Account Executive - Canada 🇨🇦

About the role

You own the end-to-end commercial journey for enterprise clients in the Canadian market, driving both new business and expansion within assigned accounts. You translate complex prevention-first value propositions into clear, compelling narratives that resonate with high-level stakeholders such as founders, heads of HR, and heads of finance. You diagnose prospect pain points related to incumbent insurance models and position Alan as the single, integrated solution that closes critical gaps in the healthcare system. You proactively build market understanding by capturing feedback from customers and prospects, feeding insights directly into product and marketing teams to influence solution development. You collaborate internally with marketing to design and execute targeted campaigns, events, and sponsorship programs that amplify reach and engagement. You take initiative in creating your own outbound strategies, content, and tools to generate demand and deepen relationships without waiting for handed opportunities. You are expected to move fast in a high-growth environment, building trust and momentum through consistent, empathetic, and detail-oriented communication.

Key facts

What you'll do

Conduct discovery conversations with founders, HR leaders, and finance leaders to uncover how current health insurance models create friction and cost.

Translate Alan's prevention-first platform into tangible business outcomes, linking better employee health to reduced systemic wait times and long-term cost savings.

Build and maintain C-level relationships based on trust, transparency, and a shared vision for redefining employee health benefits.

Own the full sales cycle, from initial outreach and qualification through negotiation, contracting, and successful onboarding.

Develop deep empathy for customer challenges by actively listening and articulating how a 100% digital solution addresses real-world gaps in care.

Create proactive outbound plans that generate pipeline without relying on inbound leads or pre-approved scripts.

Represent Alan at industry conferences, community events, and internal sessions to strengthen brand presence and thought leadership.

Collaborate with marketing to design campaigns and content that speak directly to the priorities of HR and Finance decision-makers.

Use customer feedback to influence product enhancements, ensuring the platform continues to solve evolving client needs.

Maintain rigorous pipeline management and forecasting to support company growth targets and strategic initiatives.

Champion a builder mindset by writing your own playbooks, testing new channels, and iterating based on real-world results.

Work in close proximity with the Toronto-based sales team to align on best practices, share wins, and drive collective performance.

Requirements

You may be a great fit at Alan if you have 2 to 8 years of experience as an Account Executive in B2B technology sales.

You demonstrate full fluency in English, and fluency in French is a strong advantage in the Canadian context.

You have experience across the entire deal cycle, including proactive prospecting, negotiation, and contracting.

You have a proven track record of overachieving quotas and taking ownership of complex, multi-threaded sales engagements.

You are comfortable selling to HR and Finance leaders who are evaluating systemic solutions to long-standing healthcare challenges.

You have experience working within high-growth technology companies where speed, adaptability, and ownership are essential.

You are comfortable receiving feedback and operating within a coaching culture that emphasizes continuous improvement.

You hold the LLQP license required for the role, and the company will cover the cost and provide the time needed to obtain it.

You are excited to build new markets and verticals, and you prefer action-oriented environments where writing the playbook is more appealing than reading one.

Nice to have

You moved from SDR or BDR to AE faster than your peers, demonstrating early acceleration and impact.

You have a history of overachieving your quotas and consistently delivering above expected results.

You bring experience from high-growth startups or scale-ups where agility and ownership are highly valued.

You have sold to HR or Finance leaders in previous roles, especially within health or insurance-adjacent industries.

You have experience winning deals where French language capability is an advantage in Canadian markets.

You are comfortable giving and receiving feedback and thriving in environments with a strong coaching culture.

You have a genuine interest in prevention and digital health innovation that improves access and outcomes.

Practical notes

The role requires in-person collaboration, with an expectation to work from the office 4 to 5 days per week in Toronto.

You will need the LLQP license for life and accident sickness insurance; the company covers the cost and provides dedicated study time.

This position is based in Toronto, Ontario, Canada, and follows full-time employment terms.