Customer Support Engineer

Tailscale

2d•$97,000 - $121,000•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

Competitive total compensation package including base salary, equity incentive plan, and variable commission (for quota-based roles).
Comprehensive group benefits with no waiting period for health, vision, dental, and more for you and your family.
Remote first company with flexibility to work from anywhere with wifi.
Participation in virtual and in-person social events.
Corporate co-working program access.
Annual company retreat, team off-sites, and opportunities for in-person collaboration.
$1500 USD annually for professional development.
Mentorship, coaching, and internal promotion opportunities.
Flexible, paid time off program.
Build-your-own home office setup including a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1000 USD for workstation customization.
Generous parental leave program with top-ups for up to 26 weeks.