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. This role reports 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.
• Partner cross-functionally to identify recurring friction points and advocate for product improvements.

What We Are Looking For

• Tinkerer’s Mindset: Deep curiosity for how things work (homelabs, open-source, personal projects).
• Networking Fundamentals: Solid understanding of DNS, IP addressing, firewalls, and routing.
• Troubleshooting: Proficiency across macOS, Windows, Linux, and mobile OS.
• Communication: Excellent written skills with the ability to explain complex concepts with empathy.
• Tooling: Familiarity with Jira and Slack.

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.
• Development: $1,500 USD annual professional development budget.
• Work-Life Balance: Flexible paid time off and a build-your-own home office setup ($500 stipend + monthly internet reimbursement).
• Family Support: Paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing).
• Retirement: Employer-funded retirement contributions (up to 0.75% match).