Customer Support Engineer (Tier 1)

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

About The Role

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 1) to join our growing team of support professionals. You will serve as the face of the company for a large portion of our community, handling a broad range of tickets that will help flex your technical muscles. As a Tier 1 engineer, you’ll be part of a distributed team focused on delivering excellent support and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Tier 1 Support Team Lead and will play a key role in our journey.

Responsibilities

• Act as the primary technical resource for less complex issues, resolving a wide range of configuration and networking challenges to keep users unblocked.
• Manage a high-velocity ticket queue with a consistent focus on meeting targets for time to first response and time to resolution.
• 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.

Requirements

• Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions.
• Demonstrate a foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing.
• Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS’s.
• Some familiarity with Jira and Slack to manage internal workflows and communicate effectively with the team and customers.
• Exhibit excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity.
• Maintain a proactive approach to learning new technologies and staying current with evolving infrastructure tools.

Pay

US Pay Range: $63,000—$99,000 USD

Benefits

• 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, covering health, vision, dental, and more for you and your family.
• Remote-first company with the flexibility to work from anywhere with Wi-Fi. Access to virtual and in-person social events and a corporate co-working program (e.g., WeWork).
• Employer-funded retirement contributions with a dollar-for-dollar match, up to 0.75% of eligible compensation annually.
• Annual company retreat, team off-sites, and opportunities to collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore.
• $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off program supporting work-life integration.
• Build-your-own home office setup: company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid parental leave program with top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).