Founding Senior Customer Engineer

About the role

Tailscale is on the lookout for a Founding Senior Customer Engineer to spearhead the establishment and growth of its Customer Engineering team in Singapore, as well as the wider APAC region. This position will initially focus on hands-on problem-solving and ensuring outstanding customer experiences. As the team evolves, you will have the opportunity to recruit and mentor 1-3 Customer Engineers, influencing the team's culture and setting technical standards. This is a unique chance to develop a regional function from scratch, providing continuous support for a global clientele.

Key facts

What you'll do

• Take the lead in expanding and recruiting for the customer engineering team based in Singapore.
• Set the tone for Tailscale's company culture and operational practices in the new regional office.
• Supervise daily support operations for a small team of 1-3 Tier 1 and Tier 2 Support Engineers.
• Oversee the hiring process, onboarding, technical mentoring, and career progression for your direct reports in the region.
• Organize in-office collaboration time to foster teamwork and support the integration of new hires.
• Keep an eye on the regional support queue to ensure compliance with service level agreements, prioritizing APAC tickets while also contributing to the overall health of the global queue.
• Act as an internal escalation point for intricate technical challenges and demanding customer situations.
• Work closely with the VP of Customer Engineering to ensure that regional team objectives align with the overarching global strategy.
• Analyze support data and customer satisfaction metrics to identify trends and insights for leadership.
• Enhance support workflows and internal tools in collaboration with the Support and Customer Experience Operations teams.
• Conduct regular quality assurance assessments of support tickets to guarantee technical accuracy and maintain a consistent brand voice.

Requirements

• A minimum of 6 years of experience in a technical support role within a SaaS environment.
• Proven experience in leading teams through technical expertise, coaching, or formal mentoring.
• Demonstrated ability to build teams or establish operational processes in a new region or startup environment.
• Strong foundational knowledge of networking principles, including TCP/IP, DNS, firewalls, and routing.
• Familiarity with networking and security concepts is essential.
• Experience with identity management systems and SSO integrations, such as Okta, Azure AD, and Google.
• Prior experience in supporting customers across various operating systems, including Linux, MacOS, and Windows.
• Proven capability to manage and optimize support workflows and tools effectively.
• A data-driven approach, with the ability to track and respond to metrics such as Customer Satisfaction (CSAT), Time to First Response (TTFR), and Time to Resolution (TTR).
• Excellent communication skills to convey technical concepts clearly to both customers and internal teams.
• Ability to excel in a fast-paced environment while juggling multiple priorities.

Nice to have

• Previous experience in people management.
• Knowledge of Kubernetes (k8s) is a plus.

Skills & tools

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

Practical notes

• This position requires overlapping work hours with NAMER and EMEA regions for effective onboarding during the initial three months, as well as for ongoing internal collaboration.
• Occasional travel within the APAC region is anticipated, along with potential trips to North America for internal meetings and global conferences.
• The compensation package includes a competitive base salary, equity options, and a comprehensive benefits package.
• Benefits encompass health, vision, and dental coverage, employer-funded retirement contributions (up to 0.75% of eligible compensation), a $1500 USD annual professional development budget, paid time off, a home office setup allowance ($500 USD and a company-owned laptop), and generous parental leave policies (20 weeks for birthing parents, 16 weeks for non-birthing parents).
• Tailscale also organizes an annual company retreat and team off-sites to promote in-person connections among team members.