About League League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health.

League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.

Position Summary: League is looking for a Principal Security Engineer to serve as the senior technical leader within our Security Engineering organization. This role entails designing and driving security architecture across a rapidly AI-native engineering environment, in close partnership with Product Security and Security Operations. Product Security owns day-to-day security reviews and vulnerability management; Security Operations owns detection and response.

This role sets technical direction and design for the organization's most complex and novel systems, including AI/agentic architectures, and serves as the connective tissue that makes the broader security function more effective. 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.

Requirements

into engineering practice 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 Able to strategically influence across peer functions and ensure alignment to overall Security objectives Track record of influencing engineering decisions and behaviour without formal authority over the teams involved CANADA APPLICANTS ONLY: The Canada-specific

Compensation

range below for this full-time position is exclusive