Customer Success Engineer

Summary

Join Tailscale as our founding Customer Success Engineer and 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. This role requires a combination of technical proficiency, problem-solving skills, and an empathetic customer-centric approach. You will report directly to the VP of Customer Experience and will be responsible for leading onboarding, providing technical support, conducting QBRs, building customer relationships, and serving as the voice of the customer internally. The role demands strong technical skills, excellent communication, and the ability to manage multiple accounts effectively. Tailscale offers a competitive compensation package and comprehensive benefits.

Requirements

• 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, 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

Responsibilities

• 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, escalate 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

Benefits

• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles)
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• All-remote with the opportunity to work from anywhere —enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you)
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! We encourage all Tailscalars to take 4-6 weeks of vacation annually
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks