Customer Support Engineer

Tailscale

2d • CA$129,980 - CA$162,140 • Remote

About The Position

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 2) to join our growing team of support professionals. You will serve as the face of the company for teams and companies using Tailscale, handling a broad range of tickets that will help flex your technical muscles. As a Tier 2 engineer, you’ll be part of a distributed team focused on delivering excellent support to our customers 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.

Requirements

• 4+ years of experience in a technical support role within a SaaS company, with demonstrated experience handling escalated or enterprise-tier accounts.
• 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.
• 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.
• Basic experience troubleshooting Kubernetes environments, including familiarity with pod networking, namespaces, and common CLI tools such as kubectl.
• 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.

Responsibilities

• Serve as the primary escalation point for technically complex tickets raised by paying customers, taking full ownership through to resolution.
• Diagnose and troubleshoot advanced Tailscale-specific issues like ACL misconfigurations, subnet routing/exit node configurations, and integration with identity providers (e.g. Okta, Azure AD).
• Manage a ticket queue with a consistent focus on SLA adherence, ensuring timely first responses and resolutions.
• 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.
• Own escalations of technically complex tickets from Tier 1, including those originating from free-tier users, ensuring issues beyond Tier 1's scope are resolved efficiently and thoroughly.
• Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions.

Benefits

• Comprehensive group benefits with no waiting period. Take advantage of 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 wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you).
• 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 professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• 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. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed