Forward Deployed Engineer

About this role

Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! 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.

From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role 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 Team Lead, Customer Success Engineers.

Key Responsibilities Design and build novel solutions to complex customer challenges that fall outside Tailscale’s standard deployment patterns (e.g., prototyping custom integrations, tooling, and network architecture; using structured experimentation and testing to validate solutions for bespoke client uses) Turn one-off customer solutions into repeatable, reusable assets such as reference architectures, deployment frameworks, and tooling, that can be applied across the broader customer base.

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.