Team Lead, Customer Engineering

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 customer engineering operations. As Team Lead, Customer Engineering in this region, you will serve as a player coach responsible for building a high-performing customer engineering team from the ground up and establishing Tailscale’s unique company culture locally. You will manage daily operations for a team of 8-10 Customer 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 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 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.

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.