Jobs at Tailscale

Manage and mentor multiple small engineering pods building and operating the control plane. Provide technical leadership, drive cross-functional product outcomes, hire and grow engineers, oversee on-call and incident response, and ensure high-availability production services while fostering an inclusive, remote-friendly engineering culture.

Own an enterprise sales territory, generating new business and expanding existing accounts. Manage the full sales cycle, from outbound prospecting through close, while developing strategic account plans and navigating complex technical, security, procurement, and legal processes. Build relationships with security, infrastructure, engineering, compliance, and executive stakeholders. Lead cross-functional teams and drive customer adoption, organizational standardization, and long-term account growth.

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.

Own and grow an enterprise sales territory through self-sourced pipeline generation, new customer acquisition, and account expansion. Lead full-cycle sales, strategic account planning, executive and technical stakeholder engagement, complex procurement and security reviews, and cross-functional account teams. Position Tailscale as a secure connectivity and modern networking platform, drive adoption, and build long-term enterprise relationships while consistently exceeding quota.

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.

Develop and maintain Tailscale’s control plane, relay infrastructure, identity integrations, open-source client code, and backend services. Design, test, document, and operate scalable software, emphasizing observability, security, incident response, customer escalations, and system stability. Collaborate asynchronously with engineers, product managers, and designers while contributing to product strategy and the full product lifecycle.

Develop and maintain Tailscale’s control plane, relay infrastructure, identity integrations, open-source client code, and backend services. Design, test, document, and operate scalable software with strong observability and security. Participate in incident response and customer escalations, improve system efficiency and stability, and collaborate asynchronously with engineers, designers, and product managers throughout the product lifecycle.

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

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.

Own and negotiate commercial agreements across customers, vendors, partners, marketplaces, technology, data protection, and confidentiality matters. Advise Sales and go-to-market teams on deal structure, risk, and contracting strategy. Build scalable templates, playbooks, approval processes, and self-service resources. Partner with Security, Privacy, Product, Engineering, Finance, and Operations on technology transactions, global matters, revenue considerations, and risk management. Improve contracting efficiency and support broader legal priorities.

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.

Own and continuously improve onboarding and ongoing enablement programs for revenue team hires. Design scalable role-specific learning paths, manage program logistics and LMS content, partner with sales leaders and cross-functional stakeholders, track ramp and competency metrics, and iterate based on data and feedback. Pilot AI-driven learning tools while supporting skill development, product launches, process rollouts, certifications, and career progression 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.

Build and maintain production-grade dbt data models and pipelines across ingestion, transformation, and visualization. Develop reliable datasets supporting reporting, analysis, finance, revenue recognition, and company decision-making. Collaborate with Finance, Engineering, Sales, Product, and Marketing to understand data needs, improve manual workflows, validate data accuracy, and create scalable solutions using modern data tools.

Lead Tailscale’s Developer Relations Engineering team while remaining hands-on with integrations, prototypes, demos, open-source projects, workshops, tutorials, and technical content. Own the team roadmap, coach technical contributors, collaborate cross-functionally on launches and product feedback, and measure developer engagement, activation, adoption, and business impact. The role requires strong software engineering, developer advocacy, program management, communication, and experience working in public developer ecosystems.

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, 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.

Design, build, test, document, and optimize Tailscale’s client-side networking software. Develop connectivity features involving routing, VPNs, subnet routers, exit nodes, and NAT traversal; apply secure, scalable architectures; diagnose complex customer network issues; support escalations; collaborate across product and engineering teams; and contribute to open-source networking projects.

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.