Enterprise Account Executive - Remote Eligible

Enterprise Account Executive

This senior commercial role focuses on driving strategic growth across enterprise insurance clients by selling advanced data, connectivity, and AI-powered risk digitization solutions. You will manage complex, high-value sales cycles, working closely with C-level stakeholders and functional leaders across carrier and MGA organizations. The role combines new business acquisition with expansion of existing strategic accounts, requiring a strong consultative approach and deep understanding of customer operations. You will be responsible for developing tailored account strategies, accelerating decision-making cycles, and ensuring long-term client success. Operating in a highly competitive and relationship-driven environment, you will also act as a key market-facing voice, feeding insights back into product and go-to-market strategy. This is a high-impact, senior-level position where ownership, autonomy, and commercial excellence are essential.

Accountabilities:

• Develop and execute strategic account plans for key enterprise clients, identifying stakeholders, priorities, and growth opportunities
• Manage full-cycle enterprise sales processes from prospecting to negotiation and closing of complex deals
• Expand existing accounts while actively pursuing new enterprise-level insurance clients
• Build and maintain strong relationships with C-level executives and senior functional leaders
• Apply consultative selling techniques to align client challenges with tailored solution offerings
• Accelerate sales cycles by addressing objections, building business cases, and driving internal alignment with customers
• Provide accurate forecasting, pipeline updates, and sales reporting to leadership
• Gather and communicate market insights, including competitive intelligence and industry trends
• Collaborate with internal teams to align customer needs with product roadmap and marketing strategies
• Represent the organization at industry events, conferences, and client engagements

Requirements:

• 10+ years of sales experience with a strong track record in consultative, solution-based selling
• 5+ years of experience in the insurance industry or selling software solutions to large enterprise clients
• Proven success in exceeding sales quotas and driving new business growth
• Strong understanding of insurance industry workflows, distribution models, and market dynamics
• Experience managing complex enterprise accounts and engaging C-level stakeholders
• Proficiency with CRM systems such as Salesforce
• Excellent negotiation, presentation, and relationship-building skills
• Strong analytical and strategic thinking abilities
• Ability to manage multiple priorities and complex sales cycles simultaneously
• Bachelor's degree or equivalent professional experience
• Experience with tools such as Slack and enterprise collaboration platforms is an asset

Benefits:

• Highly competitive total compensation with uncapped earning potential (target total cash compensation exceeding CAD $200,000+)
• Comprehensive medical, dental, and vision coverage
• Paid vacation, holidays, wellness days, and a paid birthday day off
• Flexible hybrid or remote work arrangements within Canada
• Strong performance-driven commission structure with significant upside potential
• Career development opportunities in enterprise sales and insurtech innovation
• Inclusive and collaborative culture focused on autonomy and impact
• Participation in industry events and professional networking opportunities