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.

Own the vision, 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, pricing, packaging, success metrics, and integrations. Partner with engineering, design, operations, and go-to-market teams while engaging technical customers and guiding products from strategy through adoption and revenue impact.

Lead a team of Commercial Account Executives focused on customer expansion revenue. Responsibilities include hiring and onboarding, coaching reps, managing pipeline and forecasts, supporting prospecting and complex deals, developing a repeatable sales playbook, and partnering cross-functionally to increase customer adoption. The role will establish Tailscale’s Toronto sales hub and requires working from the Toronto office three 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. Synthesize analyst intelligence and market trends into recommendations for Product Marketing, Product, Engineering, and leadership. Develop analyst-facing materials, support market research, track program effectiveness, and strengthen the company’s positioning across cybersecurity, networking, infrastructure, AI, and emerging technology markets.

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.

Own the vision, strategy, and roadmap for Tailscale’s Identity portfolio, including authentication, authorization, SSO, SCIM, access policies, and user management. Lead admin and end-user experiences across the console, API, and clients. Partner with engineering, product, and design, develop customer insights, and translate customer, support, and competitive signals into priorities. Ensure identity services are secure, reliable, intuitive, and integrated across Tailscale’s platform.

Own the vision, strategy, roadmap, and operator experience for Tailscale’s networking features, including App Connectors, DNS, Funnel, and Tailscale Services. Partner with go-to-market, customer success, and solutions engineering teams on strategic customer commitments. Develop customer insights, define product requirements, launch products, and iterate using data. Simplify complex networking systems through effective object models, defaults, configuration experiences, documentation, and error messaging.

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, tooling, runbooks, go/no-go decisions, and operational metrics. Partner with engineering, product, TPM, and support teams to identify risks, coordinate planning, maintain release schedules, and drive scalable process improvements. Requires strong technical fluency in software delivery, deployment pipelines, branching, feature flags, and production operations.

Lead and mentor software engineering teams across multiple product pods. Provide technical direction, oversee production services and operational readiness, manage on-call and incident response, support hiring and career development, and drive cross-functional planning and delivery. The role requires strong people-management experience, technical judgment, production-service expertise, and the ability to work asynchronously in a distributed 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.

Develop and improve Tailscale’s security and privacy features, identify and resolve technical vulnerabilities, conduct security audits, perform threat modeling, and guide engineering teams on secure coding. The role spends at least half its time writing software and requires knowledge of application security, web vulnerabilities, client-side security, API flaws, cryptography, and networking protocols.

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.

Build and maintain core billing software, including subscription and usage-based pricing, metering, rating, reconciliation, reporting, and third-party billing integrations. Ensure billing data integrity, observability, reliability, and high availability. Collaborate with product, finance, sales, support, and engineering teams on custom billing requirements, lead incident response, contribute to architecture and design reviews, and mentor engineers.

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.

Own and scale Tailscale’s Product operations, including roadmap health, launch readiness, documentation, onboarding, feature request management, customer insight systems, operating rhythms, and product metrics. Partner with Product, GTM, Support, Data, and company leadership to identify operational gaps, establish standards, influence prioritization, and build scalable systems. The role requires autonomous execution, strategic judgment, cross-functional alignment, and strong communication in a remote-first environment.