Team Lead, Customer Support

About Tailscale Tailscale is building the new Internet 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. Job Description Tailscale is seeking its first hire in Singapore to establish and lead our APAC support operations. As Team Lead, Customer Support in this region, you will serve as a player coach responsible for building a high-performing support team from the ground up and establishing Tailscale’s unique company culture locally. You will manage daily operations for a team of 8-10 Support Engineers, ensuring world-class service for our APAC users while helping to provide follow the sun coverage for our global customer base. This role reports to the VP of Customer Engineering and requires a technical expert who is equally passionate about solving complex networking problems and mentoring others in a collaborative environment. Key

Responsibilities 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. What We Are Looking For 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 As a company, we strive to maintain fair and equitable