Forward Deployed Engineer

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🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

⏰ Full Time

🟡 Mid-level

🟠 Senior

👷🏻‍♀️ Engineer

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• Lead and manage onboarding for new strategic customers, providing training and resources for long-term success • Provide technical support across Tailscale's platform, including configuration, integration, troubleshooting, and issue resolution • Conduct quarterly business reviews to assess usage, success metrics, and future goals • Identify opportunities for deeper customer engagement and horizontal expansion • Build customer relationships as a trusted advisor and recommend best practices based on use cases and business outcomes • Relay customer feedback and insights to product and engineering teams • Collaborate with sales, product, engineering, and support teams to ensure smooth handoffs and customer success • Develop and maintain technical documentation, FAQs, and customer self-service guides

🎯 Requirements

• 6+ years in a technical role, including at least 2 years of customer-facing experience • Experience working with enterprise customers in a consultative capacity • Strong understanding of networking, VPNs, and security principles • Experience with cloud infrastructure including AWS, GCP, and Azure • Experience with Docker, Kubernetes, and other DevOps technologies • Prior customer-facing technical experience as a Technical Support Engineer, Solutions Engineer/Architect, or Customer Success Engineer at a SaaS company • Ability to explain complex technical concepts to audiences ranging from non-technical stakeholders to engineers • Strong written and verbal communication skills • Analytical mindset and troubleshooting skills • Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track • Strong time management and organizational skills • Ability to collaborate cross-functionally with product, sales, and engineering teams

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self • Competitive total compensation package including a base salary, equity incentive plan and variable commission for quota-based roles • Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family • Fully remote work environment • Virtual and in-person social events • Corporate co-working program • Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation • Annual company retreat and team off-sites • $1500 USD annually for professional development • Mentorship, coaching, and internal promotion opportunities • Flexible paid time off program • Company-owned laptop (Mac or PC) • Monthly home internet reimbursement • $500 USD workstation customization allowance • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents