Founding Senior Customer Engineer

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. About the Role Tailscale is seeking a Founding Senior Customer Engineer to establish our Customer Engineering presence in Singapore and across APAC. Initially, this will be a hands-on role focused on solving complex networking problems and delivering an exceptional experience for our customers. As the regional function grows, you’ll hire and onboard 1–3 Customer Engineers, helping shape the team’s culture, working practices, and technical standards. It’s an opportunity to build from the ground up, lead through expertise and example, and help provide follow-the-sun coverage for our global customer base. This is a full-time position based in our Singapore office, with two days per week in the office. Additionally, this role is expected to overlap with NAMER and EMEA hours as needed to onboard successfully during the first 3 months and on an ongoing basis to resolve issues that require internal collaboration. Key Responsibilities Serve as the founding regional hire for the Singapore customer engineering 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 1-3 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. Experience & Qualifications 6+ years of experience in a technical support role within a SaaS environment. Experience leading through technical expertise, coaching, or formal mentoring; previous people-management experience is beneficial but not essential. 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. Expectations include travel within APAC as needed to perform the role as well as travel to North America from time to time for internal meetings and global conferences. As a company, we strive to maintain fair and equi…