Principal Security Engineer

Join League as a Principal Security Engineer, where you will be the senior technical leader within our Security Engineering organization. You will design and drive security architecture across a rapidly AI-native engineering environment, partnering closely with Product Security and Security Operations. Your role will involve setting technical direction and design for the organization's most complex systems, providing technical mentorship, and translating technical risk into business terms for leadership and compliance stakeholders. Enjoy flexible medical and dental plans, generous leaves, and a supportive work environment.

• Design and drive security architecture across a rapidly AI-native engineering environment, in close partnership with Product Security and Security Operations.
• Set technical direction and design for the organization's most complex and novel systems, including AI/agentic architectures, and serve as the connective tissue that makes the broader security function more effective.
• Provide technical mentorship to Security Software Engineering and to individuals within Product Security and Security Operations, raising technical capability across the broader security function.
• The right person for this role doesn't wait for a ticket. They show up in design conversations, ask the right question at the right moment, and leave engineering and security colleagues alike more capable than they found them - all while being a strategic cross-functional partner that people enjoy collaborating with
• Experience collaborating within a broader security organization (partnering with product/application security and security operations functions) rather than as a sole practitioner owning every function end-to-end
• Track record of influencing engineering decisions and behaviour without formal authority over the teams involved
• Experience operating in a regulated environment (HIPAA, HITRUST, SOC 2, PIPEDA, or equivalent), including translating compliance requirements into engineering practice
• 8+ years in security engineering, with demonstrated depth in at least two of: encryption/key management, IAM, cloud security architecture, application security
• Able to strategically influence across peer functions and ensure alignment to overall Security objectives
• Direct, hands-on experience securing AI-integrated systems including LLM applications, coding agents, or MCP-style tool integrations; not just familiarity with the concepts
• Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered
• If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you