Role overview

Alan is building a new standard in prevention-focused insurance by integrating insurance, prevention, and care into a single digital experience. As an Account Executive in Toronto, you will own the complete sales cycle, from initial outreach through customer onboarding, working with founders and senior leaders in HR and finance to demonstrate how a fully digital solution addresses gaps in the current healthcare system.

Key responsibilities

Manage full sales cycles from prospecting through contract closure, primarily targeting founders, heads of HR, and heads of finance.
Conduct outbound prospecting and build market relationships through community events, conferences, content creation, and other channels that deepen your understanding of customer pain points.
Present Alan’s digital health solution as an answer to frustrations with incumbent insurance providers.
Gather feedback from prospects and customers and communicate market insights back to the product team to inform development priorities.
Collaborate with marketing on campaigns, events, sponsorships, and initiatives that resonate with your target market.
Take ownership of lead generation and market development rather than relying on inbound pipelines alone.

Requirements

Two to eight years of experience as an Account Executive in B2B technology sales.
Full fluency in English; French language skills are strongly preferred.
Demonstrated experience across all stages of the deal cycle, including prospecting and contracting.
Comfort with feedback and a coaching-oriented culture, with a builder’s mindset that prioritizes writing your own playbook over following an existing one.
Strong written communication skills and attention to detail, with the ability to create presentations and one-pagers independently.
An outcomes-focused, action-oriented approach; you take initiative to create value rather than waiting for support structures to be in place.

What makes this role worth considering

You’ll join a team of over 1,000 people working on a mission to transform healthcare through prevention. Alan already partners with 40,000+ companies and serves more than 1 million members. The sales team works in-person 4-5 days per week from a prime downtown Toronto office (King and Yonge) with free lunch and collaborative spaces designed to fuel proximity and customer focus. Every team member is paired with a dedicated coach from day one to support your growth and impact.

Additional highlights

Competitive base salary plus equity, with no commission structure to keep incentives aligned with customer success.
Alan covers the cost of obtaining the LLQP license required for the role.
Monthly transit pass, generous RRSP matching, and access to healthcare insurance through Alan’s Canada app.
Flexible leave policy with no pre-approval required, extended parental leave, and a coaching culture embedded across the organization.