Jobs at Tailscale

Develop and operate Tailscale’s control plane, relay infrastructure, identity integrations, open-source client code, and backend services. Responsibilities include designing, testing, documenting, and scaling software; improving observability, stability, and efficiency; participating in incident response; handling customer escalations; and applying security-first practices. The role also involves collaborating with designers and product managers, contributing to product strategy, and working independently in a fully distributed environment.

Own and negotiate commercial agreements, advise Sales and business teams on deal structure and risk, and develop scalable contracting processes. Partner with Security, Privacy, Product, Engineering, Finance, and Operations on technology transactions, data protection, AI, pricing, and revenue matters. Support international transactions, improve negotiation efficiency through metrics and processes, coordinate outside counsel, and contribute to the growth of Tailscale’s commercial legal function.

Leads and builds Tailscale’s global legal function, advising executives and cross-functional teams on corporate governance, product, privacy, data, AI, security, intellectual property, employment, commercial, compliance, and international matters. Establishes legal strategy, processes, systems, and risk frameworks; hires and develops legal staff; manages outside counsel; supports strategic partnerships and corporate initiatives; and translates complex legal and regulatory issues into practical business guidance.

Owns revenue-team onboarding and ongoing enablement programs from pre-boarding through continuous development. Responsibilities include designing role-specific learning paths, managing program logistics and LMS content, partnering with sales leaders and cross-functional teams, measuring ramp and competency outcomes, and improving programs using data and feedback. The role also pilots AI-powered learning tools in a remote-first environment.

Build and maintain production-grade dbt data models and pipelines across ingestion, transformation, and visualization. Partner with Finance, Engineering, Sales, Product, and Marketing to deliver reliable data for reporting and decision-making. Improve manual workflows, validate data accuracy, and design scalable solutions using modern data modeling practices. Support financial and revenue-related analytics, including ARR and revenue recognition, while balancing immediate fixes with long-term architecture.

Lead Tailscale’s Developer Relations Engineering team, roadmap, and technical programs. Build integrations, demos, example applications, open-source projects, workshops, tutorials, and developer tooling while remaining hands-on with coding and technical problem-solving. Partner cross-functionally to improve product adoption, surface developer feedback, support launches, and measure DevRel impact. Coach technical contributors, prioritize investments, and translate complex networking and security capabilities into compelling developer experiences.

Design, build, and operate global networking infrastructure, including Funnel and DERP relay services and open-source dataplane code. Develop networking features, improve scalability and reliability, troubleshoot complex connectivity issues, support incident response and escalations, and apply security-focused engineering practices. Collaborate asynchronously with engineering and product teams while contributing to hosted services and client capabilities.

Design, build, test, document, and optimize Tailscale’s client-side networking software. Develop connectivity features for clients, subnet routers, exit nodes, and customer integrations using networking protocols and security-focused engineering. Diagnose complex network issues, support customer escalations, collaborate with product and engineering teams, contribute to open-source projects, and improve software scalability, reliability, performance, and maintainability across platforms.

Source and engage exceptional talent across technical and business functions, including Engineering, Product, Design, GTM, and G&A. Develop targeted sourcing strategies, conduct talent research and market mapping, engage passive candidates through personalized outreach, assess pipeline health, and build inclusive candidate pipelines. Collaborate with Talent Acquisition Partners and hiring teams while improving sourcing tools, workflows, data quality, automation, and AI-enabled practices.

Own full-cycle recruiting from intake through offer across engineering, product, design, go-to-market, general and administrative functions. Develop sourcing strategies, assess candidates, negotiate offers, advise hiring managers, use recruiting data and market intelligence, and improve hiring processes. This contract role requires managing multiple complex searches in a fast-moving, distributed technology environment while delivering strong candidate experiences.

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.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for vulnerabilities, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security analysis, and serving as an infrastructure-level subject matter expert during security incidents.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Extend visual identity, build reusable templates and design systems, present concepts, incorporate feedback, and manage multiple priorities. Collaborate with marketing, content, product marketing, web, developers, and other designers to deliver polished, consistent creative assets.

Provide Tier 1 technical support by resolving configuration and networking issues, managing a high-volume ticket queue, meeting response and resolution targets, and maintaining strong customer satisfaction. Troubleshoot across macOS, Windows, Linux, and mobile operating systems, explain technical concepts clearly, and collaborate with Customer Experience, Product, and Engineering teams to identify recurring user issues and improve the customer experience.

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.

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.

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.