tailscale
Customer Support Engineer
At a Glance
- Location
- Canada
- Work Regime
- remote
- Experience
- 4+ years
- Posted
- 2026-06-26T15:41:59-04:00
Key Requirements
Required Skills
Domain Knowledge
- SaaS
Benefits & Perks
salary, equity, and comprehensive benefits. The salary range displayed on each job
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.
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.
Responsibilities
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.
Support Engineer (Tier 2)
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.
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.