Customer Success Engineer Remote Work (United States)

Job Title: Founding Customer Success Engineer

Company: Tailscale

Location: Fully Remote

Salary Range: $200,000 - $250,000 USD

About Tailscale:
Tailscale is redefining the Internet with software that makes it easy to securely connect people and their devices, no matter where they are. From hobbyists to multinational corporations, Tailscale empowers teams of all sizes to protect their networks, share internal tools, and more.

Founded in 2019 and backed by Accel, CRV, Insight, Heavybit, and Uncork Capital, we?re a fully distributed team building a safer, more sensible Internet.

Role Overview:
As the Founding Customer Success Engineer (CSE) at Tailscale, you?ll play a pivotal role in bridging technical solutions with customer needs. You?ll help strategic customers onboard, adopt, and succeed with Tailscale?s products. Acting as a trusted advisor, you?ll manage technical support, drive customer engagement, and collaborate internally to ensure an exceptional customer experience.

Key Responsibilities:

Lead onboarding processes for strategic customers, ensuring successful adoption.
Provide expert technical support, assisting with configuration, troubleshooting, and integrations.
Conduct quarterly business reviews (QBRs) to discuss metrics, usage, and future goals.
Build and maintain strong relationships with customers, offering tailored best practices and recommendations.
Collaborate cross-functionally to relay customer feedback and improve the product experience.
Develop technical documentation, FAQs, and guides to empower customers.

What We?re Looking For:

Experience: 6+ years in technical roles, with at least 2 years in customer-facing positions (e.g., Solutions Engineer, Sr. Support Engineer).
Domain Knowledge: Strong understanding of networking, VPNs, and security principles. Experience with cloud infrastructure (AWS, GCP, Azure), Docker, Kubernetes, and DevOps tools.
Communication Skills: Ability to explain complex technical concepts to diverse audiences. Strong verbal and written communication skills are essential.
Problem-Solving: Analytical mindset with excellent troubleshooting abilities.
Customer Focus: Passion for delivering exceptional customer experiences and fostering long-term relationships.
Collaboration: Ability to work cross-functionally with product, engineering, and sales teams.
Preferred Skills: Familiarity with Scrum/Agile frameworks, experience supporting US customers, and knowledge of enterprise software solutions.

What We Offer:

Compensation: Competitive base salary, equity incentive plan, and performance-based commissions.
Comprehensive Benefits: Health, vision, dental coverage, and more from day one.
Work Flexibility: Fully remote work with access to coworking spaces and annual company retreats.
Professional Growth: $1,500 annually for development, mentorship opportunities, and internal promotions.
Generous PTO: Flexible paid time off program (encouraged 4-6 weeks annually).
Parental Leave: Up to 26 weeks of top-up parental leave.
Home Office Setup: Choose your laptop (Mac or PC), monthly internet reimbursement, and $1,000 to customize your workstation.

Why Join Tailscale?
At Tailscale, we?re building the future of the Internet while fostering an inclusive, flexible work environment. Join our global team of innovators and help shape a safer, smarter Internet for everyone.

How to Apply:
Ready to make an impact? Submit your application today and take the first step toward becoming part of our forward-thinking, collaborative team.