Forward Deployed Engineer - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. Founded in 2019 and fully distributed, we are backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

As a Forward Deployed Engineer, you will 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, helping them onboard, driving long-term adoption, and providing expert technical guidance.

Key Responsibilities

• Onboarding: Lead and manage the onboarding process for new strategic customers, providing training and resources for long-term success.
• Technical Support: Diagnose and resolve issues across the platform, assisting with configuration, integration, and troubleshooting.
• Strategic Engagement: Conduct QBRs to review usage, success metrics, and identify opportunities for expansion.
• Trusted Advisor: Build strong relationships, providing best practices and recommendations based on specific business outcomes.
• Voice of the Customer: Relay feedback to product and engineering teams to improve the user experience.
• Cross-functional Collaboration: Work with sales, product, and support teams to ensure smooth handoffs and escalate critical issues.
• Documentation: Develop and maintain technical documentation, FAQs, and guides to facilitate self-service.

What We Are Looking For

• 6+ years in a technical role with at least 2 years of customer-facing experience (e.g., Solutions Engineer, Sr. Support Engineer).
• Experience working with enterprise customers in a consultative capacity.
• Strong understanding of networking, VPNs, and security principles.
• Proficiency with cloud infrastructure (AWS, GCP, Azure) and DevOps tools like Docker and Kubernetes.
• Excellent communication skills with the ability to explain complex technical concepts to diverse audiences.
• Analytical mindset with strong troubleshooting and organizational skills.

What We Offer

• Competitive total compensation package (base salary, equity, and variable commission).
• Comprehensive group benefits with no waiting period.
• Remote-first environment with support for home office setup and internet reimbursement.
• $1,500 USD annual professional development stipend.
• Employer-funded retirement contributions (matching up to 0.75% of eligible compensation).
• Generous paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing).
• Flexible paid time off and opportunities for in-person connection via company retreats and team off-sites.