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 based in Toronto, you will drive full sales cycles with mid-market and enterprise companies, connecting decision-makers to solutions that address gaps in the current healthcare system. The company serves over 1 million members across 40,000+ partner organizations globally.

Key responsibilities

Manage complete sales cycles from initial prospection through customer onboarding, primarily engaging with founders and heads of HR or Finance.
Identify pain points with existing insurance providers and demonstrate how a fully digital solution can address critical healthcare system gaps.
Build market relationships through outbound outreach, community events, industry conferences, content creation, and other channels that deepen your understanding of customer challenges.
Gather feedback from prospects and customers and share insights with product teams to inform feature development and service improvements.
Collaborate with marketing to design and execute campaigns, events, sponsorships, and initiatives that resonate with your target market.
Proactively generate pipeline and leads through direct action rather than relying on inbound lead distribution.

Requirements

Two to eight years of experience as an Account Executive in B2B technology sales.
Full fluency in English; proficiency in French is strongly preferred.
Demonstrated experience across all stages of the deal cycle, including prospection and contract negotiation.
Comfort with feedback and a coaching-oriented culture where continuous development is expected.
Ability to work in-office four to five days per week to support team collaboration and customer focus.
Willingness to obtain the LLQP license, which the company will fund and support.

What makes this role worth considering

You will work within a rapidly expanding organization of over 1,000 employees that is reshaping how healthcare is delivered globally. Alan’s Toronto office is located in the heart of the financial district with on-site amenities including free lunch, and the sales team operates in a close-knit, collaborative environment. Beyond competitive base salary and equity, you receive comprehensive benefits including an employer RRSP matching program, access to Alan’s healthcare coverage, flexible paid leave, one-on-one coaching from day one, and extended parental leave for all new parents.