Customer Support Engineer (Tier 2)

• Serve as the face of the company for teams and companies using Tailscale, handling a broad range of tickets that flex your technical muscles. • Join a distributed team focused on delivering excellent support to customers and proactively solving friction alongside the wider CX team and Product/Engineering. • Act as the primary escalation point for technically complex tickets, including those passed up from Tier 1. • Report directly to the Support Team Lead and play a key role in the journey ahead. • Work remotely from anywhere in the United Kingdom at a fully distributed company.

• Have 4+ years of experience in a technical support role within a SaaS company, with demonstrated experience handling escalated or enterprise-tier accounts. • Bring a natural tinkerer's mindset and deep curiosity for how things work, likely shown through personal projects, homelabs, or open-source contributions. • Know networking fundamentals strongly, including TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing, and apply that knowledge to real-world troubleshooting. • Troubleshoot proficiently across macOS, Windows, Linux, and mobile platforms. • Have worked with identity providers and SSO integrations such as Okta, Google Workspace, and Azure AD as they relate to device or user authentication. • Have basic experience troubleshooting Kubernetes environments, including pod networking, namespaces, and common CLI tools such as kubectl. • Be familiar with log analysis and CLI-based diagnostic tools to investigate issues independently before escalating. • Write excellently, explaining complex technical concepts with empathy and clarity. • Be familiar with Jira and Slack for managing internal workflows and collaborating across distributed teams. • Take a proactive approach to learning new technologies and staying current with evolving infrastructure tools.

• Have hands-on familiarity with Tailscale or comparable networking and VPN products such as WireGuard or traditional VPNs. • Have mentored junior support colleagues through ticket reviews and escalation guidance. • Have contributed to public documentation or knowledge bases. • Have run a homelab or contributed to open-source networking projects.

• Serve as the primary escalation point for technically complex tickets raised by paying customers, owning them through to resolution. • Diagnose and troubleshoot advanced Tailscale-specific issues such as ACL misconfigurations, subnet routing and exit node configurations, and identity provider integrations with Okta or Azure AD. • Manage a ticket queue with consistent focus on SLA adherence, delivering timely first responses and resolutions. • Drive positive user outcomes and maintain high CSAT scores through clear, helpful, accurate technical guidance. • Balance a high volume of daily ticket replies while keeping the technical depth needed to troubleshoot complex networking issues. • Partner cross-functionally to identify recurring friction points and advocate for user experience improvements. • Own escalations from Tier 1, including those from free-tier users, resolving issues beyond Tier 1's scope efficiently and thoroughly. • Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions.

• Receive a competitive total compensation package including base salary and an equity incentive plan. • Access comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family. • Work remote-first with support for virtual and in-person social events and a corporate co-working programme at WeWork or similar spaces. • Get employer-funded retirement contributions matched dollar-for-dollar, up to 0.75% of your eligible compensation annually. • Attend the annual company retreat and team off-sites, connecting with teammates across Canada, the US, the UK, and Singapore. • Spend $1,500 USD annually on professional development, alongside mentorship, coaching, and internal promotion opportunities. • Take flexible paid time off that supports whatever life throws your way. • Build your own home office with a company-owned laptop of your choice, monthly home internet reimbursement, and $500 USD to customise your workstation. • Take paid parental leave top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents.

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices wherever they are. Teams of every size, from hobbyists to multinational corporations, use Tailscale to protect their networks and share access to internal tools. The company was founded in 2019, is fully distributed, and is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.