Alan is building a vertically integrated health partner uniting insurance and healthcare into one seamless system. Globally we have 35,000 customers, 1 million members and $1B+ revenue.

In Canada, we’re early, and growing fast bringing a $6B+ global company into a new market.

Our mission: Help people live in good health to 100 years old while helping employers feel proud, turning health benefits from a cost centre into their most valuable investment.

🚀 Your mission

You're not here to shadow. You're here to build.

Canada is a new market. The expansion is being written and you'll help write it.
Supporting the Chief of Staff, and leadership in Canada, you'll work alongside the GM of Canada, the sales team, marketing and more to unlock growth, driving alignment on strategy, building new processes internally and externally and building new products.

You will be highly involved in key challenges for Alan, and will be asked to support high added value tasks for Alan.

Possible projects include:

As such, you can’t be exhaustive on the missions you will perform as an intern, as you can be asked to help on almost any subject.

Sales

• Join customer and prospect calls - learn the full sales cycle firsthand

• Build workflows that help the team scale across Canada

• Build internal AI tools used by sales, marketing, and leadership

• Support partnership opportunities and business outreach

• If you want to build something real - you are.

Examples of past intern projects

• Helped organise founder and HR events in Toronto — contributed to invite lists, contacted companies, and supported conversations that generated real pipeline for the sales team

• Researched new customer segments in Canada — built target lists, analysed competitors, and supported go-to-market plans for new verticals

• Created AI tooling to accelerate our GTM plans

Your profile

• Analytical & business sense — frame the right questions, make sound decisions in ambiguity, think at the company level

• Execution & collaboration — own projects start to finish, direct yourself and others toward outcomes

• Versatile & organized — switch contexts without losing quality, deliver with precision and minimal hand-holding

• Be concise - each word matters

Must have

• Business / Commerce / Economics / Engineering or similar

• Strong communication

• Comfortable with ambiguity

• Wants to learn sales, GTM, or strategy

Nice to have

• B2B / SaaS / insurance / health exposure

• Strong interest in healthcare

• Built something yourself — club, project, startup, side hustle

Perks

• Free lunch at King & Yonge office

• Direct exposure to GM, Chief of Staff, and sales leadership

• Alan health coverage

• Real responsibility from week one

We hire builders, not resumes.
If this sounds like you, apply — even if you don’t check every box.