Customer Support Engineer

Tailscale is recruiting a full-time Customer Support Engineer for a remote position based in the United Kingdom, where you will provide advanced technical assistance to users of all sizes.

What This Role Involves

This Tier 2 Customer Support Engineer opportunity places you at the forefront of customer interactions for teams relying on Tailscale, addressing a wide spectrum of technical enquiries that demand both depth and clarity. You join a fully distributed support group reporting to the Support Team Lead, collaborating routinely with customer experience, product and engineering colleagues to eliminate pain points before they escalate. The work revolves around ownership of sophisticated cases drawn from both free and paying users while upholding excellence in response quality and user confidence.

Responsibilities

• Serve as the principal escalation contact for intricate technical tickets submitted by paying customers and retain full ownership until each is resolved.
• Examine and correct advanced Tailscale configuration difficulties such as access-control-list errors, subnet routing, exit-node setups and identity-provider integrations including Okta and Azure AD.
• Administer an active case queue while prioritising adherence to service-level agreements through swift initial replies and thorough closures.
• Secure favourable user results and elevated satisfaction ratings by furnishing accurate, understandable technical direction.
• Sustain a high daily volume of ticket answers while preserving the analytical expertise needed for complex networking problems.
• Work across functions to surface recurring friction and champion enhancements that improve the overall user experience.
• Assume responsibility for escalations received from Tier 1, encompassing free-tier submissions that exceed first-line capability, and drive them to efficient conclusion.
• Coach Tier 1 colleagues through constructive ticket reviews, escalation advice and contributions to shared documentation.

Skills & Qualifications

• Four or more years of technical support experience inside a SaaS organisation, including proven handling of escalated or enterprise-level accounts.
• Practical exposure to Tailscale itself or comparable networking and virtual-private-network technologies (such as WireGuard or conventional VPNs) is strongly preferred.
• A natural experimenter’s outlook and deep curiosity about system behaviour, typically evidenced by personal projects, home laboratories or open-source participation.
• Confident command of networking essentials—TCP/IP, DNS, subnetting, firewalls, NAT traversal and routing—together with the skill to apply them in live troubleshooting scenarios.
• Ability to diagnose problems across macOS, Windows, Linux and mobile platforms.
• Background with identity providers and single-sign-on arrangements (Okta, Google Workspace, Azure AD) that govern device or user authentication.
• Basic competence troubleshooting Kubernetes environments, covering pod networking, namespaces and everyday command-line utilities such as kubectl.
• Routine use of log analysis and command-line diagnostic tools for independent investigation prior to escalation.
• Excellent written communication that explains technical concepts with empathy and precision.
• Familiarity with Jira and Slack for internal workflow management and collaboration inside distributed teams.
• Proactive habit of mastering new technologies and remaining current with evolving infrastructure tools.

Working at Tailscale

Tailscale supplies software that makes secure interconnection of people and their devices straightforward no matter where they are located. From individual enthusiasts to large multinational organisations, users of every scale depend on the platform daily to protect networks, share internal resources and accomplish more. Founded in 2019 and operating as a fully distributed company, Tailscale is supported by Accel, CRV, Insight, Heavybit and Uncork Capital. The United Kingdom base-salary range for this Customer Support Engineer role is £76,630 to £95,590. Compensation packages also incorporate equity and a full suite of benefits, and the firm is committed to fair, equitable pay practices. Applicants are warmly encouraged even when they do not satisfy every listed criterion. Team members enjoy an inclusive and flexible remote-first culture, comprehensive health coverage from day one, employer-matched retirement contributions up to 0.75 percent of eligible pay, a yearly professional-development allowance of 1500 USD, customisable home-office equipment including laptop choice and a 500 USD setup budget, monthly internet reimbursement, flexible paid leave, paid parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents), company retreats and in-person collaboration opportunities across multiple countries, plus access to co-working spaces. Hiring decisions remain human-led with AI-assisted screening only; reasonable adjustments are available throughout the process.

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