Customer Success Engineer

About Tailscale

Tailscale is building the new Internet, making it easy and secure to interconnect people and their devices, regardless of location. Our software is trusted by teams of all sizes, from hobbyists to multinational corporations, to protect their networks and provide secure access to internal tools. Founded in 2019 and operating as a fully distributed company, we are backed by leading venture capital firms and are committed to creating an internet that is simple, sensible, and safe.

Job Description

As a Customer Success Engineer (CSE) at Tailscale, you will serve as the critical link between our advanced technical capabilities and the evolving needs of our most strategic customers. Your primary focus will be ensuring customer success with Tailscale's products, guiding them through onboarding, fostering long-term adoption, and providing expert technical guidance throughout their journey. This role demands a blend of technical expertise, adept problem-solving skills, and a deeply empathetic, customer-centric approach to empower our clients fully.

Key Responsibilities

• Lead and manage the onboarding process for new strategic customers, ensuring rapid understanding and adoption of Tailscale. Provide comprehensive training and resources to set customers up for sustained success.
• Deliver expert technical support to customers, diagnosing and resolving issues across the Tailscale platform. Assist with configuration, integration, and troubleshooting to ensure seamless 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 broader adoption.
• Cultivate strong, trust-based relationships with customers, acting as a valued advisor. Help customers optimize their use of Tailscale by identifying best practices and providing tailored recommendations based on their specific use cases and desired business outcomes.
• Serve as the internal voice of the customer, relaying crucial 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 smooth handoffs, escalate critical issues effectively, and champion customer success across the organization.
• Develop and maintain a robust repository of technical documentation, FAQs, and guides to facilitate customer self-service. Share valuable insights and best practices with both customers and internal teams.

What We Are Looking For

• 6+ years of experience in a technical role, with a minimum of 2 years in a customer-facing capacity (e.g., Solutions Engineer/Architect, Sr. Support Engineer).
• Proven experience working with enterprise customers in a consultative manner.
• A strong understanding of networking concepts, VPNs, and security principles. Experience with cloud infrastructure (AWS, GCP, Azure) and tools like Docker, Kubernetes, and other DevOps technologies is highly desirable.
• Prior experience in a customer-facing technical role, such as Technical Support Engineer, Solutions Engineer/Architect, or Customer Success Engineer at a SaaS company.
• Exceptional ability to clearly explain complex technical concepts to a diverse audience, ranging from non-technical stakeholders to engineers. Strong written and verbal communication skills are essential.
• An analytical mindset and proven troubleshooting skills, with the ability to approach complex technical issues methodically and critically.
• A genuine passion for delivering outstanding customer service and a strong focus on building enduring customer relationships.
• Ability to effectively manage multiple customer accounts, prioritize tasks, and keep projects on track. Excellent time management and organizational skills are key.
• A collaborative mindset and the ability to work effectively cross-functionally with product, sales, and engineering teams to achieve shared customer success goals.

Compensation & Benefits

• Tailscale offers a competitive total compensation package, including base salary, equity, and comprehensive benefits.
• The CAN Pay Range (OTE) is $201,000 - $335,000 CAD, reflecting target On-Target Earnings (OTE), inclusive of base salary and variable compensation tied to quarterly sales targets.
• Comprehensive group benefits with no waiting period for health, vision, dental, etc., for you and your family.
• Remote-first company culture with flexibility in work location and opportunities for virtual and in-person social events.
• Corporate co-working program access.
• Opportunities for in-person connection through annual company retreats and team off-sites.
• $1500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off program.
• Build-your-own home office setup: company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1000 USD for workstation customization.
• Generous parental leave program with top-ups for up to 26 weeks.

About the Culture

• An inclusive, flexible environment where authenticity is valued.
• A commitment to diverse voices and backgrounds.
• A competitive total compensation package including base salary, equity, and variable commission (for quota-based roles).
• Support for personal and professional growth.
• We strive to maintain fair and equitable compensation practices.

Tailscale is committed to an accessible and inclusive hiring process. Please contact your recruiter if you require accommodation. Our hiring process utilizes AI-assisted tools, but all hiring decisions are made by people. Please beware of fraudulent communications; legitimate emails will only come from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io addresses.