Who you are
- 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 the job involves
- 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
- 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 recent 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)
- 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
Benefits
- Fair rewards: Generous equity packages complement your base salary, for permanent contracts only
- Flexible Office: Amazing office space at our HQ, sponsored co-working hubs or a full-remote experience with home office equipment sponsorship, we want you to live where you’re the happiest
- All the tools you need: Top-of-the-range equipment: Macbook Pro, keyboard, laptop stand, monitor, and Bose noise-cancelling headphones
- Flexible vacation policy and flexible working hours: Organise your time as you wish
- Delightful healthcare insurance: Extremely comprehensive health insurance - 100% of the contribution covered by Alan for you and your family, for permanent contracts only
- Transport: Country-specific commuter benefits
- Learning & Training opportunities: A highly flexible Training policy free books and a budget to attend and speak at conferences if the opportunity arises
- Parental leave: Extended parental leave for all new parents, for permanent contracts only
📌 Strategy and Operations (Toronto)
🏢 Alan
📍 Toronto