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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.

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.

Own Tailscale’s web experimentation program across high-traffic pages. Set the roadmap, testing standards, statistical decision rules, and platform governance; design and run high-impact pricing and homepage experiments; validate tracking and results; maintain the experiment knowledge base; report findings to marketing leadership; and coach teams on hypothesis quality, test design, and interpretation. The role partners with web, development, design, product marketing, and analytics in a remote-first environment.

Build Tailscale’s internal AI-enablement tools, workflows, guardrails, and practices. Partner with engineering leadership and technical teams to define the AI roadmap, evaluate coding agents and models, improve developer velocity and quality, and drive safe adoption. The role includes internal tooling, developer advocacy, documentation, impact measurement, and collaboration across engineering and non-engineering teams.

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.

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.

Own the full new-business sales cycle from prospecting through closed-won deals. Generate pipeline through inbound leads and self-sourced opportunities, educate prospective customers, build trust, manage forecasts in Gong and Salesforce, and support customers across time zones. Attend and organize industry events, analyze market trends, and help develop Tailscale’s startup sales playbook. The role is hybrid in Vancouver, requiring three days per week in the office.

Own the full new-business sales cycle from prospecting through closed-won deals. Generate approximately one-third of the pipeline, manage inbound leads, engage senior technical buyers, educate prospects, and build customer trust. Analyze market and customer trends, organize sales activities and forecasts in Gong and Salesforce, support customers across time zones, and represent Tailscale at local and industry events. The role is hybrid in Toronto, requiring three in-office days per week.