Jobs at Tailscale

Lead Tailscale’s global communications function, including product, corporate, internal, executive, crisis, international, and media communications. Build market visibility and thought leadership around secure connectivity, networking, cybersecurity, and AI infrastructure. Develop media and journalist relationships, oversee agencies and awards, advise executives, manage high-stakes communications, and hire a high-performing team while establishing scalable processes and performance measurement.

Build Tailscale’s internal AI-enablement tools, workflows, guardrails, and documentation. Partner with engineering leadership and teams to define the AI roadmap, evaluate coding agents and models, improve adoption, and measure effects on velocity and quality. The role involves developing internal developer-facing automation, teaching and influencing engineers, identifying high-leverage AI opportunities, and promoting safe use of AI-generated code in a distributed engineering organization.

Own strategic enterprise accounts with 10,000+ employees, developing account plans, generating pipeline, managing complex six- and seven-figure SaaS deals, building executive relationships, and driving expansion. Partner cross-functionally with SDRs, Marketing, Engineering, Product, Customer Success, Legal, Finance, and leadership. Maintain accurate forecasts and CRM records while helping establish Tailscale’s enterprise sales playbook.

Own and improve Engineering, Product, and Design operational processes, including bug tracking, incidents, reliability, escalations, planning, reviews, and project tracking. Build Jira and Snowflake dashboards, analyze operational health data, identify trends, and implement process improvements. Partner with technical leadership in a remote startup, coordinate cross-functional initiatives, support retrospectives, and bring structure to ambiguous projects.

Build and operate infrastructure and shared engineering services for internal teams and Tailscale’s product. Responsibilities include improving observability, CI/CD, cloud infrastructure, managed services, Kubernetes, and service automation; designing, testing, and documenting software components; participating in incident response; supporting customer escalations; and improving system efficiency, scalability, and stability.

Own Tailscale’s web experimentation program across high-traffic pages, setting the roadmap, testing standards, governance, and decision rules. Design and run high-impact experiments, particularly for pricing and the homepage, validate measurement quality, maintain the experiment knowledge base, report insights to marketing leadership, and coach cross-functional contributors. The role requires strong experimentation statistics, web development skills, analytics proficiency, and the judgment to determine when testing is appropriate.

Partner with Account Executives on enterprise sales cycles by leading technical discovery, architecture, demos, proofs of concept, security reviews, and early adoption. Design secure Tailscale solutions for hybrid, multi-cloud, and on-premises environments, advise networking and security stakeholders, support pipeline and quota outcomes, and provide customer feedback to Product, Engineering, and go-to-market teams. Occasional travel of approximately 10–20% is required.

Develop and maintain Tailscale’s open-source client and backend networking software. Design, test, document, and optimize networking components, distributed systems, and overlay routing features. Own services through observability, incident response, and customer escalations while collaborating with product managers and designers. Apply security-first practices and improve system efficiency, scalability, and stability in a fully remote, asynchronous startup environment.

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 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.

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.

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 technical and specialized talent across engineering, product, design, GTM, and G&A functions. Build targeted sourcing strategies, conduct talent research and market mapping, create personalized outreach, assess passive candidates, and develop inclusive pipelines. Collaborate with Talent Acquisition Partners and hiring teams, use sourcing data to evaluate pipeline effectiveness, and improve tools, workflows, automation, and AI-enabled practices.

Own full-cycle recruiting across Engineering, Product & Design, Go-to-Market, General & Administrative, or cross-functional portfolios. Develop sourcing and recruiting strategies, assess candidates, negotiate offers, advise hiring managers, use market intelligence and recruiting data, and improve hiring processes and candidate experience in a distributed technology environment.

Partner with Account Executives to drive new commercial business by leading technical discovery, solution architecture, demos, and POCs. Guide complex deals, align technical and business objectives, provide product and GTM feedback, and build scalable enablement resources, demo environments, and solution blueprints for the SE team.

Drive product positioning, messaging, launches, and sales enablement for Tailscale. Conduct customer research, competitive analysis, and create collateral, demos, and enablement to generate pipeline and support revenue teams.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for weaknesses, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security, incident containment, and technical security analysis while collaborating with engineering teams in a distributed startup environment.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Apply and evolve the visual identity, create reusable templates and design systems, collaborate cross-functionally, present concepts, incorporate feedback, and manage multiple projects while delivering polished, production-ready work.

Serve as a technical, customer-facing engineer for strategic enterprise customers: lead onboarding, provide hands-on configuration and troubleshooting, run QBRs, drive adoption and expansion, relay customer feedback to product/engineering, and produce technical documentation to enable self-service and long-term success.