Jobs at Tailscale

Build and evolve Tailscale’s customer-facing documentation platform, including docs-as-code tooling, content publishing pipelines, API documentation, search, and integrations with engineering and product systems. Implement designs, improve performance and scalability, support contributors through GitHub, automate documentation workflows, and research emerging documentation and LLM trends. The role requires full-stack development with TypeScript, JavaScript, React, Python, HTML, CSS, CI/CD, testing, and scripting.

Develop and scale integrated account-based marketing campaigns for Enterprise and Mid-Market audiences. Own strategy, audience segmentation, messaging, paid LinkedIn advertising, personalized landing pages, direct mail, gifting, Sales outreach, and performance optimization. Partner with Sales, GTM Operations, Product Marketing, Content, Events, and Partner Marketing to drive account engagement, meetings, pipeline creation, and progression.

Build and lead the frontend architecture for Tailscale’s next-generation web console. Responsibilities include developing shared frontend infrastructure, cross-origin authentication and session systems, testing strategies, unified product experiences, developer tooling, deployment workflows, and accessible UI patterns. The role partners across design, growth, infrastructure, and engineering, provides technical leadership and mentoring, and participates in an on-call rotation.

Design growth-focused product experiences across activation, onboarding, monetization, expansion, and referrals. Develop experiment concepts, prototypes, and minimum-viable solutions; collaborate with product managers, researchers, and engineers; interpret experiment results; and advocate for user-centered improvements while maintaining high design quality.

Lead technology and integration partnerships from opportunity identification through technical discovery, solution design, commercial alignment, launch, and adoption. Collaborate with partners, customers, Product, Engineering, Sales, Legal, Finance, Marketing, and Customer Success. Evaluate APIs, architectures, authentication, security requirements, and data flows while developing business cases, negotiating agreements, and influencing cross-functional stakeholders. Focus areas include PAM, VPN, AI, security, identity, infrastructure, developer tools, and related technologies.

Leads Tailscale’s global communications function, including product, corporate, internal, executive, crisis, international, and media communications. Builds narratives for technical products, develops journalist and emerging-media relationships, supports executive thought leadership, and manages awards and recognition programs. The role hires and develops a communications team, oversees agencies, partners cross-functionally on sensitive issues, and establishes scalable communications processes and measurement.

Build and lead Tailscale’s internal AI enablement capabilities, including developer tools, workflows, coding-agent practices, evaluation processes, and safety guardrails. Partner with engineering and other teams to identify high-impact AI opportunities, drive adoption, measure productivity and quality outcomes, and communicate recommendations to leadership. The role requires hands-on software engineering, internal tooling, AI coding-tool expertise, strong communication, and comfort working independently amid ambiguity.

Own and improve operational processes across Engineering, Product, and Design, including bug tracking, incidents, reliability, escalations, planning, reviews, dashboards, and retrospectives. Analyze operational health data, identify trends and process gaps, communicate actionable insights, and implement improvements. The role requires hands-on execution, cross-functional coordination, technical engineering knowledge, comfort with ambiguity, and independent work in a remote startup environment.

Build and operate infrastructure and core software components supporting Tailscale’s product and internal teams. Responsibilities include improving observability, CI/CD, cloud infrastructure, managed services, Kubernetes operations, scalability, stability, and automation. The role includes incident response, customer support escalations, cross-functional collaboration, documentation, and end-to-end ownership of infrastructure projects in a fully remote startup environment.

Develop and maintain open-source client code and backend services focused on networking features. Design, test, document, and optimize distributed networking components, improve scalability and stability, support observability and incident response, handle customer escalations, and apply security-first engineering practices. Collaborate asynchronously with engineers, product managers, and UX/UI designers throughout the product lifecycle.

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.

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.

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.

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.

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 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.