Customer Support Engineer (Tier 1)

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About Tailscale

Tailscale is making safe connection effortless 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's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

If you’re passionate about solving technical issues and providing high-quality support to a diverse community of users, this is the role for you. We’re seeking a motivated Support Engineer (Tier 1) to join our growing team of support professionals. You will serve as the face of the company for a large portion of our community, handling a broad range of tickets that will help flex 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 Tier 1 Support Team Lead and will play a key role in our journey.

Key Responsibilities

Act as the primary technical resource for less complex issues, 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

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.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

CAN Pay Range

$84,420 — $132,660 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. And that flexibility in how and when you work empowers our team to integrate work and life.