Product Security Engineer - Tailscale

About Tailscale

Tailscale is building the new Internet by providing software that securely interconnects people and their devices, regardless of location. Our solution is used by individuals and large corporations alike to protect networks and share access to internal tools. Founded in 2019 and operating as a fully distributed company, we are backed by leading venture capital firms.

Job Description

We are seeking a talented Software Engineer specializing in security and privacy to join our growing product security team. You will play a key role in advancing Tailscale's product security and privacy features, ensuring our platform remains safe and robust as we scale. Success in this role requires agility, strong collaboration skills with highly technical teams, and comfort working asynchronously.

Key Responsibilities

• Enhance the security and privacy of Tailscale by identifying and implementing security/privacy features, bug fixes, and defense-in-depth measures across the codebase.
• Conduct security audits of Tailscale features, identify weaknesses, propose mitigations, and drive them to resolution.
• Support engineering decisions through threat modeling and security analysis.
• Spend at least 50% of your time writing software, focusing on implementation rather than purely operational or governance tasks.

What We Are Looking For

Technical Skills

• Proficiency in at least one programming language (Go is used at Tailscale).
• 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 or application platform security
• Penetration testing
• Threat modeling and prioritization
• User experience design or research
• Digital forensics and incident response
• Deep understanding of web application vulnerabilities (e.g., OWASP Top 10), client-side security, and common API security flaws.
• Ability to collaborate with engineering teams to promote secure coding practices and provide security guidance and training.
• Knowledge of cryptographic primitives and protocols.
• Knowledge of common networking protocols.

Team Fit

• Ability to provide and receive constructive feedback.
• Capacity for both independent work and collaboration.
• Flexibility to adapt to the dynamic nature of a startup.
• A risk-based approach to building security controls, balancing expertise with practical, usable solutions.

Compensation & Benefits

• CAN Pay Range: $218,420 - $302,840 CAD
• Competitive total compensation package including base salary, equity, and benefits.
• Comprehensive group benefits with no waiting period (health, vision, dental).
• Remote-first company with flexibility and options for co-working spaces.
• Support for personal and professional development ($1500 USD annually).
• Generous parental leave program.
• Home office setup support ($1000 USD for workstation customization, company-provided laptop, internet reimbursement).
• Inclusive and flexible work environment.
• Opportunities for in-person connection through retreats and off-sites.
• Flexible, paid time off.