Implementation Engineer

<div class="content-intro"><p><strong>About Tailscale </strong></p> <p>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.</p></div><p><span style="font-size: 12pt;"><strong>Job Description</strong></span></p> <p>As an Implementation Engineer (IE) at Tailscale, you are the primary architect of a customers’ first experience with our product. Reporting to the CSE Team Lead, you will sit at the intersection of Pre-sales, Support, and Product with the mission of value attainment for our customers. You will manage a high volume of accounts across commercial and enterprise segments, guiding them through the critical first 30 days of their journey. This is a high-impact, technical role designed for someone with intellectual curiosity, empathy, strong networking fundamentals, and a passion for helping customers solve complex connectivity/security challenges with Tailscale. You will ensure that Tailscale becomes a foundational part of our customers’ infrastructure from day one.</p> <p><span style="font-size: 12pt;"><strong>Key Responsibilities</strong></span></p> <ul> <li>Own the end-to-end technical onboarding journey for a high volume of accounts, with a relentless focus on ensuring customers reach Time To Value (TTV) in under 30 days.</li> <li>Provide hands-on guidance for technical configurations, including Identity Provider (IdP) integration, Tailnet administration, ACL policy definition, and MDM deployments.</li> <li>Partner closely with AEs and SEs to ingest technical requirements from the pre-sales cycle and ensure a seamless transition to active usage.</li> <li>Act as a critical feedback loop for the Product and Engineering teams by identifying recurring friction points or bugs during the onboarding phase and advocating for fixes.</li> <li>Maintain rigorous data hygiene within sales (SFDC) and CSP tooling to provide visibility into onboarding completion rates, TTV, and overall customer health metrics.</li> <li>Bridge the gap between initial setup and long-term support by facilitating clean handoffs to the Support and Post-sales teams once adoption milestones are met.</li> <li>Define and refine onboarding success metrics, including the development of post-onboarding surveys and in-product adoption targets.</li> </ul> <p><span style="font-size: 12pt;"><strong>What We Are Looking For</strong></span></p> <ul> <li>2–4+ years of experience in a technical, customer-facing role such as Technical Support, Implementation, or Solutions Engineering</li> <li>Strong foundational knowledge of networking concepts including the OSI model, DNS, routing, and VPN operations (experience with Tailscale preferred)</li> <li>Proficiency in installing software across diverse operating systems, including Linux, Windows, macOS, and iOS/Android (experience with Mobile Device Management is a plus)</li> <li>Strong skills in diagnosing, troubleshooting, and resolving issues related to networking</li> <li>Ability to read and modify JSON or YAML configs for ACL and Kubernetes deployments</li> <li>Exceptional organizational skills with a proven ability to manage a high volume of concurrent tasks across multiple revenue segments without compromising quality</li> <li>Clear and empathetic communication style, with the ability to translate complex networking concepts into actionable steps for technical and non-technical stakeholders alike</li> <li>A builder’s mindset, meaning you enjoy solving technical puzzles and are motivated by seeing a customer successfully deploy a solution you helped architect</li> </ul ... (truncated, view full listing at source)