Implementation Engineer

Tailscale Inc.

Job Overview

Location

Remote (Canada)

Job Type

Full-time

Full Job Description

📋 Description

• As an Implementation Engineer at Tailscale, you are the primary architect of a customer’s first experience with the product, ensuring they achieve Time To Value (TTV) in under 30 days by guiding commercial and enterprise accounts through technical onboarding.
• You will own the end-to-end technical onboarding journey, providing hands-on guidance for Identity Provider (IdP) integration, Tailnet administration, ACL policy definition, and MDM deployments, while partnering with AEs and SEs to ensure seamless transitions from pre-sales to active usage.
• You will act as a critical feedback loop for Product and Engineering teams by identifying recurring friction points or bugs during onboarding and advocating for fixes, while maintaining rigorous data hygiene in SFDC and CSP tooling to track onboarding completion rates, TTV, and customer health metrics.
• You will bridge the gap between initial setup and long-term support by facilitating clean handoffs to Support and Post-sales teams once adoption milestones are met, and define/refine onboarding success metrics including post-onboarding surveys and in-product adoption targets.
• 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 — serving hobbyists to multinational corporations with a mission to create an easy, sensible, and safe Internet.
• You will learn and achieve deep expertise in networking fundamentals, zero-trust security architectures, enterprise identity systems, and customer success workflows, while developing skills in technical advocacy, cross-functional collaboration, and scalable onboarding process design.

🎯 Requirements

• 2–4+ years of experience in a technical, customer-facing role such as Technical Support, Implementation, or Solutions Engineering
• Strong foundational knowledge of networking concepts including the OSI model, DNS, routing, and VPN operations (experience with Tailscale preferred)
• Proficiency in installing software across diverse operating systems, including Linux, Windows, macOS, and iOS/Android (experience with Mobile Device Management is a plus)
• Ability to read and modify JSON or YAML configs for ACL and Kubernetes deployments
• Exceptional organizational skills with a proven ability to manage a high volume of concurrent tasks across multiple revenue segments without compromising quality
• Clear and empathetic communication style, with the ability to translate complex networking concepts into actionable steps for technical and non-technical stakeholders alike

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self, with flexibility in how and when you work to integrate work and life
• A competitive total compensation package including base salary, equity incentive plan, and variable commission (for quota-based roles)
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family
• Remote-first company culture — most teams work fully remotely, with access to virtual and in-person social events and corporate co-working programs (e.g., WeWork)
• Support for personal and professional development with $1,500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities
• A build-your-own home office setup: company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1,000 USD to customize your workstation

Skills & Technologies

Kubernetes

Linux

iOS

Android

Remote

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Tailscale Inc.

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About Tailscale Inc.

Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.

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