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 envi