About this role.
Tailscale is seeking a Founding Senior Customer Engineer to establish its Customer Engineering presence in Singapore and across APAC. This hands-on role involves solving complex networking problems, managing a pod of Tier 1 and Tier 2 engineers, and leading hiring, onboarding, and coaching. The position requires deep networking expertise, experience with identity management and SSO, and a data-driven mindset to optimize support operations. The successful candidate will help shape team culture and provide follow-the-sun support for global customers, with eventual expansion to 1–3 directs.
Role DNA
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Job Complexity
4/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Founding Senior Customer Engineer position at Tailscale. With over six years of experience in technical support and customer engineering within fast-paced SaaS environments, I have developed a deep expertise in networking fundamentals, DNS, firewalls, and identity management integrations like Okta and Azure AD. I am particularly drawn to the opportunity to build Tailscale's APAC team from the ground up, as I have previously established onboarding processes and led technical mentoring in startup settings. My hands-on approach, combined with my ability to analyze support metrics and drive SLA adherence, equips me to deliver exceptional customer experiences while fostering a collaborative team culture. I look forward to the possibility of contributing to Tailscale's mission and expanding its global footprint.
Sample interview questions
In a previous role, a customer was experiencing intermittent connectivity issues across multiple branches. I traced the problem through packet captures and discovered a misconfigured firewall rule that was dropping certain UDP traffic. I worked with the customer's network team to adjust the rule, implemented monitoring, and verified resolution by analyzing logs over several days. This reduced their ticket volume and improved trust in our support.
First, I would learn the existing global workflows and SLAs to ensure alignment. Then I would establish local processes, document them, and identify key metrics like CSAT and TTR. For hiring, I would focus on technical aptitude and cultural fit, and create a structured onboarding program that includes shadowing senior engineers globally. I would also foster a collaborative environment by scheduling in-office time and regular feedback sessions.
A customer was frustrated about a recurring bug that impacted their production environment. I listened actively, acknowledged the impact, and set clear expectations for the next steps. I coordinated with our engineering team to implement a workaround while a permanent fix was developed, and provided daily updates to the customer. The fix was deployed within a week, and the customer later sent a positive CSAT response and renew expanded their contract.
Key metrics include Customer Satisfaction Score (CSAT), Time to First Response (TTFR), and Time to Resolution (TTR). I would also track ticket deflection and backlog bounce. To improve them, I would identify common issues and create knowledge base articles, implement AI-assisted prioritization, and ensure proper staffing for APAC hours. Regularly reviewing ticket quality and providing coaching to engineers helps maintain high technical accuracy and consistency.
I dedicate time each week to reading technical blogs, participating in community forums, and experimenting with new tools in a lab environment. I also take online courses on emerging technologies like service meshes and Zero Trust networking. For my team, I encourage sharing knowledge through weekly tech talks and documentation reviews to ensure everyone remains up to date.
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 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.
Experience & Qualifications
- 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.
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale’s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire’s base salary. Individual offers may vary based on experience and skill set.
Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!
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.
- Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- 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, the United Kingdom, and Singapore. 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 $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).
Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Please be aware that legitimate emails from Tailscale’s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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