Founding Senior Customer Engineer

About the role

Tailscale is looking for a Founding Senior Customer Engineer to establish and grow its Customer Engineering presence in Singapore and the broader APAC region. This role begins with hands-on problem-solving and delivering excellent customer experiences. As the team expands, you will recruit and mentor 1-3 Customer Engineers, shaping the team's culture and technical standards. This is an opportunity to build a regional function from the ground up, providing follow-the-sun support for a global customer base.

Key facts

What you'll do

• Lead the initial expansion and recruitment for the Singapore customer engineering team.
• Establish Tailscale's company culture and operational practices within the new Singapore region.
• Oversee daily support operations for a group of 1-3 Tier 1 and Tier 2 Support Engineers.
• Manage hiring, onboarding, technical mentoring, and career development for direct reports in the region.
• Coordinate in-office time to encourage team collaboration and support new hires.
• Monitor the regional support queue to meet service level agreements, focusing on APAC tickets and contributing to global queue health.
• Serve as an internal escalation point for complex technical issues and challenging customer situations.
• Collaborate with the VP of Customer Engineering to align regional team goals with the global strategy.
• Analyze regional support data and customer satisfaction feedback to identify trends for leadership.
• Improve support workflows and internal tools in partnership with Support and CX Operations.
• Conduct regular quality assurance reviews of tickets to ensure technical accuracy and consistent brand voice.

Requirements

• 6+ years in a technical support position within a SaaS environment.
• Experience leading through technical expertise, coaching, or formal mentoring.
• Demonstrated experience building teams or establishing operational processes in a new region or startup.
• Strong technical understanding of networking fundamentals including TCP/IP, DNS, firewalls, and routing.
• Familiarity with networking and security concepts.
• Experience with identity management and SSO integrations such as Okta, Azure AD, and Google.
• Prior experience supporting customers across various operating systems like Linux, MacOS, and Windows.
• Proven ability to manage and optimize support workflows and tooling.
• Data-driven mindset, capable of tracking and acting on metrics like CSAT, TTFR, and TTR.
• Excellent communication skills to explain technical concepts to both customers and internal stakeholders.
• Ability to thrive in a fast-paced environment while managing multiple priorities.

Nice to have

• Previous people-management experience.
• Knowledge of Kubernetes (k8s).

Skills & tools

• TCP/IP
• DNS
• Firewalls
• Routing
• Okta
• Azure AD
• Google SSO
• Linux
• MacOS
• Windows

Practical notes

• This role requires overlapping with NAMER and EMEA hours for successful onboarding during the first 3 months and for ongoing internal collaboration.
• Travel within APAC is expected as needed, with occasional travel to North America for internal meetings and global conferences.
• The compensation package includes base salary, equity, and comprehensive benefits.
• Benefits include health, vision, dental, employer-funded retirement contributions (up to 0.75% of eligible compensation), a $1500 USD annual professional development allowance, paid time off, a home office setup allowance ($500 USD and company-owned laptop), and paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing parents).
• Tailscale offers an annual company retreat and team off-sites for in-person connection.