Customer Success Engineer

Customer Success Engineer (CSE)

About Tailscale

Tailscale is building the new Internet by providing software that enables secure interconnection of people and their devices, regardless of location. Used by individuals and multinational corporations alike, Tailscale helps teams protect networks, share internal tools, and more. Founded in 2019 and operating as a fully distributed company, Tailscale is backed by leading venture capital firms including Accel, CRV, Insight, Heavybit, and Uncork Capital. We are committed to building a future for the Internet that is easy, sensible, and safe.

Job Description

As a Customer Success Engineer (CSE) at Tailscale, you will serve as the crucial link 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, guiding them through onboarding, driving long-term adoption, and providing expert technical guidance throughout their journey. This role requires a blend of technical proficiency, problem-solving acumen, and an empathetic, customer-centric approach to ensure customers are fully empowered to leverage Tailscale's capabilities. You will report directly to Zach Buchheit, Team Lead, Customer Success Engineers.

Key Responsibilities

• Lead and manage the onboarding process for new strategic customers, ensuring rapid understanding and adoption of Tailscale. Provide training and resources designed for long-term success.
• Offer expert technical support to customers, diagnosing and resolving issues across Tailscale's platform. Assist with configuration, integration, and troubleshooting to ensure smooth implementation.
• Conduct Quarterly Business Reviews (QBRs) with customers to review usage, success metrics, and future goals. Utilize these touchpoints to identify opportunities for deeper engagement and horizontal expansion.
• Build strong, trusted advisor relationships with customers. Help customers optimize their use of Tailscale by identifying best practices and providing recommendations tailored to 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 drive product improvements and enhance the overall customer experience.
• Collaborate closely with sales, product, engineering, and support teams to ensure seamless handoffs, escalate critical issues, and drive customer success across the organization.
• Develop and maintain a repository of technical documentation, FAQs, and guides to facilitate customer self-service. Share insights and best practices with both customers and internal teams.

What We Are Looking For

• 6+ years in a technical role, with a minimum of 2 years in a customer-facing capacity (e.g., Solutions Engineer/Architect, Senior Support Engineer, etc.).
• Experience working with enterprise customers in a consultative manner.
• A 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 diverse audiences, from non-technical stakeholders to engineers. Strong written and verbal communication skills are essential.
• An analytical mindset and adept troubleshooting skills, with the ability to think critically and methodically to resolve complex technical issues.
• A passion for delivering exceptional customer service and a strong focus on building long-term customer relationships.
• Proficiency in managing multiple customer accounts, prioritizing tasks, and keeping projects on track. Strong time management and organizational skills are key.
• A collaborative mindset and the ability to work cross-functionally with product, sales, and engineering teams to achieve customer success.

Compensation and Benefits

Tailscale offers a competitive compensation package including base salary, equity, and comprehensive benefits. The salary range displayed represents the target range for a new hire's base salary. Individual offers may vary based on experience and skillset.

US Pay Range (OTE - On Target Earnings): $150,000 - $250,000 USD (inclusive of base salary and variable compensation tied to quarterly sales targets)

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We value diverse voices and backgrounds and believe flexibility empowers our team to integrate work and life.
• A competitive total compensation package, including base salary, equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period for health, vision, dental, and more for you and your family.
• Remote-first company culture, with options for virtual and in-person social events, and a corporate co-working program.
• Opportunities for in-person connection through an annual company retreat, team off-sites, and collaborative travel.
• Support for personal and professional development, including $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off (PTO) program to support life events and personal needs.
• A personalized home office setup, including a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1000 USD for workstation customization.
• Generous parental leave program with top-ups available for up to 26 weeks from your first day.