Job Overview
Location
Remote (United States)
Job Type
Full-time
Category
Customer Success
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As a Customer Success Engineer at Tailscale, you will serve as the technical bridge between the company’s networking platform and its most strategic customers, ensuring they achieve their goals through expert guidance, onboarding, and ongoing support.
- • Day to day, you will lead customer onboarding, provide technical troubleshooting and configuration assistance, conduct Quarterly Business Reviews (QBRs), build trusted advisor relationships, and act as the voice of the customer to internal product and engineering teams.
- • Tailscale is a fully remote, distributed company founded in 2019 that is building a simpler, safer way to interconnect people and devices across networks, backed by top-tier investors and used by organizations of all sizes worldwide.
- • In this role, you will deepen your expertise in enterprise networking, cloud infrastructure, and customer advocacy while developing strategic consultative skills and influencing product direction through real-world customer feedback.
🎯 Requirements
- • 6+ years in a technical role with at least 2 years of customer-facing experience (e.g., Solutions Engineer, Support Engineer, or similar)
- • Strong understanding of networking, VPNs, and security principles, plus experience with cloud platforms (AWS, GCP, Azure) and DevOps tools like Docker and Kubernetes
- • Ability to clearly explain complex technical concepts to both technical and non-technical audiences, with strong written and verbal communication skills
🏖️ Benefits
- • Competitive total compensation package including base salary, equity, and variable commission (OTE: $150,000–$250,000 USD)
- • Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for employees and families
- • $1,500 USD annual professional development stipend, plus mentorship, coaching, and internal promotion opportunities
- • Remote-first work environment with flexible hours, home office setup support (company laptop, internet reimbursement, $1,000 stipend), and access to WeWork spaces
- • Generous parental leave program offering up to 26 weeks of top-up leave from day one
Skills & Technologies
About Tailscale Inc.
Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.
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