Act as the main escalation contact for complex tickets from paying customers, managing them from start to finish.
Identify and resolve advanced Tailscale-specific problems, including ACL misconfigurations, subnet routing, exit node setups, and identity provider integrations like Okta and Azure AD.
Oversee a ticket queue while consistently meeting SLA targets for initial responses and resolutions.
Achieve high customer satisfaction scores by delivering clear, accurate, and empathetic technical guidance.
Handle a high volume of daily ticket replies without sacrificing the technical depth needed for complex networking issues.
Work with cross-functional teams to pinpoint recurring user pain points and advocate for product improvements.
Manage escalations of technically challenging tickets from Tier 1, including those from free-tier users, ensuring thorough resolution of issues beyond Tier 1's capabilities.
Mentor Tier 1 colleagues through ticket reviews, escalation advice, and contributions to documentation.

At least 4 years of technical support experience in a SaaS company, including handling escalated or enterprise-level accounts.
Solid understanding of networking fundamentals such as TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing, applied to real-world troubleshooting.
Proven ability to troubleshoot across multiple operating systems including macOS, Windows, Linux, and mobile platforms.
Experience with identity providers and SSO integrations like Okta, Google Workspace, or Azure AD for device or user authentication.
Basic experience troubleshooting Kubernetes environments, including pod networking, namespaces, and CLI tools like kubectl.
Familiarity with log analysis and CLI-based diagnostic tools for independent issue investigation before escalation.
Excellent written communication skills to explain complex technical concepts with empathy and clarity.
Familiarity with Jira and Slack for managing internal workflows and collaborating across distributed teams.
Proactive approach to learning new technologies and staying updated with evolving infrastructure tools.

Hands-on experience with Tailscale or similar networking or VPN products like WireGuard or traditional VPNs is strongly preferred.
Natural curiosity and tinkering mindset, demonstrated through personal projects, homelabs, or open-source contributions.

A competitive total compensation package including base salary, equity incentive plan, and variable commission for quota-based roles.

Remote (Worldwide) — Canada, United States, United Kingdom, Singapore

An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package including base salary, equity incentive plan and variable commission (for quota-based roles).
Comprehensive group benefits with no waiting period: health, vision, dental, and more for you and your family.
Remote first company—most teams work fully remotely; enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage corporate co-working program to visit WeWork or similar spaces.
Employer-funded retirement contributions: Tailscale matches retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation.
Connect with other Tailscalars IRL: attend annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, United States, United Kingdom, and Singapore.
Support for personal and professional development: $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
Paid time off and a healthy work-life integration with flexible paid time off program.
Build-your-own home office setup: choose your own company-owned laptop (Mac or PC), receive monthly home internet reimbursement, and $500 USD to customize workstation.
Paid parental leave program: 20 weeks for birthing parents, 16 weeks for non-birthing parents.

Tailscale is hiring a Customer Support Engineer (Tier 2)