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. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

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 and solving technical issues for our diverse community of users. You will report directly to the Tier 1 Support Team Lead.

Key Responsibilities

• Act as the primary technical resource for configuration and networking challenges.
• Manage a high-velocity ticket queue, meeting targets for time to first response and resolution.
• Drive positive user outcomes and maintain high CSAT scores.
• Balance high-volume ticket replies with deep-dive technical troubleshooting.
• Partner cross-functionally to identify recurring friction points and advocate for product improvements.

What We Are Looking For

• A natural tinkerer’s mindset (demonstrated through personal projects, homelabs, or open-source).
• Foundational understanding of networking (DNS, IP addressing, firewalls, routing).
• Proficiency in troubleshooting across macOS, Windows, Linux, and mobile OS.
• Familiarity with Jira and Slack for internal workflows.
• Excellent written communication skills with the ability to explain complex concepts with empathy.
• A proactive approach to learning new technologies.

What We Offer

• Competitive Compensation: Base salary, equity incentive plan, and comprehensive benefits.
• Remote-First Culture: Work from anywhere with a corporate co-working program and annual company retreats.
• 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 career growth, mentorship, and coaching.
• Work-Life Balance: Flexible paid time off and a build-your-own home office setup ($500 stipend + monthly internet reimbursement).
• Parental Leave: Paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents).