About TailscaleTailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be.

About the Role
We’re seeking a talented software engineer, specializing in security and privacy, to help grow our product security team. The abilities to think on your feet, collaborate with highly technical teams, and be comfortable working asynchronously are essential. Improve the security properties of Tailscale by identifying opportunities for security and privacy features, bug fixes, and defense-in-depth, and implementing them across our codebase. Audit Tailscale features for technical security weaknesses, identifying mitigations or solutions, and driving them towards resolution. Support engineering decisions with threat modeling and security analysis and expertise. You will spend at least 50% of your time in this role writing software vs purely operational or governance security responsibilities. Proficiency developing in at least one programming language (Tailscale uses Go) G. iOS, Android, web, Windows, macOS, Linux) Prior experience in a safety-related technical role, e.application security or application platform security penetration testing digital forensics and incident response Deep understanding of web application vulnerabilities (e.
OWASP Top 10), client-side security,



and common API security flaws Collaborate with engineering teams to promote secure coding practices and provide targeted security guidance and training Knowledge of common networking protocols Take a risk-based approach to building security controls, balancing your security expertise and broad technical skillsets with practical, usable solutions Tailscale's compensation package includes base salary, equity, and comprehensive benefits. 218,420
- $302,840 CAD An inclusive, versatile environment where you can be your authentic self. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). Take advantage of coverage for health, vision, dental, and more for you and your family Remote first company —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in‑person social events, and leverage our corporate co‑working program to visit WeWork (or other similar spaces near you). Some roles require in‑office collaboration depending on team needs, which will be clearly noted in the

job description
. Employer‑funded retirement contributions. Tailscale will match your retirement contributions dollar‑for‑dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. Attend our annual company retreat, participate in team off‑sites, and collaborate in person with teammates across Canada,



the United States, the United Kingdom, and Singapore. We support intentional in‑person connection through team travel and distributed collaboration. Support for your personal and professional development. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world A build‑your‑own home office setup. Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top‑ups (20 weeks for birthing parents, 16 weeks for non‑birthing parents). If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI‑assisted tools to help screen and assess candidates. We are not currently able to provide relocation support for this role. We are not currently able to provide immigration support for this role. As set forth in Tailscale’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law. S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service‑connected disability. An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.
An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.

📌 Security Software Engineering (Winnipeg)
🏢 Tailscale
📍 Winnipeg