Role overview

Alan is building a new standard in prevention-focused insurance, integrating insurance, prevention, and care into a unified experience. As General Manager Associate in Canada, you will serve as the strategic right hand to the Canada General Manager, owning cross-functional strategic initiatives from conception to execution. You’ll be instrumental in establishing Alan’s operational foundation across Canadian provinces while working with a global leadership platform.

Key responsibilities

Establish and maintain Canada’s operating cadence, including monthly business reviews, quarterly business reviews, and weekly leadership pulses that synthesize input from nine business communities into actionable decisions.
Build new operational capabilities from the ground up, including new products, processes, and reporting systems such as virtual care expansion and pipeline management dashboards.
Lead insurance and regulatory execution across provinces, managing provincial licensing, regulatory filings, and clinical licensing requirements that represent formal commitments to regulatory bodies.
Develop and implement AI automation tools to enhance your own productivity, such as automating weekly reporting, hiring pipeline digests, and regulatory monitoring systems.
Create strategic documentation and business cases that enable decision-making across the organization, such as expansion plans and staffing proposals.
Provide operational coverage for senior leaders during absences and manage adjacent responsibilities including hiring processes, intern management, and office operations.
Maintain alignment between Canadian operations and the broader European organization while collaborating with General Manager Associate peers across five countries.

Requirements

Between one and four years of professional experience in consulting, banking, mergers and acquisitions, high-growth startups, or as a founder.
Demonstrated ability to combine strategic thinking with hands-on execution, moving from direction-setting to implementing models, refining processes, and managing administrative tasks.
Exceptional written communication skills, with the ability to distill complex situations into clear, concise summaries suitable for senior decision-making.
Proficiency with artificial intelligence tools, using them to extend your capabilities and productivity rather than outsource your thinking.
Strong organizational abilities, time management discipline, and capacity to work autonomously on projects from start to finish with minimal oversight.
Entrepreneurial mindset with comfort navigating ambiguity and willingness to take ownership beyond formal role boundaries.
Commitment to healthcare transformation and the mission of prevention-focused care.

What makes this role worth considering

Based in Toronto’s financial district at King and Yonge, you’ll be part of a global organization of over 1,000 people serving more than 1 million members. The role is designed with a minimum two-year horizon to build compounding impact, positioning you for advancement into community or functional leadership. You’ll receive dedicated coaching from day one and work within a culture that emphasizes personal growth and long-term development.