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General Manager Associate - Canada 🇨🇦

Alan - Toronto, ON, Canada - In-office - posted 2026-09-29

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Alan is a prevention-focused insurance company integrating insurance, prevention, and care into a single user experience. The company serves 1M+ members across 40K+ partner companies and has reached €800M+ in ARR, operating across France, Spain, Belgium, and Canada with 1000+ employees. As General Manager Associate for Canada, you will be the Canada GM's strategic right hand, owning Strategy & Operations end-to-end with accountability for outcomes. This is not a support role but a seat with real ownership of strategic initiatives. Key responsibilities: - Own Canada's operating cadence: manage MBRs, QBRs, and weekly pulse meetings, synthesizing inputs from nine communities into actionable narratives and decisions for leadership. - Build new operations from scratch: design and launch new products, processes, and reporting systems (e.g., virtual care expansion, pipeline dashboards); define, execute, and hand over to operational teams. - Own insurance and regulatory execution: manage provincial licensing, regulatory filings, and clinical licensing for new provinces—these are commitments to regulators, not internal deadlines. - Build AI tooling: automate your own work using AI agents for real operational tasks (e.g., weekly reporting automation, hiring pipeline digests, regulatory monitoring). - Lead through influence and clarity: write documentation that enables others to make decisions independently; keep Canada and European operations aligned. - Step in where needed: cover for leaders during absences, run hiring loops, manage interns, and support adjacent business needs like office operations. You will work daily with Canada's leadership and leverage the global Alan platform, collaborating with GM Associate peers across five countries. The role is built on a minimum two-year horizon, designed to compound real impact and serve as a springboard to leading a community or function. You'll have a dedicated buddy and coach from day one. Requirements: - 1–4 years of experience in consulting, banking, M&A, high-growth startups, or as a founder. - Strategic thinking paired with hands-on execution: ability to set direction and then build models, fix processes, and deliver on time. - Exceptional written communication: can distill complex quarters into concise, board-ready narratives. - Real command of AI tools to extend your output and thinking; you'll be asked to demonstrate proficiency. - Strong organization, time management, and autonomy; ability to run projects start-to-finish with precision and minimal oversight. - Entrepreneurial mindset: comfortable with ambiguity and taking ownership beyond your formal remit. - Mission-driven: genuine desire to transform healthcare in Canada. - Based in Toronto and able to work in-office 5 days per week. - Plus factors: French language skills, international team experience, or background in scale-ups, healthcare, or insurance. Note: The posting explicitly welcomes earlier-career applicants who have demonstrated real ownership (e.g., companies started, teams led, shipped work).

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