Forward Deployed Engineer

Tailscale

71d • CA$201,000 - CA$335,000 • Remote

About The Position

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.

Requirements

• 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

Nice To Haves

• Bachelors degree in CS or CE a plus

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. Use these touchpoints to identify opportunities for deeper engagement and horizontal expansion.
• Build strong relationships with customers, acting as a trusted advisor. Help customers optimize their use of Tailscale by identifying best practices, and by 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 to help improve the product and the customer experience.
• 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.

Benefits

• Base salary
• Equity incentive plan
• Variable commission (for quota-based roles)
• Comprehensive group benefits with no waiting period (health, vision, dental, and more for you and your family)
• Employer-funded retirement contributions (Tailscale will match retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation)
• Support for personal and professional development ($1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities)
• Flexible, paid time off program
• Build-your-own home office setup (company-owned laptop, monthly home internet reimbursement, $500 USD for workstation customization)
• Paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: High school or GED