Simple, secure networks for teams of any scale. Built on WireGuard.
Toronto, Ontario
For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.
Remote · Canada
The Commercial Legal Counsel will lead day-to-day commercial legal support, negotiating a broad range of agreements and partnering with cross-functional teams to manage risk. They will also build and improve contracting processes, templates, and playbooks to support the company's growth.
Remote · Canada
The Head of Legal will build and lead the company's legal function, serving as a trusted advisor to executives on complex business and legal matters. They will establish legal priorities, manage risk, and oversee the development of scalable processes and team capabilities.
Remote · Canada
You will own and continuously improve onboarding and enablement programs for the revenue team, from pre-boarding through ramp and continuous skill development. You will partner with leadership to identify skill gaps, manage program logistics, and use data to iterate on learning initiatives.
Remote · Canada
You will design and maintain clean, scalable, production-grade data models while working across the full data pipeline from ingestion to visualization. You will collaborate with cross-functional teams including Finance, Engineering, and Sales to deliver reliable data solutions that support decision-making.
Remote · Canada
Lead the Developer Relations Engineering team to create technical content, integrations, and tools that drive developer adoption. Partner with product and engineering teams to influence strategy and translate developer feedback into actionable product improvements.
Remote · Canada
Design, construct, and maintain global networking infrastructure including Funnel and DERP relay services. Ensure operational excellence through automation, observability, and proactive troubleshooting of complex connectivity issues.
Remote · Canada
Design, build, and maintain core client-side networking software while evolving connectivity features for various network integrations. Provide architectural insights and resolve complex network connectivity issues to ensure scalability and a superior customer experience.
Remote · Canada
You will drive growth initiatives including onboarding, monetization, and user expansion by testing hypotheses through minimum-viable solutions. You will collaborate with product, engineering, and research teams to iterate on designs based on experiment results and user feedback.
Remote · Canada
The Talent Acquisition Sourcer will partner with hiring teams to develop and execute targeted sourcing strategies across various functions including Engineering and Product. They will identify passive talent, build inclusive pipelines, and use data-driven insights to optimize search outcomes.
Remote · Canada
Lead full-cycle recruiting for complex searches across various business functions including Engineering, Product, Design, and GTM. Partner with hiring managers to develop effective sourcing strategies, manage interview processes, and ensure a high-quality candidate experience.
Remote · Canada
Develop and maintain the Tailscale Windows client using the Windows App SDK, WinUI, C#, and Go. Contribute to cross-platform code while implementing new features and maintaining compatibility across Windows versions.
Remote · Canada
You will partner with product-minded engineers to transition prototypes into production-grade software while ensuring high standards for security and reliability. Additionally, you will work directly with customers to integrate Tailscale solutions and maintain the operational practices required for agent-generated code.
Remote · Canada
You will design, build, and maintain core software components while ensuring the scalability and stability of system resources. Additionally, you will participate in incident response and collaborate with cross-functional teams to improve infrastructure and observability.
Hybrid · Vancouver
Generate qualified sales opportunities through high-volume outbound prospecting across phone, email, and LinkedIn. Partner with Account Executives to execute territory plans and schedule high-quality discovery meetings.
Remote · Canada
Design and implement security controls across cloud, OS, and Kubernetes environments to defend against threats. Audit infrastructure for security weaknesses and drive resolutions while performing threat modeling and security analysis.
Remote · Canada
The Brand Designer will own creative projects from concept to delivery, ensuring high-quality assets across web, social, and marketing channels. They will also partner with cross-functional teams to evolve design systems and maintain a cohesive visual identity.
Remote · Canada
Act as the primary technical resource for resolving configuration and networking challenges while managing a high-velocity ticket queue. Partner cross-functionally to identify recurring friction points and advocate for improvements to the overall user experience.
Remote · Canada
The Forward Deployed Engineer acts as a technical bridge for strategic customers, managing onboarding, driving product adoption, and providing expert guidance. They also serve as the voice of the customer internally to influence product development and ensure long-term success.
Remote · Canada
Create high-impact technical content that drives growth by leveraging search insights, customer questions, and emerging industry trends. Collaborate with cross-functional teams including product, engineering, and marketing to produce accurate, useful educational resources for enterprise audiences.
Hybrid · Toronto
Lead and coach a team of account executives to manage existing customer expansion within the commercial segment. Collaborate with marketing, product, and sales engineering teams to refine sales processes and accelerate pipeline growth.
