Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We’re building a future for the Internet that is easy, sensible, and safe, just like it used to be. Founded in 2019 and fully distributed, we’re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. We’re seeking a motivated Support Engineer (Tier 1) who is passionate about solving technical issues and providing high‑quality support to a diverse community of users. This role is the face of the company for a large portion of our community, handling a broad range of tickets and flexing your technical muscles. As a Tier 1 engineer, you’ll be part of a distributed team focused on delivering excellent support and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Support Team Lead and will play a key role in our journey. Key Responsibilities Act as the primary technical resource for our free user community, resolving a wide range of configuration and networking challenges to keep them unblocked. Manage a high‑velocity ticket queue with a consistent focus on meeting targets for time to first response and time to resolution. Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance. Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues. Partner cross‑functionally to identify recurring friction points and advocate for improvements to the user experience.



What We Are Looking For Bring 1–4+ years of experience in a technical support or customer‑facing role, with a track record of solving technical problems. Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open‑source contributions. Demonstrate a foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing. Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS’s. Some familiarity with Jira and Slack to manage internal workflows and communicate effectively with the team and customers. Exhibit excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity. Maintain a proactive approach to learning new technologies and staying current with evolving infra tools. CAN Pay Range $84,420 – $105,860 CAD What We Offer An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. Flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota‑based roles).



Comprehensive group benefits with no waiting period. Coverage for health, vision, dental, and more for you and your family! Remote first company. Most of our teams work fully remotely. Enjoy a change of scenery wherever you can get Wi‑Fi, participate in virtual and in‑person social events, and leverage our corporate co‑working program to visit WeWork (or similar spaces near you). Some roles require in‑office collaboration depending on team needs, which will be clearly noted. Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off‑sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in‑person connection through team travel and distributed collaboration. Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for career development, or take advantage of mentorship, coaching, and internal promotion opportunities. Paid time off and a healthy work‑life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! A build‑your‑own home office setup. Choose your own company‑owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customise your workstation. Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top‑ups for up to 26 weeks. As set forth in Tailscale’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law. #J-18808-Ljbffr

📌 Support Engineer (Tier 1) Remote (Canada) - C$84,420 - C$105,860 A Year - Remote
🏢 Tailscale
📍 Toronto