About this role
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 missionYou'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.
SalesJoin 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 projectsHelped 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 profileAnalytical & 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 haveBusiness / Commerce / Economics / Engineering or similar
Strong communication
Comfortable with ambiguity
Wants to learn sales, GTM, or strategy
Nice to haveB2B / SaaS / insurance / health exposure
Strong interest in healthcare
Built something yourself — club, project, startup, side hustle
PerksFree 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.