Customer Support Engineer (Tier 1) - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe.

About the Role

We’re seeking a motivated Support Engineer (Tier 1) to join our growing team. You will serve as the face of the company, handling a broad range of tickets that will help flex your technical muscles. You will be part of a distributed team focused on delivering excellent support and proactively solving friction by partnering with our broader CX, Product, and Engineering teams.

Key Responsibilities

• Act as the primary technical resource for less complex issues, resolving configuration and networking challenges.
• Manage a high-velocity ticket queue, meeting targets for time to first response and time to resolution.
• Drive positive user outcomes and maintain high CSAT scores through clear, helpful, and accurate technical guidance.
• Balance high-volume ticket replies with the technical depth required to troubleshoot complex networking issues.
• Partner cross-functionally to identify recurring friction points and advocate for user experience improvements.

What We Are Looking For

• Tinkerer’s Mindset: Deep curiosity for how things work (homelabs, open-source contributions, or personal projects).
• Networking Fundamentals: Foundational understanding of DNS, IP addressing, firewalls, and routing.
• OS Proficiency: Experience troubleshooting across macOS, Windows, Linux, and mobile OSs.
• Communication: Excellent written skills with the ability to explain complex technical concepts with empathy.
• Tooling: Familiarity with Jira and Slack for workflow management.
• Proactive Learning: A commitment to staying current with evolving infrastructure tools.

What We Offer

• Competitive Compensation: Base salary, equity incentive plan, and comprehensive benefits.
• Remote-First Culture: Work from anywhere with a monthly home internet reimbursement and a $500 workstation customization budget.
• Benefits: Comprehensive health, vision, and dental coverage with no waiting period.
• Retirement: Employer-funded retirement contributions (matching up to 0.75% of eligible compensation).
• Professional Development: $1,500 USD annually for your growth, plus mentorship and coaching.
• Work-Life Integration: Flexible paid time off and generous paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing).
• Connection: Annual company retreats, team off-sites, and corporate co-working program access.