Customer Support Engineer (Tier 2)

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, like it used to be. 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 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. Key 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. What We Are Looking For 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. As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Range $129,980—$162,140 CAD Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! What We Offer An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents). Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.