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Tailscale

Founding Senior Customer Engineer

Tailscale

Founding Senior Customer Engineer at Tailscale, focusing on customer support in Singapore and APAC. Leading team expansion and technical mentoring for exceptional customer experience.

Posted 8/1/2026full-timeSingapore • 🇸🇬 SingaporeSeniorWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates strong leadership in building and managing technical support teams within a SaaS environment, with a focus on operational excellence and customer satisfaction. Proficient in networking fundamentals and identity management, ensuring effective support workflows and team collaboration.

Highest-signal resume keywords
Technical Support ManagementNetworking FundamentalsIdentity ManagementData-Driven MindsetExcellent Communication Skills

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Technical SupportNetworking FundamentalsTCP/IPDNSFirewallsRoutingSSO IntegrationsOktaAzure ADLinux
Soft Skills
CoachingMentoringTeam CollaborationProblem SolvingAdaptability
Tools & Technologies
Customer Support ToolsCSAT MetricsSupport WorkflowsInternal ToolingKubernetes
Industry Keywords
SaaSAPACCustomer EngineeringOperational ProcessesStartup Environment

Tech Stack

Tools & technologies
AzureDNSFirewallsKubernetesLinuxMacOSTCP/IP

About the role

Key responsibilities & impact
  • 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.

Requirements

What you’ll need
  • 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.

Benefits

Comp & perks
  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package.
  • Comprehensive group benefits with no waiting period.
  • Remote first company—most of our teams work fully remotely.
  • Employer-funded retirement contributions.
  • Connect with other Tailscalars IRL.
  • Support for your personal and professional development.
  • Paid time off and a healthy work-life integration.
  • A build-your-own home office setup.
  • Paid parental leave program