Jobs at Tailscale

Leads Commercial Account Executives focused on expanding existing customer relationships. Responsibilities include hiring and onboarding a Vancouver sales team, coaching representatives, driving expansion revenue, managing pipeline and forecasts, supporting customer deals, developing repeatable sales playbooks, and collaborating cross-functionally to increase product adoption.

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.

Own the strategy, roadmap, and business growth of Tailscale’s Workload Connectivity product. Lead Kubernetes, ephemeral workload, AI agent, and cloud infrastructure connectivity initiatives; define developer experiences, integrations, pricing, packaging, and success metrics. Collaborate with engineering, design, operations, and go-to-market teams while engaging developers and platform engineers to drive adoption, retention, and revenue.

Own and grow Tailscale’s analyst relations program by managing analyst inquiries, briefings, evaluations, research participation, and relationships. Translate analyst feedback and market intelligence into actionable recommendations for Product Marketing, Product, Engineering, and leadership. Develop analyst-facing materials, monitor emerging technology categories, support market research, maintain intelligence repositories, and track program effectiveness. The role requires strong communication, analytical, organizational, relationship-building, and project management skills within B2B technology, with interest in cybersecurity, networking, infrastructure, and AI.

Own the vision, strategy, and roadmap for Tailscale’s networking features, including App Connectors, DNS, Funnel, and Tailscale Services. Lead operator experience across the admin console and CLI, translate complex networking systems into intuitive product surfaces, partner with go-to-market and customer-facing teams, and develop customer insights across users ranging from homelab operators to large enterprises. Drive end-to-end product ownership, from strategy and requirements through launch, measurement, and iteration.

Own the vision, strategy, and roadmap for Tailscale’s Identity portfolio, including authentication, authorization, lifecycle management, SSO, SCIM, access policies, and user management. Lead operator and end-user experiences across the admin console, API, and clients. Partner with engineering, product, design, and customers to prioritize improvements and deliver secure, intuitive identity capabilities for developers, administrators, and enterprises.

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.