Forward Deployed Engineer

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. Founded in 2019 and fully distributed, backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

As a Forward Deployed Engineer, 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. The role will report directly to the Team Lead, Customer Success Engineers.

• 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.
• 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.
• 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.
• Develop and maintain a repository of technical documentation, FAQs, and guides to help customers self-serve.

• 6+ Years in a 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.
• Strong written and verbal communication skills.
• Analytical mindset and troubleshooting skills.
• A passion for delivering excellent customer service.
• Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track.
• A collaborative mindset and ability to work cross-functionally.

US Pay Range (OTE): $150,000—$250,000 USD. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. Benefits include: health, vision, dental coverage; employer-funded retirement contributions with dollar-for-dollar match up to 0.75% of eligible compensation; flexible paid time off; $1500 USD annually for professional development; home office setup with $500 USD and monthly internet reimbursement; paid parental leave (20 weeks for birthing parents, 16 weeks for non-birthing parents); annual company retreat and team off-sites.

Apply via the Greenhouse job posting.