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Sales Lead - Canada

Alan

Alan

Sales & Business Development
Toronto, ON, Canada
Posted on Dec 16, 2025

Location

Toronto, ON, Canada

Employment Type

Full time

Location Type

On-site

Department

Acquisition

🚀 Your mission

For our Canada growth, we're looking for a Sales Lead (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 🇨🇦

  • 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, sponsorships 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.

⭐️ Eligibility criteria ⭐️

  • 8+ years in Sales

  • 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

  • Ownership: you’re hands on even when leading a crew – you lead by example but also create a strong structure

  • Builder: opening new markets or verticals excites you. Writing the playbook is more exciting to you than reading one.

  • Ownership: you don’t sit back and wait, you go out and create value through action

  • Communication: love written communication & sweat the details

  • Initiative: you are OK to build your own decks, 1-pagers, and content. You don’t need a 100-person sales team to make an impact from Day 1

  • Outcomes focused: no-ego doer & scrappy; you want to put your name on something meaningful in healthcare.

  • Thrive In-Person: when you’re not out with customers, we’re in office 5-days-per week