Apply on company website Remote (Canada) Remote (Global) Full-time USD 129,980 – 162,140 / year

Tailscale is hiring a Customer Support Engineer

Requirements

  • 4+ years of experience in a technical support role within a SaaS company, with demonstrated experience handling escalated or enterprise-tier accounts
  • Strong working knowledge of networking fundamentals - TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing - with the ability to apply this knowledge to real-world troubleshooting scenarios
  • Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile platforms
  • Experience working with identity providers and SSO integrations (e.g. Okta, Google Workspace, Azure AD) as they relate to device or user authentication
  • Familiarity with log analysis and CLI-based diagnostic tools to independently investigate issues before escalating
  • Excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity
  • Familiarity with Jira and Slack to manage internal workflows and collaborate effectively across distributed teams
  • Maintain a proactive approach to learning new technologies and staying current with evolving infra tools

Nice to Have

  • Hands-on familiarity with Tailscale or comparable networking/VPN products (i.e. WireGuard, traditional VPNs) strongly preferred
  • Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions
  • Basic experience troubleshooting Kubernetes environments, including familiarity with pod networking, namespaces, and common CLI tools such as kubectl

Work Arrangement

Remote (Worldwide)

Additional Information

  • Founded in 2019 and fully distributed
  • Backed by Accel, CRV, Insight, Heavybit, and Uncork Capital
  • 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
Required Skills
Jira
Job Details
Location Remote (Canada)
Work mode Remote (Global)
Employment Full-time
Salary USD 129,980 – 162,140 / year
Category other
Posted 12 days ago
Application On company website
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About company
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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.
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