Jobs at Tailscale

Manage and expand existing customer accounts through upsells and renewals. Build pipeline, forecast revenue, educate customers on product features, drive adoption, and create mutual success plans. Partner with Solutions Engineering, Customer Success, Support, Marketing, and Product teams while presenting to senior stakeholders and managing multiple opportunities to quota attainment.

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.

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.

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.

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.

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.

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 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.

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. 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.