Strategy and Operations - Canada 🇨🇦 at Alan (Toronto, Canada)Strategy and Operations - Canada 🇨🇦

Health can’t wait. Not for symptoms to get worse. Not for a six‑month appointment. Not for a system to catch up. But that’s exactly how healthcare works today. You wait, until you can’t. Alan exists to end the wait. Health is a universal right, and we believe this right can only become real when it’s coupled with prevention. We need to stop treating health as something we repair and start treating it as something we build, every day. It’s not solely a question of willpower. It’s the healthcare system itself that needs to work for everyone, in a sustainable way. So we are building the new standard in prevention insurance. Alan is the first company that integrates insurance, prevention, and care into a single, acclaimed user experience. We are on an incredible journey to build a global leading company, with a unique culture. We already partner with 40K+ companies of all sizes, serving more than 1M+ members, and have reached €800M+ in ARR. Prevention as the new norm. That's what we're building with our team of 1000+ people. If it speaks to you: we're hiring across France, Spain, Belgium, and Canada. And beyond. ⭐️ The role You are the Canada GM's right hand. Not a support role: you own strategic initiatives end to end and are accountable for the outcome, not the slide deck.

This seat owns Strategy & Operations: the operating cadence, the operational build-out of a young insurer, and the regulatory execution that lets Alan operate province by province. You'll work daily with Canada's leadership and draw on the global Alan platform, including GM Associate peers in five countries.

🎯 Your mission Your core missions:

• Own Canada's operating cadence. MBRs, QBRs and the Canada Weekly pulse: turn inputs from nine communities into the narrative and decisions leadership acts on.
• Build new operations from scratch. New products, processes and reporting (e.g. virtual care expansion, pipeline and quota dashboards): define, launch, hand over.
• Own insurance & regulatory execution. Provincial licensing, other filings and clinical licensing for new provinces. These are commitments to regulators, not internal deadlines.
• Build your own AI tooling. Automate your own job with agents that do real work (e.g. automate weekly reporting, hiring pipeline digests, regulatory monitoring).
• Lead through influence and clarity. Write the docs that let others decide without you (e.g. the business case for a 2nd GM Associate, summer interns, staffing BC expansion) and keep Canada and Europe aligned.
• Step in where the business needs you. Cover leaders when they're out and pick up adjacent work (e.g. running hiring loops, managing summer interns, running the Toronto office).

💪 You may be a great fit if you have

• 1-4 years in consulting, banking, M&A, a high-growth startup, or as a founder.
• Strategic thinking with hands-on execution. You set direction, then build the model, fix the process and file the renewal on time.
• Exceptional written communication. You can turn a messy quarter into three paragraphs a board will act on.
• A real command of AI tools, used to extend your output, not replace your thinking. We'll ask you to show us.
• Strong organisation, time management and autonomy. You run projects start to finish with precision and little oversight.
• An entrepreneurial mindset. Comfortable with ambiguity, you take ownership beyond your remit.
• Mission-driven. You want to transform healthcare in Canada.
• Based in Toronto and in our office 5 days a week.
• As a plus: French, international team experience, or a background in scale-ups, healthcare or insurance.

Earlier in your career? Apply anyway. If you've shown real ownership (a company you started, a team you carried, work that shipped), we'd rather see your application than screen you out on a number.

🚀 What this role leads to The role is built on a minimum two-year horizon: long enough to compound real impact, and the springboard to leading a community or function. You'll have a buddy and a coach from day one.

🙌 Perks & benefits

• Competitive salary + equity - B0-C1, ($96-140k CAD) see the salary & equity grid.
• Monthly TTC pass, and a generous employer matching program for your RRSP.
• Excellent health coverage through Alan's own app.
• Office at King & Yonge in the financial district, with free lunch.
• Flexible leave, no pre-approval needed.
• Personal growth through coaching. Every Alaner has a dedicated coach from day one. Read about our coaching culture.