Role overview

Alan is building a new standard in prevention-focused insurance that integrates coverage, prevention, and care into a unified digital platform. As an Account Executive based in Toronto, you will own the complete sales cycle, from initial prospection through client onboarding, working with founders and senior leaders at companies of all sizes to show them how Alan’s digital-first approach addresses gaps in traditional health insurance.

Key responsibilities

Drive full sales cycles from prospection through contract signing, primarily engaging with company founders, heads of HR, and heads of Finance.
Build market relationships through outbound outreach, community events, industry conferences, and online content creation to deepen your understanding of client pain points.
Identify how Alan’s prevention-focused model solves specific problems clients face with incumbent insurers and communicate that value proposition clearly.
Gather feedback from prospects and customers and share insights with the product team to inform how Alan evolves to serve market needs.
Collaborate with marketing to develop campaigns, events, sponsorships, and other initiatives that resonate with your target market.
Generate your own pipeline and leads through proactive effort rather than relying on inbound sources.

Requirements

Two to eight years of experience as an Account Executive in B2B technology sales.
Full fluency in English; French language skills are highly valued.
Demonstrated experience managing all stages of the deal cycle, including prospection and contract negotiation.
Comfort with a coaching-oriented culture and openness to regular feedback.
Proactive, builder mindset that thrives on opening new markets or creating sales approaches from scratch rather than following established playbooks.
Strong written communication skills and attention to detail.
Willingness to create your own materials and content without waiting for support resources.

What makes this role worth considering

Alan operates with a distinctive culture centered on coaching and personal development; every team member is paired with a dedicated coach from day one. The Toronto sales team works in-person four to five days per week in an office located in the heart of the financial district at King and Yonge, with free lunch and collaborative space designed to strengthen team connection. The role offers competitive base salary plus equity with no commission structure, ensuring alignment with customer needs rather than transactional incentives, plus the company covers the cost of your required LLQP license and provides healthcare benefits through Alan’s own platform.