[Hiring] Forward Deployed Engineer @Tailscale

Role Description

As a Forward Deployed Engineer at Tailscale, you’ll be the bridge between our technical capabilities and the needs of our most strategic customers. You will work directly with customers to ensure their success with Tailscale’s products, helping them get onboarded, driving their long-term adoption, and providing expert technical guidance throughout their journey. This role requires a combination of technical proficiency, problem-solving skills, and an empathetic customer-centric approach to ensure customers are fully empowered to leverage the power of Tailscale. The role will report directly to the VP of Customer Experience.

Key Responsibilities

• Lead and manage the onboarding process for new strategic customers, ensuring they quickly understand and adopt Tailscale.
• Provide training and resources that set customers up for long-term success.
• Offer technical support for customers, diagnosing and resolving issues across Tailscale's platform.
• Assist with configuration, integration, and troubleshooting to ensure smooth implementation.
• Conduct QBRs with customers to review usage, success metrics, and future goals.
• Build strong relationships with customers, acting as a trusted advisor.
• Help customers optimize their use of Tailscale by identifying best practices and providing recommendations based on their specific use cases and desired business outcomes.
• Serve as the voice of the customer internally, relaying feedback and insights to the product and engineering teams.
• Work closely with sales, product, engineering, and support teams to ensure smooth handoffs, escalate critical issues, and drive customer success across the organization.
• Develop and maintain a repository of technical documentation, FAQs, and guides to help customers self-serve.
• Share insights and best practices with both the customer and internal teams.

Qualifications

• 6-8+ years in an engineering or technical role with minimum 2 years of customer facing experience (Solutions engineer/architect, Sr. Support Engineer, etc.).
• Experience working with enterprise customers in a consultative capacity.
• Strong understanding of networking, VPNs, and security principles; experience with cloud infrastructure (AWS, GCP, Azure) and tools like Docker, Kubernetes, and other DevOps technologies.
• Prior experience in a customer-facing technical role such as Technical Support Engineer, Solutions Engineer/architect, or Customer Success Engineer at a SaaS company.
• Ability to clearly explain complex technical concepts to a diverse audience, from non-technical stakeholders to engineers.
• Strong written and verbal communication skills are a must.
• Analytical mindset and troubleshooting skills, with the ability to think critically and methodically to resolve complex technical issues.
• A passion for delivering excellent customer service and a strong focus on building long-term customer relationships.
• Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track.
• Strong time management and organizational skills are key.
• A collaborative mindset and ability to work cross-functionally with product, sales, and engineering teams to deliver customer success.
• Bachelor's degree in CS or CE a plus.

Requirements

• As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels.
• Tailscale's compensation package includes base salary, equity, and comprehensive benefits.
• The salary range displayed on each job posting represents the target range for a new hire's base salary.
• Individual offers may vary based on experience and skill set.
• For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.
• CAN Pay Range (OTE): $201,000 — $335,000 CAD.

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including a base salary, an equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, including coverage for health, vision, dental, and more for you and your family!
• Remote first company—most of our teams work fully remotely.
• Employer-funded retirement contributions, with Tailscale matching your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Paid time off and a healthy work-life integration with a flexible, paid time off program.
• A build-your-own home office setup, including a company-owned laptop and $500 USD to customize your workstation.
• Paid parental leave program, with top-ups for birthing and non-birthing parents.