Job Description

This position is posted by Jobgether on behalf of a partner company. We are currently looking for an Enterprise Account Executive in Canada.

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:

You will be responsible for driving enterprise sales growth, managing strategic accounts, and building long-term relationships across the insurance ecosystem while executing a consultative, value-driven sales approach.

• 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:

This role requires extensive enterprise sales experience within the insurance or enterprise software sector, with a proven ability to manage complex, consultative sales cycles.

• 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

How Jobgether works:
We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.
We appreciate your interest and wish you the best! Why Apply Through Jobgether?
Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.
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