Customer Success Engineer

Tailscale is building the new Internet 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.

As Customer Success Engineer (CSE) 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.

• 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, elevate 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.

• 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 Dev Ops 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

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package.
• Comprehensive group benefits with no waiting period.
• Remote first company—most of our teams work fully remotely.
• Connect with other Tail scalars in person with annual retreats, off‑sites, and distributed collaboration.
• Support for your personal and professional development.
• Paid time off and a healthy work‑life integration.
• A build‑your‑own home office setup.
• Generous parental leave program from your first day.

As set forth in Tailscale’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law.

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