive mitigations to resolution, and spend significant time writing secure software (50%+ coding). Collaborate with engineering teams to promote secure coding and provide guidance and training.

Create technically accurate, growth-focused educational content (tutorials, guides, demos, comparisons) that helps enterprise and developer audiences discover, evaluate, and adopt Tailscale. Monitor communities and search signals, collaborate with product and engineering, optimize existing content, and build an AI-first program to drive self-serve revenue and product adoption.

Serve as the technical lead for strategic customers: onboard, train, troubleshoot, and drive adoption of Tailscale. Build relationships, conduct QBRs, recommend best practices, escalate product feedback, and maintain customer-facing documentation to enable long-term success and expansion.

Execute and QA marketing campaigns: build landing pages and emails, manage a 500k+ newsletter, coordinate webinars, maintain marketing automation/CRM workflows, pull performance reports, and document repeatable processes to scale operations.

Build and maintain internal engineering services and automation to support product teams. Improve observability, CI/CD, infrastructure as code, and cloud-managed services. Own running services, participate in incident response, collaborate cross-functionally, and drive reliability, scalability, and efficiency improvements.

Lead frontend architecture and platform work for a unified web console: design app structure, cross-origin auth and session infrastructure, shared UI/platform abstractions, testing strategy, developer workflows, and tooling. Collaborate with product, design, growth, and infrastructure teams, provide technical leadership, mentor engineers, and participate in on-call rotation.

Drive technical success with channel partners by leading discovery, architecture, demos, and POCs for partner-sourced and co-sell deals. Enable partners via training, blueprints, and scalable assets, advise on zero-trust, identity integrations, cloud/hybrid deployments, and collaborate cross-functionally to grow partner-sourced revenue.

Partner with the VP of Engineering to maximize effectiveness by managing calendars, meetings, travel, communications, and cross-functional coordination. Own executive operations, prepare briefing materials and presentations, track actions and dependencies, coordinate offsites and events, and improve administrative systems. Work closely with leaders across Engineering, Product, Design, Finance, Legal, People, Marketing, and the CTO Chief of Staff to ensure timely execution and continuous improvement in a distributed, remote-first environment.

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.

Lead and resolve high-severity post-sales technical escalations through deep-dive investigation, reproduction, and engineering handoff. Own customer calls, collect logs/evidence, file bug reports, monitor patterns, and improve tooling and runbooks in partnership with Support and Engineering.

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

Lead the dataplane product vision and roadmap, spanning WireGuard, DERP, relays, subnet routers, exit nodes, and connectors. Define customer-facing performance and reliability SLOs, drive regional capacity and relay operations, own operator tooling and admin/CLI surfaces, partner across engineering, GTM, and customers, and represent Tailscale externally on dataplane strategy and deployments.

Work on an AI-native Strategic Projects team to turn prototypes (LLM gateways, proxies, sandboxes) into production-grade services. Own hardening, error handling, observability, operational tooling, security review practices, and customer integrations. Use coding agents and LLMs heavily, collaborate with product-minded engineers and reference customers, and ensure prototypes meet production reliability and maintainability standards. Remote role with light travel (<10%).

Owner of the developer experience for Tailscale-native apps: define reference architectures, SDK and CLI product strategy, improve onboarding and docs, run internal dogfooding, partner with engineering and GTM, and engage external developers to drive adoption.

Design, build, and operate Tailscale's global Funnel and DERP relay infrastructure. Implement and improve networking features in the open-source client dataplane, troubleshoot complex connectivity issues, integrate observability, participate in incident management, and drive reliability, scalability, and security for hosted services.

Manage and mentor multiple small engineering pods to deliver and operate high-availability production services. Provide technical direction, lead incident response and on-call rotations, hire and grow the team, and collaborate cross-functionally with product and design to drive short- and long-term planning.

Manage end-to-end sales compensation operations including monthly commission processing, audits, and CaptivateIQ administration. Partner with Revenue Leadership, Finance, and Payroll on compensation design, quota modeling, and incentive strategy. Deliver analytics and reporting on attainment, payouts, and quota performance while improving systems, automations, integrations, and operational governance.