Job Overview
Location
Remote (Canada)
Job Type
Full-time
Category
Cybersecurity
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As a Security Infrastructure Engineer at Tailscale, you will play a critical role in strengthening the security posture of a company building the new Internet by making secure device interconnection simple and safe for users worldwide.
- • Your day-to-day responsibilities will include designing and implementing security controls across cloud platforms, OS, Kubernetes, networks, and CI/CD pipelines; auditing infrastructure for vulnerabilities; improving security properties through threat modeling and defense-in-depth strategies; and spending 25-50% of your time writing software to enhance security features in Tailscale’s codebase.
- • You will join a fully distributed, mission-driven team backed by top-tier investors, working alongside highly technical engineers to protect networks and enable secure access to internal tools for users ranging from hobbyists to multinational enterprises.
- • In this role, you will deepen your expertise in cloud and infrastructure security, contribute to meaningful security improvements in a widely used product, and grow as a technical leader by shaping security strategy and incident response practices across a modern, security-first organization.
🎯 Requirements
- • Expertise in securing cloud platforms (e.g., AWS), particularly multi-cloud environments and cloud-agnostic system design
- • Proficiency in at least one programming language (Tailscale uses Go) and Infrastructure as Code tools such as Terraform or Ansible
- • Prior experience in infrastructure security, security operations, threat modeling, or digital forensics and incident response
- • Familiarity with container security, orchestration security, authentication/authorization, and internet/web security fundamentals (WAF, TLS, PKI, DNS)
- • Knowledge of operating system internals, networking protocols, and ability to act as a Subject Matter Expert during security incidents
🏖️ Benefits
- • Competitive total compensation including base salary, equity, and variable commission (for quota-based roles)
- • Comprehensive group health, vision, and dental benefits with no waiting period
- • $1,500 USD annual professional development stipend, plus mentorship and internal promotion opportunities
- • Remote-first work environment with flexible hours, home office setup support ($1,000 USD stipend + monthly internet reimbursement + company laptop)
- • Generous parental leave top-ups for up to 26 weeks from day one, paid time off, and opportunities for in-person connection via company retreats and team off-sites
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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