Founding Account Executive - Canada

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 32,000+ companies of all sizes, serving 700k+ members, and have reached $750M+ in ARR.

Our team of 600 people (still growing) operates across France , Spain , Belgium , and we're launching Canada now!

How we do it ?

About

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

• Mission is the Boss: We have a mission-first focus with long-term thinking, where all employees act as owners seeking the company's success above all else.
• Member & Customer-led: We are obsessively focused on solving customer problems and creating delightful experiences while building trust.
• Excellence like Athletes: We maintain high standards and talent density, using the Keeper Test to ensure exceptional performance.
• Enlightened Despots: We combine distributed ownership with accountability, empowering decision-makers while maintaining responsibility.
• Radically Transparent: We make information accessible and written-first, promoting async communication while protecting sensitive data.
• Kind, Methodic Optimists: We collaborate genuinely without ego, support teammates, and maintain positive intent while assuming the best.
• Empathetic Challengers: We give direct feedback with empathy, praise strengths, and focus on growth through candid communication.
• Bold & Creative Contrarians: We think differently to achieve greatness, challenge expertise with first principles, and embrace calculated risks.
• Disciplined Executors: We focus on making good decisions quickly, maintain accountability, and break down problems into manageable pieces.
• Fight for Simplicity: We eliminate unnecessary processes, stay concise and articulate, and maintain smart frugality while solving problems pragmatically.
  
  

Your mission

As a Founding Account Executive in Canada, you will be at the heart of Alan's growth in Canada and best positioned to lead our team moving forward if you overachieve.

You will take our GM's outbound model that has built >$10M ARR in pipeline and build the processes & rigour around it to scale us nation-wide. We are currently building the GTM team around you, with Growth Marketing & CS planned for this year.

You must be willing to do the full sales cycle from prospection to onboarding & success. You’ll need to be scrappy, low-ego (there’s no work below us) and buy into our mission of improving the healthcare system in Canada.

You’ll need a builder mentality and have a passion for creating frameworks, strategies, decks & tools to get the job done.

You’ll need to help us identify new markets & verticals, adapt global playbooks to Canadian nuances and bring the voice of the customer into every conversation we have.

We also expect you to look at the big picture and help us grow and improve as a company. For that, you’ll have to be real team players even beyond your role. You’ll be expected to challenge us to improve our products, our methods and our strategy, and get involved in other projects and initiatives relevant to growing our customer base.

For this opportunity, we are aiming to hire within the C0-D level range of compensation that includes salary, equity, amazing benefits & perks.

Please note that this role does not include a commission component (shocking, we know) and will require you to get your LLQP license for all of Canada (including Quebec).

Your main responsibilities will include:

• Work directly with the Canada GM to achieve our ambitious targets in Canada
• Build, refine and extend our understandings of our buyer personas
• Create lead lists, prospect using cold emails & calls, hold demo calls and close deals with our target customers
• Manage and extend our CRM to ensure quality reporting & data standards
• Track, measure, and report on sales effectiveness; adjust strategies based on Canadian market dynamics
• Collaborate with Marketing and Product teams to maximize lead generation and product feedback for Canadian market
  
  

️ Who you are ️

You may be a great fit at Alan if you have/are:

• 3-5+ years of experience in B2B sales, preferably with a SaaS company, in challenging environments
• Experience selling to HR stakeholders at SMBs with 25-100 employees
• Strong empathy for customers and passion for personal development & growth
• Highly organized with exceptional follow-up skills
• Ability to create high-touch strategies adapted to each prospect
• Deep understanding of value drivers in health & insurance businesses
• Ability to manage influence through persuasion and negotiation
• Desire to learn fast, work in fast-paced environments and make an impact from day 1
• Super passionate about healthcare and benefiting the health experiences for Canadians
• Can both build strategic plans with a leadership team and do the work yourself!
• Think analytically and can communicate clearly in English with the team
  
  

Nice to have:

• Experience collaborating with internal teams (Strategy, Sales Ops, Marketing, Product, Success)
• Methods for challenging others to improve product and strategy constructively
• Based in (or willing to relocate to) Toronto
• Knowledge of French is a plus
  
  

Why joining us?

• Unique opportunity to contribute to the launch of a global healthcare player in Canada
• Provide a meaningful generational change to Canadians healthcare experiences
• Grow a business in a new country from 0-1
• Ability to own from the first few months as much of our >$10M+ ARR growing pipeline as you can take on
• Best balance of scrappy and thriving start-up environment while being part of a fluid global powerhouse
• The chance to develop into a leader and be part of the founding team in Canada
  
  

Perks & Benefits

• In office: amazing office space right in the heart of the financial district (King & Yonge) to work closely and collaboratively with your colleagues 4-5 days per week in-person!
• All the tools you need: Macbook Pro, keyboard, laptop stand, monitor, and Bose noise-canceling headphones.
• Flexible leave policy: we trust Alaners to take the holidays they need, and no pre-approval is required.
• Delightful healthcare insurance: great benefits through Alan’s Canada app!
• GRRSP. Generous employer matching program!
• Transport: monthly Toronto Transit Commission pass or other equivalent commuter benefits.
• Learning & Training opportunities: a highly flexible training policy, free books and budgets to attend and speak at conferences if the opportunity arises.
• Personal growth through coaching: At Alan, coaching isn't just a perk - it's core to who we are. Every Alaner is paired with a dedicated coach from day one, who helps maximize their impact, nurture engagement, and navigate Alan's values to develop their full potential. Learn more about our coaching culture.
• Parental leave: extended parental leave for all new parents.
  
  

Important note: we hire people, not roles.

If you're excited about this opportunity but don't check every box, we'd love to hear from you. Everyone, no matter how underrepresented, should feel free to apply as it can only bring learnings or success.

If you identify yourself as a woman: Did you know that research shows women often apply only when meeting 100% of requirements?

Remember, this is just a guide, not a checklist.

We'll be thrilled to receive your application!

Check out our About Alan and Career pages, as well as our Medium, blog and Glassdoor page for more info.