Solutions Engineer (Singapore) - Commercial

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. Job Description Tailscale is seeking an experienced, highly technical, and commercially driven 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. 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. What We Are Looking For 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