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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 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.

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.

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.

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.