Team Lead, Customer Support

🕒 May 14

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• Manage day-to-day support operations for a team of 8-10 Support Engineers. • Lead the onboarding, technical mentoring, and career coaching for all direct reports. • Conduct regular 1:1s and performance management reviews to ensure team alignment and growth. • Oversee the support queue to ensure SLA/SLO adherence, including response and resolution times. • Act as an internal escalation point for both complex technical issues and difficult customer situations. • Align team activities and outcomes with the strategic roadmap set by the VP of Customer Engineering. • Partner with Support and CX Operations to refine workflows and improve internal tooling like Jira, Incident.io, Kapa.ai, and PagerDuty. • Perform regular QA reviews on tickets to maintain technical accuracy and brand voice. • Analyze support data and customer feedback (CSAT) to identify and report trends to leadership.

🎯 Requirements

• 4+ years of experience in a technical support role within a SaaS environment • 1+ years of experience in a leadership, management, or formal mentoring capacity • Strong technical background in networking fundamentals (TCP/IP, DNS, firewalls, and routing) • Proficiency with networking and security concepts (k8s a plus) • Experience with identity management and SSO integrations such as Okta, Azure AD, and Google • Previous experience in supporting customers across OS’s (Linux, MacOS, Windows, etc) • Proven ability to manage and optimize support workflows across processes and tooling • Data-driven mindset with the ability to track and act on metrics like CSAT, TTFR, and TTR • Excellent communication skills for translating technical concepts to both customers and internal stakeholders • Ability to thrive in a fast-paced environment while managing multiple competing priorities

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self. • A competitive total compensation package. • Comprehensive group benefits with no waiting period. • Remote first company—most of our teams work fully remotely. • Connect with other Tailscalars IRL. • Support for your personal and professional development. • Paid time off and a healthy work-life integration. • A build-your-own home office setup. • Generous parental leave program from your first day.