Jobs at Tailscale

Manage and grow existing customer accounts through upsells, renewals, product education, adoption, forecasting, and quota attainment. Build pipeline, create mutual success plans, present to senior stakeholders, and collaborate with Solutions Engineering, Customer Success, Support, Marketing, and Product teams. The role requires a strong understanding of technical or developer-focused products, particularly in a product-led growth environment.

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.

Expand and renew existing customer accounts through upsells, adoption, forecasting, and pipeline management. The role involves educating customers on product features, creating mutual success plans, presenting to senior stakeholders, and partnering with Solutions Engineering, Customer Success, Support, Marketing, and Product. The position requires managing multiple opportunities, meeting quota, and participating in recorded customer meetings. It is based in Vancouver with three required in-office days per week.

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.

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 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.

Develop and maintain open-source client code and backend services focused on networking features. Design, test, document, and optimize distributed networking components, improve scalability and stability, support observability and incident response, handle customer escalations, and apply security-first engineering practices. Collaborate asynchronously with engineers, product managers, and UX/UI designers throughout the product lifecycle.

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 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.

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.

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.

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.

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.

Own full-cycle recruiting from intake through offer across engineering, product, design, go-to-market, general and administrative functions. Develop sourcing strategies, assess candidates, negotiate offers, advise hiring managers, use recruiting data and market intelligence, and improve hiring processes. This contract role requires managing multiple complex searches in a fast-moving, distributed technology environment while delivering strong candidate experiences.

Partner with Account Executives to drive new commercial deals by leading technical discovery, solution architecture, demos, and POCs. Serve as trusted advisor across stakeholders, co-own pipeline and quota outcomes, produce enablement assets, and provide product and GTM feedback. Focus on networking, zero-trust, IAM, PAM, and cloud architecture.

Drive product positioning, messaging, and go-to-market for Tailscale by collaborating with product, sales, and marketing. Launch features, create sales enablement content, perform competitive analysis, represent PMM at events, and measure pipeline and revenue impact.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for vulnerabilities, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security analysis, and serving as an infrastructure-level subject matter expert during security incidents.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Extend visual identity, build reusable templates and design systems, present concepts, incorporate feedback, and manage multiple priorities. Collaborate with marketing, content, product marketing, web, developers, and other designers to deliver polished, consistent creative assets.