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Customer Support Engineer

1 month, 1 week ago
Canada
Full-time
Senior
Technical Support Engineer
Customer and Technical Support
DNS JIRA Kubectl Kubernetes Linux macOS TCP/IP
Apply Now
Tailscale

Tailscale

Tailscale is a zero config VPN service that simplifies network security and connectivity for teams of any scale, offering easy deployment, minimal latency, and compatibility with existing services.

Diversified Telecommunication Services
51-250
Founded 2019
$115M raised
View All Jobs 22

Description

  • Serve as the primary escalation point for technically complex tickets and own them through resolution.
  • Diagnose and troubleshoot advanced Tailscale issues, including ACL misconfigurations, subnet routing, exit nodes, and identity provider integrations.
  • Manage a ticket queue while meeting SLA expectations for first response and resolution times.
  • Provide clear, accurate technical guidance that drives positive customer outcomes and strong CSAT scores.
  • Handle a high volume of daily ticket replies while maintaining depth in troubleshooting networking issues.
  • Partner cross-functionally to identify recurring friction points and advocate for product and experience improvements.
  • Support escalations from Tier 1, including issues from free-tier users, and resolve them efficiently and thoroughly.
  • Mentor Tier 1 team members through ticket reviews, escalation guidance, and documentation contributions.

Requirements

  • 4+ years of experience in a technical support role within a SaaS company.
  • Experience handling escalated or enterprise-tier customer accounts.
  • Hands-on familiarity with Tailscale or comparable networking/VPN products such as WireGuard or traditional VPNs preferred.
  • Strong knowledge of networking fundamentals, including TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing.
  • Ability to troubleshoot across macOS, Windows, Linux, and mobile platforms.
  • Experience with identity providers and SSO integrations such as Okta, Google Workspace, or Azure AD.
  • Basic experience troubleshooting Kubernetes environments, including pod networking, namespaces, and kubectl.
  • Familiarity with log analysis and CLI-based diagnostic tools for independent issue investigation.
  • Excellent written communication skills with the ability to explain complex technical concepts with empathy and clarity.
  • Familiarity with Jira and Slack for internal workflow management and collaboration.
  • A proactive approach to learning new technologies and staying current with evolving infrastructure tools.
  • A natural tinkerer’s mindset and curiosity demonstrated through personal projects, homelabs, or open-source contributions preferred.

Benefits

  • Competitive total compensation package with base salary, equity, and variable commission for quota-based roles.
  • CAN pay range of $129,980 to $162,140 CAD.
  • Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for employees and family.
  • Remote-first work environment with flexibility in how and when you work.
  • Annual $1,500 USD professional development budget, plus mentorship, coaching, and internal promotion opportunities.
  • Flexible paid time off program.
  • Company-owned laptop choice, monthly home internet reimbursement, and $1,000 USD home office setup budget.
  • Generous parental leave with top-ups for up to 26 weeks from day one.

Interested in this position?

Apply directly on the company website

Apply Now

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