Jobs at Tailscale

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.

Manage and expand existing customer accounts through upsells, renewals, product education, adoption support, forecasting, and revenue delivery. Build pipeline, develop mutual success plans, and present to senior stakeholders. Collaborate with Solutions Engineering, Customer Success, Support, Marketing, and Product teams. The role requires quota attainment, technical or developer-product sales experience, and participation in recorded customer meetings. It is hybrid in Toronto, requiring three in-office days weekly.

Manage and expand existing customer accounts through upsells, renewals, product education, adoption support, forecasting, and mutual success planning. Build pipeline, own account revenue targets, and collaborate with Solutions Engineering, Customer Success, Support, Marketing, and Product. The role requires customer presentations, opportunity management, quota attainment, and participation in recorded meetings. It is hybrid in Toronto with three in-office days per week.

Manage and mentor software engineering teams across multiple product pods. Provide technical direction, guide design decisions, oversee production services and incident response, and drive planning across short- and long-term horizons. Responsibilities include recruiting, performance management, career development, cross-functional collaboration, engineering culture, operational reliability, and fostering inclusive, psychologically safe teams in a fully remote startup environment.

Own and improve Tailscale’s software release management process, including release cadence, readiness criteria, rollout coordination, go/no-go decisions, tooling, documentation, and operational metrics. Partner with engineering, product, TPM, and support teams to identify risks, coordinate planning, keep releases on schedule, and drive scalable process improvements.

Develop and implement security and privacy improvements across Tailscale’s codebase. Audit features for vulnerabilities, conduct threat modeling and security analysis, drive mitigations, and promote secure coding practices through guidance and training. The role spends at least half its time writing software and requires expertise in application security, web and API vulnerabilities, cryptography, networking protocols, and platform development.

Build and maintain core billing software, including subscription and usage-based pricing, metering, rating, reconciliation, reporting, and third-party billing integrations. Design distributed, event-driven systems, ensure data integrity and observability, support billing incidents, and collaborate with product, finance, sales, and support teams. Provide technical leadership, participate in architecture reviews, mentor engineers, and own features throughout the product lifecycle.

Owns Tailscale’s Product operations model, including roadmap health, launch readiness, documentation, onboarding, feature requests, customer insight, operating rhythms, and product data strategy. Partners with Product, GTM, Support, Data, and company leadership to identify operational gaps, improve planning and prioritization, establish scalable processes, and drive alignment in a remote-first environment.

Build and evolve Tailscale’s customer-facing documentation platform, including docs-as-code tooling, content publishing pipelines, API documentation, search, and integrations with engineering and product systems. Implement designs, improve performance and scalability, support contributors through GitHub, automate documentation workflows, and research emerging documentation and LLM trends. The role requires full-stack development with TypeScript, JavaScript, React, Python, HTML, CSS, CI/CD, testing, and scripting.

Develop and scale integrated account-based marketing campaigns for Enterprise and Mid-Market audiences. Own strategy, audience segmentation, messaging, paid LinkedIn advertising, personalized landing pages, direct mail, gifting, Sales outreach, and performance optimization. Partner with Sales, GTM Operations, Product Marketing, Content, Events, and Partner Marketing to drive account engagement, meetings, pipeline creation, and progression.

Build and lead the frontend architecture for Tailscale’s next-generation web console. Responsibilities include developing shared frontend infrastructure, cross-origin authentication and session systems, testing strategies, unified product experiences, developer tooling, deployment workflows, and accessible UI patterns. The role partners across design, growth, infrastructure, and engineering, provides technical leadership and mentoring, and participates in an on-call rotation.

Design growth-focused product experiences across activation, onboarding, monetization, expansion, and referrals. Develop experiment concepts, prototypes, and minimum-viable solutions; collaborate with product managers, researchers, and engineers; interpret experiment results; and advocate for user-centered improvements while maintaining high design quality.

Lead technology and integration partnerships from opportunity identification through technical discovery, solution design, commercial alignment, launch, and adoption. Collaborate with partners, customers, Product, Engineering, Sales, Legal, Finance, Marketing, and Customer Success. Evaluate APIs, architectures, authentication, security requirements, and data flows while developing business cases, negotiating agreements, and influencing cross-functional stakeholders. Focus areas include PAM, VPN, AI, security, identity, infrastructure, developer tools, and related technologies.

Leads Tailscale’s global communications function, including product, corporate, internal, executive, crisis, international, and media communications. Builds narratives for technical products, develops journalist and emerging-media relationships, supports executive thought leadership, and manages awards and recognition programs. The role hires and develops a communications team, oversees agencies, partners cross-functionally on sensitive issues, and establishes scalable communications processes and measurement.

Own and improve operational processes across Engineering, Product, and Design, including bug tracking, incidents, reliability, escalations, planning, reviews, dashboards, and retrospectives. Analyze operational health data, identify trends and process gaps, communicate actionable insights, and implement improvements. The role requires hands-on execution, cross-functional coordination, technical engineering knowledge, comfort with ambiguity, and independent work in a remote startup environment.

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 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.

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.