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Head of Sales

Job in Toronto, Ontario, C6A, Canada
Listing for: Alan
Full Time position
Listed on 2026-01-01
Job specializations:
  • Management
    Business Management, Business Analyst
Salary/Wage Range or Industry Benchmark: 150000 - 200000 CAD Yearly CAD 150000.00 200000.00 YEAR
Job Description & How to Apply Below

Who we are

You. Better. With Alan.

Alan's vision is to make prevention the new norm of care for all.
Our mission is to help people live in good health to 100 while helping employers feel proud, turning health benefits from a cost centre into their most valuable investment.

We're building a vertically integrated health partner that seamlessly unites insurance and smart healthcare delivery into one system.

By connecting all aspects of care - private, public, and direct to consumer
- we create the most member-centric healthcare experience. Through deep engagement, we empower everyone to overcome day-to-day health obstacles and live healthier lives.

We partner with 35K+ companies of all sizes, serving more than 950K+ members
, and have reached 680M+ in ARR.

Our team of 700+ people (still growing) operates across France , Spain , Belgium , and Canada .

How we do it ?

People joining Alan are always surprised and delighted by our innovative working method. We have a set of cultural values that guide our approach to work, such as:

What drives us - We're obsessed with helping members live healthier
  • Mission is the Boss
    : long-term thinking, mission above all else
  • Member & customer-led
    : obsessed with solving problems and delighting users
How we build excellence - We hire the best and empower them to succeed
  • Champions of excellence
    : extremely high standards and talent density
  • Distributed ownership
    : everyone owns their decisions and results
  • Radically transparent
    : all information accessible, written-first, async decisions
How we grow together - We improve through honest feedback and bold thinking
  • Optimistic alchemy
    : optimists who collaborate with genuine care
  • Empathetic challengers
    : direct, caring feedback to help each other grow
  • Bold contrarians
    : think differently, try new approaches
⚡ How we move fast — We fight complexity and focus on what matters
  • Disciplined execution
    : decisive action with compounding focus
  • Fight for simplicity
    : high-impact processes, smart frugality
Your mission

For our Canada growth, we're looking for a Head of Sales to build our upcoming Sales team across Canada!

  • This will be a game-changer for Alan as we move from being Toronto focused to expanding across a country of 41M people and CAD $64B+ – with the industry growing 7.5% vs. 2023!
  • You’ll be responsible for a Sales team of ~9 individuals (and rising) completing full sales cycles from prospection to onboarding;
  • This role will include setting the structure in line with the global cadence as we organise the first sales team in Canada;
  • You’ll be bringing the incredible Alan experience to Canada and have the opportunity to become a lead within the team;
  • Part of our mission is to show how Alan a 100% digital solution can help close critical gaps in the health system - Alan is the first insurer since the 1950s for Canadians;
  • We’re looking for someone to create, innovate and execute our go-to-market strategy;
  • Think of creative ideas that push us to achieve our EOY goals - through outbound, hosting community events, attending conferences, writing content online & any other channel that increases your empathy and understanding of the market’s challenges. Be creative, ambitious and we're here to help you grow;
  • You’ll work closely with our Growth / Marketing Lead to build relevant campaigns, events, sponsor ships and other initiatives - nothing is off the table for us to build the most successful team;
  • You won’t wait for anything leads/strategies/ideas - you’ll go create them through action.

We are aiming to hire within the D-F level range of compensation that includes salary, equity, amazing benefits & perks.

Please note that this role compensation model is made of a base salary + Equity (learn more) and will require you to get your LLQP license for all of Canada.

⭐ Is it you we’re looking for?
  • At least 8 years of Sales experience
  • At least 2 years of team lead experience
  • Sustained great performance in your current role
Nice to have
  • You’re super ambitious and willing to be scrappy & autonomous in launching a new market segment
  • You have experience coaching others and supporting their growth
  • You want to open a new market segment in a bilingual country (French is a bonus)
Your profile
  • Ow…
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