Job Overview
Location
Remote (Canada)
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 critical bridge between technical capabilities and the strategic needs of enterprise customers, ensuring their long-term success and adoption of Tailscale’s secure networking platform.
- • Day to day, you will lead customer onboarding, provide technical support and troubleshooting, conduct quarterly business reviews, act as a trusted advisor, relay customer feedback to product and engineering teams, and collaborate cross-functionally with sales, support, and engineering to drive customer outcomes.
- • Tailscale is building the new Internet by making secure device interconnection simple and safe for users ranging from hobbyists to multinational corporations. Founded in 2019 and fully distributed, the company is backed by top-tier investors and operates with a remote-first culture across Canada, the U.S., and the U.K.
- • In this role, you will develop deep expertise in enterprise networking and cloud technologies, strengthen your consultative and communication skills, influence product direction through customer insights, and grow into a trusted technical advisor shaping how organizations adopt zero-trust networking at scale.
🎯 Requirements
- • 6+ years in a technical role with minimum 2 years of customer-facing experience (e.g., Solutions Engineer, Sr. Support Engineer)
- • 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 DevOps technologies
- • Ability to clearly explain complex technical concepts to diverse audiences, from non-technical stakeholders to engineers
- • Analytical mindset and troubleshooting skills with methodical approach to resolving complex technical issues
- • Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track with strong time management and organizational skills
🏖️ Benefits
- • Inclusive, flexible remote-first environment where you can be your authentic self
- • Competitive total compensation package including base salary, equity, and variable commission (OTE: $201,000–$335,000 CAD)
- • Comprehensive group benefits with no waiting period (health, vision, dental, and more)
- • $1,500 USD annual professional development stipend, plus mentorship and coaching opportunities
- • Paid time off and healthy work-life integration with flexible PTO policy
- • Build-your-own home office setup: company-owned laptop (Mac or PC), monthly internet reimbursement, and $1,000 USD for workstation customization
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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