Jobs at Tailscale

Own the full sales cycle for new business: prospect, qualify, and close deals with senior technical buyers. Manage inbound leads and self-source pipeline, run outreach campaigns, organize and attend events, support customers across time zones, and track pipeline and forecasts in Gong and Salesforce to hit quota.

Perform high-volume outbound prospecting to generate qualified pipeline, own target account portfolios, research and engage technical and executive buyers via phone, email and social, schedule discovery meetings for Account Executives, and use modern sales tools to meet activity and pipeline goals.

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.

Partner with Account Executives to drive new commercial deals by leading technical discovery, solution architecture, demos, and POCs. Serve as trusted advisor across stakeholders, co-own pipeline and quota outcomes, produce enablement assets, and provide product and GTM feedback. Focus on networking, zero-trust, IAM, PAM, and cloud architecture.

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.

Drive product positioning, messaging, and go-to-market for Tailscale by collaborating with product, sales, and marketing. Launch features, create sales enablement content, perform competitive analysis, represent PMM at events, and measure pipeline and revenue impact.

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.

Build and maintain internal AI enablement tools, workflows, and guardrails to help engineers use coding agents and LLMs safely. Evaluate models, partner with teams to apply AI, track adoption and impact, and provide documentation, coaching, and advocacy to increase engineering velocity.

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.

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.