Hybrid Senior Account Executive – Mid-Market

Posted 3 hours ago

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About the role

  • Mid-Market Account Executive driving sales transformation through outcome-based selling for the modern insurance brokerage. Engaging with mid-sized organizations, promoting AI technology in their operations.

Responsibilities

  • Business Case & Value Mapping
  • Full-Cycle Strategic Sales: Own the journey from initial introduction to long-term partnership.
  • Economic Value Mapping: Move beyond features to build a comprehensive Business Case. You will quantify the Cost of Inaction for prospects—calculating the dollar value of broker time lost to manual notes and the potential cost of an undocumented E&O claim.
  • Consultative Discovery: Use diagnostic sales techniques to uncover deep-seated operational friction.
  • Champion Building & Multi-Threading: Navigate the Power Map of a brokerage.
  • Mutual Action Plan (MAP) Orchestration: Act as a consultant-lead project manager for the buying process, ensuring all stakeholders are aligned on the path to value realization.
  • AI Strategy Advocacy: Educate traditional leaders on how Conversational AI creates a competitive advantage, specifically through automated CRM updates and real-time compliance tracking.

Requirements

  • 5–7+ Years of Consultative B2B Sales: Proven experience in Mid-Market deals where the Product is secondary to the Business Transformation.
  • Advanced Financial Literacy: You are comfortable building an ROI model in a spreadsheet and presenting it to a CFO or Principal.
  • Solution-First Mindset: You have mastered a methodology (e.g., Challenger, Gap Selling, or Sandler) that prioritizes solving a business problem over pitching a product.
  • Storytelling & Vision: The ability to take complex AI technology and weave it into a narrative of The Modern Brokerage.
  • Process Rigor: High CRM discipline and a Manager of the Business mentality. You know your numbers, your conversion rates, and your path to quota.
  • Bonus Experience Vertical Expertise: Deep understanding of the Insurance or Financial Services landscape.
  • Technical Integration: Experience discussing how voice/AI data flows into Agency Management Systems (AMS) like Applied Epic or Vertafore to create a Single Source of Truth.

Benefits

  • Uncapped Commission: Significant accelerators for over-performance.

Job title

Senior Account Executive – Mid-Market

Job type

Experience level

Senior

Salary

CA$85,000 - CA$105,000 per year

Degree requirement

Bachelor's Degree

Location requirements

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