About this role.
Tailscale is seeking an experienced Founding Solutions Engineer to lead technical sales and customer engagement across the APAC region from Singapore. This role combines deep technical expertise in networking and zero-trust security with sharp commercial acumen to drive complex deals and build scalable solution architectures. As the first SE in the region, you will work closely with Account Executives, contribute directly to product development, and help establish Tailscale's culture and technical strategy in APAC. The position requires strong fundamentals in networking, IAM, and hands-on coding, along with the ability to navigate ambiguity in a fast-growing startup.
Role DNA
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5/5Autonomy Level
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Founding Solutions Engineer role at Tailscale. With over five years of experience in solutions engineering for high-growth networking and security platforms, I have consistently translated complex technical challenges into successful customer outcomes. My strong background in zero-trust architectures, IAM integrations, and hands-on coding aligns perfectly with this role's blend of technical depth and commercial impact.
I thrive in ambiguous, early-stage environments and have experience building regional technical strategies from the ground up. I am eager to bring my passion for secure, simple networking to Tailscale and help establish a world-class customer engineering presence across APAC. I look forward to the opportunity to contribute to your mission of building a new, safer Internet.
Sincerely, [Your Name]
Sample interview questions
In a previous role, I was the first SE in the APAC region. I started by mapping the local market, identifying key customer pain points, and building a standard demo environment tailored to regional needs. I also set up feedback loops with product and sales teams to ensure insights were shared, creating a structured yet flexible approach that could adapt as the business grew.
I would first run a discovery workshop to understand each stakeholder's core objectives and pain points. Then I would map those needs to specific product capabilities, clearly demonstrating value for each party. By building a solution architecture that addresses the most critical business outcomes and maintaining transparent communication, I can align everyone toward a common goal.
I treat the POC as a critical sales activity, so any code I write is directly tied to unblocking the customer's adoption. I would prioritize tasks by impact: first resolving the blocker, then documenting the fix for the product team, and finally ensuring the demo and next steps with the customer are still on track. This requires strong time management and collaboration with engineering.
I have designed and deployed zero-trust access solutions for enterprise clients, integrating with IdPs like Okta and Azure AD using SAML and OIDC. I've also worked with mTLS, device posture checks, and network segmentation. My hands-on experience ensures I can lead technical evaluations and troubleshoot complex authentication issues effectively.
I prioritize clear documentation and regular syncs. I would establish shared channels for tracking customer issues, use asynchronous updates for global visibility, and schedule overlapping hours with NAMER/EMEA teams when needed. By building trust and ensuring everyone has access to the same information, we can deliver consistent service and avoid silos.
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 an experienced, highly technical, driven Founding Solutions Engineer to partner with Sales in establishing and accelerating our business expansion across the APAC region. Based in Singapore, this individual will serve as our founding Solutions Engineer in the region and will report directly into the VP of Customer Engineering.
In this role, you will co-own a regional book of business with AE’s, driving complex multi-stakeholder deals, uncovering core organizational pain points, and engineering robust solution architectures. Beyond direct sales engagement, you will be a critical anchor for building out technical engagement across the region and collaborating closely with other newly emerging customer-facing technical teams in Singapore, such as Customer Support. This position sits at the center of technical depth and sharp commercial acumen with a mission to translate platform features into long-term customer trust and measurable business outcomes.
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
- Act as the pioneering technical voice for Tailscale in APAC, cultivating market presence, initiating customer engagement frameworks, and defining regional technical execution strategies.
- Partner closely with AEs to identify, qualify, design, and close new commercial opportunities, managing the regional pipeline effectively to hit and exceed quota outcomes.
- Lead discovery workshops, deliver tailor-made product demonstrations, and manage technical POCs that resolve technical objections and shorten sales cycles.
- Engage in direct R&D activities such as writing code, developing custom tool integrations, and contributing fixes or features directly back to Tailscale’s core product to solve deep technical barriers for strategic regional customers.
- Document and synthesize critical field insights, architectural trends, and regional product requirements to provide structured feedback that informs product, engineering, and GTM strategies.
- Build reusable demo environments, solution blueprints, technical whitepapers, and objection-handling documentation to uplevel the global Solutions Engineering organization.
- Collaborate with adjacent customer-facing technical teams simultaneously building out in Singapore to ensure tight feedback loops, consistent service delivery; partnering together to actively establish and anchor Tailscale’s company culture in the region.
- You will focus on building partner relationships that drive measurable results
Experience & Qualifications
- 4-5+ years of experience in a customer-facing Sales Engineer, Solutions Engineer, or Solutions Architect capacity supporting high-growth networking, security, or enterprise cloud software platforms.
- Proven success navigating ambiguity as a founding regional hire or operating within an early-stage, high-growth startup culture where process construction and individual ownership are required.
- Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills.
- Comprehensive understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC).
- Hands-on experience designing, provisioning, or troubleshooting infrastructure within major cloud environments (AWS, GCP, and/or Azure) and container environments (Docker, k8s).
- Technical storytelling capacity, with an ability to link technical architectural decisions directly to strategic customer/business outcomes, and executive value propositions.
- Outgoing communicator with strong interpersonal skills, capable of syncing seamlessly across fully distributed global engineering teams and regional sales groups.
- 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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