Forward Deployed Engineer

Responsibilities

• Lead and manage onboarding for new strategic customers, ensuring rapid understanding and adoption of Tailscale.
• Provide training and resources that support long-term customer success.
• Offer technical support across Tailscale’s platform, including configuration, integration, troubleshooting, and issue resolution.
• Conduct quarterly business reviews (QBRs) covering usage, success metrics, and future goals.
• Identify opportunities for deeper customer engagement and horizontal expansion.
• Build trusted customer relationships and provide recommendations based on specific use cases and desired business outcomes.
• Represent customer feedback and insights to product and engineering teams.
• Collaborate with sales, product, engineering, and support teams on handoffs, escalations, and customer success.
• Develop and maintain technical documentation, FAQs, and self-service guides.

Requirements

• 6+ years of experience 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 and DevOps technologies.
• Prior experience in a customer-facing technical role at a SaaS company, such as Technical Support Engineer, Solutions Engineer or Architect, or Customer Success Engineer.
• Ability to explain complex technical concepts to non-technical stakeholders and engineers.
• Strong written and verbal communication skills.
• Analytical and methodical troubleshooting skills.
• Strong customer-service orientation and relationship-building skills.
• Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track.
• Collaborative approach to working cross-functionally.

Compensation and Benefits

• Target compensation range: $201,000–$335,000 CAD OTE (on-target earnings), inclusive of base salary and variable compensation tied to quarterly sales targets.
• Compensation includes base salary, equity incentive plan, and variable commission for quota-based roles.
• Comprehensive health, vision, dental, and other group benefits with no waiting period.
• Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually.
• $1,500 USD annual professional-development allowance.
• Flexible paid time off.
• Company-owned laptop, monthly home-internet reimbursement, and $500 USD for workstation customization.
• Paid parental leave top-ups of up to 20 weeks for birthing parents and 16 weeks for non-birthing parents.
• Remote-first work environment with coworking and team-connection programs.