Team Lead, Customer Support

🕒 May 20

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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

• Serve as the founding regional hire for the Singapore support team, leading the local expansion and recruitment efforts. • Build and establish Tailscale’s company culture and operational standards within the new Singapore region. • Manage day-to-day support operations for a pod of 8-10 Tier 1 and Tier 2 Support Engineers. • Lead the hiring, onboarding, technical mentoring, and career coaching for all direct reports in the region. • Coordinate in-office time to foster team collaboration, establish the local office environment, and support new hires. • Oversee the regional support queue to ensure SLA/SLO adherence, focusing on APAC specific tickets and partnering on global queue health. • Act as an internal escalation point for both complex technical issues and difficult customer situations. • Partner with the VP of Customer Engineering to align regional team outcomes with the broader global strategy. • Analyze regional support data and customer feedback (CSAT) to surface trends and insights to leadership. • Refine support workflows and internal tooling in collaboration with Support and CX Operations. • Conduct regular quality assurance reviews on tickets to maintain high technical accuracy and a consistent brand voice.

🎯 Requirements

• 6+ years of experience in a technical support role within a SaaS environment • 2+ years of experience in a leadership, management, or formal mentoring capacity • Proven experience building teams or establishing operational processes in a new region or startup setting • 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. • 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.