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Security Software Engineer

Tailscale Inc.

Job Overview

Location

Remote (Canada)

Job Type

Full-time

Full Job Description

📋 Description

• As a Security Software Engineer at Tailscale, you will play a critical role in strengthening the security and privacy of a product that enables secure, seamless connectivity across devices and networks worldwide. Your work will directly contribute to making the Internet safer and more reliable for users ranging from individual developers to large enterprises.
• Day to day, you will identify and implement security and privacy improvements across Tailscale’s codebase, conduct security audits of features, perform threat modeling, and collaborate with engineering teams to drive secure coding practices. At least half of your time will be spent writing software, ensuring your contributions are hands-on and impactful.
• Tailscale is a fully remote, fast-growing startup founded in 2019, backed by top-tier investors, and dedicated to rebuilding the Internet with a focus on simplicity, security, and usability. The company fosters a culture of trust, transparency, and technical excellence, with teams distributed across Canada, the U.S., and the U.K.
• In this role, you will deepen your expertise in application security, cryptography, and secure software development while influencing the security posture of a widely used product. You’ll have the opportunity to grow as a technical leader, shape security best practices, and work on meaningful challenges at the intersection of networking, privacy, and software engineering.

🎯 Requirements

• Proficiency in at least one programming language (Tailscale uses Go)
• Proficiency developing for at least one application platform (e.g., iOS, Android, web, Windows, macOS, Linux)
• Prior experience in a safety-related technical role such as application security, penetration testing, threat modeling, or digital forensics and incident response
• Deep understanding of web application vulnerabilities (e.g., OWASP Top 10), client-side security, and common API security flaws
• Knowledge of cryptographic primitives and protocols and common networking protocols
• Ability to give and receive constructive feedback, work independently and collaboratively, and adapt to a dynamic startup environment

🏖️ Benefits

• Competitive total compensation including base salary, equity, and variable commission (for quota-based roles)
• Comprehensive group benefits with no waiting period (health, vision, dental, and more)
• $1,500 USD annual professional development stipend plus mentorship and coaching opportunities
• Remote-first work culture with flexibility to work from anywhere with Wi-Fi
• Annual company retreat, team off-sites, and support for in-person collaboration across Canada, the U.S., and the U.K.
• Build-your-own home office setup: company-owned laptop (Mac or PC), monthly internet reimbursement, and $1,000 USD for workstation customization

Skills & Technologies

Linux

iOS

Android

Remote

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Tailscale Inc.

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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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