×
Register Here to Apply for Jobs or Post Jobs. X

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
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…
Note that applications are not being accepted from your jurisdiction for this job currently via this jobsite. Candidate preferences are the decision of the Employer or Recruiting Agent, and are controlled by them alone.
To Search, View & Apply for jobs on this site that accept applications from your location or country, tap here to make a Search:
 
 
 
Search for further Jobs Here:
(Try combinations for better Results! Or enter less keywords for broader Results)
Location
Increase/decrease your Search Radius (miles)

Job Posting Language
Employment Category
Education (minimum level)
Filters
Education Level
Experience Level (years)
Posted in last:
Salary